Betting on Yourself is a Kind of Misery

On ambition, pain, and the quiet war of creating something real

“The marine corps teaches you how to be miserable. This is invaluable for an artist. Marines love to be miserable. Marines derive a perverse satisfaction in having colder chow, crappier equipment, and higher casualty rates than any outfit of dogfaces, swabjockies, or flyboys, all of whom they despise. Why? Because those candyasses don't know how to be miserable.

The artist committing himself to his calling has to be miserable. The artist committing himself to his calling has volunteered for hell, whether he knows it or not, he will be dining for the duration on a diet of isolation, rejection, self-doubt, despair, ridicule, contempt, and humiliation. The artist must be like that marine: he has to know how to be miserable. He has to love being miserable. He has to take pride in being more miserable than any soldier, or swabbie, or desk jockey, because this is war, baby, and war is hell.” ― Steven Pressfield, The War of Art

Have you ever been confronted by an insight that makes your heart skip and your soul flare? Most recently, that was me on page 68 from The War of Art. It gave voice to a low-grade fever that I’ve been living with for years. The small, persistent thrum of discomfort I’ve tried to medicate with achievement, ambition, and self-help material.

Is there something wrong with me? Will I ever be satisfied? Why does fulfillment feel like a fight?

I founded a company from my gut. Not because it was safe or obvious – but because I felt pulled. The kind of pull that doesn’t care if you’re tired, broke, or newly postpartum. All the while, I still assumed I was in pursuit of happiness – because that’s what we’re told we should want. Even though over the years, deep down, happiness has never felt like enough. When it arrives, it’s sweet but fleeting. When it’s static, it begins to rot in place. I wasn’t wired to rest in contentment. I was wired to build, stretch, risk, ache. And suddenly, it clicked: aliveness – not happiness – is what I’ve been seeking all along.

Aliveness is being on FaceTime with your manufacturer at 3am because the labels are misprinted, and fulfillment starts at 8. It’s crying in the bathroom at the Starbucks across the street so your team doesn’t hear you – after yet another closed door – then walking into your next meeting like you weren’t just gutted. It’s watching competitors flourish while you’re choosing between payroll and a production run. It’s hearing “no” for the 47th time and wondering if the 48th might kill you – or finally crack something open. It’s waking up with that sick feeling that you might lose everything and doing it anyway.

That one shift in language – from happiness to aliveness – changed me. It gave shape to my choices and quieted the inner voice insisting I was doing life wrong. It gave me permission to want what I actually want. Aliveness is brutal, but it’s real. And I’d rather be broken open by truth than soothed by ease.

Reading Pressfield made me feel less alone. Like maybe there’s a whole secret world of people – artists, founders, builders – who know that betting on yourself is a kind of misery. We do it anyway. Not because we love pain, but because we love becoming.

That’s the part no one tells you: your dream will demand more from you than you think you have. And still, somehow, it will feel like home.

So if you’re optimizing for peace or joy or stability – I honor that. Truly. But if you’re chasing the thing that keeps you up at night, welcome to the arena. There’s no map here. But there is a pulse. If you follow it, it will show you exactly who you are.