The future of work was, is, and always will be about content — creating it, managing it, and protecting it for business use.

I’ve always loved prediction season because predictions are fun.

They feel like work, but allow you to indulge in a bit of whimsy and speculation without having to worry about being wrong.

They’re even better when you get them right!

12 years ago, a Gartner analyst I know (Hanns Kohler-Kruner) invited a large number of folks in the ECM* (enterprise content management) industry to make predictions about the future of work for research Gartner was conducting at the time (never read that research).

Doing some overdue spring dead-heading of old content on LinkedIn (along with seeing if anything is worth refreshing) and started reading the short essay I wrote in response to Hanns’ request.

Much to my surprise, I was actually mostly right. And while we’re still too early for 2027 prediction season, I thought I’d share anyway.

Below is my original post, along with combined responses from Claude and ChatGPT for accuracy and my grade (and no, I didn’t tell them to grade on a curve!). The stuff from the robots is in brackets.

The Future of Work – All About Content

Unlike George Jetson, I’m pretty sure we won’t be able to fly our car to the office, push a red button, and then relax until it’s quitting time (barring our blustering boss pushing HIS button to yell at us). Work will still be work. How we get it done . . . that might be a lot cooler.

Two things first off. One, half of everything everyone writes will be collectively wrong — I’m still waiting on my flying car. Two, we should be clear that we’re focused on office/knowledge work. While technology will of course affect tracking, assigning, etc. other work; digging a ditch is still digging a ditch.

[Holds up. Software wraps around more work now, but the ditch is still a ditch.] Me again: I will add here that robots work autonomously in warehouses and I do think that there’s potential for automating manual work outdoors with robots as technology continues to improve.

The future of work will be reliant upon effective creation and maintenance and then distribution of content/information/documents/data (pick a word). The companies that take this fire hose of information and point it in the right direction will be the ones that win.

[Arguably more true now than in 2014. Every shiny AI demo is still sitting on top of content, data, documents, workflow, and retrieval. The model isn’t the moat. The plumbing is. Sadly, nobody wants to talk about the plumbing.]

I’m going to assume that we’ll get the maintenance and storage of content mostly right going forward, otherwise, we should all buy stock in storage companies now.

[Partial credit. Storage got cheap and abundant. Findability, governance, and basic “where did we save that” remain a mess in most organizations.]

I think we’ll get to a heads up display for work, which will make the “office” even more portable than now. To interface with this HUD, we’ll have some combination of input from eye tracking or direct “jacking” into brain waves.

[Directionally correct, early on timing. Apple Vision Pro ships with eye tracking and is pitched at productivity; Meta’s Orion points the same direction. Brain-wave input remains clinical and experimental, not something anyone uses to clear their inbox. Call it right in concept, a decade optimistic on adoption.]

I think from a marketing standpoint; companies will be able to slice and dice a huge amount of data from customer interactions to pinpoint and deliver targeted ads/offers (whatever you want to call them) to consumers at point of sale/point of looking in the aisle (if you have your mobile device/embedded chip turned on); geographically or online.

[Full marks. Retail media is its own category now. Every major grocery chain runs an ad network. Transaction, loyalty, and behavior data drive targeting at the moment of intent. The embedded-chip line reads less like a joke than it did in 2014.] Me again: This was inspired by a conversation I had had with the guy who created the software that spat out those personalized ads/coupons on the back of your grocery store receipt.

I think Facebook and/or Google will be less about “the Web” and more about delivering that customer data to advertisers.

[Right in substance. Alphabet closed 2025 at $402.8 billion in revenue, most of it still advertising; Meta’s revenue is overwhelmingly ad-driven. “Less about the Web” is the part that needs a tweak — Search is still the cash register — but both companies are fundamentally ad and data businesses with products as the delivery mechanism.]

[Note: this might be more today than the future.] Unlike the other brackets, this was an original aside.

[Accurate self-catch. This was already underway in 2014.]

I think we’ll stop worrying about the bullshit divide between work and personal and finally acknowledge that because the office is so portable, office hours really don’t mean much beyond some basic, core ability to be able to meet with your team at a mutually convenient time. There will be times when 9 to 5 is needed. Other times, the ability to be untethered to a cubicle but still connected will unleash a huge wave of productivity — and maybe even decrease the amount of time we all spend in rush hour (a productivity saving all by itself).

[The most optimistic paragraph in the piece, and where it misses hardest. Portability happened — roughly a quarter of US. paid workdays are remote — but the divide didn’t dissolve. It collapsed into always-on. Late-night meetings are up, cross-time-zone work expanded, and the boundary is worried about more now, not less. Right on the technology. Wrong on what humans would do with it.]

Despite 1 and 4, the value of face-to-face, real-time meetings (virtually or IRL) will continue to be a powerful way to collaborate.

[Correct. Hybrid won. Pure async didn’t.]

Paper — or at least some sort of digital paper — will continue to be with us. People like to write stuff down.

[Right. Quocirca survey data still puts printing as necessary for a clear majority of SMBs, and paper note-taking remains stubbornly popular among the people supposedly living in the future.] Me again: Recent AIIM research shows about 50% of all business processes run on paper. The supply chain industry remains almost entirely paper-based; and with something like 100 documents for a single container and with the average container ship ferrying 10,000 – 20,000 containers . . . that’s a LOT of paper, ripe for automation.

Cultural issues will hold productivity back more than technology. Dilbert’s Pointy-Haired Boss (hmmmm, any resemblance to Cosmo Spacely?) will still be with us and not all companies will be able to be truly creative as C-level continues to focus on productivity measures that just don’t matter.

[The piece’s most durable prediction. Gallup’s 2026 report shows global employee engagement dropped to 20% in 2025, the lowest since 2020, with disengagement pegged at roughly $10 trillion in lost productivity in 2024. Technology keeps improving. Management keeps underperforming. The culture lag is the real bottleneck, and it has been for decades.]

And, as Gregg Easterbrook says in his brilliant Tuesday Morning Quarterback column: All predictions wrong or your money back.

[Not all wrong. No refund issued.] I am delighted to just now discover that he still writes the column here; and I just subscribed. Now just need football season to hurry up and get here! WhoDat!

Roughly 7 right, 2 half-right, 1 early.

Final grade: B+. Strongest on ad-tech targeting, paper not dying, the primacy of culture over technology, and the portability of office work. Weakest on assuming portability would feel like freedom rather than a longer leash. Would be an A- with slightly less cheerful naivete about what humans do with always-on tools.

Your turn. Dig up something you wrote 5, 10, 12 years ago. Read it. Grade it. You’ll probably be more right than you remember — and wrong in ways that are useful to notice. Hit reply and tell me what you found. Love to see what y’all come up with.

Thanks for reading, comments, criticisms, and witticisms welcomed.

Nobody knows.

That’s the answer. I’ve been comfortable saying that for decades even though as an editor and content marketing pro it always feels like people think I’m being glib when I do.

Nobody — not the guru with the $997 course, not the algorithm whisperer on LinkedIn, not the marketing professor with a shelf full of textbooks — knows what “just right” is for your content. Not precisely anyway. The honest ones will say it anyway rather than trying to tap-dance their way through an impressive 2 minute discourse that boils down to “I don’t know for sure.”

The fear that you’ll get it wrong — too long, too short, too often, too infrequent, too much, not enough — is one of the most effective forms of procrastination I’ve ever seen. Researching can look like strategy. It feels like diligence. But it’s just paralysis by analysis.

I’ve written about pieces of this before — the “great” trap, the goldfish myth, the barking problem – but not altogether.

Here’s how they fit. Let’s go.

The “Too Long” Myth Is Still Bullshit

Let’s start with length, because this is the one that won’t die.

“Keep it short. People don’t read anymore. Attention spans are shrinking.”

No. People don’t read your shitty, self-involved content that serves you and not them. That’s a different problem entirely.

I’ve been watching content performance metrics since me, the mail room guy (now a successful Web designer), and my managing editor built our first website together in 1998. Longer content that’s actually useful consistently outperforms shorter content on time-on-site, engagement, and conversions.

And the data keeps backing this up. Long-form content of 3,000+ words performs 2.5 times better than shorter pieces. The average content length for the top 10 Google search results is approximately 2,200 words. Posts over 2,000 words generate three times more backlinks and shares than shorter ones. Content Marketing Institute data shows long-form articles get 75% more time-on-page than short pieces.

On the other hand, the average blog post length actually shrank in 2025 — down to about 1,350 words, decreasing for the second year in a row. So the average is getting shorter while the best-performing content is getting longer.

Why? Because AI is pumping out short, mediocre content at industrial scale. The floor is flooded with machine-generated filler, and it’s pulling averages down. Meanwhile, the stuff that actually works — the content people read, share, link to, and act on — keeps getting longer and more substantial.

While I remain dubious that anyone can always tell if something is created by GenAI, we all at least say we want human content. Stats show that human-generated content receives 5.44 times more traffic than AI-generated content.

The competitive advantage of writing something real and useful and long enough to actually help someone is widening, not shrinking. There’s less competition at the top because fewer people are willing to do the work.

Meanwhile, 60% of adults binge-watch TV regularly. I once turned on the first episode of Cobra Kai around 9 on a Friday night and looked up at 4 a.m. having finished the entire first season.

We pay attention to things we find interesting. That’s it. That’s the whole secret.

If it’s short and shitty, people won’t read it. If it’s long and good, they might. Length is not the problem. Usefulness is the variable.

But There ARE Broad Targets

I’m not saying anything goes. There are general guidelines that work across platforms, and if you’re just getting started, they’re worth knowing — not because they’re sacred, but because they get you unstuck.

For blog posts, 500 words is enough to make a single point. I’ve been telling people that for over two decades and it still holds. It’s short enough to write quickly but long enough to actually say something. For meatier pieces that you want to perform in search and get shared, the research points to 1,600 to 3,000 words — but that’s not every post you write. Though one effective strategy is to only write long, well-researched posts. Yeah, it really does depend on your goals, time, budget, skills, market, and so on.

For newsletters, one useful idea per issue. That’s the bar. “Here’s one question we get all the time. Here’s the cleanest answer I have. Here’s what to do if you need more help.” Done.

For social posts, shorter tends to win because you’re fighting a feed, not a reader’s attention span. But even there — a longer LinkedIn post that tells a real story will outperform a punchy one-liner with nothing behind it. One interesting wrinkle: LinkedIn carousels — the PDF-style posts — earn a median engagement rate of 21.77%, which is 196% higher than video and 585% higher than text posts. Highest of any format on any platform in a recent Buffer analysis of 45 million+ posts. That’s a format thing, not a length thing — which is exactly the point. The “rules” are platform-specific and format-specific, not universal.

For video, I recommend a length ladder: 7–10 seconds for a teaser, 20–30 seconds to answer one question, 60–90 seconds for a full explainer. Record once, cut three ways, and let the audience tell you which one they actually watch. Full disclosure: I give this advice but haven’t mastered the multi-cut workflow myself yet. I’m still learning. But the principle is sound — and it’s supported by the data. Videos under two minutes have a 70% higher completion rate than videos over five minutes.

These are starting points. Guardrails. Training wheels. They exist to get you moving without running into a ditch, not to define or limit you. In time, you’ll be riding in the ditch and jumping the guardrails – but you have to start first.

Frequency: The Other Goldilocks Problem

How often should you publish? The honest answer: I don’t know. Neither do you. Neither does anyone — until you start.

There is a “that’s just too much” level every newsletter reaches. But no one knows where that line is until they cross it. Your audience might want to hear from you more than you think. Don’t limit your reach voluntarily.

Start monthly. Twice a month if you can sustain it. Stick to that for three months. Then pay attention. Are people opening? Clicking? Replying? Unsubscribing in unusual numbers?

Increase the frequency until more folks than normal unsubscribe from an issue. Congratulations — you’ve found “too much.” Dial it back one notch. That’s your Goldilocks zone. For now.

Because it moves.

Here’s what the data actually says, and it’s worth knowing: MailerLite analyzed over 12 billion emails in 2025 and found that sending frequency has less impact on unsubscribes than sending irregularly. Sending less than once a month was the biggest driver of unsubscribes — not sending too often. More frequent senders (weekly, twice a week, even daily) actually had lower unsubscribe rates.

Separately, Campaign Monitor’s research shows newsletters should land somewhere between once a month and twice a week, and there isn’t much difference in open rates across that entire range. Brands sending 4–8 emails per month tend to hit the best balance.

You don’t need to worry about frequency until you actually publish one. Then another and another. Create a cadence you can stick with. Give yourself deadlines. Meet those deadlines. Publish.

If you get to the point that you really need to worry about sending “too much,” congratulations, you’re kicking ass and taking names.

Again: Be. Consistent.

If you’re reading this and realizing your newsletter is one of those things you keep meaning to start — or restart — but the “just right” question keeps freezing you up, that’s exactly the problem I built Newsletter in a Box to solve. I handle the writing, the strategy, and the showing up on schedule so you can stop agonizing and start publishing. Hit reply (bryant@simplyusefulmarketing.co) if you want to know how it works

Volume: The Barking Problem

Volume in content marketing has two meanings: output and promotion.

So let’s tackle output first. We just covered frequency for newsletters, but this applies to everything. Blog posts, social posts, videos, all of it. There’s a middle ground between publishing nothing and flooding every channel like a bot high on Red Bull and Sour Patch Kids with a quota. Brands published an average of 9.5 posts per day across all networks in 2024. The resulting saturation sets up a vicious cycle of doing more than your competitors who then do more than you and then you . . . until customers start to tune you out or hit block and unsubscribe.

But most small businesses and solopreneurs are nowhere near that problem. They’re not posting too much. They’re barely posting at all. If you’re agonizing over whether three LinkedIn posts a week is “too many” or if two newsletters a month is “spamming,” you’re worried about a problem you don’t have.

The second meaning is promotion — how loudly and how often you share what you’ve already made. This is where most people I talk to fall down (including folks who know better). They publish something, share it once, and move on. They want the work to speak for itself. I operated that way for years. It doesn’t work. You have to share your content more than feels comfortable. You have to ask for the sale or the meeting. You have to bark.

Not like an over-caffeinated chihuahua barking or the bot on a sugar high. But you do have to open your mouth.

The Goldilocks zone here isn’t about finding a magic posting schedule. It’s about whether you have something worth saying each time you show up. “Post with purpose” sounds like a bumper sticker, but it’s the actual answer. One thoughtful post beats three that exist because someone told you to post daily.

Rule of thumb: share at least one thing daily, even if it’s engaging with someone else’s content. And when you publish something you’re proud of, share it more than once. I promise that there are more people who would be interested in seeing it than already saw it.

Quality: The Trap That Eats Everything

And then there’s the “great” problem.

A lot of writing and marketing advice tells you to create “great content.” I’m all for great content. I’d love to write one great thing. But trying to be great before you’ve published a damn thing is how you end up frozen.

I’ve been there. When I took over as editor of a professional magazine at 26, I wanted every issue to be perfect. I had to figure out how to get out of my own way. And when I moved into content marketing years later, the same problem came back.

The truth is that even the greats aren’t always great. Drew Brees won games with 37 seconds on the clock and also threw interceptions that ended seasons. The Eagles have some incredible songs and some you skip every time. As my favorite greatest hits album title — from Primus — says: They Can’t All Be Zingers.

Focus on being useful and you might get to great on the way.

The AI flood actually makes this argument stronger than it was a year ago. As one analysis put it: the more machines produce fast, standardized, context-free content, the more humans crave analysis, experience, and deep thinking. Long-form, human-written content is becoming a marker of expertise — not because long is inherently better, but because anything real stands out (reinforcing the “longer can be better” point I made earlier).

One sobering note worth sitting with: the average bounce rate for content pages in 2026 is 45%. Nearly half of visitors leave without engaging. Quality alone doesn’t guarantee attention — distribution and trust still matter. But that’s not an argument against quality. It’s an argument that you need both: something worth reading AND the willingness to put it in front of people.

The Goldilocks zone for quality isn’t a fixed standard. It’s “better than the bots, and actually helpful to a real person.” That bar keeps moving, but it’s achievable for anyone willing to do the work.

Two Contradictory Things That Are Both True

Here’s where it gets uncomfortable, because I need you to hold two ideas in your head at the same time.

First: Follow the broad guidelines. They exist to get you started and unstuck. Don’t overthink. Don’t wait for perfect. Just do it — and over time, you’ll develop a feel for what works. You’ll build a filter. “This is me” on one side, “this isn’t me” on the other.

I can’t tell you exactly how that filter develops.

There’s no secret. Do it. Do it again. Evaluate. Tweak. Revise. At some point you’ll be writing and you’ll just know if it’s right or wrong.

Second: When that filter tells you to break the guidelines — break them. Want to write something longer than the “best practices” say you should? If you believe in it and you believe your audience will get something from it — do it. No one knows your audience better than you do.

Slavish devotion to rules is as bad as having no rules at all. The guidelines are there to remove the fear, not to replace your judgment.

Mini Content Lesson

Before letting you go, a quick mini-lesson in content creation. I noted in the intro that I’ve touched on each of the topics above, but not as a single post to have them all in context. NEVER think of a piece of content in isolation. Note that this is a reflexive skill/habit built over 30 years and I still get it wrong at times; so be kind to yourself if you’re just beginning to create content.

You can bundle pieces together to build something new (Notes into a newsletter post for example). Or take something large and pull it apart (a webinar could turn into a blog post, a series of social posts, a Q&A post – with each Q&A as its own Note or Tweet; you could also bundle the content from a webinar series into a larger ebook or whitepaper).

For instance, this newsletter could turn into:

1. Each section as a standalone post on LinkedIn

2. Shorter snippets to share on Notes

3. A short, Simply Useful Marketing Minute video

4. A chapter in an ebook on online writing advice

5. Go deeper into each section and create more in-depth posts

6. Compile those posts with a bit of connection tissue and it’s a short ebook.

It’s not always effective or worthwhile to pursue every permutation of what you can do, but it is a good idea to think of how you can use/reuse what you publish.

So What the Hell Is “Just Right”?

It’s a moving target. Sometimes it doesn’t exist at all. And the search for it — the endless calibrating, the reading one more article about optimal post length, the tweaking before you’ve even shipped anything — is itself a form of procrastination.

The only way to find your version of “just right” is to publish, pay attention, and adjust. Over time, patterns emerge. You’ll notice what your audience responds to. You’ll develop instincts you can’t fully explain but learn to trust.

That’s the Goldilocks zone. It’s a feel, not a number.

And the only way to create that feeling is to start publishing and pay attention to what happens. You’ll never find “just right” by reading “just one more” article about it.

