Unreasonable.

Why choices that look wrong build lives that feel right.

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This essay was originally published here.

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The best financial decision of my life was taking a job that paid $18,000 less than the one I already had.

I was 28. My mom had emailed me the Craigslist ad. A door-to-door sales gig in New York City, for a company nobody had heard of, in a city I couldn’t begin to afford, and I was already drowning in credit card debt.

Every reasonable person in my life told me to pass. I’m glad I didn’t listen to one of them.

Over the last twenty years of my life, my seemingly unreasonable choices have been responsible for almost everything good that’s happened to me.

This is something I think about a lot. How the choices that yielded the most positive results were never the ones that made sense on paper.

And maybe you’re thinking that taking risks and “having courage” are, of course, the choices that lead to the good stuff. But I don’t think it’s really about that. I think it has to do with how choices compound over time and what happens when you make too many reasonable choices in a row.

Think about it. The status quo looks a little something like this:

Go to a good school and get good grades, take the reasonable job, say yes to the city the job wants you to move to, meet the guy or gal, date and get married, take the promotion, move again, have the kids, send them to good schools, take the next promotion, buy the house, and mow the yard.

On it goes.

And the fact is, every one of those choices is reasonable. Nobody could blame you for saying yes to the stuff that makes sense.

But there’s a catch. Because every time you make a reasonable choice, it makes the next decision a little easier to make too, without thinking.

It doesn’t matter if you’re facing a decision about the industry you’re in, the promotion you’re offered, or the titles you acquire along the way. Each next choice comes with a little less friction, every time. Another promotion? It’s more money. Sure. Move closer to the office? Will make life more efficient. Yeah, I don’t love the industry, but this offer from a competitor is pretty compelling. I should look at it.

The aggregate total of all these reasonable choices creates a long chain. Each choice you make is one link, and each link makes the next choice a bit more automatic.

Then somewhere around year 10 or 15 or 20, there’s so much momentum that breaking the chain feels downright irresponsible. Reckless even. So most people will never break the chain, and they just keep trucking along. What’s the worst thing that could happen?

But one day you wake up 40 years later and realize you built your entire life this way, on autopilot, one reasonable choice at a time. And a lot of people who wake up there don’t like the life they find themselves in.

The chain you linked together isn’t actually the problem, though. My old college roommate, Dave, has been at the same medical company in the same city he grew up in for the last 23 years. He’s married, has the kids, and from everything I hear, he’s happy as a clam. Last time I asked a buddy how Dave was doing, I heard, “He’s exactly the same as he was 20 years ago.” And that wasn’t an insult. Because the chain Dave built and the life Dave wants point in the same direction. I admire that.

But for a lot of people, the chain is building in the opposite direction of the life they really want. But they can’t see it happening because each link they added was so small and so logical that they never stopped to question the direction the chain was going.

This happened to me early in my career. When I graduated from college, I got into pharmaceutical sales because that’s what my Dad had done my whole life. I had a nice, American, middle-class childhood, and I figured that’s what I’d build for my family someday.

But unlike my Dad, I wasn’t good at the job and got fired pretty fast. And with one pharma job on my resume, I felt like my choices started to narrow. So I applied for another pharma job and met the same demise a few years later. So I started applying again. Same industry, another terrible small town, same logic behind the choice. Three jobs, three nowhere towns, and three firings later, I was the biggest loser in my friend group.

That Craigslist ad my mom sent me was for a startup called ZocDoc, and I had absolutely no business taking that job. I was already crushed by credit card debt, had a résumé full of firings, and I had a second offer sitting right in front of me that was, by far, a more reasonable choice. It was a sales job at a big medical device company back home in Cleveland that paid more than I was making. The reasonable choice was obvious. Take the Cleveland job, live near (or with) my family, pay down my debt, and turn my career around. If I’d polled all my friends and former colleagues at the time, nobody would have voted for New York.

But I said yes to New York.

I moved into my friend Mara’s apartment in Bushwick, Brooklyn. She had four other roommates, and I slept on a futon in the living room, next to a rolling rack that held my entire wardrobe.

I woke up for my first day in a city I couldn’t afford.

Within a few months of living in NYC, I was selling more ZocDoc subscriptions than anyone on the team, and I was good at something for the first time in my career.

The company was growing fast, and we finally needed an office manager. Our CEO recruited a no-nonsense cocktail waitress he’d met in Chicago, talking her into moving to New York to work for a company she’d also never heard of. That waitress’s choice was just as unreasonable as mine. She’d just rented a new apartment in Chicago, painted the walls with her boyfriend of five years, and settled in for good. Then she left all of it to move to Brooklyn.

Her name was Jennifer Kelly, and we’ve been married for 12 years.

