The Optimization Trap (And Why You Should Fall Into It Anyway)

A pestilence is spreading one time-saving life hack, morning routine, and productivity protocol at a time. Falling victim to this pestilence causes people to race through their work day and have no agency left for themselves—all they can do is park themselves as a consumer in front of a screen. And do it all over again.

The myth is that when you're pushing yourself you must be getting somewhere. The thing with being in a hurry is that it means you don't like where you are.

Largely, this is an American thing. In most of the world, it isn't so much of an issue. But if you’re in the US and you happen to peer over the hills headed westward into California, you're bound to find a bonafide infestation of it. God help you.

It’s just armor

The Huberman protocols, the Tim Ferriss life hacks, the Silicon Valley microdosing and intermittent fasting and cold plunges and "sunlight in your eyes" and bulletproof coffee, for god's sake.

I had my Tony Robbins days. I unleashed the ol' Giant Within. And here's the thing: it did some good. It also did some damage.

I was prey, honestly. I didn't have a father figure, so I spent my early life looking for one, like turning over the bottoms of rocks to search for insects and finding them here and there in these life-optimizers. Each one seemed to really be living their custom-branded secret: do this morning routine, optimize this system, and you'll become the man you're supposed to be.

But that stuff is just armor. The armor is compelling because it promises significance in a world that feels insurmountably hard. It's a certain model of lifestyle—usually masculine, always quantified, forever promising that if you just dial in one more variable, you'll finally arrive. Sure, you optimized your finances, but what about “maxing out your spirituality?” Eventually I learned it's just an image. It's hollow. It's a lie, in fact.

The real revelation came when I actually pursued it all the way through. I wanted to become my ideal self, really live the life of my dreams. And by actually pursuing that image to its energetic conclusion, the whole quest gradually fell away as less interesting than what was underneath. Some people learn this easily or know it intrinsically. Good for them. The rest of us have to burn through the whole program for awhile.

Luddites

I've been thinking about Thomas Pynchon's essay on Luddites lately (the one from 1984). He writes about how “the love/hate that grows up between humans and machinery” comes from letting machines multiply our effect without understanding the cost.

For him the real issue wasn't the machines but "the concentration of capital that each machine represented, and...the ability of each machine to put a certain number of humans out of work."

Sound familiar?

The optimization industrial complex promises to make your human soul worth more. To multiply your effect. To make you Bad and Big. But, well, I'll tell you: the most interesting people I know are not orienting their life to win based on quantity. They prioritize things like creative flow, depth of relationship, the pursuit of new experiences and new challenges.

Sometimes you just need to build the perfect system and then light it on fire to see what can grow from the ashes.

Career suicide as life strategy

For some reason, changing pursuits is scary—or, like, shameful. It’s dangerous to discuss in any terms beyond the LinkedIn-sanitized version where you "leverage transferable skills" and "pivot strategically." I mean the real thing—where you wake up one day and realize you've been playing someone else's song for so long you've forgotten you have your own voice.

The optimization bros will tell you to find your "zone of genius" or your "unique ability." But that's still armor—a shinier, more expensive version, but armor nonetheless. It’s armor (even though they use a lot of the right words) because it’s outward-oriented. Your gift is something you’re supposed to impose on the world and in exchange the world grants you validation that you’re successful or good enough.

Angela Duckworth talks about grit, but what about anti-grit? The wisdom to quit? The courage to say "I was wrong about everything" at 35, 45, 55? In my experience achieving a basic level of competence at something completely new doesn't have to take that long. You can take up totally different endeavors in life. It's like cross training—the more you do, the more variously skilled you become, and the better you're able to do whatever else you’d like to focus on next.

Sure, mastery takes time and can't be optimized. But it's totally possible to dive into something at any point and achieve some degree of mastery. People steer clear of it because it’s scary and humbling to be mediocre at something you care about. There need be no limits to growth that matters when optimization is not the dogma.

Herminia Ibarra's research on career transitions shows that people who successfully reinvent themselves do it through experimentation. They become unoptimized professionals. They can carry accounting into art, engineering into empathy work, teaching into tech.

Impostor syndrome means you're finally doing something that matters enough to scare you. If you're doing it right, it shouldn't matter whether you feel like you fit in or not.

You know what I think you should optimize? Not your whole life, that's for sure. Optimize what doesn't matter. Carve out more space for what does.

Invisible alchemy

Think about Florence in 1494 or whatever. People had this strange notion of doing not just a single thing. There were gentlemen scientists. A banker decided he wants to understand beauty. A painter decided to cut open corpses. A philosopher decided to write comedy. Nobody's pure. Nobody's optimized. Everyone's stealing from everyone else's discipline. The Renaissance wasn't about life hacking.

To insist on the miraculous is to deny to the machine at least some of its claims on us.

Thomas Pynchon

The miraculous isn't efficient. It's not scalable. It's not something Andrew Huberman can package into a protocol. The miraculous happens when you stop trying to be a better version of someone else's idea of you and start being a worse version of something nobody's seen before.

What, pray, do I mean by that rather convoluted sentence? Any phase of adoption or apprenticeship is bound to be humbling, but it's also the source of absolute nectar when it stems from your choice to step toward a new part of yourself.

Depth Charges

Here's what optimization culture gets wrong: it assumes the goal is to be received well, to be understood quickly, to be valued immediately. The Tim Ferriss model is about winning bro games faster, and it misses the fact that the biggest gains come from compounding interest—consistent discipline over time. When you rush, it feels like you're doing more than you are. What about the work that takes twenty years to make sense? What about becoming someone for whom experiences get received rather than recorded for the podcast?

Cal Newport talks about deep work, but I'm talking about deep being. Ignore the Instagram version where you document your authenticity with sunrise photos and journal prompts. I like the kind where you pursue truth even when it takes you on the trodden path for a while, then off into the untrodden without praise, without metrics, without proof of concept.

You get what you want, eventually. Then you want something else. Then you become something else. Tony Robbins is great, but he never mentions much about the ephemeral.

The AI thing

I'm working on a weekend course—a writing marathon course that's coming out soon. And another on AI, once I figure out how to structure it. Because here's what I know: AI is a tool, but people who ape into it without cultivating their own creative discipline will use it in a way that atrophies the very thing they have most to offer.

The optimization mindset loves AI because it's the ultimate hack. Why learn when you can prompt? Why struggle when you can generate?

We went from "don't die with your song inside you" to how to build better life support systems that keep people playing music they don't discover until too late will turn out to be someone else's song. Or no one's song. Just the average of all songs, optimized for engagement.

The hard work is the point. Why make pottery by hand when you can go to Ikea? Because in the discipline, you discover yourself.

Pynchon’s Luddites weren't really anti-technology. They were pro-human, pro-miracle, pro-the-kind-of-badass-that-comes-from-actual-work.

The machines are coming, man. But as long as we remember that the point is actualization, we’ll survive and so will our unique creative voice.

Even if those voices are weird.