P.S. If this whole piece made you think “I know I need a newsletter, I just don’t have time to figure all this out” — that’s literally why Newsletter in a Box exists. One conversation and I can tell you if it’s a fit. Email me at bryant@simplyusefulmarketing.co and we’ll talk.

No music today, just one of the innumerable Justice League Chicago Fire SVU shows in background (I’m at my Mama’s). Though here are a few sources for further reading.

Sources for content length

• https://www.averi.ai/how-to/10-content-marketing-trends-for-2026-(and-what-they-mean-for-startups)

• https://www.georgescifo.com/2025/10/the-definitive-guide-to-content-length-best-practices-for-2026/

• https://www.content-managers.com/insights/how-to-measure-content-performance/

• https://www.amraandelma.com/top-long-form-vs-short-form-content-statistics/

Frequency Sources

• https://www.mailerlite.com/blog/email-cadence-and-frequency-best-practices

• https://blog-origin.mediashower.com/blog/how-often-should-i-send-newsletters/

• https://nucleusmarketing.org/mastering-newsletter-timing-best-practices-for-frequency-timing-and-performance-benchmarks/]

In Greek mythology, the Moirai — the three Fates — controlled every mortal life. Clotho spun the thread. Lachesis measured it. Atropos cut it. Even Zeus couldn’t overrule them.

It’s a fun story if you’re inclined to enjoy mythology. However, waiting on fate is a terrible marketing strategy.

If you’re waiting for customers to find you — waiting for the right person to stumble across your website, or hoping your name comes up in conversation at the right moment — you’re handing your business plan to three fickle goddesses with a pair of shears. To market your business, you need a plan. Whether that’s a complex strategy with ad spend, multiplatform outreach, and a website that converts — or something simpler, like a clear offer on a landing page and a newsletter that builds trust (and an audience) over time — the common denominator is action.

Not hope.

Not fate.

Action.

I don’t believe in fate. Or “meant to be.” I think that belief leads to a learned powerlessness — an excuse to stop doing the work because the universe will sort things out.

But I do think we massively underestimate the role of chance. Not fate. Not manifestation. Just the plain, dumb reality that small random events can bend the entire arc of a life.

There’s science behind this. In 2018, a team of Italian researchers simulated a thousand careers over 40 years and found that the most successful people weren’t the most talented — they were moderately talented people who encountered the most lucky random events. Talent did play a role; in that a talented individual is better equipped to take advantage of a fortuitous event; but it wasn’t close to a guarantee of success. Their takeaway: we miss a critical piece of the success picture when we focus only on personal ability. FYI, it’s a fascinating article Read it here: Scientific American

The old line attributed to Seneca — “luck is what happens when preparation meets opportunity” — is partly right. You do need to be prepared enough to recognize a good thing when it shows up. But the showing-up part? You can’t schedule that.

Two stories of random chance (and my choices) sending my life down entirely separate paths.

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The No Way Pile. In 1994, I applied for an editorial internship at AIIM, a professional trade association. Got the job. A few years later, I became editor. While cleaning out the office, I found the intern applications. My resume was in a manila folder with “No Way” written on the outside. Now, I knew I wasn’t the first intern. John Harney had brought in a journalism student who was apparently so annoying she was dumped after 2 weeks. Never asked him why he pulled me in after that. But that one act set the course of my career for the next 20-plus years (and even now as I’m back in that industry).

The Alternator. Sophomore year at Southern Miss. I was supposed to drive to Jackson to visit a woman I’d been writing letters to all summer. My alternator died. The replacement part was supposed to come in Thursday, car fixed Friday, I’d be on my way. Part didn’t come in.

So I ended up in my buddy Jason’s dorm room that evening. Called Rebecca, told her I couldn’t make it. Literally as I hung up the phone, a woman named Candice walked in from the party next door, slid down the wall (she was a wee bit buzzed and took a wrong turn to the bathroom), and we started talking. Two weeks later, she smacked me on the head with a rolled-up program at a campus concert. I crawled over the seat and sat next to her. We were together from that night in 1990 until 2007. Two daughters. One grandson.

If the alternator part had arrived on time, I drive to Jackson. I never meet Candice. My daughters don’t exist. Everything after that moment is different.

Fate? Nah, just a logistical failure of a part not arriving on schedule.

Chance put me in Jason’s room that night. But I still had to talk to the woman who slid down the wall. John pulled my resume from the No Way pile — but I still had to show up and do the work once I got the interview.

You can’t control the random events. But you can be ready to take advantage of them when they arrive. And in marketing, you don’t have to wait for chance to put you in front of people. You can go build something that does it on purpose.

The Fates are fickle. Your marketing shouldn’t be. Stop waiting for Clotho to spin you some customers. Go build something.

PS — If you’ve been meaning to start a newsletter but keep waiting for the right moment, the right template, the right name that’s the Fates laughing at you while Atropos sharpens her shears. I help businesses build newsletters that show up consistently so you’re not relying on chance to bring customers to your door. Reply to this email or hit me at bryant@simplyusefulmarketing.co and let’s create your own fate.

Here’s something nobody selling AI wants you to think about too hard: every promise being made about enterprise AI — agents, copilots, RAG, agentic workflows, whatever the vendors are calling it this quarter — depends on a foundation that doesn’t exist in most organizations.

Not because the AI is bad. Because the information underneath it is a tottering tower of redundant, outdated, trivial, ungoverned, mislabeled, duplicated, scattered, and often unfindable content.

ROT, if you want the acronym. Redundant, outdated, trivial. The IDP (intelligent document processing; formerly ECM, formerly Document Capture, and even more formerly, microfilm and micrographics) industry has been talking about ROT for decades. It hasn’t gotten better. It’s gotten worse — there’s just more of it now, spread across more systems, with AI piled on top like a penthouse suite bolted onto a building with no plumbing.

I know this because I’ve been watching this industry not fix these problems for 30 years from a position of editor, marketer, and ghostwriter.

I started in the industry as an editorial intern at AIIM in February 1995. True story: when I was cleaning out the office a few years later after becoming editor, I found my resume in the “No Way” pile. I stumbled into this industry sideways through an open screen door — and never totally left.

One of the things that has stuck with me across all of those years is how little things have changed at the core. I recall a “paperless workflow” poster in the editor’s cube when I started that, with some slight updating, wouldn’t be out of place today. The one thing I wish had changed — and it hasn’t — is the gap between the need for what the IDP industry produces and the actual implementation of those tools by organizations.

That gap is about to matter a lot more than it used to. Because every promise being made about AI depends on the stuff this industry has been trying to get organizations to do for three decades.

I recently saw a conversation about trying to find research on converging information management teams with knowledge management teams inside large enterprises. A big multinational had asked an industry analyst (who has been in the industry since the late 80s) if any such research existed. He couldn’t find any.A practitioner who’d tried it at a large retailer said the two teams couldn’t even get past the fact that they didn’t share the same vocabulary. They worked at it for a while, got busy with their own goals, and drifted apart. I recalled suggesting something similar to AIIM leadership 16 or 17 years ago and they weren’t interested.

If the professionals whose literal job is managing information can’t converge their own teams — inside organizations that know they need to — what hope does a generic enterprise have of getting AI-ready across departments?

Note: I used both Claude and ChatGPT to compile this. Everything here is pulled directly from my thinking. The comparison of 2014 to today’s issue is all genAI, but pulled directly from the ebook (explained immediately below) or sites I directed the tools to look at. It’s my work, including most of the language. For those interested, I explain what I did at the end of this tome.

The Comparison Test: 2014 to Today

In 2014, I pulled together an ebook to market the AIIM conference that year. I stumbled across it last week and had the thought “Huh, I wonder how much of what’s in there are the exact same issues as now.” The title was “From InfoChaos to Information Opportunity.” It was a preview of the AIIM Conference – each speaker and sponsor contributed a short piece that we published online and then used in the ebook. I edited the thing and gave the designer instructions for what I wanted it to look like. I remember the conversations back then and they’re the same ones the industry is having today. The ebook (I’ve embedded it below) covered governance, fragmentation, findability, cloud sprawl, legacy workarounds, workflow exceptions, paper, metadata, change management, and the eternal struggle to get business value out of unstructured content.

I directed both Clause and ChatGPT to read it and then pointed it at what current vendors and analysts like AIIM, Gartner, McKinsey, Deep Analysis, Hyland, OpenText, IBM, Forrester, and others are talking about right now.

The overlap is not subtle.

Of the 10 big problem areas from the 2014 ebook. About 8 of them are still being discussed in almost identical terms. If you allow for the AI-era vocabulary swap — “information chaos” becomes “AI-ready data,” “ECM” becomes “content intelligence,” “information governance” becomes “AI governance” — it’s closer to 9 out of 10.

The industry has been better at changing labels than solving root problems.

Here’s the list.

1. Governance, retention, privacy, and compliance

Still the same fight. The 2014 ebook treated governance as foundational — eDiscovery risk, privacy exposure, the absence of real retention policies. Johnny Lee’s chapter was literally titled “I Don’t Need Governance” with the parenthetical “(or lower ediscovery costs or access to my content or...)” — that sarcastic tone tells you how far behind organizations were – 12 years ago.

In 2026, AIIM’s Global Summit has an entire opening keynote on AI governance and regulatory compliance — the EU AI Act, ISO 42001, cross-border data rules. Gartner predicts half of all organizations will adopt zero-trust data governance by 2028 because AI-generated content is creating a whole new class of unverified information to manage. And Gartner’s 2026 Magic Quadrant for data and analytics governance platforms has expanded significantly into unstructured data governance — something the 2025 edition barely touched.

Different acronyms. Same risk. Same organizations dragging their feet.

2. Fragmentation and silos across repositories

In 2014, the problem was file shares, SaaS silos, Dropbox, laptops, and phones. Alan Pelz-Sharpe — who is still covering this industry, now through Deep Analysis [Note: I’ve know Alan since the late 90s and currently do some marketing work for Deep. On the bullshit scale of 1 to 10; he’s a zero.] — called it a “Polar Vortex” of fragmentation that had dumped a pile of problems in its wake. The goal of one master file, stored and managed in one location, was a worthy ECM goal, he said, but it proved too impractical for most.

Today, AIIM’s own research says the average enterprise manages over ten information management platforms. Forrester says organizations store content across an average of 21 systems. Hyland’s new CEO — who came from the structured data world at Informatica — says content management was “perennially a black box.” His exact framing: large language models now allow you to give structure to unstructured data, so you can do the things we’ve been doing with structured data — without structured data. That’s a vendor pitch for solving a problem the industry identified a decade ago.

Same problem. More tabs open

3. Findability, metadata, search, and dark data

The 2014 ebook had an entire section on metadata being taken for granted. Another chapter complained about dark data straining IT budgets “for no good reason.” People couldn’t find anything, and the metadata that would have helped them didn’t exist or wasn’t maintained.

In 2026, AIIM is still centering “knowledge enrichment” and “knowledge discovery” as conference tracks. OpenText is selling tools to automate metadata tagging and surface content across repositories. The AIIM/Deep Analysis Market Momentum report found that unstructured data knowledge bases are spread across multiple applications. And according to recent industry research, only 11% of organizations have high metadata management maturity.

Twelve years of progress and we’re still swimming in information we can’t properly classify or find. That’s not a technology gap. That’s an effort gap. The technology exists. It has for a while. People just haven’t done the work.

4. Cloud, mobile, remote work, and BYOD versus control

The 2014 ebook was already panicking about information leaking through personal email, unmanaged devices, and free sharing tools. Monica Crocker’s chapter — one of the best in the ebook, a person with a sense of humor writing about a real problem — described how Land O’Lakes “grasped the cloud in a panic” because employees were storing company content on thumb drives and personal accounts. Her line about what happens when you don’t build an official solution stuck with me: people will “staple together a tar paper shack without adequate sanitary facilities and invite their friends to live there, too.”

That was 2014. Today the leak surface includes AI embedded in browsers, desktops, and operating systems. Shadow IT has become shadow AI. Gartner’s 2026 CIO survey found that 84% of enterprises expect to increase GenAI funding this year — but the governance to match that spending doesn’t exist yet. The devices changed. The control problem didn’t. And the tar paper shacks now have chatbots in them.

5. Legacy systems and poor usability driving workarounds

The ebook said it plainly: when the official system is painful, people route around it.

I wrote about this in 2022 when I did a presentation for the AIIM Florida Chapter. One of the things that sticks out to me across 30 years is that gap between the need for what this industry produces and the implementation of those tools by organizations. The technology exists. It works. People just don’t use it because it’s a pain in the ass — or it was implemented without anyone asking the people who would have to use it what they actually needed.

In 2026, Hyland is still pitching migrations from legacy ECM to its unified cloud platform. OpenText is positioning its AI Data Platform as a way to “activate” content trapped in old systems. The word “activate” is doing a lot of heavy lifting there — it means the content has been sitting around doing nothing. For years. In systems people hate.

Meanwhile, Hyland’s CEO is adamant that delivering AI and cloud value “should not start with a content migration” — which tells you that’s exactly what some organizations are being told to do. And if migrations are still the conversation in 2026, the legacy problem hasn’t gone anywhere.

6. Workflow and process automation that breaks on exceptions

In 2014, ibml’s Dan Lucarini warned about “casual capturers” passing errors directly to the most expensive workers in the loop — underwriters getting bogged down with missing paperwork because the capture step was pushed out to people who didn’t know what they were doing. BancTec said it simply: connect content and process.

In 2026, Forrester makes what it calls a critical and often-overlooked point: AI agents need clear, step-by-step instructions to perform enterprise tasks reliably, and in most organizations, that process knowledge still lives in fragmented workflows, undocumented tribal knowledge, and unofficial workarounds. Forrester’s readiness test is blunt: ask yourself if you know exactly where to find the documentation for how your organization actually does the work. If the answer is “no” — and it usually is — your AI agent is going to be about as useful as a new hire on day one with no onboarding, no training, and no one to ask.

I’ve been saying this for a while: companies are generally shit about understanding workflows, and agentic AI will depend on workflows and workflow orchestration to provide actual business value. Color me dubious of that happening any time soon.

The happy path gets automated. Real work still lives in the exceptions.

7. Paper, manual intake, re-keying, and accuracy problems

The 2014 ebook explicitly complained about re-keying and the stubborn persistence of paper. I.R.I.S.’s Frank Tiedt literally listed “time spent re-keying data” as a top business problem and noted that it was “tedious, time consuming and generates arthritis.” I appreciated the honesty.

In 2026, the AIIM Global Summit agenda includes a session on a nonprofit — Boys Hope Girls Hope — that had to digitize decades of paper records before it could even begin to use AI for classification and routing. And the AIIM/Deep Analysis research found that 58% of organizations report capture inconsistencies and 62% report incomplete data.

Are we getting closer to a paperless office? I’ve been asking that question for 30 years. Paper never really died. Neither did manual entry and the errors that come with it. The industry still talks a big game about transformation while plenty of core processes remain stubbornly manual.

Here’s an “ebook” I created for World Paperfree Day in 2012. I’ll try to download and embed, but the interwebs are being finicky. Click the image to see the whole thing. Scanners are faster. Capture/recognition tools are WAY better. Same problems exist.

8. People, process, change management, and executive sponsorship

Technology was never the whole issue. The 2014 ebook’s chapter on zero-based information governance laid out eight tenets, and the first three were executive mandate, cultural attention, and personal accountability. Deborah Juhnke wrote that without those three things, information governance initiatives fail. Early technology purchases, she said, mask the problem and often fall short of full implementation.

In 2026, McKinsey says nearly two-thirds of firms have failed to scale their AI projects. Forrester describes a “vicious cycle” where lack of employee trust leads to weak governance, which leads to perpetually deprioritized data cleanup, which leads to AI tools that underperform — which further erodes trust. Around and around it goes.

Different decade, same management failure mode. And it’s the one that matters most because you can’t buy your way out of it. You never could.

9. Getting business value out of unstructured content

In 2014, John Mancini’s keynote (John was AIIM’s president at the time) framed four questions for the industry, and the last was the simplest: how do we get any business insight out of all the information we’re gathering?

In 2026, that same question shows up wearing much fancier trousers. It’s now called “AI-ready data,” “content intelligence,” “RAG,” “knowledge enrichment,” and “agentic AI.” Gartner predicts that through 2026, organizations will abandon 60% of AI projects because their data isn’t ready. Hyland says 80% of enterprise content is usually unstructured, disorganized, and incomplete. AIIM’s own mission statement is still centered on helping organizations “manage and prepare unstructured data for AI and automation.”

The Hyland CEO framed it well: content management was perennially a black box. CIOs would ask him at Informatica what he could do for their unstructured data. Now that LLMs exist, the answer is theoretically “a lot.” But only if that content is clean, governed, and accessible. Most of it isn’t.

Same core problem. Better outfit.

10. “Social business” as a standalone theme

This is the one that feels more renamed than identical. The 2014 ebook gave it a full keynote. Pelz-Sharpe’s chapter explored what social business even meant, and whether the enterprise social networks of that era could deliver real value or were just “social for social’s sake.”

In 2026, nobody uses the phrase “social business” or talks about enterprise social networks as their own category. But the underlying concern — how people collaborate, share know-how, and connect knowledge to work — has been absorbed into broader conversations about collaboration layers, knowledge discovery, copilots, and AI-assisted work.

The problem persists. The framing doesn’t stand on its own anymore.

So You Say You Want an (AI) Revolution

Now, let me clarify something because I don’t want to come off as a Luddite screaming into the void.

AI is genuinely powerful. Not “powerful” in the way a lot of the hype around AI wants you to believe — actually, functionally powerful in specific, focused applications. GenAI and agentic AI can find connections across vast amounts of data and information that a human simply doesn’t have the time or speed to process (hello this thing thing you’re reading here). In bounded, well-scoped use cases — claims intake, invoice processing, document classification, contract review, onboarding, fraud detection — the gains are real and measurable. Deep Analysis has been saying for years that IDP was the first really profitable application of GenAI in enterprise, and that’s only become clearer since. Firms using AI-powered due diligence tools are already cutting contract review time significantly. That’s not vaporware. That’s working technology applied to a well-defined problem.

Where it works is where the content is clean, the process is documented, and the scope is narrow enough that the AI doesn’t have to guess about context. In other words: the exact conditions that most business don’t have.

And that’s the gap this whole piece is about.

AI is a useful tool. I use it every day. I’m using it right now — again this piece was almost entirely compiled using genAI, drawing on my stored thoughts and past writing. It’s a prediction engine trained on data that gives the illusion of intelligence because it does stuff really, really fast. And yes, it is extremely useful, as limited as it is.

