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Westenberg. | v1.0 | 2026

Why I quit "The Strive"

Why I quit "The Strive"
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I spent about a decade waking up at 6am and checking my follower count before I brushed my teeth. Refreshing analytics while the coffee brewed, reading Y Combinator essays, networking on Twitter and trying to reverse-engineer what made people break out. I'd look at every piece of creative work I produced and ask "will this scale?" Every night, I'd calculate the gap between where I was and where Mark Zuckerberg was at my age, or Marc Andreessen, or Om Malik, or Ryan Holiday etc etc etc - which is an unhinged thing to do.

But I did it all the time.

I was obsessed with whatever it was that would come Next. After all of this, after I had made it, after I'd stopped "plateauing" and reached my potential.

This is what I've come to call The Strive.

And you know it too, even if you've never called it that. It's the obsession with making it, going viral, founding a billion-dollar company, becoming the next TBPN, raising millions of dollars, getting profiled in Wired, landing on the Forbes 30 Under 30 list (or, for those of us who aged out, the Forbes 40 Under 40 list that doesn't exist but should). The Strive is what makes people put "serial entrepreneur" in their Twitter bio. It's what makes a 24-year-old describe their note-taking app as "disrupting knowledge work." It's what kept me awake at 2am calculating how many followers I needed per week to hit my Q3 growth target.

Back in the 70's a researcher named Philip Brickman studied lottery winners and found that people who won big were no happier than anyone else within a few months. He called it the "hedonic treadmill." You get the thing, the feeling fades, you chase the next thing.

The Strive is the hedonic treadmill all over again, but it comes with a mandatory pair of white sneakers and a Claude Max subscription.

How the machine works

From the outside, The Strive it looks like that thing we call passion; but from the inside it feels like a crushing, soul destroying anxiety disorder.

You set a goal, and with a bit of luck and a whole lot of blood, you hit it, and you feel good for somewhere between 4 hours and 2 days (and I'm being generous with the 2 days), and then it fades and you set a bigger goal because the old one, the one you were sure would change everything, turned out to be a thing that happened and nothing more.

I hit 10,000 followers once and felt good for about an afternoon, and I got published in an outlet I'd been pitching for months and the dopamine lasted maybe 36 hours before I was back at my laptop, pitching the next thing.

Your brain's ~wanting system and your brain's ~liking system are separate circuits, and the wanting system is bigger and louder and more connected to everything else.

As it turns out, dopamine fires for the chase, not for the catch.

Infrastructure

The Strive doesn't live in your head alone - no, it has infrastructure. It has an entire litany of podcasts, and conferences, Twitter threads, and LinkedIn posts, co-working spaces, and pitch competitions, and all of it keeps you sprinting.

Everyone around you is Striving, too. And when you stop, you feel like you're falling behind. But falling behind who? People who are also on the treadmill, also wondering why their last win didn't stick?

Once you're in it, opting out feels like abject failure. If you're not growing, you must be dying, if you're content, you must be complacent. Peace and satisfaction are a disease that infests the uninitiated.

Well, I went to the events and read the books (the ones with single-word titles like "Grit" and "Hustle") and optimised my mornings and tracked my habits with an app that gave me a score, and I tweeted through it, and I cold-emailed strangers to ask if I could "pick their brain," which is a phrase that should be fucking illegal.

It got me nowhere.

What it costs

You're told to calculate the upside: money, status, influence. You're told to weigh that against the "sacrifice," which is always framed as temporary. Grind for a few years, miss some dinners, put some relationships on hold. There's a finish line out there and once you cross it you get to enjoy things.

But this is bullshit! There's no finish line! That's the trick, and it's a damned good one!

I watched a friend raise a Series A and immediately start losing sleep over Series B. I know someone who hit a million in annual revenue and couldn't enjoy it because all he could think about was getting to 10. Every finish line is a checkpoint. You cross it and the next one appears, further away, higher up. This is intentional design.

What The Strive actually cost me was a large number of physical years. Years I spent optimising instead of living, years I spent going to networking events instead of seeing friends, building an audience when I could have been reading a book for fun. I worked on things that were always about to become The Thing that Mattered, and they never quite did. And even if they had, it wouldn't have been enough. It would never, ever have been enough.

Enough

What if the right scale for interesting work is whatever scale that lets you keep doing it? What if a good idea doesn't need to become a billion-dollar company? What if it can be a good idea that you work on because it's interesting and it pays your rent?

Kahneman and Deaton published a study in 2010 showing that after about $75,000 a year (probably closer to $100,000 now), more money doesn't make your day-to-day life feel any better. Your abstract "life satisfaction" might tick up, but the actual texture of your days doesn't change.

You can't ask "how much is enough?" inside The Strive's framework because "enough" is a word it doesn't recognise.

I run a solo creative studio called Studio Self. I write things I love writing. I work with clients I actually like. I pick projects that challenge my brain in ways I find interesting and I turn down the ones that don't. I am not optimising for maximum revenue. I am not building a unicorn. I am unlikely to go down in history.

