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9 / Every obsession has a legacy.

November 13, 2022

Welcome to Issue #9!

What do you find so interesting that it out-competes Netflix for your attention?

People are astoundingly unique thanks to non only our genetics but all the stuff that happened to us—and because of us—that shaped who we are. And I’m convinced that when someone’s bored or stuck or feeling trapped or any other flavor of unmotivated, it’s because we’re not putting that peculiar combination of experience to good use.

The things we’re interested in are the clues to becoming more aware of what makes us so damned unique. For example, it took me a while to realize that my interests—learning and listening to other people, writing, making stuff look pretty, and wondering how to make work prosperous for employers and employees—could be combined into not only a real career but one with more freedom and lightness than anything I’d ever done before.

So how do you unlock an insight like that? That’s where my question, what do you find so interesting that it could beat Netflix in a competition for your attention, comes in.

Maybe your answer is nothing. But if you think for a second about what might happen, most of us can find some clues.

Whatever this thing is, we have a lot of words for it. Obsession is the most common. Brie Wolfson calls it person-problem fit. Robert Greene calls it your life’s task. It’s been called a calling. Tim Urban calls it the non-negotiable bowl at the top of your yearning hierarchy.

But my favorite is a monomaniacal preoccupation.

Why Does it Matter? People who find something to be monomaniacally preoccupied with—something that would out-compete whatever their Netflix-equivalent attention siphon is—are unusually motivated and have a history of producing great work regardless of their field.

  • Historian Dean Keith Simonton, who may have studied the nature of genius and greatness more than anyone else, believes that almost all human motivation boils down to “a single activity, a monomaniacal preoccupation.”
  • Similarly, the poet David Whyte says, “the antidote to exhaustion is not rest; it is wholeheartedness.”

The Bottom Line: Gallup reports only 34% of U.S. employees feel engaged at work, and I can’t help but wonder if some of that has to do with heaps of monomaniacal preoccupations awaiting claiming. This week I’m going to skip over how one finds an obsession and skip straight to what to do with one once you’ve found one.

Big Idea #9: The Obsession Tree


Every obsession has a legacy, and we can choose to ignore it or embrace it and save ourselves years of painstaking rediscovery and reinvention.

Imagine a family tree, but on this tree, the people aren’t connected by birth and heredity. Their obsessions connect them. Unfortunately, we aren’t born with our hard drives pre-loaded with all the stuff our obsession ancestors figured out before we showed up on the scene.

If you feel like you get it, skip to the practice section. But if I’ve learned anything from non-fiction authors, you have to say what you’re trying to say in ten or twelve different ways to get a book deal, so here’s another way to think about it.

In a lot of video games, your character’s level and power increase as you complete missions. You start at zero, and there’s usually a max level of 20-100. But in life, it’s like the person who discovered the wheel went from level 0 to level 1 in their life, but you can go from level 0 to level 2,356 by studying what all the other wheel-obsessed folks did before you showed up.

Another way is to think of the generational transfer of obsessions as a baton, an Obsession Baton.

Obsession Batons aren’t some magical objects we can pick up, but they’re choices imbued with incredible power. As we pick up our batons, we can look back and learn from those who handed them to us. Or we can take the sicko-route and ignore history and risk letting our branch of the tree wither and crumble.

And if that wasn’t enough, here’s another way to put it (I can nearly hear Penguin’s agents scrambling, can you?): I’ve sometimes heard tracing the lineage of your intellectual heritage as “going to the source.” As in following a river upstream to find the source of the water. The further upstream you go, the further ahead you’ll be able to see (because elevation, you know).


Anyone can, at any moment, begin to map both the lineage of who’s held the obsession baton before you and your other living intellectual relatives.

Einstein needed to study Newton and Galileo, Faraday and Maxwell. Still, in Hendrik Lorentz’s 1905 paper, a man only twenty-six years his senior, he discovered equations he needed to develop his Theory of Relativity.

As a CEO, your obsession may be a customer problem. So who was obsessed with it before you? Who is obsessed now?

As a designer preoccupied with typography, you’re sure to realize that Matthew Butterick is carrying a baton for typography, and so are Kris Sowersby and the team at Klim Type Foundry.

It gets really cool when you’re carrying two batons from different fields, and you get to mash them up in a sort of industrial version of combining two cuisines in delicious fusion.

The point is simple: when you find something that beats Netflix in a battle for your attention, two places you can look to further your knowledge are to the past—who’s been obsessed before—and to the community of others who share your obsession.

Reads & Resources


For years, Beth Scheer at Homebrew has been writing helpful long-form guides for startup founders on topics like diversity, immigration, benefits, onboarding, compensation, sourcing talent, and performance management. Each one is awesome. This one on executive coaching is so good that I recommend any potential client I speak with read it before we talk, and it’s a great place to point people out if they have questions about coaching.

From Twitter

Alex Hormozi, the founder of, tweeted, “Biggest cost reduction that took me too long to learn: Pay A-players 1.5x market rate to get 5x the output of a B-player.” This is wisdom that goes way back. Frederick Winslow Taylor, an early management theorist in the late 1800s and early 1900s, called this the “paradox of high wages and low costs.” Many incorrectly think of high wages as a cost, reducing overall profits. Still, the idea is that when great people are incentivized right, the interests of the employee and employer are aligned, leading to a general increase of the pie being split.


I read and listen to just about anything Matt puts out these days. Before I was a coach, I’d refresh the Google Doc for The Great CEO Within, waiting for a new chapter to drop. Today, I regularly refer to Matt’s methodology and tactics for building companies with my clients. He shares his ideas generously, and I love how sincerely he cares about building great companies that work for the employers and the employees. My favorite part of this episode comes early when he talks about how he makes a bet with CEOs he coaches that ends up helping them become aware of just how often fear is driving them to misjudge situations.


This is one of my most heavily highlighted books of all time. The book’s author is Tim O’Reilly, who created one of the first e-commerce marketplaces on the web, coined the term “open source,” and founded O’Reilly Media, the publishing company behind the technical books with the animals on the covers. It’s one part of history, arriving at some conclusions about “how we got ourselves here,” and then another part, “what to do about it.” My favorite part is where he describes “the market” as humanity’s first AI, one few of us are conscious of spending our lives feeding.

Dice Roll

Last year I bought almost every gift I gave friends and family off this list. The list is full of delicious items I didn’t even know existed, and the gifts were all hits. I tweeted Rand and Amanda to ask if they’d be doing a 2022 version, and they confirmed they would. But for those of you who want to get started earlier, this is the ticket.

That’s all for this week. I’m looking forward to what’s next!