But AI doesn’t think for you. It can’t. It’s a server in a rack . . . somewhere.

Now apply that same thinking to the enterprise AI narrative.

I keep hearing that AI is going to take over everything. That it’s going to replace knowledge workers, eliminate back-office staff, and automate the enterprise. And the executive class is sprinting to make that narrative real — or at least to use it as cover for headcount cuts they wanted to make anyway.

Here’s a question worth asking: is anyone pushing the “AI will devastate entire career paths” narrative who doesn’t have a financial stake in that being true? Altman, Amodei, Nadella — they’re running companies with billions in infrastructure bets that only pay off if adoption is fast, broad, and deep. That doesn’t make them wrong about the long arc. It makes them unreliable narrators about the timeline.

And the timeline is where reality gets interesting.

Deloitte’s 2026 State of AI report found that only 25% of organizations have moved even 40% of their AI pilots into production. Talent readiness sits at 20%. Governance at 30%. Data management at 40% — and these numbers actually decreased compared to last year. Companies are less prepared than they were 12 months ago, even as they set more ambitious goals. PwC’s 2026 Global CEO Survey found 56% of CEOs report getting “nothing” from their AI adoption efforts. And MIT says 95% of generative AI pilots fail to move beyond the experimental phase.

Meanwhile, 60% of hiring managers admit they emphasize AI’s role in reducing hiring because it sounds better than citing financial constraints. When New York gave companies a legal form to formally attribute layoffs to automation, zero out of 160 companies — including Amazon and Goldman Sachs — checked the box. Companies are publicly blaming AI for cuts they won’t legally attribute to AI.

The hype is doing the damage the technology hasn’t earned yet.

But AI can’t do any of that on a foundation this shaky.

Here’s why I’m dubious, and it ties directly to the 10 problems above:

AI agents depend on documented workflows. Most organizations don’t have them (problem #6). Forrester says process knowledge lives in tribal knowledge and unofficial workarounds. You can’t agent your way through a process that isn’t written down. I read recently about an AI agent on a website negotiating a cut-rate deal with a customer — 8,000 pounds (was in the UK) of service for 2,000. It could have even been two agents negotiating with each other. That’s what happens when you deploy agents without understanding the workflows they’re supposed to follow.

AI models depend on clean, governed, findable data. Most organizations don’t have that either (problems #1, #2, #3, #9). Gartner says 63% of organizations either don’t have — or aren’t sure if they have — the right data management practices for AI. Only 11% have high metadata management maturity. The average enterprise manages content across 10+ platforms with manual processes bridging the gaps. That’s not a foundation for an AI revolution. That’s a foundation for a very expensive AI disappointment.

AI readiness depends on people and change management. The hardest problem of all, and the one technology can’t solve (problem #8). McKinsey says nearly two-thirds of firms have failed to scale their AI projects. Forrester’s “vicious cycle” — distrust leads to weak governance leads to bad data leads to bad AI leads to more distrust — is the same people-and-process failure mode this industry has been watching for decades.

AI still needs the basics the IDP industry sells. You simply can’t digitally transform an organization — with or without AI — without capture and process automation tools. That was true when I was writing about it in 2022 (or 1995). It’s true now. Every agentic workflow, every RAG deployment, every copilot rollout depends on documents being captured, classified, indexed, stored, governed, and retrievable. If you can’t find the right document, your AI can’t either.

Deep Analysis put it best in a recent piece: “We are not here to stop the AI train; we are here to lay the tracks so it doesn’t derail spectacularly at the first curve.” They describe the AI opportunity for information management professionals as requiring “intelligent guerrilla warfare” — not grand head-on assaults but strategic, essential infiltration. Making governance, structure, and the ethics of information impossible to ignore. Because without that foundation, as they put it, “this entire glittering AI edifice is built on a ghost — the ghost of messy, uncontrolled, and profoundly dangerous data.”

That’s not my hyperbole. That’s an analyst firm that has been covering this market for decades. And, again, I know these guys and do work with them. They are some of the smartest folks I’ve ever met whose work and advice has been informing the IDP industry for decades. In short, they’ve shaped it.

Behind every customer-facing automation, there’s some poor monkey in the background pushing all the right buttons to provide that good customer experience (I’ve been that monkey on the back-end of HubSpot automations). The “promise” of AI agents talking to each other is supposedly going to remove this pain from us. Given that companies are generally shit about understanding workflows and agentic AI will depend on workflow orchestration to provide actual business value — color me dubious of that happening any time soon.

So AI will absolutely automate parts of the enterprise. It already is in bounded, well-scoped use cases — claims intake, invoice processing, document classification, onboarding. The kind of tightly defined, document-heavy work this industry has been chipping away at for decades. Celonis — the sexy process mining company — touts invoice processing and accounts payable as part of their platform. Same low-hanging fruit capture vendors have been picking for 40 years (40 is not a typo, this stuff has been around for a long time). Some things never change.

But the broad, sweeping, “AI is coming for everyone’s job next Tuesday” narrative? That requires clean data, strong governance, documented processes, good metadata, findable content, and systems people actually use. Most organizations don’t have any of those things. They didn’t have them in 2014. They don’t have them now.

The Lazy Marketer Problem Isn’t New Either

One more thing, because I see this playing out in my own world of marketing, especially content marketing.

The lazy marketer (and the cheapskate C-suite) who skimps on marketing — who views it as a checkbox, not a differentiator — has always looked for cheap shortcuts. Content mills outsourcing to Fiverr for $12 blog posts. Keyword stuffing. Stenography “reporting” that just restates a vendor press release. None of this is new. AI just allows that process to move faster with worse results if there’s no human intelligence, filtering, and taste applied.

Having been on the receiving end of marketing slop from IT vendors for most of my career starting in the mid-90s, I can un-merrily report that people often write worse than AI. Because if genAI is giving us average, that means it’s trained on even worse content than what it spits out.

The same dynamic playing out at the enterprise level — executives hoping AI will compensate for missing effort — is playing out in marketing too. The exec who says “why are we paying a content person when AI can write blogs” is making the same mistake as the law firm that stops hiring junior associates. They’re cutting based on the demo, not the results.

But that’s a piece for another day.

The Word Salad Hasn’t Helped

The word salad changes every few years. ECM became content services became intelligent information management became IDP became “AI-ready content.” I once jotted down all of the phrases used for process and capture technology — intelligent capture, intelligent document capture, intelligent automation, hyperautomation, digital transformation, capture 2.0, process automation, intelligent process automation, intelligent document automation, digital process automation — and I found vendors using multiple combinations in the same paragraph on the same Web page. If there’s any whiff of AI, the product is “intelligent.”

Here’s one I copied from a vendor website a few years ago:

“Hyperautomation with Intelligent Document Processing, Business Process Management, Robotic Process Automation, Automated Governance, and Integration.”

I’m not making that up. That is from an actual vendor website. They intentionally pushed “publish” on that garbage.

What does that even mean? I have no idea. And I’ve been reading about and/or covering this stuff for 30 years.

For the vendors out there: what’s that confusion doing to your customers?

The constantly changing terminology doesn’t just cause confusion. I suspect it has actively hurt industry adoption over the years. Every time the industry renames itself, organizations have to re-learn what they’re buying. That friction adds up. And now AI is layered on top of that confusion, promising to solve problems that require the very tools organizations couldn’t figure out how to buy under the previous three names.

The Honest Version

When a CEO announces that AI will transform the company by Q3, what I hear is: “I don’t have the patience to fix the foundation, so I’m going to pretend the foundation doesn’t matter.”

It matters.

Given how slowly companies have addressed these problems over the past 12 years — the past 30, if I’m being honest — expecting AI to sweep through the enterprise like wildfire is not a plan. It’s a fantasy. AI will move quickly in narrow, well-defined lanes where the content is clean, the processes are documented, and the governance is in place. (Or it’ll move quickly and the press will have a field day covering those clusterfucks.) It will move slowly everywhere else.

And “everywhere else” is most of the enterprise.

This is actually good news for IDP vendors if they frame it right. Every organization that wants to use AI needs what this industry sells first. The capture, the classification, the indexing, the governance, the workflow automation — all of it. AI doesn’t replace the need for information management. It makes the need for information management urgent in a way that two decades of conference keynotes never could.

The opportunity isn’t “AI will do it all for you.” The opportunity is “you literally can’t do AI without doing this first.”

Like everyone, I’m probably wrong. Just not in the way it looks like I’ll be wrong.

I don’t think AI is going away or slowing down in capability. I think the organizations trying to use it are going to keep tripping over the same problems they’ve been tripping over since 2014 — and since 1994, if I’m being honest. The technology will keep getting better. The foundations will keep lagging behind. And the gap between the keynote and the cubicle will keep being wider than anyone with a financial stake in AI wants to admit.

2014’s information chaos is 2026’s AI-readiness problem. Same mess. Better branding.

I’m heading to the AIIM Global Summit in Baltimore at the end of April since that’s where I live (well, at least the lobby, not paying to go). If you’re an IDP or information management vendor and your marketing sounds like the word salad I just described — or worse, sounds like every other vendor in the space — I can help with that. Social ghostwriting, newsletter ghostwriting, content strategy grounded in 30 years in this industry. Reply to this email or reach me at bryant@simplyusefulmarketing.co.

For more on the specific challenges facing AI and automation adoption in this space, I’d recommend reading Deep Analysis — particularly their pieces on the lengthy hikes awaiting AI in 2026, the demand for hyper-specificity, and how information management professionals can avoid losing the opportunity AI presents. They’re one of the few analyst firms that don’t buy into the bullshit. While you can accuse me of bias, I’d say the same if I weren’t working with them. I don’t pander to anyone.

How I Compiled This.

I did not “write” this, yet this is all me just the same. So I’m in a Slack group of folks I knew from my time at AIIM — analysts, users, consultants (some of the smartest folks in the IDP industry you can find). There’s an underlying “why the hell don’t more companies pay attention to this shit” vibe in some of the conversions. (Talk to a vendor in the industry, you’ll get the same vibe.)

I was literally looking for something else and noticed that 2014 sneak peek. So I though, “Hmmm, genAI is good for brute force comparison, let me run this against what’s out there today.” So I did. I had ChatGPT read it and compile the main themes. Then directed it to look at those themes relative to what’s out today across a few vendors, AIIM, analyst, and consultant sites. I was like, “Well, shit, that’s pretty good.” So I ported it over to Claude, and ran it through again. After a few tweaks, you’ve read the result.

It is me. Other than the 10 point comparison, which is almost entirely AI, the rest is pulled directly from my thinking and words — which is a combo of prompts (thinking and framing), a webinar presentation and article based on that I wrote, the preview document (which was conceived, assigned, and edited by me; except for the vendor stuff, John had done that), and various other snippets and background AI research I’ve done in both GPT and Claude.

As for the 10 point comparison — that’s exactly where the power of AI lies. It would have taken me a full day, maybe longer, to go point by point with this. That ability to pull together massive volume is spectacular. It’s dangerous because we need to doublecheck for sanity, but . . . wow.

So while I didn’t “write” this in the traditional sense, it’s me. My words. My thinking. My edits on anything GPT/Claude popped out that I didn’t like. I’m pretty sure I won’t “write” many things like this, but it can be useful in some situations.

For anyone interested, this is the AIIM 14 ebook that inspired this thing.

Aiim14

5.43MB ∙ PDF file

Download

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Musical Interlude

Amy Winehouse from Jools Holland (a fantastic UK music show). Sigh. Wish she HAD taken rehab seriously. What a fucking loss.

Joss Stone. I love the Dusty Springfield original. My favorite Dusty is after this, but Joss does a good job on this cover. She’s pretty great. Been a few years since I’ve listened to her.

But, OMFG, Dusty . . . She of course rules on the above song, but this . . . yeah, baby. Do yourself a favor, hit a road trip and push play on Dusty in Memphis or a day when you’re doing some cooking.

Have loved this Trampled By Turtles Song since I first heard it on the The Way Way Back (a movie that I thought was a comedy because I saw Steve Carrell; it is funny, but not a comedy). Anyway, this song rules (the soundtrack is good top to bottom too).

Come into the world alone

And you go out of the world alone
But in between, there’s you and me
Oh-oh

Man, if that ain’t life and the desire to connect, I don’t know what is.

Just as I was scheduling, Etta popped up. I’m not one of those “oh, music was so much better when . . . “ but, damn, you ain’t getting better than this.

This is the first in an occasional series I’m calling Marketing and the Movies. The concept is simple — I watch (or rewatch) a movie I love or have always wanted to see, and any time an action, plot twist, or character decision reminds me of a marketing lesson, I write it down.

First up: the 1963 classic, Jason and the Argonauts, with the superb Ray Harryhausen’s animation. Questionable acting, glorious stop-motion animation, and a surprising number of useful things to say about running a business.

If you enjoy a Greek myth and like a sword and sorcery movie, this one’s for you. I know, I know; not everyone’s cup of tea but the article will still be worth your while.

Let’s go.

Make People Feel Special and They’ll Do Hard Things for/with You

To select the crew of the Argo, Jason holds what is basically an Olympic competition — archery, discus, the works. This is a journey to the end of the earth. Nobody knows if they’re coming back alive. And yet people are competing for the right to go.

Because they feel special. They feel chosen.

If you make someone feel like they’re part of something worth doing, they’ll go out of their way to help you. That applies to customers, collaborators, and anyone you want on your ship.

Brains Over Brawn

After the competition, Hylas arrives late and misses his spot on the Argo. He challenges Hercules for a place. Hercules selects discus throwing and points out to sea at a large rock. “No man has ever hit that rock with a disc.” Hercules, because he’s Hercules, hurls a disc a quarter mile and clangs it off the rock.

Hylas — slim, not muscular — takes his disc and skips it across the water like a frisbee. It bounces right off the rock.

Brains over brute strength.

Sometimes when you’re staring at a problem, stop bashing your head against the wall. Take a step back. Look at it from a different angle. Check if the wall ends two or three feet to your left and just walk around it. If you can’t go around, go over, under, or through. There’s usually a unique solution — you just have to stop relying on pure force long enough to find it.

Believe in Your Abilities

Jason was transported by Hermes to Mount Olympus where Zeus gave him his quest and also five chances to call on Hera for help. Zeus also offered to hand-pick his crew and give him a ship. Jason refused — he knew he had a plan and could handle it himself.

Don’t use help you don’t need. If you can do it, do it — especially if there are strings attached to the offer.

But Also: Get Help When You Need It

Hera is the figurehead (though at the back of the ship – look, I didn’t film it), for the ship. In tight, impossible spots, Jason talks to Hera through it. No one on earth is a god, obviously, but there’s no shame in learning from someone who knows more than you do. And if you can pay with money rather than time, you’re one step closer to where you want to be.

Get help when you need it. You probably need it more often than you think.

The Gods Are Fickle

The gods in this movie are basically watching TV and meddling. Zeus and Hera are married and constantly competing, and, really, the entire pantheon is essentially an inbred trailer park soap opera — only worse, because they have actual power over people’s lives.

But they do have power. And they use it.

In our lives, there are powerful forces that shape the world we’re in — market shifts, algorithm changes, economic headwinds — that you can’t control and sometimes can’t even see. It’s trite, but still true. You can’t always fight the current. Sometimes you just have to go with it, and just hope you can stay roughly on course — or simply don’t drown.

Don’t Take More Than Is Given

Hera directs the Argonauts to a safe island to repair the ship. Simple instructions: fix the boat, drink some water, don’t take anything, be on your way.

Hercules finds a treasure room underneath a giant bronze statue — Talos — and helps himself to whatever catches his eye.

Talos, naturally, tries to kill all of them.

Don’t take more than is given. Just be decent and don’t be greedy.

Everyone Has a Weakness

Talos is a hundred-foot-tall bronze golem with a big sword. Impervious to everything the Argonauts throw at him. But like a lot of mythology, the monster has a weak spot — he’s full of some kind of boiling liquid, and there’s a plug in his heel. Jason sneaks behind him, loosens the cap, the oil flows out, and Talos goes down.

Everyone has a weakness. You, me, your competitor. Know your own and guard against them. And, not to change the light-hearted nature of this post, understanding your competitors’ weaknesses is also a damn good thing.

On a more positive spin, you also need to understand your customers’ pain because your job is to provide a product or service that soothes it or makes it go away.

Sometimes You Have to Stop, Pause, and Reset

Talos picks up the Argo and drops it into the sea. The ship gets torn a new asshole. So because Hercules was a greedy idiot (if you read mythology he’s not nearly as charming as the guy in the Disney movie), they have to take even more time to repair the ship.

Sometimes you get stuck. You make a wrong choice. You anger the wrong giant iron golem. It happens. Take a step back, recalibrate, move on.

Ignore the Heads. Go for the Heart.

You know the Hydra myth. Cut off one head, two more grow back. Jason finally kills it by ignoring the heads and stabbing the thing in the body.

Same thing in marketing.

We all live under the illusion that we make decisions rationally. We very, very rarely do. We make an emotional decision and then retroactively apply logic and data to justify what we’ve already decided.

I’m not saying lie or make outlandish claims. But your writing should appeal to emotions — appeal to how your product will make someone feel, paint a picture of how their life will be different. Once you’ve got them by the heart, the head will usually follow.

If your newsletter reads like it was written for heads instead of hearts — all features, all logic, no feeling — that’s the kind of thing Newsletter-in-a-Box is built to fix. I help you find the stories and angles that actually make people care. If you’re curious what that would look like for your business, reply or email me at bryant@simplyusefulmarketing.co.

Be Helpful and Make Connections

Later in the movie, Jason rescues a woman from a shipwreck near the Clashing Rocks. Turns out she’s the high priestess of Colchis — and she ends up saving his life at the end. And, of course, she falls in love with Jason.

You never know when the person you helped out of a jam turns out to be the one who opens a door for you later.

The friends you make online — on Substack or LinkedIn or wherever — probably aren’t high priestesses. (If you are, please friend me.) My high school English teacher used to say, “Friends are like shoes; you’ve got them, use them,” which still makes me laugh. There’s truth in it, though. True friends will support you. And even if a friendship never “comes in handy,” it’s never a bad thing to have a friend.

Be Direct

Near the end of the movie, the king has cornered Jason and his men by a temple. His command to the hydra/dragon teeth skeletons is simple: “Kill them. Kill them all.”

Sometimes the most direct course is the best one. (It didn’t work out for the king, but that’s beside the point.)

Tell people what you want them to do. When you’re clear and direct, you’ve got a better chance of them actually doing it. Don’t hide the fact that you’re a business with something for sale — even if you’re a business of one. Especially if you’re a business of one.

