What Actually Made Me Stop Caring What People Think
Every article says to go travel alone and come back free. I did that, came home, and signed a lease on a store. What actually worked was failing in public and finding out nothing happened.
Every article about this says the same thing. Go travel alone. Get lost somewhere far away. Come back free.
I did that. It didn’t work.
I flew to Costa Rica, spent four months living out of a backpack, felt more like myself than I had in years, came home, and immediately signed a commercial lease on a retail store because that’s what a responsible adult in his late twenties was supposed to be doing.
So no, the trip didn’t cure me. Something else did, and it was a lot less fun.
2020 is where it starts
I was on unemployment like millions of other people. Stuck at home, no plan, no particular idea what came next.
What I actually got out of that year wasn’t clarity. It was space. It was the first time in my adult life I wasn’t running on autopilot, and when the noise stops you start hearing questions you’ve been outrunning.
Whose life is this. Why does so much of it feel like a performance.
There was no big moment. I didn’t wake up one day a changed man. I just slowly got less interested in keeping up the act.
What caring had already cost me
Approval is expensive and it doesn’t send you a bill.
I’d wanted to travel for years. Not vacation. The long, unglamorous kind. And I kept not doing it, and I always had a reason, and none of the reasons were the real one.
The real one was this: what would people think if I just left. What if they decided I was irresponsible. What if I failed and came crawling back.
So I stayed. I made plans, and then I made more plans. None of it was actually going anywhere. I was just doing a pretty convincing impression of a guy doing the right thing.
The trip was not the fix
I did eventually go. In 2021 my lease was ending and I’d just finished my degree and I had a free place to stay in San José, so I went, which is a much less heroic origin than the one I used to tell.
Those four months were the best thing that had happened to me in a decade.
And then I came home and opened a store, took on inventory and rent and fixed costs, and built a life I couldn’t leave.
That’s the part that matters. If travel really rewired me, the rewiring should have shown up in the very next decision I made. It didn’t. I went straight back to doing what looked correct from the outside.
Travel showed me something. It didn’t yet cost me anything to ignore it.
What actually did it
The store failed in six months.
A few weeks later I filed for bankruptcy. Less money than I’d started with, more debt, and nothing to show for a year of my life except a lease I couldn’t afford and an inventory I couldn’t move.
What if I fail and come crawling back. Remember that one?
That was it. The exact scenario. The thing I’d spent years arranging my life to avoid, and it happened, and it was on paper. Bankruptcy filings are public record, which is a fun thing to find out in your late twenties. There was no keeping it private.
And then a strange thing happened, which is nothing.
The world did not respond. Nobody convened. Whatever judgment existed, I never had to sit in it, because everyone was busy with their own lives. A week later I was still a person. Same guy, smaller bank balance, and most of what was left of the process turned out to be waiting for mail. That was the big reckoning I’d been dreading for years.
Then I put everything I owned in a Nissan Altima and drove west, and slept in that car for the better part of a year while people I’d gone to school with were buying houses.
That’s what finished the job. Not the travel. Failing in public, and finding out the punishment I’d been dodging my whole adult life mostly lived in my head.
You cannot reason yourself out of caring what people think. I tried for years. It goes away when the thing you were afraid of actually happens and you’re still standing.
Free guide · Work a Season
That year ran on seasonal jobs with housing included.
How I landed the Yellowstone and Alta jobs with housing included, written down step by step.
I still care
Of course I do. Anybody who tells you they’ve fully stopped is either lying or not paying attention.
The difference is that I notice it now. I catch it before it takes the wheel. That old version of me still shows up, the quiet one who wants everyone comfortable and nobody upset, and he still has opinions about what I’m doing. He just doesn’t get a vote anymore.
I feel the discomfort. I don’t obey it. Most days, anyway.
The current test
I’m 32. In February I’m leaving the United States on a one-way ticket with a $12,000 budget for the year.
I’m at the age where people around me are buying houses and having kids and getting the promotion, and I’m going to go live in Albania and see how cheaply I can do it. Some of the people in my life think this is a great idea. Some of them clearly think it’s a phase I should have grown out of.
The old version of me would have shaped the plan around that second group. Softened it. Given it a respectable justification. Called it a sabbatical.
Instead I’m publishing the whole thing, including the money, in public, in advance, where anyone can watch me miss the number.
I wouldn’t call that confidence. I’ve just already had the embarrassing outcome once, and it turned out to be pretty survivable.
What I’d actually tell you
Not “go travel alone.” Most people can’t, and it didn’t work for me anyway.
Here’s the real version: the thing you’re afraid people will think about you has almost certainly already happened to someone you respect, and they’re fine. The fear usually isn’t the outcome. It’s being seen having the outcome. And look, people might judge you. Some of mine probably did. It just cost me a whole lot less than I’d spent years assuming it would.
Deciding to stop caring never worked for me. Doing the scary thing, living through whatever came after, and noticing I was still fine did.
Start small if you need to. But start with something that could actually cost you a little face, because the ones that can’t don’t teach you anything.
I leave on February 21, 2027, and I’m publishing every dollar of it. Drop your email below if you want to watch me test this in public. The day-to-day goes on Instagram.
Thanks for reading
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I’m Dylan. One honest email a month: what it cost, what worked, and the places worth your time. You also get my free field guide, First 24 Hours in a New Country.
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