Aggressively Human: Online Business in the Age of AI, Algorithms & Automations The expert's paradox
The longer you’ve been doing your work, the harder it can be to explain it.
In this episode, we talk about what we’re calling the expert’s paradox: why people with real experience often struggle to publish clearly, while less-experienced voices seem perfectly comfortable shipping simple advice. We see the seven-part blog post that will take 21 hours to write, and know we can’t stop with the simple AI-generated “5 simple tips” framework. We look at how this shows up in content, marketing, and tool recommendations—and why experts tend to freeze once they can see all the nuance at the same time.
We talk about the Dunning–Kruger effect, the difference between tutorials and diagnostic thinking, and how to deal with the pressure to finish the entire framework before saying anything publicly. We also talk about what helps: publishing before things feel complete, letting ideas change in public, and using content as a working asset rather than a polished performance.
And hear Jessica use the question “what’s the best CRM” to map out a content strategy in real-time, and Meg and Jessica compare chemistry (we think?) to your content organization philosophy.
* Why having more experience often makes it harder to say anything short, clean, or publishable
* How we can use our content for reinforcement, not repurposing
* A Clarion Call for Expertise with “Zippie Nickie and Gnarled Bart” from Corey Wilks, Psy.D.
* Why experts feel pressure to finish the whole framework before sharing anything
* Why tutorials are easy to ship and diagnostics are slow (and why that matters)
* How publishing your work and getting your language out there changes what people search for
* Why clarity wins out over volume in 2026
* How you can use blogs and long-form content as living, updateable assets
* Content architecture: collections, pillars, and making old work findable again
* Our voice choice and how does that influence your authority
“If you have something interesting to say that you feel is different from what else is happening in your industry, that is not a sign that you are outside of the norm; that is a sign that you see something that the beginners don’t. But you cannot be cited, credited, claimed, unless you put it out into the public sphere for indexing, for retrieval, for somebody else reading it. And you can’t change the discourse if you’re not part of the discourse.” - Meg
The Expert’s Paradox by Meg Casebolt
A Clarion Call for Expertise by Corey Wilks
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