Fate Is Not a Strategy

Fate makes a great story device. It’s a terrible way to run your business.

Nothing is fated. Results come from whatever actions you take today and tomorrow. Be consistent. Keep going. Twenty years from now, when you’re kicking back on the beach in Maui, you can say it was fated — but it wasn’t. It was work.

Even Gods Get Bored

There are recurring shots of the Greek gods lounging around a pool, watching Jason and the Argonauts like it’s Netflix.

No lesson here. Just struck me as funny that even gods need something to watch. I suppose eternity gets dull.

There are no new ideas in marketing. But sometimes a 62-year-old movie about Greek myths reminds you why the old ones hold up.

Skip the disc across the water. Go for the heart, not the heads. Show up, do the work, and don’t steal from giant bronze statues.

Next month: Conan the Barbarian. Mostly just the one god; CROM!; and more swords.

Also, if you’ve got a movie suggestion; I would LOVE to hear it. I’ve got tentatively: Krull, Beastmaster, Sword and the Sorcerer, The Hobbit (the Rankin-Bass cartoon from the 70s), Excalibur, and Dragon Slayer on the list.

PS — If you’ve been meaning to start a newsletter (or restart the one that’s been collecting dust since September), I can get you from blank page to first send without it becoming your new part-time job. Reply with what kind of business you run and I’ll tell you what the lightest version looks like. bryant@simplyusefulmarketing.co

A newsletter is the most direct trust-building tool you own.

It should and can be the critical connection point with your customer.

Not a flashy one. Not a viral one. A steady, reliable one — the kind that builds trust the same way showing up on time and doing good work builds trust. Over time, people start to expect you. They start to rely on you. And when they’re ready to buy, you’re the name that comes up.

That’s what a newsletter does when it’s working. It helps. It educates. It can amuse. It earns attention instead of begging for or demanding it. And unlike social media, where a platform decides who sees what you post (yes, even here), a newsletter lands in someone’s inbox because they asked for it.

That’s a one-to-one relationship. And it’s the only one in digital marketing that you actually own.

That subscriber list is yours. And every issue you send is a chance to grow it — someone forwards it to a colleague, a reader shares it on LinkedIn. Each one of those moments adds a person to an audience you own, not one you’re renting from an algorithm.

Everything else I’m about to explain — what a newsletter is, what it isn’t, how it works — flows from that. The trust-building part is the point.

It’s a Container Word

Think of the word “book.”

The thing every book has in common is two covers with some dead trees and ink sandwiched between them. Beyond that, it could be an illustrated manuscript from the 1300s, a tabletop art book, a huge historical tome, or a 25-cent Bantam paperback from the 50s.

A newsletter works the same way.

It can be a hundred words delivered daily — Seth Godin’s been doing that for roughly 20 years now — or it can be a monthly deep-dive that runs novella-length. It can be one article, five short bits, curated links with commentary, an image followed by an essay about the image, or a combination of all of those things. It can be delivered by email, by paper, or — if you’re old enough — by fax.

The format is the least important thing about a newsletter. What matters is whether it’s useful to the person receiving it.

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Don’t Confuse the Delivery Truck for the Package

One quick distinction, because it trips people up.

Email is a delivery mechanism. It’s how most newsletters reach people. But email is not the newsletter — the same way UPS is not the thing inside the box.

And when someone says “I have a Substack” what they mean is they have a newsletter on a platform. The platform is just plumbing. If the same content lived on a WordPress site with a subscribe button, it’d work (mostly) the same way.

This matters because if you ever decide to move platforms — and you might — your content and your subscriber list are what you take with you. The platform is replaceable. The relationship with your readers is not.

A Newsletter Is Not a Sales Email

Confusing these things can cause real damage to your marketing efforts.

If someone says they have a “newsletter” and all they do is pitch you — webinar invitations, product announcements, case studies that are thinly veiled press releases — that’s not a newsletter.

That’s a pitch with a subscribe button (if you ever hear “email marketing” that’s what they’re talking about).

The mechanism is the same. The design can be identical. But the intent is completely different.

A pitch-with-a-subscribe-button delivers no value on its own. It exists entirely to make a sale. It says “buy me.”

A newsletter says “trust me — and when you’re ready, buy from me.”

A newsletter answers customer questions. It’s helpful. It’s useful. It treats the reader’s attention like the gift it is. And over time, that builds the kind of trust that makes selling easier.

Intent is the distinction between a newsletter and email marketing.

But You Do Want to Stay in Business, Right?

Being useful and making sales are not opposites.

The difference isn’t whether you sell in your newsletter. It’s whether you’ve earned the right to ask. If you’ve spent issue after issue helping people — answering their questions, giving them something they can actually use — then asking for the sale isn’t pushy. It’s natural; a next step rather than an interruption.

So within your newsletter, believe in your product. Include a CTA (call to action) — that’s marketing-speak for “ask the reader to do something,” whether it’s reply to the email, book a call, or buy the thing you sell. You should always include one. You do want to stay in business, right?

And on the back end, if you’ve got a decent email tool — HubSpot, Kit, whatever — you can see who’s opening, what they’re clicking on, and use that information to make smarter, better-timed sales outreach. The newsletter builds trust on the front end and gives you data on the back end. It’s doing double duty.

If the part you dread isn’t the writing but the figuring out — what to send, how often, where to put the ask without feeling gross about it — that’s what Newsletter-in-a-Box is built for. Reply to this email or hit me at bryant@simplyusefulmarketing.co.

A Quick Side Note: Newsletters as Products

Some newsletters are the product — people pay directly for subscriptions, or the newsletter generates ad revenue. There are plenty of those in my inbox.

That’s not what I’m talking about here.

I’m talking about the newsletter as a marketing tool — a vehicle that builds trust, connects you with your customers, and creates the conditions for sales. Similar fundamentals, different playbook.

But that’s an entirely different post.

The Fax Machine Days

The first newsletter I ever wrote (well, compiled, it was essentially condensed press releases from mail — until the late 90s/early 2000s and the email takeover, I got 3 to 4 plastic mail bins full of press releases each week) — was delivered via fax. This was 1996. Every Friday night, I spent two to two-and-a-half hours after five o’clock feeding four to five thousand names through in chunks of six or seven hundred, praying they went through.

We actually charged extra for email delivery when that became an option — because it cost us more to send emails than faxes. If that seems inconceivable today, it was the reality at the time.

Point is: newsletters aren’t new, though the tools to manage and send them are MUCH easier to use these days.

Be You

Your newsletter should sound like you. If you can take your name and logo off of it and no one can tell it’s you because you ran it through legal and marketing and three execs with conflicting styles; start over.

Make it sound like a human being who knows their business and gives a damn about their customers.

This matters more than the design, more than the platform, more than the frequency. If the personality is right, people will forgive almost everything else.

And if you’re thinking “but I’m hiring someone to write it for me, so how is it still me?” — that’s exactly the job. A good ghostwriter doesn’t replace your voice. They get it out of your head and onto the page in a way that sounds like you on your best day.

A newsletter isn’t a platform, a particular format, or an email.

It’s how you show up, stay useful, and build the kind of trust that turns readers into customers — one issue at a time.

PS — If “I’ll start a newsletter when things settle down” has been on your to-do list for more than six months, things aren’t going to settle down. I can get you from blank page to first send without it becoming your second job. bryant@simplyusefulmarketing.co

Musical Fun

A couple-three songs in the background as I pulled this together.

Between this and John Batiste at the end, I’m really missing home in SW Louisiana and needing a trip to New Orleans.

I always think this is Van Morrison

“OOOHH! OOOHH! OOOHH!” If you know, you know.

You can never go wrong listening to Bill Withers, or being lucky enough to start your day with someone who you look at, teeth unbrushed, still groggy from sleep and think “the world’s alright with me.”

I’m late to the John Batiste party, but better late than never.

No one wakes up thinking about your company.

We wake up staring at our own navels; worrying about our own problems, looking for answers to our own questions, trying to get through the day with fewer hassles and better results.

That’s not bad news for your marketing.

It’s liberating.

I co-created a sponsored webinar program in the late 2000s that is still running in essentially the same format. My role was to host, recruit an expert to present, and work with the sponsor (they got 5 minutes and a chance to chime in during the Q&A) and speaker to make sure the session flowed and the audience got value.

I must’ve given “the talk” to 60 or so sponsors over the five years I ran it. One of my regular speakers started calling it that over beers at a conference and the name stuck.

It went like this:

No one cares about you.

No one is registering to hear you talk about how wonderful your product is. They are there to understand the topic at hand and how to address a problem they have. They already know you have a product or service that can help because your logo is right there on the registration page. You need to show that you understand the business problem – the pain they have.

Lead with useful information, not speeds n’ feeds.

You can use the time as you choose because you paid for it, but if you lead with features, folks WILL tune out. I have the survey stats to prove it.

The drop-off in ratings for the folks who ignored me were brutal. We sent a survey link to everyone as we closed each webinar. Overall event approval was about a 4.5; the same for expert speakers, while slightly lower for the sponsors who listened to me.

For those that didn’t, approval dropped into the 2ish range along with comments like “awful sales pitch at the start.” I wasn’t a marketer in those days but I remain semi-curious about any difference in sponsor email outreach (they got one shot at access to the registration list) results for the majority of sponsors who listened versus the 20% or so who chose to ignore me and did their usual song and dance.

I do this for companies — build newsletters that focus on being useful instead of being loud. bduhon@simplyusefulmarketing.co

Nobody cares about your company at the start. They care about whether you understand their problem. Whether you can explain it clearly. Whether you can help.

What are their problems?

What’s keeping them up at night?

What do they despise about the current options on the market?

When you’re wrapped up in proving how smart you are or how impressive your product is, you miss the opportunity to hold a conversation. To listen. To learn. To adapt.

And there’s another benefit.

Competing on price and features makes you sound like a commodity.

Features can be copied. Prices can be matched. Buzzwords get slapped onto every damn thing in sight.

You can see that as vendors in the IDP space (intelligent document processing; where I’ve spent most of my career) slapping “AI” onto their feature set whether it belongs there or not. The result is a blur of sameness. Similar promises. Similar vague claims. Similar bloated language. Customers are left trying to figure out who actually does what — and your sales team gets to clean up the mess.

You’d think these companies would learn; they did the same thing with RPA (robotic process automation) seven years ago.

The company that stands out isn’t always the one shouting the loudest.

It’s the one making the customer feel understood.

The one explaining the problem clearly.

The one focusing on outcomes instead of jargon.

The one proving, over time, that it gives a shit.

That last part matters.

Because when you stop shouting about yourself and start showing up with useful information, something important happens.

People begin to trust you.

Not all at once. Not because of one brilliant webinar or killer LinkedIn post or clever campaign.

Over time.

Familiarity becomes trust.

Trust becomes the reason people remember you when they’re finally ready to buy.

So, yes, nobody cares about you.

Good.

That means you can stop trying to be the hero of your marketing.

Because the hero is the customer; you’re just there to help them complete their journey.

P.S. I help companies stop shouting about themselves and start saying things their customers actually care about. If your marketing is stuck in “speeds-n’-feeds” mode, let’s talk: bduhon@simplyusefulmarketing.co.

I saw a post the other day I mostly agreed with — stop buying $500 courses from people who’ve never built anything, stop wrapping empty platitudes in authority, tell the truth.

Preach.

Then came the line that made my left eyelid twitch: “Drop the funnel.”

No.

Drop the bullshit that’s been smeared all over funnels — the fake scarcity, the bait-and-switch webinars, fake countdown timers on offers that never actually expire. Drop that.

But don’t drop the funnel itself.

Because everyone making fun of funnels has one. They just call it something else — “ecosystem,” “customer journey,” “my process.” At some point, a stranger discovers you, decides you’re worth paying attention to, and eventually decides you’re worth paying. That mechanism is a funnel. Renaming it doesn’t change what it does.

The concept isn’t broken. What’s broken are the folks who use manipulation tactics to pull people into their funnels and products.

A funnel built on manipulation deserves scorn. A funnel built on being useful — showing up, earning trust, asking for the sale when you’ve earned the right — is just good business.

So don’t throw it out. Fix it.

And since “fix it” is vague advice that helps no one, let me show you what a simple, honest funnel looks like — and how to build one without spending a dime on some guru’s course.

What a Funnel Actually Is

A funnel is three stages:

Someone finds you.

Someone starts to trust you.

Someone buys from you.

That’s it. That’s the whole thing.

The reality involves more touchpoints — lead scoring, nurture campaigns, SEO, digital ads — but the skeleton is always these three stages. Tactics are legion. The process is always similar.

This image from Rand Fishkin is the foundation for how I think of funnels (because it was one of the first things I read on the topic and it stuck).

I also imagine customers as butterflies. They are blown by the wind. They fly in zig zags. They alight on this flower, then another and another.

But, somehow, they can migrate all the way from Canada to Mexico.

Every business on earth has this whether they use the word “funnel” or not.

My funnel is very simple. Someone reads one of my LinkedIn posts or Substack Notes. They’re curious enough to click through to my newsletter. They read a few issues. Somewhere in there, they realize I know what I’m talking about and that I’m not trying to sell them something every five seconds. Eventually, they reply to one of my emails or book a call. Some of them become clients.

That’s a funnel. No countdown timer. No “only 3 spots left.” No 47-minute webinar that’s actually a hostage situation. Just useful content, consistency, and a clear offer when the time is right.

Why Most Funnels Feel Gross

The problem isn’t that funnels exist. The problem is that too many of them skip the middle.

The middle is the trust part. It’s the stage where someone goes from “who is this person/company?” to “I think this person/company might be able to help me.” That takes time. It takes showing up more than once. It takes giving people something useful without immediately asking for their credit card.

Hustlebro funnels jump from “stranger” to “buy my $997 thing” in 48 hours. They manufacture urgency because they haven’t earned attention. They use psychological pressure as a substitute for trust.

That’s more like one of those antlion traps — nobody is eating except the larvae at the bottom of the funnel.

An honest funnel gives the trust stage room to breathe. Weeks. Months. However long it takes for the person on the other end to decide — on their own terms — that you’re worth their money.

You can nudge. You should ask.

But there’s a world of difference between a clear offer and a manufactured crisis.

If you’re reading this and thinking “I know I need a system but I keep not building one” — that’s the exact problem Newsletter-in-a-Box solves. I’ll help you set up a simple, honest funnel that runs on useful content instead of pressure tactics. Reply or email me at bryant@simplyusefulmarketing.co and tell me where you’re stuck.

A Simple Funnel You Can Build This Week

Here’s what a basic, honest funnel looks like for a small business. No special software. No course required. No Goo-Roo required.

Top: They Find You

Pick one platform where your customers already spend time. LinkedIn. A local Facebook group. Substack Notes. Instagram. Wherever.

Post something useful 3 to 5 times a week. Not pitches. Not “exciting announcements.” Answer questions your customers actually ask you. Share something you learned. Offer a quick tip someone can use today.

This is how strangers become aware you exist. It’s not complicated. It’s also not optional — if you’re invisible, nobody’s buying anything.

Cost: free.

Middle: They Start to Trust You

Drive people from social to a newsletter. This is the one relationship you actually own. Social platforms can throttle your reach, change the algorithm, or disappear tomorrow. Your email list is yours.

Pick a platform: Substack, Mailchimp’s free tier, Kit (formerly ConvertKit) — they all do the same basic thing at the free level. Collect emails. Send emails.

Then send something useful on a regular schedule. Weekly is great. Twice a month is fine. The cadence matters less than the consistency. Show up when you say you will. Don’t waste their time. Don’t make every email a sales pitch.

This is where trust compounds. Every issue that helps someone is a small deposit. Over time, those deposits add up until you’re the person they think of when they need what you sell.

Cost: free.

Bottom: They Buy

Include a clear offer in every newsletter. Not a hard sell — a clear one. There’s a difference.

“If you need help with this, here’s what working with me looks like.”

“I wrote a short guide that goes deeper on this — it’s $7 on Gumroad.”

“Reply to this email and tell me what you’re dealing with.”

That’s it. A sentence or two. After you’ve delivered value, you’ve earned the right to say “hey, I also do this for a living.”

For digital products, Gumroad lets you sell PDFs and downloads with zero upfront cost — they take a small cut when something sells. For services, your email address is the most sophisticated sales tool you need at this stage.

If you want something a step up from an email address as your call to action, create a simple landing page. One page. One offer. One action. Substack does this natively for newsletter signups. For anything else — a free guide, a consultation booking, a product — Carrd ($19/year) or even a single page on your existing website works fine. The landing page doesn’t need to be beautiful. It needs to be clear: here’s what you get, here’s what to do next.

Cost: free until someone pays you, which is the whole point.

Follow Up Like a Human

When someone replies to your newsletter, respond. When someone comments on your LinkedIn post with a real question, answer it. When someone DMs you, have an actual conversation.

This is where services get sold — 14-email automation sequences DO have their place, but are often overkill. Sales boils down to one human being paying attention to another human being and providing a product or service they want/need. All of these online tech tools are delivery and infrastructure. Trust is built person to person.

I realize this sounds stupidly simple. That’s because it is. The execution is where it gets hard — showing up consistently, writing when you don’t feel like it, resisting the urge to pitch before you’ve earned it. But the structure? A child could draw it on a napkin.

Cost: free forever.

The Whole Toolbox, Zero Dollars

In case you skimmed the above and want the quick-reference version:

Newsletter platform — Substack, Mailchimp free tier, or Kit free tier. Pick one. Don’t agonize.

Digital product sales — Gumroad. Free to start, they take a percentage per sale.

Landing pages — Substack (built in for newsletter signups), Carrd ($19/year), or a single page on your existing site.

Content creation — Google Docs. Or whatever you already use to type words.

Images — Canva free tier. Or your phone.

Video — your phone, turned sideways. (I learned the sideways part the hard way at a conference in 2014. We live and hopefully learn. Note: upright recording works fine for TikTok, Instagram, and YouTube Shorts.)

Tracking — a spreadsheet. Name, date, what happened, what’s next. You don’t need a CRM until you have enough clients to justify one.

Total startup cost: $0.

Total ongoing cost: your time and your willingness to show up.

The Funnel Isn’t the Enemy

Dishonesty is the enemy. Impatience is the enemy. Treating people like conversion metrics instead of humans with problems — that’s the enemy.

The funnel is just the shape that commerce takes when it works. Someone finds you. Someone trusts you. Someone pays you. That’s been true since before the Internet existed and it’ll be true long after whatever platform we’re arguing about today is gone.

