Weekly Wisdom #342 - The curse of knowing too much

Expert Fallacy, Curse of Knowledge, Steal Like an Artist & Making Friends While Traveling

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Happy Sunday!

Just a few weeks ago I spent an evening talking to a guy at a hostel in El Salvador. He’d recently left a chaotic life — street racing, selling drugs, the whole thing — and was now traveling the world, editing videos, figuring out what’s next.

At some point he asked what I did. I gave the short version: I build software tools, write online, run a newsletter.

His response: “That’s incredible. I wouldn’t even know where to start.”

And I almost said “it’s not that hard” — but I caught myself. Because to him, it genuinely seemed like a different world. The things I take for granted — vibe coding with AI tools, understanding SEO, building a product — are mysteries to most people.

There’s a name for this. The curse of knowledge. Once you know something, you can’t un-know it. You lose the ability to see it as hard, which means you undervalue what you’ve learned.

I see this constantly in the communities I’m in. People who know more about AI, or marketing, or building products than 95% of the population — but they don’t think of themselves as experts because they compare themselves to the other people in the room.

Austin Kleon writes about this in Steal Like an Artist. His advice is to share your work and your process even when you feel like a beginner, because you’re always one step ahead of someone.

The uncomfortable implication: if you’re sitting on knowledge and not sharing it — or not selling it — you’re leaving something on the table. Not because you need to become a guru. But because there are people who’d pay for the shortcut you already took.

One interesting side note from traveling: making friends on the road is shockingly easy. Everyone’s in the same situation — new place, no existing network, open to meeting people. It’s a reminder that the barriers we feel to connection are mostly environmental, not personal. Change the environment, change the outcome.

What do you know that feels obvious to you but would be genuinely useful to someone a few steps behind?

Have a great week!

Graham

📚 Book Notes: Steal Like an Artist — Austin Kleon​

Short book, big ideas. Kleon’s core argument is that nothing is truly original — creativity is about taking what exists and combining it in your own way.

The useful bit: you don’t need to be an expert to create. You just need to be one step ahead. Teach what you just learned. Share what you just figured out. The people right behind you need your perspective more than the perspective of someone who’s been doing it for 20 years and forgot what it was like to start.

📖 Article: ‘Hemingway Didn’t Say That’ (And Neither Did Twain Or Kafka)​

We attribute wisdom to people who already seem wise. Lincoln, Twain, Einstein — they get credit for things they never said because we want the quote to carry authority. It’s the expert fallacy in reverse: we assume the expert said the smart thing, even when they didn’t.

Fun read. Makes you question every motivational quote you’ve ever shared.

From the Blog

📝 I Quit My PM Job 6 Months Ago — When I left, I didn’t feel like I knew enough to build a business. Six months later, it turns out I knew plenty. The gap was confidence, not competence.

📝 Memory and Task Systems: Giving Your AI Agent a Brain — I wrote this thinking everyone already knew this stuff. The response told me otherwise.

🔗 Things I Found Interesting

​Why Garry Tan’s Claude Code setup has gotten so much love, and hate — The YC CEO sharing his exact AI coding workflow is a great example of the Kleon approach. Share your process. Some people will love it, some will criticize it — both mean it resonated.

​How I code with agents, without being ‘technical’ — Ben Tossell built products without traditional coding skills. He’d be the first to tell you he’s “not technical.” His users wouldn’t agree.

​OMA completes expansion of New York’s New Museum (Dezeen) — OMA mirrored the original SANAA building with something that’s connected but has its own identity. Nice metaphor for building on what came before you.

​World’s first commercial green H2 project powered by surplus renewables — Green hydrogen from surplus wind energy. The kind of infrastructure project that doesn’t get the attention it deserves.

📣 Quote

“Start copying what you love. Copy copy copy copy. At the end of the copy you will find yourself.” — Yohji Yamamoto

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