How to Flounder Mode with Brie Wolfson
Hyperlegible 013: On Brie's good day together with Kevin Kelly
Find Hyperlegible 013 with
on YouTube | Spotify | Apple PodcastsWhile you’re there, and I’m sorry to ask but it really does help: like, comment, and subscribe.
Today’s Not Boring is brought to you by… Vanta
Vanta helps growing companies achieve compliance quickly and painlessly by automating 35+ frameworks, including SOC 2, ISO 27001, HIPAA, and more.
Start with Vanta’s Compliance for Startups Bundle, with key resources to accelerate your journey: step-by-step compliance checklists, case studies from fast-growing startups, and on-demand videos with industry leaders.
How to Flounder Mode
Hyperlegible 013: Brie Wolfson, Flounder Mode
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. If you don’t get the Colossus Review, get it.
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, whose career is even more varied than Brie's. Her description of his lifetime of doings is three big paragraphs long, and it doesn’t even mention a couple of the essays that have had a big impact on me: The Case for Optimism and Scenius, or Communal Genius. As a small taste: he’s building a 10,000-year clock, inspired Futurama's death clock, started WIRED magazine, and launched a project to catalog all living species that’s now being run by the Smithsonian.
Kelly calls his style of work “Hollywood Style.”
Brie called her essay about him 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 unlike any profile I’ve read. 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.
We talk about how Brie wrote this piece the way she did, and why it’s one of the very few pieces about Kevin Kelly that he’s actually read.
And we go deep on what it takes to do Flounder Mode well. There is a thin line between Flounder Mode and aimlessness, and we came to the conclusion it has something to do with turning your curiosity into output; not just consuming interesting things, but creating from them. It probably has something to do with taste, too.
Flounder Mode isn’t easy. Both Brie and I have struggled with it, as she captures beautifully in the essay and as we discuss in depth. It’s hard to see your peers doing more understandably bigger things than you. And it’s up-and-down: sometimes, people love what you’re doing, sometimes, they don’t care. Brie calls it magnet-on, magnet-off.
But I think that if it’s true that AI does more of the basic work that humans do, more people will work in Flounder Mode. We will have the luxury of following our curiosity, and curiosity is something that the LLMs seem to lack. It’s human.
Because we’re human, and competitive, the hard part is learning to be content with a less legible path, and to take satisfaction in the exploration itself. Brie’s profile, Kelly’s life, and our conversation, is the starting point for a bigger conversation that I’m sure we’ll be having more frequently in the years to come.
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. Getting to have conversations like this is one of the benefits of Flounder Mode.
Transcript and Links:
If you’re the reading type, I used Claude to turn the messy YouTube transcript into something well-formatted and clean:
Hyperlegible 013 with Brie Wolfson - Transcript
As always, you can find the full conversation wherever you like by subscribing to Not Boring Radio:
YouTube:
Spotify:
Apple Podcasts:
While you’re there, give us a like, comment, and subscribe so we can bring great essays to more people.
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!"
You can find this and all of the articles we discuss on Hyperlegible in one place thanks to our sponsor, Readwise - Visit readwise.io/hyperlegible for a free trial and get all Hyperlegible articles automatically added to your account: https://readwise.io/hyperlegible
Big thanks to Brie for joining me and to Jim Portela for editing!
That’s all for today. We’ll be back in your inbox tomorrow with a Weekly Dose.
Thanks for listening and watching,
Packy