Build something simple. Make it useful. Stop apologizing for having a way to turn attention into revenue.

That’s running a business, not manipulation.

The people telling you to “drop the funnel” will keep selling to you through theirs. The difference between them and you is that you’ll be honest about it.

PS: If you read all of that and thought “I should really get my newsletter going” but you know you won’t do it alone — that’s exactly who I built Newsletter-in-a-Box for. One conversation and I can tell you what the lightest version looks like for your business. bryant@simplyusefulmarketing.co

In 2020, freshly out of my second marriage (and with VERY limited dating experience) I started online dating.

Tinder. Match. eharmony. Plenty of Fish.

There were a few others, I forget. I was, as the song has it (see below) “looking for love.”

What I didn’t expect was that it would eventually fix my head around sales outreach. That connection didn’t hit me until over a year ago — and it’s only really starting to click now. But it’s clicking. And it’s sticking.

I’m an introvert. Shy, especially around women I’m attracted to. I can talk to a stump when I’m in the right mood, but walking up to someone and starting something? Not my natural habitat.

Online is. I feel comfortable there. Online dating apps are, I think, a genuine gift to shy guys like me — a place where the opening move is built into the structure and I could just be myself in writing, which is where I often express myself best anyway.

And it’s worked. I’ve had good relationships come out of it. The most recent one lasted a year and felt like — well. It felt like possibly the one for the rest of my life.

She ended it.

So. You figure out pretty quickly that it’s a numbers game, and you only need one yes, and sometimes you get the yes and it still ends, and then you’re back at it.

Which, as it turns out, is also a pretty accurate description of selling.

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Selling IS Personal

Making a pitch as a company of one is intensely personal in a way that selling for a bigger brand isn’t. When I reach out to a potential client, I’m not just presenting a service. I’m presenting myself. My judgment. My track record. My taste.

Which means rejection can sting beyond the professional surface.

Do enough outreach and the spiral is easily started. You second-guess your approach, your offer, your copy writing, your entire reason for existing as a human on this planet. (OK, maybe not that last part. But the self-doubt is real.)

I’ve never much cared what people think of me. There’s a small list — maybe a dozen people, if that — whose opinions actually matter to me. But I’d still let the mechanics of outreach — the silence, the non-responses, the ignored follow-ups — get into my head anyway.

Here’s what I’ve carried over from online dating pitches to online sales pitches:

The no’s don’t matter — you were never going to meet them anyway. The person who doesn’t respond to your outreach was not going to become a client. The silence is information, not a verdict. Move on.

Cast a wider net than feels comfortable. Some of my more interesting dates came from “I’m not sure, but maybe” swipes. You don’t know what a good fit looks like until you actually talk to someone. Don’t per-reject people on their behalf. Say an enthusiastic “yes” to at least a conversation.

Online interest doesn’t always equal in-person chemistry. Some conversations that start great go nowhere. A promising discovery call can fizzle. That’s not failure — it’s fit. Move on without drama.

There’s no perfect. There is perfect for you. You’re not looking for a universally acclaimed client. You’re looking for someone whose problem you can actually solve and who values what you do. Smaller target. More useful.

Rudeness is a gift. I was once called an “Amazon-chaser” on a dating app because I’m 5’6” and had the nerve to message a tall woman. My reaction, in order: LOL, then — whew, dodged that bitch bullet.

Someone who leads with cruelty tells you exactly who they’d be to work with. Take the information and move on.

And then there’s honesty, which I’ve come to think is the most important filter of all.

I met someone for breakfast once who had a significantly different relationship with her profile photos than with reality. I wasn’t expecting perfection — real people have bellies and jiggle and I’ve got my own situation going on — but the gap between the photos and the actual person was, well, large.

We had a nice conversation (and Captain Crunch waffles!). That was it.

Here’s the thing: if someone is willing to misrepresent themselves in a situation where you’re going to find out the truth the moment you show up — that’s not just vanity. It’s a tell. Someone who fudges the easy stuff will fudge the harder stuff.

Same goes for clients. Early dishonesty — about budget, about timeline, about who actually makes decisions — is a preview of the engagement. Pay attention to it.

Honesty is gold. In dating and in business.

A newsletter does the same thing a good dating profile does — it lets people decide if they like how you think before either of you commits to a conversation. If you've been avoiding outreach because pitching cold makes your skin crawl, a newsletter is the warm version. That's what Newsletter-in-a-Box builds. Reply or email me at bryant@simplyusefulmarketing.co if you want to know what the lightest version looks like for your business.

None of this makes outreach fun. It’s still a grind. It doesn’t make the silence after a pitch feel great, or the end of something that mattered feel like anything other than what it is.

But “a grind I can do” beats “a thing I dread and avoid.”

Most people who don’t respond aren’t rejecting you. They’re busy, or distracted, or the timing is off. It’s not personal.

It rarely is.

What do you do? You get back up on that horse and keep on riding until you get where you want to go.

P.S. — If you're the kind of person who read this whole thing and thought "yeah, but I still don't know what I'd write about" — that's the first thing we figure out together. It's usually easier than you think. bryant@simplyusefulmarketing.co

Musical Coda

The sub-heading is a nod to one of my favorite love songs, Looking for Love. Enjoy! I always forget that it’s in Urban Cowboy, also a great movie.

I believed “marketing is evil” for the first 15 years of my career.

Then over two years or so my role slid from magazine editor to social media and online community manager and then into content and inbound marketing.

I quickly realized that while marketing CAN be evil, it doesn’t have to be. Shouldn’t be, for that matter.

Marketing is about serving your customers and potential customers. Believing that marketing is “just” something you have to do prevents your business from doing as well as it could.

Now, some people just want shortcuts and will use marketing to say anything they need to move someone closer to a sale.

Others degrade their marketing efforts for more understandable reasons.

They “tried” and it didn’t work — usually meaning they wrote a few blog posts, didn’t get immediate results, and decided marketing was a waste.

It’s hard to tie ROI directly to marketing, so it’s an easy cut in favor of the sales team.

Or, as in my case, they were exposed mostly to bad marketing and assumed that’s all it was.

As an editor of a trade press magazine, I was on the receiving end of a lot of bad marketing and PR — focused on features, larded with over-the-top language (THE BEST, leading, cutting-edge, unique, seamless) for the first 12 or so years of my career.

Over time, I began to notice a difference between companies that treated marketing with respect and those that treated it as a checkbox on the way to customers and the bank.

Here’s what the research shows — and more importantly, here’s what I’ve watched happen in practice.

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What “Necessary Evil” Thinking Actually Produces

When a business decides marketing is a cost center and obligation, you can see it. The strategy deck might be fine, but the marketing output itself suffers.

Budgets get cut first because marketing is hard to tie to a specific sale. The sales team has a number. Marketing has... awareness? Engagement? Good luck defending that in a budget meeting.

So spending gets squeezed, which means the work gets cheaper. Which means more cold outreach, more interruptive ads, more low-value email blasts to lists that haven’t been touched in two years, more mindless AI or Fivrr content. More “we need leads NOW” thinking that treats potential customers as a disposable contributor to your bottom line rather than people trying to solve a problem.

The content, if there is any, becomes a press release in a trench coat. Features. Awards. “We’re pleased to announce.” Random pictures of staff in the same t-shirt doing community service.

Nobody asked. Nobody cares.

Customer questions go unanswered because nobody’s job is to answer them publicly. The blog, if it exists, hasn’t been updated since 2024. The newsletter went out — sporadically — seven times and then quietly died.

Meanwhile, the sales team is out there trying to build relationships with people who’ve never heard of you or already formed an opinion about your company based on sloppy marketing.

Even worse: the companies trying to save money by treating marketing as a necessary evil are almost certainly spending more than the companies investing in it properly. More on acquisition. More on interruptive ads. More replacing churned customers they could have kept. They think they’re being fiscally responsible. Nope. They’re just paying for it across multiple line items, so the true costs stay hidden.

This is the slow bleed of “necessary evil” thinking. It doesn’t always kill a business; it just keeps one from growing as much as it could.

Why This Costs You Money

Edelman’s 2025 Trust Barometer puts it plainly: trust now equals price and quality as a purchase consideration. Not “nice to have.” Equal footing with the two things businesses have always competed on. And 71% of global consumers say trust is a “buy or boycott” factor — meaning distrust doesn’t just mean someone ignores you, it means they actively go elsewhere and sometimes tell people why.

Here’s the number that should keep “necessary evil” thinkers up at night: 79% of B2C leaders believe their customers trust them. Only 52% of customers agree. That gap — nearly 30 points — is what happens when you assume goodwill you haven’t actually earned.

(I went deeper on the trust-ROI connection in a previous issue — worth a read if you want the full picture. Click here to read.)

On the retention side: Bain & Company found that a 5% increase in customer retention can increase profits between 25% and 95%. And it costs somewhere between 5 and 25 times more to acquire a new customer than to keep an existing one. The “necessary evil” approach typically optimizes hard for acquisition — the expensive end — while quietly destroying the conditions that make retention possible.

One more: Content Marketing Institute found that content marketing costs 62% less than traditional marketing while generating three times more leads. The cheap, interruptive tactics that “necessary evil” thinking defaults to are, somewhat ironically, more expensive and less effective than just being useful.

None of this is complicated. It’s just easier to ignore when you’re staring at a quarterly number.

What the Other Approach Actually Looks Like

It’s not complicated, which I think is part of why people resist it. There’s no secret framework here.

You show up consistently with something useful. You answer the questions your customers are already asking — the ones your sales team hears every day, the ones sitting in your service inbox, the ones showing up in your site search. You write like a person, not a committee. You make offers, clearly, to people who actually want what you’re selling.

That’s it.

A quick example of what this looks like in practice. When I was helping copier dealers with their marketing, the billing team at one dealer was asked every single month to explain invoices to confused customers. We created a short blog series answering those questions. Cut support calls. Gave the billing team something to point people to. Built a small but real amount of trust with customers who previously just felt frustrated.

The “necessary evil” company never writes that post. The trust-oriented company writes it, publishes it, and keeps benefiting from it for years.

If you just read that copier billing example and thought "we have something like that" — questions your team keeps answering, problems your customers keep running into — that's a newsletter waiting to happen. Not a big production. Just useful answers, sent regularly, to people who want them. That's what Newsletter-in-a-Box is. Reply or email me at bryant@simplyusefulmarketing.co and tell me what question your customers keep asking.

The companies that do this well don’t have bigger budgets or better writers. They have a different assumption underneath everything: that marketing’s job is to serve the customer, not to drag them toward a sale. The goal is still ultimately a sale (this is business after all), but you get there by helping, not hustling.

Over time, this compounds. People remember you when they’re ready to buy. They refer you because you helped them. They forgive mistakes because you’ve built up goodwill instead of just hunting them for leads.

None of this is fast. That’s why the “necessary evil” crowd doesn’t do it. They want the shortcut. The problem is the shortcut costs more and produces less.

The Companies That Get This Are Pulling Away From You

Some businesses will read this and shrug. They’ll keep treating marketing as a line item to minimize, a necessary evil to tolerate, a checkbox before the “real work” of selling.

And some of those businesses will be fine — for a while. Markets can carry a mediocre marketing program if the product is strong enough or the competition is weak enough.

But those conditions don’t last. And when they change, the businesses that have been quietly compounding trust — showing up, being useful, treating customers like people — will be in a completely different position than the ones that were just running plays.

Marketing that helps people isn’t a moral stance. It’s a business strategy. A boring, unsexy, works-every-time business strategy.

The companies treating it as a necessary evil are betting that shortcuts compound the same way consistency does.

They don’t.

P.S. — You don't need a content strategy to start. You need one customer question and 15 minutes. The strategy part comes after you've been showing up for a while. bryant@simplyusefulmarketing.co

You’ll write (or record) words that people will hate.

You’ll write great stuff no one will read.

You’ll write what you think is crap that will take off like a rocket.

I was reminded of this yesterday, listening to Sirius in the car. The host on one of the country stations gave a short back-story about the song “I Swear.”

If you listened to the radio at all in 1993 and 94, you probably heard it – either the John Michael Montgomery country version or the All-4-One R&B version (embedded below for those who missed/don’t remember it – it’s a good song).

The song won two Grammy Awards in 1995 – Best Country Song and Best Pop Performance by a Duo or Group with Vocal.

But it took five years before it was picked up and recorded after being written in the late 80s by Gary Baker and Frank Myers.

Timing. Luck. The Tides. Who knows what cosmic confluence needs to happen before something takes off.

There’s only one guarantee – if you don’t write, if you don’t record; you will never have a hit.

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What’s This About Zingers?

One of my favorite album titles is They Can’t All Be Zingers; Primus’ greatest hits compilation (why there’s a beaver playing banjo leading this article off is answered below).

The title always makes me giggle a bit, but also makes me think. Across nine studio albums, people loved much fewer of their songs than they recorded.

Think about any band you love – there are at least a few songs you don’t hate, but skip more often than not.

They can’t all be zingers.

Willie Nelson wrote “Crazy”; an absolute classic and definite zinger. He also has over 150 albums, with 75 plus solo studio albums. They aren’t all “Crazy.”

So you twiddling your thumbs because you “don’t know what’s going to work” is pointless.

If Hollywood studios miss with their films after focus groups and test screenings …

If even best-selling artists fail to connect with every song …

Then you are entitled to a few clunkers along the way.

Wait, scratch that, here’s the reality: you WILL have a few clunkers along the way.

And you just need one. Hit; not clunker. Gary Wills had a 30-odd year career as a singer-songwriter with two hits:

I enjoy Nick Hornby’s novels. In About a Boy, the main character lives an idle life because his Dad wrote a single hit jingle and he lives off of the royalties decades later.

Gary Baker did spent a 30-odd year career as a singer/songwriter with two hits to his name – “I Swear” and “I’m Already There” (recorded by Lonestar). Most of that career was was spent working out of the spotlight. You can make a living being quietly competent behind the scenes.

Not everything can be a zinger. Not everyone can be a superstar.

You will never know with 100% certainty what people are going to want to read (or listen or watch or whatever) from you.

So take a swing because you never know when you’ll connect.

I swear.

You won’t know what your zinger is until you start shipping. Newsletter-in-a-Box exists for people who know they should be showing up consistently but keep not doing it. I’ll help you build the thing and keep it going — and then keep you going. Done-with-you or done-for-you. Reply or email me at bryant@simplyusefulmarketing.co and tell me what you’re working with.

As for the beaver, one of my all-time favorite song titles is on this album: “Wynonna’s Big Brown Beaver.” Get your head out of the gutter! It’s not about THAT!

Before writing this, I would have bet money that it was Boyz II Men who covered “I Swear.”

Focusing on “going viral” is a sucker’s game. I’ll explain why, but first, a story about why I despise with the heat of a thousand dying suns trying to “go viral.”

“We need rock stars so we can go viral.”

“Oh, FFS,” I thought. “Here we go with this crap.”

This was 2010. The association I worked for had canned the magazine but kept me on to build an online community. Leadership was convinced the way to grow was to recruit “rock star” bloggers.

I made the boring argument — backed by a decade’s worth of reader surveys from my editor days — that we’d grow by publishing a steady flow of useful content for the people we served.

“NO! WE NEED ROCK STARS!”

I did manage to recruit a few. Most dropped off within a year, because we couldn’t offer anything beyond “exposure,” and rock stars don’t need exposure. We would’ve been smarter to recruit homegrown experts and turn them into rock stars over time (which is what I did on the down low, though no one hit “rock star” status).

We did manage to “go viral” once.

I read the post before it went live and thought, “Good piece. We’ll get our usual 600 to 700 views.”

Nope.

The topic was TIFF v. JPEG as the better format for image output in a document scanning implementation. It became the most-read post in the program, racked up ~75 comments, pulled hundreds of thousands of views per year, and people stayed on the page for around 10 minutes.

Which is exactly why “let’s go viral” is not a strategy.

Because you just never freaking know what’s going to hit.

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“Let’s Go Viral”

Here’s the most useful translation of what people mean when they say this:

“a sudden spike in reach outside our normal audience.”

That’s it. Not “steady growth.” Not “qualified leads.” Not “trust.” A spike. Which they mistakenly believe will magically turn into growth, leads, and trust.

And yes, before anyone asks: people still ask for this. Look around and you’ll marketing agencies and platforms churning out “how to go viral” toolkits and playbooks — because there’s still a market for the fantasy.

If you want a quick reality-check on why the request won’t die: 58% of consumers say they “believe the hype when a product goes viral,” and almost half say they’ve purchased a product based on an influencer recommendation.1

Not captured in that survey data is the pain and effort of trying to force “viral content” into existence like you’re smacking the bottom of a glass ketchup bottle, hoping something, anything splurts out.

So let’s talk about what’s actually happening when something “goes viral,” especially when you’re a smaller account.

What Does “Viral” Mean? It’s Slippery

“Viral” doesn’t have one agreed-upon definition. People use it to mean any of these:

• a post gets shared far beyond your usual audience

• a larger account (or a few) amplifies it

• the platform surfaces it (recommendations / For You / suggested posts)

• a post hits a big number, even if it doesn’t lead to anything durable

So when someone says “we want to go viral,” the most important follow-up question is:

“Viral in what way — and what do we want to happen after the spike?”

“Viral” Is a Distribution Event

Most “viral” moments aren’t engineered because the content was so inherently brilliant it escaped the gravity well of the platform algorithm on pure merit.

They happen because distribution happens.

A bigger account shares it. A few people with reach pile on. The platform surfaces it. Someone reacts to it. Suddenly your post is in a room you weren’t invited into.

It’s amplification — not your genius — that turns “a post” into “a viral post.” BuzzSumo notes that if just five influencers share something it can cause it to explode.2

That matches what most of us have seen with our own eyeballs.

A small account posts something solid. It does… fine.

Then a larger account quotes it, reframes it, reacts to it — and suddenly it’s “viral.”

So if you’re running a small brand and you’re wondering why your great post didn’t immediately set the Internet on fire…

It’s because quality alone is not a distribution strategy.

Content Matters, But That’s Just Turning the Key in the Ignition

The content matters — but often after distribution happens.

Here’s the simplest way I think of it:

• Distribution creates exposure.

• Quality determines what happens next.

Quality is what turns exposure into something durable: people staying, subscribing, trusting, buying later.

But quality doesn’t guarantee distribution.

And distribution doesn’t guarantee business results, either.

A “viral” spike can be the wrong audience, the wrong attention, the wrong expectations. It’s like eating empty calories — that bag of Starburst was great, but you still need to eat a healthy meal.

One reason this is so hard to control: sharing is social. Seeing other people share something makes you more likely to share it too — and to do it sooner.3

So no, I’m not telling you “to hell with content.”

