I advised 100+ solopreneurs in the last three years. Wanna know what NONE of my clients was? A dilettante. An amateur. Someone who needs more knowledge before they sell what they’re selling.
Sure, some of them were new solopreneurs, but they were not newbies in their craft.
And that’s a problem. Or, better said, an obstacle.
Not in our work. Expertise is the very thing clients pay us for. It’s what allows us to recognize patterns others miss, diagnose problems in minutes instead of hours, and make decisions that look almost magical to people watching from the outside.
It becomes an obstacle when we sit down to explain what we know.
The more experienced you become, the less your brain stores isolated facts and the more it starts storing patterns. A junior marketer might see a low email open rate and wonder whether they should rewrite the subject line. I look at the same numbers and instinctively connect deliverability, audience expectations, positioning, list hygiene, offer-market fit, timing, previous campaigns, and half a dozen other variables.
That ability is exactly what makes you an expert.
It’s also exactly what makes creating profitable content so difficult.
I’ll tell you more about that and how to fix it in a second, after a quick message from one of my favorite partners, one of the few people in this space who means it when she says “BS-free”.
And, if you run a service business, do yourself a favor and RUN, don’t walk to this. It will help you understand what kind of leverage you need beyond vanity metrics.
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Tappers vs listeners
Did you know that the curse of knowledge has already been studied for decades? In one of the foundational papers on this topic, three economists discovered that, once we know something, it becomes surprisingly difficult to imagine what it feels like not to know it. We unconsciously assume other people possess far more context than they actually do.
One of my favorite demonstrations of this comes from psychologist Elizabeth Newton’s research at Stanford.
Participants were divided into “tappers” and “listeners.” The tappers would choose a well-known song such as Happy Birthday and tap its rhythm on a table. Before starting, they predicted that listeners would correctly identify the song roughly half the time.
The actual success rate was a staggering ~2.5%.
The experiment has become famous because it perfectly illustrates what happens inside the expert’s mind: the person tapping isn’t hearing random knocks, but the entire melody, the lyrics, the rhythm, and perhaps even memories associated with the song. All of that context exists only inside their own head.
The listener hears someone enthusiastically assaulting a wooden table.
That’s what expertise feels like: every time you write about your work, you’re the tapper. Now imagine carrying that invisible orchestra into every newsletter, LinkedIn post, or YouTube script you publish.
By the time you’ve spent ten or fifteen years in your field, you’ve forgotten hundreds of intermediate steps because your brain has compressed them into shortcuts. Cognitive scientists refer to this process as chunking: instead of processing dozens of individual pieces of information, experts organize them into larger mental units that can be retrieved almost instantly.
Chess masters don’t analyze thirty-two separate pieces every time they look at a board. Experienced radiologists don’t inspect every square millimeter of an X-ray one by one. They recognize familiar configurations almost immediately because their brains have spent years building those mental chunks.
That’s wonderful for solving problems and terrible for explaining them because your audience hasn’t built those chunks yet.
This creates something I think every expert feels but rarely names.
There’s a cognitive tax attached to creating content
Most people assume writing is hard because they can’t find the right words, but that’s rarely the problem. The difficult part happens long before the first sentence appears on the screen.
For a piece of content to be profitable and to land, you need to answer these questions first:
- How much context does my audience need before this makes sense?
- Which assumptions have I accidentally skipped?
- Is this concept actually obvious, or has it simply become obvious to me because I’ve repeated it for a decade?
- Where exactly does their understanding stop?
None of these questions involve writing. They’re acts of perspective-taking. Every piece of content requires you to temporarily step outside your own expertise and reconstruct what it felt like before you knew everything you know today.
And yes, that’s mentally expensive.
Yet, the trade-off is even more expensive: if you don’t pay this cognitive tax, your audience will. BUT your audience is not forced to do it; they can simply choose to scroll past your content if it becomes too taxing.
Ironically, beginners don’t pay this tax nearly as often.
Someone who’s been freelancing for six months usually writes about whatever they learned yesterday. And it works because their audience is only a few steps behind them, so the distance they need to bridge is relatively small.
Experts face the opposite problem: their audience isn’t six months behind; they’re often ten years behind, and that’s a much wider gap to cross.
Which brings me to something I’ve noticed over and over again in my consulting work.
The better someone is at their job, the more likely they are to dismiss their own best ideas
During strategy sessions, clients constantly apologize before sharing an observation: “This is probably too obvious.” Then they say something they’ve been telling clients for years.
At this point, I need to interrupt them because they’ve just handed me the central idea for an entire newsletter — sometimes even for their central thesis.
And they’re always surprised: “But everyone knows that.”
Nope. Everyone around you knows that.
You’ve spent years immersed in your own professional bubble. Your clients haven’t. If they already understood what you understand, they wouldn’t be paying you.
Your expertise has become so familiar that your own brain no longer registers it as valuable. This is habituation: repeated exposure reduces our conscious attention to something. The idea hasn’t become less useful. It has simply become less noticeable to the person who’s been living with it for years.
This has two really nasty effects:
- The pieces of content you’re most proud of aren’t your best ones; at least not in terms of conversion rate. They’re usually written for your peers (and their level of understanding), not your audience’s.
- When you ask yourself, “What should I write about this week?” you will often end up with mediocre content because your brain starts searching for novelty. Meanwhile, the ideas your audience would gladly pay to hear have become practically invisible to you.
So how do you fix this? “Better content ideas” is not the solution (what does that even mean?!).
You need to find better ways to notice the ideas you already have
In other words, you need to create enough distance from your own expertise that you can see it again.
That’s much harder than it sounds because you cannot simply decide to forget fifteen years of experience, and you can’t unknow what you know.
What you can do is build systems that continuously force your thinking back into your audience’s world.
Start by documenting EVERY:
- Client question
- Objection
- Misconception
- Moment where someone says, “Wait… can you explain that?“
- Social media comment that asks for clarification
Write.Them.Down!
I promise you that you will start seeing patterns after a while. I use these patterns to do two things:
- Create new content (like this newsletter) whenever a question/challenge pops up ±3 times.
- Create products and offers whenever a question/challenge pops up ±6-10 times.
Real talk: becoming a BETTER expert is amazing; please don’t take this lightly. Just consider this: if you were in academia, you could write without caring whether your audience gets you or not. After all, your readers can do some more research to catch up — that’s the whole point of academia.
If, however, you are running a business, being a profitable expert has two components: the expertise itself and the ability to temporarily set aside what you know enough to meet your audience where they are, then walk them forward one insight at a time.
Candidly, I mostly wrote this for myself
(and two recent strategy session clients.)
I also fall into this trap quite often. I think most topics I come up with are bland, over-explained (by me or others), and pretty much common knowledge.
Writing for an audience whose expertise is in other fields without treating them like toddlers is not easy. My go-to is this: I know you’re smart, so I don’t dumb down my writing (heck, I even quote scientific studies).
I also know that (most of) you don’t have my 20 years of marketing background, so I tone down the talk about advanced funnels and cryptic acronyms that no one outside this field gets (nor should they).
What helps me the most is the documenting I mentioned above: whenever I feel the need to overcomplicate things, I take a look at the suggestions I already received and realize I have to take a step back.
Community Spotlight
Do you know of any qualitative AND quantitative reports on brand messaging? I didn’t know of any, either — until my friend and fellow Council member, Laurel Carpenter, launched it. It’s the report that will tell you how many people have an actual differentiating factor on their website, among many other interesting finds. Grab it here!
