Maybe it is about the money

Hey honeys and hustlers,

Today, I’m bringing you some words from Pete Cybriwsky, the writer behind the Re:Pete newsletter. I first came across Pete’s work on Substack notes as he was posting about Ahoy, his latest data art project that visualizes how far around the world you’ve traveled (currently only available on the App Store). Merging data, tech, and art is such a unique creative business, and I’ve been enjoying following his journey to building products. Today’s article is his perspective on building a creative business and leaving his full-time job, something many people ask me about, but even fewer actually follow through with. I hope you find it insightful.

You can find the original article here.

There’s a particular tone people use when they talk about quitting their jobs. Half dreaming, half disclaiming. Like they’re asking for permission to try something different. They’ll say they want more freedom. A chance to pursue a passion they’ve thought about forever. But almost always, they follow it with: “I just can’t give up the salary.” And maybe that’s fair.

Maybe it is about the money.

Not can’t, as in survival. Can’t, as in status and structure. The comfort of knowing exactly how your value is measured, what that value can buy, and how it’s supposed to grow over time. And I get it. Almost three years ago to the day, I left my well-paying, comfortable job. Since then, I’ve had this same conversation over coffee or lunch with at least 30 or 40 friends who wanna “take the leap”. Almost always, they don’t. And I can’t blame them at all. The part no one really talks about is what comes after you quit. Not the freedom. The low-status part.

Split the check?

Three years ago, I left my well-paying, comfortable consulting job to explore the idea of turning personal data into art.

And even with that, I’ve been privileged. Before I left, I told my parents I wanted to build a company that turned personal data into art. They, understandably, had no fucking clue what I was talking about. But they let me move back in to save some money. That gave me an in-between space where I could still live near New York City, see friends, and keep my life mostly intact.

I was (and am) extremely fortunate.

I had savings from my first job. I had family support. I had no major medical emergencies or caregiving responsibilities. I didn’t have chronic health issues or surprise hospital bills hanging over me. I had enough of a cushion to try, and nothing in this time that forced me to stop. But it’s hard socially, too. Especially in the prime of your 20s.

• Spending 15 of the last 36 months in your childhood bedroom

• Missing birthdays, concerts, ski trips

• Saying “no” to weeknight dinners with friends because they’re too expensive

• Watching everyone else post vacation photos while you’re heads-down in your apartment, wondering if this is a huge mistake

It all came with immense tradeoffs: tens of thousands in forgone salary, deferred goals, and a foggy sense of when (or if) things would stabilize. And, of course, a lot of questions from people all of the fucking time.

Why do we measure everything in dollars?

The one I still don’t have a clean answer to: Why is money always the metric, even when it’s not the goal?

Even among entrepreneurs, it’s often just a new scoreboard. The corporate title gets replaced by "$50K MRR" in their Twitter bio or a flashy seven-figure raise. Founders leave their jobs in search of freedom and end up prioritizing growth at all costs.

I’m not saying they’re wrong. I get why those metrics matter and why people post them. It’s proof that you’re building something real. That it’s working. It highlights the product to draw in more customers. There’s a tangible value in sharing these things. It also publicly validates the risk you took paid off, signaling success to your peers. But I keep wondering why that’s the metric we keep returning to obsessively, even when we often say we’re chasing something else entirely.

Learning to love low-status

This is where Cate Hall’s recent essay on low-status work comes to mind. She writes about learning to sing—how if you’re a bad singer, and you want to get better, the path forward is awkward, uncomfortable, loud, and, most regrettably, public.

You have to do the thing badly, in front of others, until you do it less badly.

And it’s not just that it’s embarrassing. It strips away the identity you’ve built around being a competent and high-achieving person. You lose the title, the salary, the trajectory. For a while, all that’s left is the work to be done.

You’re no longer who you were, and you’re not yet who you want to become.

Entrepreneurship, or any independent path, works the same way. We all imagine the version where it worked. This creative success story we conjure up in our minds. But most people want to skip the brutal part. The bad vocals. The stretch where life feels smaller, quieter, and you can’t tell if it’s progress or just a very expensive stall. But, as Cate eloquently points out, the payoff of low-status work makes life undeniably richer (in meaning and sometimes in actual dollars) than the theoretical world in which we did the thing.

Do we ever really make it?

A friend—someone I’d call a very successful non-tech entrepreneur—recently asked if I’d ever felt like I’d “made it”. I could tell the question came from a place of unease in their own work, the same unease I feel at times too. What followed was a great conversation and reflection. I said: yes, but no. (what a cop out answer by me) My original goal was to stop climbing a corporate ladder I didn’t want to be on. In that sense, I do feel successful.

I’ve:

• Created a ~10M user consumer app

• Made what might be the most viral data art piece ever (5M+ personalized versions — I think that’s gotta be a record?)

• Exhibited work, won awards

• Launched several apps

• Pioneered my own form of interactive data art

And, at the time of writing this, I actually feel closer than ever to realizing the dream and seeing it take off (!!!) But have I done everything I set out to do? Not even close. And some of these projects and freelance gigs have paid much better than others. None of which pay better than my old corporate job (…yet). There’s still so much I want to build. The difference now is that I feel qualified to build them. And I’m even recognized by peers in my field as someone who can. A lot of entrepreneurs we admire, who’ve gone on to build wildly successful companies, didn’t get it right the first time. Or even the second. Some built three or four companies that didn’t quite land before one finally did.

The early work is ugly, but it is essential to eventually succeed.

Ironically, since going out on my own, I’ve been offered roles I never would’ve been considered for—iOS development, full-stack engineering, and growth strategy. All jobs that would pay more than the one I left. Because I left. So in a way, the “risk” created more upside than I expected. Just not in the straight line you read about in a LinkedIn post or can concisely explain over a cup of coffee. Success is not some binary outcome. But still — when, if at all, is the decision ever universally validated? I definitely have people who care about me who openly wonder if it is time for me to hang it up 😅 (I am extremely appreciative of you)

Survivin’

These days, I make enough to live in New York City and keep going. I’m doing work I care about. It’s challenging. It’s a mixed bag of opportunities, none of which would exist if I had:

• Committed to building something I didn’t care about just for the money, or

• Stayed in my job until I could guarantee immediate upside upon departure

And still, I catch myself wondering every day:

• Should I be further along?

• Should I be building something bigger, faster, more obviously impressive?

• Should I be saving more in case of an emergency?

• Am I putting other goals at risk? Am I putting my relationships at risk?

It’s hard to tell whether those doubts are coming from me, from the dozens of conversations with others, or from some definition of success I thought I had left behind.

Maybe it is about the money

And yet, money is an important metric. It keeps you going. It sets the floor. It unlocks options. There’s a part of me that believes the cliché—that your 20s are for trying, failing, and exploring—is true. But there’s another part that wonders if stepping away from optimizing for money is seen as stepping away from adulthood altogether. I am happy. And I want to believe that if you’re happy and healthy, you’ve won. That the number doesn’t matter at some point. That the risk and the work are their own kind of reward. But I don’t know.

Maybe it is about the money.