I’m telling you content is not the lever people think it is when they say “make it go viral.”

My Favorite Example of Why Content Stickiness Matters

Here’s what gets left out of most “viral” analysis:

Even when a single piece of content does explode, the creator only benefits if there’s something there to catch people when they land.

Early YouTube beauty is a perfect example.

Michelle Phan posted makeup tutorials in the early days of YouTube. And at some point, one video hit big enough that it got the attention of Lancôme — in her telling, Lancôme’s head of PR found her video while searching YouTube; it had about 500,000 views, and that led to them reaching out.

But the “viral moment” isn’t the whole story.

The reason that moment mattered is because she didn’t have one video. She had a body of work. People could watch the viral one… then binge another… then another… then subscribe — because there was already a little universe to step into.

If she’d had three videos total, that spike could’ve been a sugar high: exciting, then gone.

That’s the point:

The content doesn’t cause virality most of the time.

But when virality happens — by luck, amplification, timing, whatever — content is what keeps people around.

It’s the difference between:

• “Wow, that was a neat video,” and

• “Wait, this person has 40 more like this… I’m sticking around.”

A Quick Nuance So Nobody Gets Cute in the Comments

If you’re the kind of person who enjoys arguing about edge cases (I see you) — yes, not every big cascade is caused by “influencers.”

Large diffusion events can come from lots of ordinary people under the right conditions.4

Which is true.

And it changes nothing about the practical takeaway:

You can’t schedule virality.

You can’t build your marketing plan on “maybe the right person sees it and shares it.”

That’s not a plan. That’s playing the marketing lottery.

Also: many “viral” events aren’t beautiful multi-generation share chains anyway. A huge share of diffusion is shallow — closer to broadcast than contagion.5

Translation: most “viral” moments are one big shove, not a predictable chain reaction.

Why “Go Viral” Thinking Poisons Your Marketing

Look, going viral isn’t a bad thing. It’s awesome when it happens. Sugar highs don’t last, but they do feel good. Nothing wrong with that.

The problem is what it does to your behavior.

When you chase “viral,” you can start optimizing for:

• novelty over usefulness

• reaction over clarity

• spikes over compounding

• rented attention over owned attention

You start treating your work like it’s only valuable if it explodes.

And then you accidentally build a system where you’re either:

• “winning” (a spike happened), or

• “wasting time” (a spike didn’t happen)

That mindset will fry your brain.

And it pushes you toward content that feels like marketing — but doesn’t actually help anyone make a better decision.

Build Repeatable Reach Instead

If you want a goal that’s ambitious and sane, steal this:

Aim for repeatable reach, not random reach.

Repeatable reach looks like:

• a message you can say more than once without hating yourself

• a format you can produce consistently

• a network of humans who recognize your name

• an owned audience you can reach without begging an algorithm for table scraps (reminder that an email list is the one-to-one digital reach you control)

Yes, you can still try for “big” moments. But build the boring foundation underneath it.

Here are a few ways to do that without becoming a hustlebro gremlin:

1) Make your work easy for other people to share.
Short, clear, one idea. If someone has to translate it to pass it along, they won’t. Though don’t be afraid to write long either, comprehensive guides and reports can do well.

2) Build actual distribution relationships.
Not “DM me BRO” nonsense. Real relationships: partners, customers, peers, communities you contribute to. People share the work of people they recognize and trust.

3) Turn one good idea into a series.
Stop acting like every useful idea must be brand new. If something helps people, turn it into a series. Then repurpose it — a LinkedIn post, a carousel, a short video, a short ebook. Just because it isn’t sexy doesn’t mean it won’t work.

4) Put your best stuff on land you own.
Don’t build on rented land. If the platform changes, your reach shouldn’t disappear overnight.

This is why I’m annoying about newsletters. Not because newsletters are magical.

Because you own the relationship with your subscribers — not Google, not social algorithms, not whatever the platforms decide to feature this week.

My Fervent Wish

If you ask me to “make it go viral,” what I hear is:

“I don’t have the patience to play the long game. I want a quick result over the hard work of repetition.”

I get it. I’d like faster results too. I’m an impatient guy.

But the truth is simple:

We can increase the odds of going viral. It can’t be scheduled.

If you want growth you can keep, build something that compounds.

If you want a moment that makes you feel alive for 48 hours, you can chase that too.

Just don’t confuse the two.

If you’re tired of hearing “let’s go viral” like it’s something you can order off a menu — you don’t need another content brainstorm.

You need a repeatable reach system.

That’s what Newsletter-in-a-Box (NIB) is: a practical setup + operating plan that builds over time.

Newsletter-in-a-Box

Build the one marketing channel you can actually count on.

Why NIB? Because:

• You can’t schedule virality — but you can schedule a newsletter.

• You sidestep the algorithms that restrict your reach on every platform.

• Trust grows because people see you helping them over time, not shouting at them once.

• Your list is yours because subscribers opted in to hear from you — and nobody can “throttle” that relationship.

With NIB, you get the structure: what to send, how often, what to say, what to ignore, and how to keep it sustainable without turning into a full-time content goblin (I can be your content goblin).

If you want marketing you can keep — not just spikes you can screenshot — let’s have a conversation: bryant@simplyusefulmarketing.co.

How powerful is it when someone “gets you”?

In marketing, to “get” our people, to make them feel understood, we need to listen.

Basically: Listen to your customers AND anyone in your company who talks to customers.

I’m going to share a few things I’ve learned over the years about who to listen to (and a little bit of how) to get to the heart of what your customers care about (hint: it’s not you).

Even before my career slip-slided away into marketing, I thought that there are more marketers who understand the form of marketing, but not its soul.

They spend time creating emails, promotions, discounts, share on social channels, blog, and do all of the “things” that make marketing work. But they’re allergic to talking to people. The result: they lose sight of why they’re doing all of those things.

There’s no heart to it.

In my opinion, they’re usually bad listeners. They are too focused on doing what they think is right or following the latest trend instead of actively hearing from their customers.

To do a good job at marketing (especially content marketing) you have to actually care (or at least do a great job of faking caring, but, egads, what a hollow way to live).

Of course, as I often emphasize, you also need to be helpful.

Here’s what I’ve learned about listening to people — magazine readers, community members, and inbound and ghostwriting clients (and their customers) — over 30 or so years:

You can’t create great content without listening.

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1. Customer Surveys

A good way to get a large volume of responses. You can create long, intensive surveys using something like Surveymonkey. You can also create simple polls on different platforms like Substack or Twitter to ask a simple question. For example, “Is Drew Brees the greatest QB of all time?” Of course, the answer is yes.

I used these to guide my editorial calendar each year for both print and for webinars. I also used them for ego stroking by asking how well we were doing. Other than the one person who wrote, and I quote, “that Duhon guy is an ass,” feedback was 99% positive. If I had known about it at the time, I would’ve used feedback to create a kickass net promoter score to use in marketing.

2. Conferences and Events

If your company hosts or attends events (online events count!), talk to customers while you’re there. It’s a great spot to have random conversations that lead to marketing insights.

Events also provide great opportunities to grab a ton of customer testimonials.

Before the AIIM Conference in 2014, I set up dozens of appointments with folks who had taken the Certified Information Professional test to record video testimonials. I asked each of them, “Why are you an information professional?”

My favorite response remains Baron’s, “Because amateurs don’t get paid.” These videos are also an example of “go ahead and give it a try” because I didn’t know to turn my phone sideways to capture video full screen — we live and (hopefully) learn.

We then used these to help market the program.

Note: schedule interviews in advance, but leave gaps in your schedule to allow chance and serendipity to work their magic.

Bonus note: Scope out one or two relatively quiet meeting spots in advance. Have water handy for throats with a tickle and leave enough time between meetings so folks aren’t waiting for you, you have time for the occasional bio break, and so you have enough time to physically get from place to place (events can get hectic, plan well).

3. Social Media

Instead of simply blasting out your stuff on [insert your favorite social channel here], don’t miss the opportunity to have conversations with people. I used to host semi-regular tweetchats as community manager at AIIM. They were fun, rapid-fire ways for me to get ideas for blog posts (and summations of the tweetchats also became blog posts, and tweets).

More importantly, they helped to create a sense of community among the AIIM tribe. There are folks I met online that have become friends.

Social listening has gotten easier to do at scale. Tools now roll up mentions, themes, and sentiment across channels so you can spot patterns faster than manual scrolling.

4. Site Statistics

This isn’t listening exactly, but paying attention to your Web and marketing statistics can confirm what you hear. Statistics will tell the story of what folks are interested in. What blog topics are hitting? Where is the most action on your website? Where are they spending time? In numbers, your customers are telling you what they’re interested in with every click (or no clicks). You just have to know how to listen.

“Listening” can include watching behavior, not just reading words. Heatmaps and session recordings can show where people hesitate, rage-click, and bail — which often points to confusion, missing info, or a trust gap.

5. Comments

An obvious one. Scan your comments, wherever they are (Yelp, Google, blog posts, social media, etc.), like you’re a miner panning for gold nuggets. Respond to every comment. Mine for patterns in customer questions – then answer them!

6. The Sales Team

OK, yes, sales people can be . . . self-absorbed assholes who care more about their bonus than anything else.

Talk to them anyway (and, I suppose, they aren’t all like that).

The smart salespeople are the ones who understand their customers. They can feed you invaluable tidbits about customer points of pain, objections to buying, what language turns them on or off, etc.

Check in with them regularly to find out why customers are buying, as well as objections, and let that information guide your marketing.

If you record sales or discovery calls, you can also listen at scale. Run transcriptions through your favorite genAI tool, looking for repeated points of contention, objections, agreements, etc. across meetings.

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7. Customer-Facing Staff (Service Reps, Help Desk, Etc.)

During the four years I helped copier dealers with their marketing, neck in neck in useful ideas with the sales team were the service reps — the guys (and they were all men) who service the machines.

They were a gold mine. While it was next-to-impossible to get them to write themselves, they could point out common customer questions that I could answer in blog posts.

These customer-facing employees can help you identify common topics that bug your customers. Then you can write a blog post, shoot a video, create a FAQ, etc. to show them how to fix the problem themselves (if that’s possible, you don’t want anyone but a skilled technician monkeying around inside a copy machine).

Another example came from the billing team at one copier dealer. They were asked every month to explain invoices by customers. We created a short blog series that they could point people to that cut down the number of times they had to answer this question.

I also learned two interesting tidbits:

1. People really did photocopy various body parts back in the day and broke the platen (that’s the glass sheet you put your paper on to be copied).

2. One guy found a dead rat inside an empty paper tray. He wasn’t happy about it.

8. Online Communities

If you have an online community (wherever it lives — Facebook page, LinkedIn group, actual community site) the marketing team should take time to drop in to hear first-hand from customers. Make friends with the community manager(s) too and regularly check in for thoughts, insights, and/or potential customer issues to use in marketing to delight customers (or defuse potential issues).

Reddit is also a gold mind for listening-inclined marketers.

Putting It All Together

My experiences have been with smaller organizations, so my approach to collecting this information has been . . . hodgepodge. That said, I DO have a system that works for me.

Since this isn’t a post on how to create an editorial calendar (another day) or filter ideas (also another day), I’ll share a few quick thoughts on what’s worked for me.

• Create a single spot to store the ideas. Truth in advertising, I’ve never managed to 100% do this. I have a paper-to-brain connection and take notes pen to paper. I get around this by having a single notebook per client/topic/product line.

• When you see the same thought/idea in multiple spots, create content about it.

• Contemplate your navel. Take time to think and doodle. Write down headlines. Brain dump topics and random ideas and thoughts inspired by all of the above. Whatever process you use that gives your brain the space to make the random connections that lead to insights — and great content.

Get going. At some point, from the jumble of conversations, ideas, your own experiences and knowledge, research, and brainstorming concrete ideas will emerge. Based on your goals, prioritize what seems most likely to carry you to those goals and start writing.

If you want a newsletter that actually sounds like your customers — and gives you a simple, repeatable system for what to write next — that’s exactly what Newsletter-in-a-Box (NIB) is for.

I’ll help you set up the structure, the cadence, and the “listening pipeline” that turns real questions into publishable issues — so you’re not staring at a blank page every month.

If you want, reply (or email me bryant@simplyusefulmarketing.co) and I’ll tell you what the lightest, lowest-lift version looks like for your business.

Musical Interlude

Edited while listening to The Curious George Soundtrack; one of my favorite movie soundtracks. Jack Johnson has the perfect vibe to go along with George; Broken and We’re Going to Be Friends are particular favorites.

I’ll do it when . . .

Insert whatever magical fairy tale you’d like to tell yourself about how you’ll start your newsletter “someday when conditions are perfect.”

They never are; never will be.

Because “perfect” is “now.”

Somewhere out there, a small business owner is staring at one of the dozens of available tools (such as Mailchimp, Substack, or ConvertKit) and thinking:

• “Once I pick the right template… I’ll start.”

• “Once I name it… I’ll start.”

• “Once I figure out the perfect font pairing… I’ll start.”

I get it. These feel like “being responsible.”

But most of the time? It’s just procrastination with better branding.

So here are 18 initially unimportant things that somehow manage to block a newsletter from ever leaving the station — and the simple move that gets you unstuck.

How do I know these? I’ve lived each and every one.

Quick note before diving in; this is from the perspective of using a newsletter as a marketing vehicle, not a newsletter as a product. While I think in general the advice works for both, some things, like a name, can be more important for a product than for a marketing method. Also, over time, these things ARE important. But, here’s the thing, the can’t BECOME important until you start.

Cool? On we go.

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1. Naming the Newsletter.

Shakespeare nailed this one. Nobody cares what it’s called. The best name possible is pointless if no one ever hears about it because you won’t publish.

Do this instead: Name it “(Business Name) Updates” — or something in the same vein — and move on.

2. Agonizing Over The Fonts.

Unless you’re writing about Web design or publishing, your readers aren’t typography critics.

Do this instead: Use the default. If you can read it on your phone, it’s fine.

3. Choosing a Perfect Template.

“Pretty” is optional. Useful is not. Most of my favorite newsletters are plain text with minimal HTML formatting (bold, italics, headers, and links) to improve flow and readability.

Do this instead: Start in plain text. Add design later if you feel like it or, better, think it will improve connection with your audience and sales.

4. Logo and Logo Placement.

No one is opening your email to admire the header or your logo.

Do this instead: Put your name in the “From” field and make the first line helpful. Create a simple header and move on with your life.

5. Writing an Epic “About” blurb.

No one needs your brand manifesto in email form via your newsletter.

Do this instead: Explain who it’s for, what they’ll get, how often you’ll send. One or two sentences will do the trick.

6. Looking for the “Perfect” Platform.

Tools don’t ship newsletters. People ship newsletters. Yes, as you grow, there are differences (pricing levels, email automations, forms, etc.) and they can be important. When you start that doesn’t matter because they all do the same thing – take your newsletter and place it into your customers’ and potential customers’ inboxes.

Do this instead: Pick a platform that can (1) collect emails, (2) send emails, and (3) allows you to export your content and subscriber list easily. Done.

7. Overthinking the Subject Line.

Subject lines ARE important. But you will never know what works with your audience until you start sending. Start (and likely end) by focusing on telling ‘em what you’re gonna tell ‘em in the subject line and then tell ‘em in the email body.

Do this instead: Subject line: “Quick tip for [problem]” or “One thing to know about [topic].” An effective first subject line can be as simple as “Welcome to our new newsletter.”

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8. Waiting Until You Have “Enough” Subscribers.

Let’s say you have zero customer emails. Start collecting them today. Now. This moment. At some point, everyone starts from zero. The threshold to start a newsletter is zero subscribers.

Do this instead: Start with whatever you have — from none to eleventy bajillion. Build from there.

9. Worrying About Month 12 Before Writing Issue 1.

That’s avoidance; not planning.

Do this instead: Plan the next 3 issues. You’ll learn more by sending than brainstorming.

10. Obsessing Over Frequency Before You’ve Published One

You don’t know what the right frequency is until you have A frequency. Start monthly (twice/month if possible). Stick to it. You can try for more (or not) once you’ve created a consistent publishing rhythm.

Do this instead: Pick one frequency you can sustain for 3 months.

11. Trying to Perfect Your “Brand Voice.”

Your brand voice is “a human who helps.”

Do this instead: Write like you talk to a customer you actually like. Develop a style guide over time, better to start without one than to never start.

12. But I Need a Lead Magnet.

You know what’s a great lead magnet? A newsletter worth reading.

Do this instead: Publish 6 issues first. Then turn the best one (or combine them) into a downloadable asset.

13. But I Don’t Know What to Write About.

Do you have customers? Do they ask questions? Congrats — you have content.

Do this instead: Keep a running list of FAQs and answer one per issue. Bonus: Read They Ask, You Answer by Marcus Sheridan for endless tips, ideas, and strategies to never run out of things to write about.

14. Fear of Sounding Like a Used Car Salesman.

Being helpful isn’t salesy. Making offers isn’t immoral, especially when you solve a problem for customers.

Do this instead: Focus on being useful, but include offers in your newsletter. And be clear about who the offer is for. Over time and as your list grows, use focused sales emails to turn subscribers into customers.

15. A Newsletter + LinkedIn + YouTube, Oh My!

I struggle sometimes to manage multiple platforms and I’ve been doing this years. You aren’t a content octopus. You’re a person trying to help their customers.

Do this instead: Pick newsletter as the home base. Learn how to repurpose and re-use content AFTER you consistently ship your newsletter. You need to be able to roll-over before you can sit up, much less walk or, eventually, run.

16. Thinking You Need “News” to Have a Newsletter.

You don’t need news. You need usefulness. A newsletter is just the label we use to describe a regular, useful communication with your audience. Something useful that your readers don’t already know will be “news” to them.

Do this instead: Focus on sharing useful information your customers can use to improve their lives. I’ve read too many vendor newsletters that were press release puffery. Boring.

17. Worrying About Unsubscribes.

Unsubscribes are not a personal attack. They’re list hygiene. There isn’t a person on the planet who appeals to everyone. Neither will you.

Do this instead: Focus on the people who stay — those are your people.

18. What If No One Reads It/What If No One Likes It?

What if they do? These are two variations of the same pointless fear. Let me burst this bubble for you now – there are some people who will despise what you write. That’s fine. They aren’t going to buy anything from you anyway, are they?

Do this instead: Create something so useful it can’t be ignored and focus on the people who like what you’re doing.

A Tiny Challenge For You

Here’s a quick way to get unstuck. You should be able to do this in 10 to 15 minutes; don’t overthink it. Do it today.