I replay that in my mind often. The Cleveland job was the reasonable and safe choice. But I can trace every good thing back to my unreasonable decision to take a chance on New York.

In 2014, I made another unreasonable decision. Six months after getting promoted to work directly for the CEO, I decided to quit. ZocDoc had become one of New York’s first “unicorns,” and I walked away to take a VP of Sales job at a company with no funding and one salesperson. My friends (and especially my buddies at ZocDoc) thought I’d lost my mind. We were on a rocket ship, after all. Why leave a sure thing to manage one sales guy at a startup nobody believed in enough to even fund?

But off I went, and I built a sales team to 150+ people doing $70 million in revenue. And eventually, a unicorn valuation of its own. Then I quit that too. Why?

To build an online business by myself. I didn’t have a team, a title, or a salary. And it was the scariest and most unreasonable thing I ever did. I’m not sure I ever thought it would work. But I went on to build an eight-figure business over seven years, and that’s where I am today.

Every one of those moves scared my friends and family at the time. But they all worked out better than the reasonable alternatives would have.

If you’re reading this and you’ve heard stories like this before, I know how this comes off.

“Guy takes risks, things work out, and now he tells others to be bold.”

I know that luck is a much bigger part of my story than I’ll ever fully grasp. But I’ve only got a sample size of this one life. And I’m not claiming that breaking your chain will work out the same way mine did.

But I do think it’s important to view the risks of unreasonable AND reasonable choices.

People usually focus on the risks of the unreasonable choice and stop there.

What if I fail?
What if this choice doesn’t work out?
What if everyone thinks I’m crazy for trying?

Those are valid concerns.

But nobody talks about the risks of sticking to the reasonable choices, compounded over decades. And I think those risks are bigger. It’s just slower and harder to feel the consequences. Because the unreasonable choices get loud, scary warnings, while the reasonable ones get decades of encouragement and approval. Every link is defensible, and everyone around you nods along and claps the whole way down.

That’s why you can’t see it happening. Because nothing ever feels like the wrong choice. You follow the chain for decades, one reasonable link at a time, and you end up deep inside a life you never really chose. Nobody warns you about it because, from the outside, everything looks great. Thumbs up.

When I realized this, I stopped asking questions the status quo wanted me to ask. Is this safe? Does the money make sense? Will people approve? Sure, those questions keep you employed, housed, and respectable. And there’s a time and a place for asking them. But they’re also the questions that build the chain over time.

So instead, I started asking a different question:

Does this life feel like mine?

And once I started asking that, I couldn’t stop. Every few years, the chain started to get predictable and easy again. Reasonable choices began stacking up, the momentum building, and my autopilot would kick in. So, I’d make the conscious choice to break the chain. Quit my job, change the business, or move somewhere else. A slight pivot here, a new business model there, pack up and move to the mountains of Upstate New York. And each time, that worried voice in my head (and my friends and family) showed up to tell me I could be making a huge mistake, or…being unreasonable. But they’ve been wrong every time so far.

The most unreasonable people I know aren’t always rich. Some run tiny businesses that venture capitalists would laugh at. Some of them just got sick of their corporate gigs and leaned into something more personal. And others just picked up their family and moved somewhere they felt most alive, and stopped feeling the need to explain their decisions. They’re not all successful by the common narrative.

But their lives are their own.

And I’d venture to guess that if you’re reading this, you know whether your life feels the way you want it to or not.

When it doesn’t, most people call it something else. Being “tired”, “overwhelmed,” and “too busy”, “going through a rough patch”, or the kind of thing “everybody” deals with.

You may have decided it’s ungrateful to even think that way. So you reach for the next link of the chain. The next promotion or the bigger house or the decision that makes total sense to everyone around you. And the chain gets one link longer and stronger.

I’m not here to tell you to blow up your life. That would be foolish. I don’t know your life. And maybe your chain and life point in the same direction, like my old college roommate, Dave. If so, that’s something to celebrate. Because most people can’t say that.

But if this essay touches a nerve, I’d encourage you not to explain it away. It’s not a weakness to question yourself. It’s just a small part of you that’s trying to figure out whether or not this life you’re living is actually yours. If it’s tracking in a direction you actually want to go.

Most people will never stop to even consider it.

Almost all of the risks you’ve been taught to fear are around unreasonable choices. Those risks are loud and obvious and pretty easy to talk yourself out of.

The risks you’ll rarely think about are the invisible ones. It’s the reasonable choice you’re about to make, without even thinking, because it’s sitting right in front of you. That choice is easy, obvious, and pre-approved by everyone.

And maybe, just maybe, very wrong.

Cheers,

Justin Welsh

P.S. This is an essay I’ve been working on for a few months and have been excited to share. I hope you enjoyed it. If you did, a Restack would be the kindest compliment you could pay. Have a great weekend.

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