By The Strive's metrics, I'm a failure. I should be raising money. I should be building a team. I should be positioning for an exit. Instead I'm writing a blog and reading comic books and playing Doom II and working on ideas that will almost certainly never make anyone a billion dollars, and I'm fine with that. Better than fine. I wake up and I'm not dreading the day. I work on things I care about. I stop working when I'm done. My brain feels alive and I have time to read for fun and I think that's worth more than a Series A.

The MASH test

The Strive doesn't believe in hobbies. In its twisted framework, everything is either productive or wasteful. Reading a comic book: wasteful. Reading a business book: productive. Playing a video game: wasteful. Building one: productive. It can't process the idea that you might do something because you enjoy it. Every hour has to be an investment. Every experience has to compound.

That is a psychotic way to live. I mean that close to literally. It's a disconnection from the basic human experience of enjoying things because they're enjoyable. A 6-year-old knows you read a book because it's fun. The Strive beats that out of you and replaces it with a spreadsheet.

I have a test for whether The Strive still owns you, and I call it the MASH test. MASH ran for 11 seasons, from 1972 to 1983. The finale pulled 105.9 million viewers, still the most-watched broadcast in American television history. It's a show about people stuck in the Korean War trying to stay human by being funny and caring about their work even though everything around them is insane.

The test: can you sit down and watch an episode of MASH on a Wednesday afternoon without feeling guilty about it?

If you can't, if you feel The Strive pulling at you, telling you that you're wasting time, that you should be producing something, that every hour not spent growing your brand is an hour wasted, then The Strive still owns you. You've handed your peace of mind to a system that will never give you permission to stop.

I can read a comic book now without running the mental math on whether I should be making content instead. I can go for a walk without listening to a business podcast. I can talk to someone without wondering if they're a useful connection. These sound like small things but mate I promise you, they're the whole game.

Why it sticks

You'd think, given everything I've described, that people would stop. But tey don't, and I didn't for a long time, even though I knew the math was bad.

Part of the reason why is survivorship bias. The Strive only shows you the people who won: the fundraise posts, the exit announcements, the profile in TechCrunch. You don't see the thousands who ground it out for five years and ended up back at a day job, older and more tired and with a credit card balance that makes them nauseous. The expected value of The Strive is way lower than it looks from the outside, but the outside is the only view you get.

Part of it is identity. Once I'd been Striving long enough, it stopped being something I did, and started being something I was. My friends were Strivers and my self-concept was "ambitious person building something." When I started pulling back, it felt like I was killing a version of myself. That's not a comfortable feeling.

But the biggest part, the part nobody wants to cop to is this: The Strive is a really good way to avoid sitting with your actual life. If you're always chasing the next milestone, you don't have to ask whether you like the way you spend your days. You don't have to look at the possibility that catching the thing wouldn't make you happy either. I think, for me, a lot of The Strive was... running, running from the question of whether any of it was what I wanted, or what I'd been told to want.

Boring on purpose

Contentment is boring. "I woke up, I wrote something I liked, I read a book, I had dinner, I went to bed" doesn't make for a great narrative. Nobody's making a podcast series about the person who decided things were just fine and they were just fine with that.

The Strive has narrative tension. Will they raise the round? Will the product launch? Will they make it? My life doesn't have narrative tension right now and I think that might be the whole point.

A life that makes a good story tends to be a life that was awful to live. The chapters people want to read about in biographies tend to be the ones the person would have skipped if they could. The Strive sounds great in the abstract. Work hard, dream big, change the world, but on the ground it's a prescription for chronic dissatisfaction, because it trains you to put your well-being somewhere in the future, always in the future, and the future never arrives.

I'd rather be bored and present than excited and perpetually somewhere else. I'd rather have a Wednesday than a narrative arc. I realise that's not a sexy position to hold. I'm directionally ok with that.

I work hard, I care about quality. I want the things I make to be good and I want to find clients who push me and I want projects that make my brain hurt in a good way.

But the specific cultural program that equates your worth with your scale, your follower count, your funding round, is a bad deal for most people. It takes the normal desire to do good work and bolts a set of impossible metrics onto it. It takes "I'd like to make a living doing something I care about" and inflates it into "you need to build an empire." Those are different things. The Strive collapses them into one.

Where this goes

"Is this enough?" is a better question than "How do I get more?" and I wish someone had told me that 10 years ago, but I probably wouldn't have listened.

I was too busy Striving.

The Strive isn't going anywhere, not any time soon. There's too much money in it, too many people selling the dream. The conferences will keep going, and the podcasts will keep recording, and LinkedIn will keep telling you that your comfort zone is where dreams go to die, which, as motivational slogans go, really is something isn't it?

But I think, I hope, the math is starting to catch up with more people. We spend years marinating in anxiety for a feeling that lasts 48 hours, on repeat, forever - and that is a bad fucking trade.

I'm going to go watch MASH now. I've got nowhere to be and nothing to optimise and I don't feel guilty about it at all.

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