1. Pick one customer question you get all the time.

2. Write 5 bullet points answering it.

3. Add one line: “If you want help with this, reply and tell me what you’re dealing with.”

That’s your first issue.

See? It doesn’t need to be complicated.

If you’d rather not do this alone…

I help businesses start newsletters — and keep them going.

If you want a newsletter that’s useful, consistent, and not a regular panic attack, reply to this email with:

• what kind of business you run

• who you want to reach

• and whether you prefer done-with-you or done-for-you

I’ll tell you what I’d do in your situation — and what it would take to make it sustainable - bryant@simplyusefulmarketing.co.

Let me get something out of the way before we go any further.

Consistency works — and it works in more places than just email (hello there, exercise!).

Show up regularly on LinkedIn with something thoughtful to say, people start to recognize you.

Publish video consistently — especially if you sound like a human and not a hostage reading a script — trust builds there too.

Long-form writing stacks. Podcasting stacks. Showing up in comment sections with something useful to add stacks over time.

There’s no one right way for everyone.

There are patterns and tools that work consistently across industry, company size, and number of customers. In my opinion, a newsletter is the single most effective way and the best starting point.

But this isn’t an argument that newsletters are the only place growth happens.

A newsletter plus LinkedIn plus video plus sharing on Substack Notes/Twitter/TikTok/Insta/WhateverComesNext all work together to increase trust and grow your business. So don’t think “either/or” think “yes/and.”

But if you’re building a marketing plan, a newsletter is often the biggest initial bang-for-your buck approach to begin.

Consistency Builds Growth

Every channel rewards consistency, but there’s a catch.

You show up. You get better. People start to expect you. You begin to make connections. And sales. One of the earliest content marketing metaphors I read was the flywheel – it takes time and effort to get it turning, but once it’s moving, it’s easier to keep it moving. The focused, regular approach is how reputations are built, in person or online; pretending otherwise is silly.

So here’s the catch.

On social platforms, consistency earns you visibility — until the platform decides it would rather promote something else, such as how LinkedIn reduces the reach of any post with a link. With search, consistency earns you traffic — until an update quietly rearranges the furniture.

It’s not personal.

It’s just how rented land works.

A newsletter doesn’t make consistency more powerful.

It makes it more durable.

Because you build and own a list of people who want to hear from you. That is a one-to-one relationship that’s hard to replicate on social – and you don’t own it there.

Establishing Trust Is Important. (Yeah, I Know: Duh.)

But how you do that has almost nothing to do with “going viral” off a single moment or piece of content.

That burst of attention isn’t growth unless you show people they can trust you enough to stick around.

Why else do you think all the hustlebros have a metric shitton* of glowing reviews plastered across their sales pages? Or why companies cram as many logos as possible onto their websites? Those are trust signals — “social proof,” if we want to use the marketing term — and they exist for a reason.

People are trying to answer a very basic question:

Can I trust you?

Most growth is slow.

You do good work. You provide good service. Your content marketing helps customers remember you — and, ideally, buy from or work with you.

Over time, they come back. And when a friend or coworker asks, “Do you know anyone who…?” your name comes up.

That doesn’t happen because you were clever. Or because you went viral once.

It happens because of familiarity and reliability compounded over time — deeply unsexy things that are wildly effective.

Compounding Is About Growth (Just Not the Kind Dashboards Love)

Compounding is absolutely about growth. Just not the kind that shows up cleanly in a weekly report.

It’s about effort carrying forward instead of letting it dry up.

With most marketing, each piece of work largely lives on its own. A post does well, then it doesn’t. A video gets attention, then slides down the feed. A campaign works, then you start planning the next one like the previous effort never existed.

Yes, your skills improve. Yes, recognition accumulates.

But a lot of the value still resets at the surface.

A newsletter behaves differently.

Every issue slightly increases the odds the next one gets opened. Every send reinforces the idea that you’re worth paying attention to. Every month of showing up reduces friction the next time you ask someone to reply, share, buy, or point someone your way.

That’s compounding growth. Quiet, predictable, and boring in the way that actually matters.

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Newsletters Force the Right Kind of Discipline

In my opinion, a newsletter forces you into a regular cadence of sharing — of building trust.

It’s not a one-off campaign. It’s not a launch.

It’s maintenance — the slow, unglamorous work of staying present in someone’s world without yelling “LOOK AT ME” every time you show up.

This is the grind. The ongoing marketing maintenance where growth actually happens.

And I say “grind” even as I genuinely enjoy creating newsletter content, for myself and for clients. Filtering the knowledge in someone’s head into something that actually lands with their audience is a fun, fascinating challenge.

But the doing of it is a grind.

A constant, ongoing showing up — daily, weekly, monthly — to serve customers.

That’s why most newsletters die. People get tired or bored or don’t see results quickly enough and the frequency drains away until the “most recent” issue is “September 25, 2025.”

And that’s exactly why the ones that stick work so well.

Why This Still Matters

Marketing tools change. Platforms shift. Tactics age out.

But businesses still grow the same way they always have — by staying visible, being useful, and earning trust over time.

Social, video, and search are how people find you.

A newsletter is where the relationship can hit that comfortable, settled place. Sure, there should be some excitement and new things; but the baseline is stable, ongoing support. That’s your newsletter.

Email is the one relationship you own that the platforms don’t get to decide who can see what you want to share.

It’s boring, owned, predictable — and very hard to replace once it’s working.

If you want growth that stacks, it’s still one of the best places to put in the work.

If you want help building one of these without making it your new part-time job, that’s what Newsletter-in-a-Box is for. I’ll get you from blank page to first send — and keep the thing alive long enough to matter — bryant@simplyusefulmarketing.co.

*I still believe “metric shitton” should be an official unit of measure.

Without a strong cultural foundation of a maniacal focus on what’s best for the customer, your marketing efforts will never be as effective as they could be.

Before Christmas last year, I did a “Marketing Advent Calendar.” It was 25 days of short statements that I believe are fundamental to any successful marketing. (Here’s a link to all of them.)

While each statement could be a post (or even a book to themselves – one of them even is), I decided to take a little time before the year accelerates to expand on each of these.

For anyone who wants to work with me, these are the marketing fundamentals my approach to marketing comes from. Even if you don’t want to work with me (I’ll be over there in the corner, rocking back and forth to sooth myself), I think these should form the bedrock of your marketing efforts too.

Without further ado, off we go.

1. Marketing Helps. It Doesn’t Manipulate.

The difference between propaganda and marketing is intent. Functionally, the tactics are identical.

Marketing designed to trick someone into buying is just propaganda tied to someone’s bonus.

Marketing designed to help someone understand a problem — and decide on an answer to that problem (of course hopefully by choosing you) — is a service.

If you actually give a damn about your customers and deliver something that helps them succeed, you don’t need manipulation.

2. Write for People; Not Algorithms.

Google search isn’t about search – it has always been an answer machine. Marketers have been trying to trick search algorithms from the beginning (remember keyword stuffing?) into directing people to their sites.

Google, along with the various social platforms, continually tweak their algorithms to get their users (that’d be us) to an answer/things we’re interested in as quickly as possible (and to shovel money into their pockets, but that’s a different post).

One core job of marketing is to explain something clearly to a human being.

When you write for an algorithm first, you end up sounding like everyone else. If you’re online often, you’ll notice when the various Internet gurus think they’ve found another way to trick the algorithm when post formatting and flow suddenly changes.

You do need to be aware of the algorithms – ignoring them entirely is dumb. But, people first; always.

3. Marketing Works Best When You Give a Damn.

You can fake expertise for a while. You can’t fake caring. It shows up immediately — in what you choose to explain, what you skip, and how patient you are with the reader.

Most bad marketing isn’t bad because it’s intentionally manipulative.

Most bad marketing is bad because the lack of care about the customer comes through in the boring, indifferent, and undifferentiated marketing crap they churn out (or pay a content mill to churn out).

If you care about your customers, show them by helping them with your marketing content.

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4. Always Be Human.

If your marketing sounds like it was written by a committee with a thesaurus addiction, change it. Humans trust humans, not mission statements.

Write like you’d explain it to a friend over coffee. If you wouldn’t say it out loud, don’t publish it.

Have a personality – your real one, don’t fake one. Human kindness and empathy can be the umami in your marketing.

5. Be Useful.

I’ve said this repeatedly because it keeps being true: stop trying to be great and focus on being useful. Useful moves people forward even if the prose isn’t perfect.

“Great” freezes people. Useful ships.

I’m biased to “useful” given my background. My career began in a professional organization as editorial intern, and became the editor a few years later. All content was centered around giving members information they could use to do their job better. Of course, had a little fun along the way, but I often told people “Ain’t nobody reading this for fun; it has to help them.”

Over time, my concept of useful has expanded to include whatever your goals happen to be. So “useful” could be making someone laugh, making someone feel, or making someone think. Come to think of it, laughter is always useful.

6. Everyone Is Guessing.

Marketing decisions all boil down to educated guesswork. Do your research to identify where your customers are, what they are interested in, and so on; but you never know for sure if an idea is going to work until you try it.

So within the bounds of time, try new things. Its not quite throwing spaghetti at a wall to see what sticks, but . . . maybe a little bit. Because anyone who tells you they’ve cracked marketing is either lying or delusional. Markets change. Platforms move the goalposts. Everyone is testing in public.

The honest brokers and experts aren’t the ones with the most certainty — they’re the ones comfortable swimming in an ocean of uncertainty.

7. Content Is King. Distribution Is Emperor.

If a newsletter only exists in one place and is never read, does it exist?

Content without distribution is a diary. Distribution without substance is spam. You need both, but they’re not the same job.

Make something worth sharing first. Then do the boring work of sharing it more than once and in more than one place.

There’s a misconception that you’ll “annoy” people if you share the same thing multiple times. There is a “too-much” threshold. What is it? That varies by audience, goals, your ability to create, etc.; but you don’t know until you get there.

But – and maybe sit down for this next line if you’re reading this on your phone at the kitchen counter – people aren’t paying attention to you 24/7. Will some people see everything you share? Maybe. But most will see your post tomorrow. Then get busy and not read anything from you for three weeks; then see everything for a week. And so on.

So make the things and then share the shit out of the things. Don’t assume you’ll annoy people with frequent sharing, but when enough folks start mentioning it THAT’s when it’s time to dial it back a bit.

8. Don’t Build on Rented Land.

We are the products on social media (Google Search is essentially an ad platform). They don’t care about you; they care about their bottom line.

The various social platforms are useful. They are also not yours.

Email is the one connection you actually control. Use the platforms to build an email list of people who want to hear from you.

9. Answer Customer Questions.

Marcus Sheridan wrote a great book on this – They Ask, You Answer (highly recommend it). Not sure what to share in your newsletter or blog? Talk to every customer-facing employee to find the questions customers are asking them. didn’t invent this — he just named it. Customers ask questions because they’re trying to decide.

Pricing. Comparisons. Risks. “What happens if…” Answer them honestly, publicly, and more than once.

And, yes, talk to customers when you get a chance to — listen in on sales calls to see where sticking points are, read the customer service inbox, trade shows (where those still exist), etc.

I found reader surveys to be a goldmine of ideas. Every year, I would simply go through the “suggestions” answers and have 20 solid feature articles, webinar topics, and online blog ideas to cover. I did have to ignore the occasional "that Duhon guy sucks” comment though (actual comment).

10. Repeat Yourself. Again. And Again.

You are bored of your message long before anyone else has even noticed it.

Just about when you’re absolutely sick and tired of your messaging is just about when folks start paying attention to it. People miss emails. They skim posts. They take a break from being online to focus on work.

Once upon a time, I would share the same tweet 3-4 each day for a few days before tapering off because the half-life of a tweet was something like 10 seconds.

Repetition isn’t laziness. It’s how you build familiarity and trust.

11. Clarity Beats Clever.

If someone has to reread a sentence to understand it, you’ve introduced friction. Friction kills decisions.

Plain language isn’t dumbing things down. It’s respecting the reader’s time.

Don’t use a dollar word when a dime will do.

12. Be Yourself.

Being authentic doesn’t mean oversharing or turning your work into a diary. It means there’s no whiplash between who you are in real life and how you show up on the page. The voice people hear in your writing should sound like the one they’d hear over coffee (or an adult beverage).

Sand down your edges and you disappear into the pile of competent, forgettable noise. Keep them, and something else happens: the right people recognize you. They lean in because it feels familiar. Human. Trustworthy.

Not everyone will like it. That’s fine. You’re not writing for everyone.

13. No One Cares About You.

No one wakes up thinking about your company, your product, or your “exciting announcement.” They wake up thinking about their problems.

The moment you stop trying to make people care about you and start showing how you care about their problem, everything changes.

Come sit on grandpa’s knee for a story. When I was an editor, I also created, hosted, and ran the content side of a sponsored webinar program. I gave every webinar sponsor the talk. Some version of:

No one cares about you. They didn’t register to hear your company history, your product pitch, or how awesome you think you are. They are here to learn about the topic and get help to solve a problem. Address the problem, don’t talk about the ever-lasting glory of your product – they know you have a product already because you’re a sponsor.

Most listened. Some didn’t. The sponsors who listened were well-rated and had more successful follow-up emails than the smaller portion who didn’t.

This was true 20 years ago. It’s true today. It’ll be true 20 years from today.

14. You Aren’t for Everybody.

I’ve used the Howard Stern theory for years.

Stern didn’t succeed by trying to be universally liked. He succeeded because the people who connected with him really connected. He was unmistakable. You always knew what you were getting, and that clarity created loyalty.

Marketing works the same way. When you try to appeal to everyone, you soften your message until it blends into the background. When you’re clear about who your work is for — and how you think — the right people recognize themselves in it.

15. Customer Attention Is a Finite Resource. Respect It.

Every email, post, or video is an ask.

An ask for at least attention, at most a purchase. We are all pressed by a bajillion distractions daily – treat your customers’ attention like the precious gift it is. And keep earning it.

When people trust you not to waste their time, they keep giving you more of it.

16. Be Nice.

As my Meme always said, “It’s easier to attract flies with sugar than vinegar.”

You don’t need to be sweet, but you should just be nice. It’s also a better way to go through life than being a stressed out ball of rage.

Default to assuming misunderstanding before malice. Of course, there will always be trolls who delight in malice. Ignore them. Or better yet, turn their negativity into a joke in your favor.

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17. Trust Is a Conversion Strategy.

Trust is a force multiplier.

When customers trust you, they buy more often, stay longer, forgive mistakes faster, and tell other people about you. They’re also more willing to pay a premium — not because you’re cheaper or louder, but because working with you feels lower-risk.

Trust turns attention into preference, and preference into revenue.

It compounds quietly over time — while everyone else is busy chasing the next burst of visibility that disappears a week later.

18. There Is No Secret Sauce.

Do the work. Do it again. Repeat. That’s it.

We all know this. Stop looking for shortcuts. Put your head down. Put in the time it takes to be good.

I’ve had this image from The Gaping Void in my office for about 15 years now to remind me to remain patient as I tackle something new.

19. It’s Not a “Click.” It’s a Person Looking for an Answer.

Dashboards are useful, but abstract. They compress real behavior into numbers so we can make the educated guesses needed to market our businesses.

But behind every click, visit, open, etc. is a person – someone trying to figure something out. Someone comparing options. Someone looking for a new direction. Someone looking for reassurance they’re not about to screw up.

That “click” is a signal that you are at least doing something right. That you got someone to pause and consider you. Write for that person.

20. Don’t Chase Shiny Objects.

There is always something new to try yet the basics of marketing haven’t changed – identify a customer problem and solve that problem.

There’s a lot guru nonsense online at the moment around solopreneurship. Every single one of them is using content marketing as a strategy. They frown on words like “funnel” even as they use funnels to acquire leads.

Don’t mistake shiny new tactics and tools as shifts in the fundamentals. You should try new tactics over time. But boring consistency beats clever novelty every time.

21. Consistency Compounds.

One post doesn’t change anything. A hundred posts do.

Do the things.

Do them again.

Repeat.

If there’s a “secret sauce,” that’s it.

22. Plain Language Wins. Drop the Insider Jargon.

If you need a glossary, you’ve already lost them. Jargon signals insecurity, not expertise. I’ve lost count of the vendor websites I’ve hit where I couldn’t tell what they did without rereading the homepage three times — and even then, I wasn’t sure. That’s failure.

Jargon doesn’t signal expertise; it signals insecurity and lazy thinking.

Clear language isn’t dumbing things down. Clarity is credibility.

23. Marketing Isn’t a One-and-Done Campaign.

Being a marketer is a bit like being Sisyphus – you keep rolling that boulder but you never quite get to the top of the hill.

Marketing doesn’t stop. You have campaigns, within marketing, but your overall marketing effort should be inseparable from your sales and overall business strategy. It’s essential. It never ends.

Though, unlike Sisyphus, you DO get to roll the boulder to the top and down the slope of a hill with successful campaigns. Then you find the next hill. Your marketing should never stop.

24. Familiarity Drives Preference.

When the stakes are high, people don’t go hunting for novelty. They choose what feels known. Familiarity lowers perceived risk and makes decisions easier — especially when no option feels perfect.

That’s why showing up matters more than being clever. Repetition builds recognition. Recognition becomes comfort. And comfort is what people reach for when it’s time to choose.

25. Marketing Is Simple. Not Easy.

The ideas are basic. The execution is hard because it requires patience, repetition, and restraint.

Do the simple things. Keep doing them. That’s how you build a successful marketing program.

You can download the original version of these, Advent-calendar style, below.

Advent All

68.3MB ∙ PDF file

Download

Download

If this sounds like how you already think about marketing — we’ll probably get along. If you want help building something durable instead of noisy, let’s talk: bryant@simplyusefulmarketing.co.

And, yes, hopefully that answer is your product and service.

Anyway, here they are, in all their glory — 25 marketing fundamentals I believe (and think) that provide the needed mindset to be successful.

And, whatever Holiday it is you celebrate (or none at all), hold your loved ones close if possible and enjoy the ending of one year and the beginning of another in a few short days.

Most people don’t avoid building a newsletter because they’re busy. They avoid them because they’re scared.

You already know a newsletter would help your business.

You subscribe to a handful and trust those businesses who supply you with information you can use. You’ve thought:

• “We should really email our customers.”

• “We have a list somewhere… right?”

• “A newsletter would help with referrals / staying top of mind / sounding like we’re still alive.”

This isn’t going to be another “Newsletters Are Magical!!!” motivation parade.

I think they are. The money flowing into newsletter platforms (like this one and Beehiv) show investors see a future and need. Research shows that a focused-on-customer-needs newsletter builds trust and that trust is a competitive advantage.

