Brie Wolfson: Learning to Love Flounder Mode from Kevin Kelly (Hyperlegible 013)

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Jul 17, 2025

Brie Wolfson, CMO of Positive Sum and Colossus and co-founder of Stripe Press, shares her journey through 'Flounder Mode,' a playful term for career paths driven by curiosity. She discusses her mentorship experience with Kevin Kelly, exploring his profound influence on her creative journey. Brie reflects on the challenges of navigating a non-linear career while comparing it to her peers' more structured paths. The conversation highlights the importance of storytelling, innovative workplace dynamics, and the value of genuine connections in personal growth.

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INSIGHT

Accepting Nonlinear Career Paths

Feeling outpaced by peers climbing traditional ladders can sting and make one feel unqualified.
Brie found comfort accepting some doors close, redefining success beyond conventional routes.

INSIGHT

Cultural Bias for Focused Careers

Society values relentless focus on one thing and views drifting as immaturity or lack of loyalty.
Polymathic careers are accepted only if they funnel into a clear focus area.

ANECDOTE

Inside Kevin Kelly's Home

Kevin Kelly's home felt like a dream childhood bedroom, full of books, models, and personal collections.
The intimate setting reflected his multi-dimensional personality and curiosity.

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How do I introduce Brie Wolfson?

Brie's website – briewolfson.com – is a good place to start. It's a treasure trove. She launched Stripe Press. She started The Kool-Aid Factory. Today, she's the CMO of Positive Sum and Colossus.

And there's so much more! She told a story on The Moth! She's written two novels. Everyone is now obsessed with "taste." Her essay, Notes on Taste, kicked off the craze. She even worked at Dandelion Chocolate just to make something with her hands.

But I'm talking to her today because she wrote a phenomenal, personal, and original essay on her day with Kevin Kelly, who's career is even more varied than Brie's.

She called it Flounder Mode.

Flounder Mode is a way of building a career by following your curiosity. It's winding, weird, and often illegible. I know something about this - I've been in Flounder Mode without having the words for it before reading Brie's essay.

The essay itself is unique. Brie spent a day at Kevin Kelly's house and had the chance to interview her hero. Instead of just writing a bunch of Kevin Kelly quotes, though, she writes about her own career, how odd it feels to be in Flounder Mode when your peers are climbing a sturdy ladder, and how comfortable Kevin Kelly seems to be working this way.

I would never have thought to write this essay this way, but it's perfect. Kevin Kelly has impacted so many peoples' careers. So it's only appropriate that Brie's profile is about how he impacted hers. By putting Kelly's words into the background, she infuses the whole essay with him.

In our conversation, we talk all about how to Flounder Mode, what it feels like, the difference between Flounder Mode and laziness, what it takes to do it well, and much more.

I've been a fan and admirer of Brie's for a long time, and I'm so happy we had a chance to get to chat.

At the end of our conversation, Brie makes a couple of recommendations:

Her favorite of her own essays: Notes on Taste⁠

One essay everyone should read: Being basic as a virtue by Nadia Asparouhova

And she gives a one-sentence takeaway from her time with Kevin Kelly: "Have fun!"

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Big thanks to Jim Portela for editing!