There are four common fears I’ve seen over and over.

They’re real. They’re human. Hell, I’ve felt all of them too.

They are all also bullshit.

Let’s unpack them so that you can put these fears behind and begin helping your customers even more than you already do.

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Fear #1: I Don’t Want to Bother People

This fear pops up like a prairie dog every time someone thinks about starting a newsletter.

You imagine your reader opening their inbox, seeing your name, and immediately flinging their laptop across the room while screaming, “HOW DARE THEY SEND ME SOMETHING RELEVANT TO MY OWN WORK?!”

But . . . Do you unsubscribe from newsletters that help you?

I’m going to guess you don’t.

You read and nod your head quietly along. You save the ones most relevant to you. And you face the day feeling ever-so-slightly more competent and informed. You ignore/unsubscribe to the others.

People aren’t bothered by useful. They’re bothered by noise.

You aren’t bothering people if your newsletter:

• answers real questions

• tells the truth about something confusing

• saves someone time

• makes someone think

• or just helps them feel less alone in the chaos

You’re becoming familiar — even trusted — in the best possible way.

You have an inbox. You know what interruption looks like.

Helping is when you show up with something they actually needed — even if they didn’t know to ask.

There’s a companion fear to this one around frequency. “I don’t want to bother them too much.”

While respecting your customers’ time is a good thing (no, a GREAT thing), you can go overboard.

There is a “that’s just too much” level every newsletter reaches, but no one knows what “too much” is until they reach it.

Fact is, your audience might want to hear from you more often. Don’t limit your reach voluntarily. Within the confines of how often you can produce a newsletter, increase the frequency until more folks than normal unsubscribe from an issue.

Congrats. You’ve found “too much,” now dial it back and enjoy the goldilocks feeling of a “just right” newsletter frequency.

Fear #2: I Don’t Know What to Say

Yes you do.

You say it all day long:

• On calls.

• In meetings.

• In emails.

• In Slack.

• Over coffee.

You’re full of answers, stories, and explanations. You are an expert in your business.

The problem isn’t ideas — it’s expectations.

You’re imagining:

• a 7-section “real newsletter”

• a beautifully formatted masterpiece

• Something Anne Handley (who writes my favorite content writing newsletter) would applaud

• Something that demonstrates your brilliance without revealing any of your insecurities

Stop. Just please stop.

Your first newsletter can be:

“Here’s one question we get all the time. Here’s the cleanest answer I have. Here’s what to do if you need more help.”

That’s it.

A newsletter is not a Broadway production; it can start out as community theater.

It’s a conversation — one helpful thing at a time.

Back in my magazine editing days, I tried for two years to get someone who had designed, implemented, and ran a document scanning operation for a mid-sized regional bank.

“But what can I write about” he kept asking.

I kept telling him you’ve forgotten more about how to run a scanning center than most folks will ever know! I still regret not being able to get him to share his knowledge.

You have valuable knowledge between your ears that will help people. So help them.

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Fear #3: What If No One Reads It?

They won’t.

At least at first.

And that’s fine.

No one reads your first newsletter because no one knows it exists yet.

But here’s the part people miss:

• The act of sending the first one makes the second one possible.

• The second makes the third make sense.

• And by the seventh or eighth, something strange happens: People start paying attention.

You cannot build trust with people you never talk to. You can’t build a relationship if you aren’t around.

There is a slight caveat to this: if you already have a list of customer emails, your first newsletter will be read. In fact, the open rate will probably be very high as existing customers open out of loyalty and curiosity.

From there, the work of earning their attention over and over begins.

Fear #4: What If We Can’t Keep It Going?

This is the fear behind the fears.

It’s also the one that will hold you to its grubby bosom as it gently strokes your hair until you murmur, “not yet, I can’t commit to this.”

While fear has you in its grasp, your competition is going full speed ahead.

But here’s what I tell every client:

Start with a cadence you can hit on your worst week, not your best one.

You don’t need daily or weekly to start with. You need “repeatable.”

You don’t need “content pillars.” You need “topics your customers care about.” (Though these overlap within a broader content marketing strategy, but that’s a much different post!)

You don’t need “a big launch.” You need to just go.

Look, sticking to a publication schedule is HARD. Every writer and marketing professional I’ve ever met struggles with this.

I’ve been doing this for just over 30 years now and the fear of deadlines and not being able to keep up is still there. Though thankfully buried deep these days.

There’s good news though. While this is often the biggest fear, it’s also the simplest to overcome (not easy, mind, but simple).

How. Have a system.

If you’re reading this and aren’t a professional writer, you probably think we faff about as we wait for inspiration to strike — that ineffable spark of creativity that leads to beautifully written words.

That’s horseshit. It’s amateur thinking.

You create a list of topics.

You create a schedule.

You write to meet that schedule regardless of if you “feel” like writing or not.

That’s the basic system for every publication yesterday, today, and tomorrow. (I’ll write about writing systems more next year.)

Systems aren’t handcuffs. They help you reduce decision fatigue, improve your consistency, and are a relief valve for anxiety.

So What Do You Do With All This Fear?

You live with it and don’t let it get in your way.

Or, as Paul Atreides from Dune would say (this is for my fellow sci-fi nerds):

I must not fear. Fear is the mind-killer. Fear is the little-death that brings total obliteration. I will face my fear. I will permit it to pass over me and through me. And when it has gone past I will turn the inner eye to see its path. Where the fear has gone there will be nothing. Only I will remain. \\— Frank Herbert, Dune

To get started, lower the stakes:

• Pick a date.

• Answer a customer question.

• Hit send.

• Do it again.

Fear shrinks when you start moving. Especially when movement results in another human saying, “Wow, thanks — this helped.”

My recommendation is to get started, which you can do on your own.

There’s nothing magical about newsletters, and there’s no secret handshake required. What trips most businesses up isn’t ability — it’s friction. Decisions pile up. Weeks get busy. The “we’ll get to it” folder grows mold.

And that’s usually where things stall.

Which brings me to why Newsletter-in-a-Box exists.

It’s for people who already have the expertise, already know a newsletter would help, and are tired of letting good intentions die in the cracks.

You bring:

• expertise

• stories

• an audience worth helping

I bring:

• a simple, repeatable system

• the writing

If this stirred up that familiar “we really should be emailing people” feeling, and you want help finally getting it off the ground without spending your Sundays staring at a blank screen, send me an email at bryant@simplyusefulmarketing.co with “fear” in the subject line.

No pressure. Just a conversation about whether this makes sense for you — or not. Regardless, hit send on something soon. Your customers are waiting to hear from you.

Content marketing isn’t complicated — but great googally-moogally, most companies insist on making it so.

Every week, someone launches a new framework, cheatsheet, formula, “ultimate guide,” AI tool, or system promising to crack the content code. Meanwhile, the stuff that works hasn’t changed since two French brothers handed out restaurant guides to sell more tires.

Strip away the jargon, trends, and platform panic, and content marketing still runs on three unchanging essentials. That’s not to say that new frameworks, etc. aren’t useful — they certainly can be!

But.

If you don’t nail these three core strategic essentials, faffing about on the edges isn’t going to make a dent for you in your market.

Here they are.

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Essential 1: Your Content Needs a Purpose

Most content fails because it’s created for the creator, not the reader.

You don’t publish because “content is important.” You publish because someone, somewhere, has a problem you can help solve.

In other words:

Customers don’t care about you; they care about their problem.

Your job is to make the connection between their pain and your expertise unmistakably clear — and to do it consistently enough that trust forms. And trust? That’s not fluff. It compounds and will make you more money over time.

Purposeful content does at least one of the following:

• Helps someone make a decision

• Reduces friction

• Saves time

• Clarifies confusion

• Moves them closer to working with you

Where should you start?

Let’s keep this as simple as possible:

• Write down three questions your customers ask the most.

• Pick one.

• Answer it simply and clearly.

The purpose is embedded when you answer customer questions.

Essential 2: Write Like a Human (and With Intent)

You don’t need to be a literary genius. You just need to not sound like a corporate press release that wandered into the nearest boardroom.

Clarity beats clever.

Consistency beats brilliance.

Jargon beats absolutely nothing.

Write like you’d explain the idea to a curious friend over a cup of tea. When you do that, you automatically sound more human, more authoritative, and infinitely more readable.

Some rules that haven’t failed me yet:

• Useful beats great. “Great” freezes you; “useful” moves you forward.

• Short sentences create momentum.

• Editing is where the writing becomes good. Time on task > sudden inspiration.

• Never be the hero. The customer is the hero; you’re the guide.

Don’t worry about writing beautifully, focus on writing something useful.

Try this today:

• Take a paragraph you wrote.

• Read it out loud.

• Anywhere you stumble? Fix it.

• Anywhere you sound like a committee? Humanize it.

• Anywhere you hear fluff? Cut it.

That’s writing with intent.

Essential 3: Distribute Strategically (Not Everywhere, and Not Randomly)

In 2014, I would’ve said: “Write well and share it.” Adorable. Naive. Wrong.

Here in 2025, you must respect this iron law of the Internet:

Social platforms are rented land. Amplify there, don’t build you home there.

LinkedIn, Substack, Instagram, X — they giveth, then they tweak the feed, and poof, they taketh away. Influence evaporates. Reach dissolves. The algorithm laughs at your pain.

So your distribution strategy should be:

• Go where your audience already hangs out

• Share generously (five-to-one is still a good rule, but be sure you repeatedly share your content)

• Be human, not promotional

• Use social to start relationships

• Invite people back to a place you own

That place is your newsletter — the ultimate long-term trust builder. No algorithm. No gatekeeper. No volatility. Just permission-based communication you control.

For instance, this Substack newsletter is my “home” online. I have had a Wordpress site before. Functionally, Substack isn’t much different.

Your true “home” — the only thing you own online — is your email list. Substack makes it easy for you to export that list as well as providing built in social tools to help you grow.

Still — we are the product on Substack. Never forget that.

Quick action you can take:

• Pick one platform your audience uses.

• Share one useful insight.

• Ask one genuine question.

• Invite people to join your newsletter for more.

That’s distribution with intention, not desperation.

Content Is Simple; Not Easy

The basic concepts are simple. Where it DOES become complicated and convoluted and contradictory is in the tactics.

SEO evolves.

Analytics get messy.

AI shifts the playing field weekly.

Different platforms require different formats.

And workflows multiply like gremlins fed after midnight.

Content marketing isn’t hard because it’s complicated.

It’s hard because it’s relentless.

You will never be “done.”

You will never reach a finish line.

And there is no “perfect,” only “published.”

If you want an edge, it isn’t brilliance — it’s stamina.

The Three Essentials, One Last Time

1. Purpose: Help someone solve something today.

2. Writing: Be human, be clear, be useful.

3. Distribution: Show up where your audience is — then bring them back home.

Content marketing rewards those who practice these three essentials with patience and persistence. Ignore them and no tactic, no AI tool, no viral post will save you.

But do them long enough, consistently enough, and people might start calling you “great.”

When really you were just purposeful and useful and relentlessly human (while sharing the hell out of your work).

If you’re serious about content that actually moves people, you need a channel you own — not another rented stage.

Start a newsletter. Newsletter-in-a-Box gets you from zero to first send in four weeks, no drama, no dithering.

Email me at bryant@simplyusefulmarketing.co and let’s build something that compounds.

Clever isn’t evil. It’s just insecure. It’s trying too hard to be smarter than your audience because you’re afraid to be clear.

Does your marketing sounds like it was written by a committee with a thesaurus addiction? Change it.

I’ve spent my career around people who are brilliant but terrified to sound “unprofessional.” Like if they use use instead of utilize, the business gods will smite them for not sounding Important Enough.

So they reach for clever. They lace every sentence with jargon, buzzwords, and “world-class, best-in-class, cutting-edge” fluff — and end up sounding exactly like everyone else.

Clever is writing to impress.

Clear is writing to be understood.

Your customers don’t wake up hoping to be dazzled by your vocabulary. They wake up thinking about their own problems: the busted workflow, the broken process, the sales pipeline that looks like a shot of the Sahara.

They don’t need you to be clever. They need you to be useful.

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My “Clever” Newsletter Subject Lines Never Were

For years I curated an ECM-focused newsletter (enterprise content management) for a professional association. Before HubSpot and the ability to run A/B tests, I would periodically “test” a clever (something I thought would be funny or tongue in cheek).

Got my teeth kicked in nearly every time I swapped out a simple, declarative, “here’s what’s inside” subject line with one that made me giggle a bit.

Opens would decrease. Shares would decrease. Click throughs would decrease.

And yet, like a goldfish swimming to the other side of the bowl and bumping my nose again, a month . . . two months and I would think “THIS time it’ll be different.”

Never was.

I was trying to show how smart and how good of a writer I was; not 100% focused on helping my readers get better at their profession.

Since then I’ve (usually) managed to focus on clear over clever.

Even without my personal experience, the research backs that up.

What the Data Says About Clear Language

A few highlights from people who’ve actually done the math:

• A 2020 plain-language study of 500 Americans found that when text was rewritten in plain language, readers understood it faster and better — message clarity scores went up by a third and retention jumped by 40%. ( Source: University of Minnesota – Plain language study summary)

• A digital agency case study showed that simply rewriting product descriptions and calls-to-action in straightforward, benefit-focused language (instead of jargon) led to a 12% boost in conversion rates in a month — less confusion at the final step, more people completing purchases. Source: BlackSheep Communications – Plain language delivers business results

• A conversion-rate study from Portent found that website readability does correlate with conversion rates: pages that were easier to read tended to convert better, reinforcing that friction in the copy shows up directly in your revenue. Source: Portent – “The Readability of Your Website is Affecting Your Conversion Rates”

• On trust: a 2024 piece from a digital services firm points out that plain language reduces misunderstandings and makes information feel more trustworthy — people are more likely to rely on information that’s easy to understand. Source: Coforma – “Use Plain Language to Build Trust”

And since we’re talking subject lines:

• Mailchimp-analysed data (summarized by Econsultancy) found that descriptive, straightforward — even “dry” — subject lines like “{Company} Jan/Feb Newsletter” consistently achieved some of the highest open rates across 40+ million emails. Source: Econsultancy – case studies on effective subject lines

• A roundup of subject-line research notes that around a third of recipients decide whether to open an email based on the subject line alone — and nearly 70% will report emails as spam purely because of how the subject line reads. Sources: Data Axle – “17 Subject Line Statistics to Transform Your Email Marketing” and Juicebox – “Recruitment Email Subject Lines”

There’s even a classic MarketingSherpa/AWeber test where “creativity vs clarity” subject lines went head-to-head — and the clear, descriptive version came out on top. Source: AfterOffers – case studies on winning subject lines

So no, it’s not just cranky old content people yelling at clouds. There’s real evidence that clear, plain language isn’t just nicer — it performs.

Why We Reach for “Clever”

Clever feels safer than clear.

Clear language is specific. It pins you down.

“We help small B2B firms get more repeat customers from their existing list”

is measurable. Someone can come back in six months and ask, “So… did that happen?”

“Empowering digital transformation through next-generation solutions” is slippery. No one knows what it means, which means no one can hold you to it.

We also reach for clever because we’re writing for the wrong audience. Instead of writing for the customer, we write for:

• the boss who loves big words,

• the peers on LinkedIn we’re trying to impress,

• the imaginary award-show judge who might give us a trophy.

The result? A lot of noise and very little signal.

Why Clear Wins

Clarity is credibility. If you need to look up a word before putting it into your marketing or sales material, your customer will likely need to as well. That’s friction. Friction kills decision-making. Clear, concise language helps to eliminate friction.

Every extra brain-cycle your reader spends deciphering a sentence is a tax on their attention. Enough tax, and they bounce.

Clear:

• Makes it obvious who you’re for and what you do.

• Makes it easy for people inside a company to advocate for you.

• Makes you sound confident instead of desperate.

When you write like a person — like you’d explain it to a friend over a drink — you make it easy for people to believe you. They can hear you. They can feel the intent behind your words. And when they feel that you’re not trying to impress them, but to help them, you become memorable.

A Simple “Clever vs Clear” Test

Grab a line from your website, proposal, or LinkedIn profile and run it through this:

1. Would my best customer say this out loud?
   If it sounds like something only a brochure would say, it’s probably clever, not clear.

2. Can a stranger repeat it after one read?
   If they can’t paraphrase it without looking, it’s too fuzzy.

3. Does it point to a concrete outcome?
   “Drive innovation” is mush. “Shorten quote-to-cash cycles” is concrete.

4. Could I explain this to a smart 15-year-old?
   If the answer is no, you’re hiding behind words.

Bonus: for subject lines, ask “If this popped up on my phone, would I instantly know why I should care?” If not, you’ve drifted back into clever.

How to Shift From Clever to Clear

You don’t need a full rebrand. You need a blue pen (I’m a bit red/green color blind, my editing pen is blue, not red) and a bit of courage.

Pick one key asset (homepage, services page, or your LinkedIn “About”) and:

• Replace big, vague words with small, specific ones.

  • “Leverage best-in-class solutions” → “Use tools that actually work.”

  • “Optimize stakeholder engagement” → “Keep your best customers coming back.”

• Swap “we” language for “you” language.

  • “We are a leading provider of…” → “You get…” / “You stop…” / “You finally…”

• Name the problem in plain English.

  • “You’re answering the same customer questions over and over.”

  • “Your CRM is full, but your pipeline is empty.”

• End with one clear next step.

  • “Book a 20-minute call to see if this would work for you.”

  • “Hit reply and tell me your biggest roadblock.”

In your email subject lines, try this tiny discipline:

write the fancy, clever version first… then force yourself to write the boring, brutally honest one. Send the honest one. Let your ego pout.

The Tiny Scary Thing That Changes Everything

Clear doesn’t mean boring. You can still tell stories, crack jokes, be yourself. It just means the story is in service of a point your reader cares about, not a performance to prove how smart you are.

Every word of your marketing either makes you the hero, or makes the customer the hero. Hint: You aren’t the hero.

The irony is, when you stop shouting about yourself — and stop trying to be the cleverest person in the inbox — that’s when people finally start listening.

If your marketing sounds more clever than clear and you’re too close to untangle it, that’s the work I do. I help small and mid-sized businesses rewrite websites, emails, and newsletters in plain language that customers actually respond to — and, if you want, we can build a simple newsletter system (Newsletter-in-a-Box) so you keep showing up consistently. If that sounds useful, hit reply or email me at Bryant@SimplyUsefulMarketing.co with “clarity” in the subject line and tell me where you’re stuck.