I spent three seasons in Vail. The first one was magic. The third one I skied maybe ten days.
That’s a quick the view and telling of why I left Vail a beautiful mountain town for the surf and beaches in Mexico. Here’s the full story.
What the First Season Felt Like
When I arrived in November 2019 I was a blank slate. New town, new job, new version of myself I was still figuring out. I’d come off a decade in corporate finance and I was bartending at a pizza place making drinks for people who’d just come off the mountain, and it was the most alive I’d felt in years.
The après-ski culture in Vail is its own thing. There are decks on the back of the mountain where people drag their skis and open beers and hang out until ski patrol kicks everyone off around 4:30. Then you ski down to town and you’re at the bar. I was working those bars. I was staying out late. I was doing the whole thing and loving it. The mountain was magic. The community was magic. The land of misfit toys — ex ski pros, people who’d lived in Costa Rica, college dropouts, kids who were supposed to follow the conventional path and instead became the best bartenders in Colorado — those were my people.
I found a relationship there. I found a rhythm. I found myself, honestly, in the way you only can when you’ve blown up your old life and are building something new from scratch.
What the Third Season Felt Like
COVID changed Vail. The shoulder seasons — those gentle months of May and early fall when you could breathe, when the town belonged to locals, when you could actually take time off — compressed into nothing. What used to be a month of recovery became two weeks, then less. Vail became a year-round destination and the workforce paid the price.
The clientele shifted too. Remote work brought people with high corporate salaries who could live anywhere and chose Vail, which drove up rents and drove out locals. The guest energy changed. I’m going to be honest about something that took me a while to admit: watching wealthy people be miserable got to me after a while. People with everything — the ski house, the gear, the vacation — treating servers like servants, taking bad days out on staff, demanding and entitled in ways that made the work feel demeaning. You are a server. You are not a servant. There’s a difference and in that third season I felt it constantly.
There’s also a darkness to ski towns that the Instagram photos don’t show. The party culture is real and it’s fun until it isn’t. The drinking, the late nights, the accessible drugs, the Peter Pan syndrome of people who’ve been there fifteen years and are still chasing the same night they had at twenty-five. I’m a healthy person. I work out. I care about my body. By the third year the appeal of ripping shots with friends and skiing hungover had completely worn off. I’d go up on the mountain alone sometimes and try to find the magic and it just wasn’t there the way it had been.
I got on the mountain maybe ten or twelve days that last winter. For someone living in Vail, that’s a sign.
I was working three jobs — the gym, the sushi restaurant, the bar — and exhausted in a way that sleep wasn’t fixing. The gym job was draining me with entitled guests who complained about pool temperatures and full yoga classes. The bar shifts I used to love felt like something to endure. I remember going into Saturday shifts dreading seeing the same faces, dealing with the same drunk energy, smiling through interactions that were costing me something.
And underneath all of it was a quieter realization: I wasn’t moving forward. I’d come to Vail telling myself I was going to figure out my own thing, start something, build something. Three years later I was bartending and picking up odd jobs — which I loved, genuinely — but there was no self-improvement happening, no path forward, no version of a future I could see clearly. The cheapest studio in town was $1,500 a month minimum. I was never going to build anything real there. I was going to stay comfortable and stagnant and that is the one thing I cannot survive.
Complacency is what drove me out of corporate. I wasn’t going to let it trap me in Vail too.
The Relationship Ending
I’d been in a relationship for about three years. He was great — as active as me, matched my energy, the kind of person who wanted to do a ten mile hike and not think twice about it. But from early on he’d talked about wanting to travel Asia and COVID had kept that dream on hold. When the world opened back up he booked his ticket.
I don’t have resentment about it. You should follow your dreams. He followed his.
But it left me alone in a town full of our shared memories at exactly the moment I was already burning out. I could have stayed. Vail is the town of boomerangs — you can leave and come back and everyone welcomes you like you never went anywhere. But staying felt like choosing stagnation twice. I needed to go somewhere new and figure out what came next.
How Mexico Happened
I’d been thinking about surfing. I’d done a trip to Portugal, learned a little, caught something. I looked at Ecuador, at Central America, at various surf towns. I talked about it out loud the way bartenders do — to everyone, all the time — and my boss at the barbecue joint heard me.
He’d owned a house in Sayulita, Mexico. Had friends with businesses there, knew the town well. He sat me down and was pretty direct: you don’t speak Spanish and you’re not ready to dive into something that extreme. He suggested Sayulita as a middle ground — English spoken, beautiful surf, enough infrastructure for someone landing alone, and connections he could offer to help me get settled.
I’d actually been to Sayulita once before, with a group of Vail people. It’s a popular trip in that crowd. And I remembered thinking it was fine — a party town, fun, did one beginner surf session and got scared when I fell, barely noticed the waves. I laughed about that later. When you visit somewhere as a tourist on a party trip you see a completely different place than the one you live in.
I said yes. Found an apartment, six month lease, somewhere around $600-700 a month. Sold the Jeep. Packed three massive bags — way too much stuff, I know better now — and booked a flight for early November.
My family was not thrilled. East Coast families have a very specific mental map of Mexico: Cancun for an all-inclusive, maybe Cabo, and then cartel news. The idea of their daughter moving there alone was not an easy sell. But I’d done enough independent things by then that it was my life and they knew it.
The First Two Weeks
I landed and the apartment wasn’t ready. I walked around town for two hours with my three massive bags waiting for them to clean it, completely alone in a place I barely knew, thinking some version of what have I done.
When I finally got in I made it feel like home as fast as I could. And then I basically didn’t leave for two weeks.
I watched a lot of TV. I ordered food and cooked quietly and let myself be still. And I want to be honest about what that stillness was, because I think people expect the big adventure story to start immediately — she landed in Mexico and hit the waves and never looked back. That’s not what happened.
I had just ended a three year relationship. I had just left a town that held three years of memories. I had just walked away from the version of myself I’d built in Colorado. My body was exhausted from three years of grinding and my brain needed to stop. The two weeks of doing nothing weren’t a failure of nerve. They were a requirement.
I remember googling “is it okay to be happy by yourself.” I’m laughing writing that but I also think it’s important to say out loud. When you’ve spent years sleeping next to someone and then you move to a foreign country alone, the aloneness is loud at first. It turns out I was fine. Better than fine. For the first time in my adult life — maybe my whole life — I had no one to please. No coworkers to perform for, no relationship to tend to, no social calendar to maintain. Just me and whatever I actually wanted to do that day.
It turned out I wanted to do a lot.
Learning to Surf
After two weeks I kicked myself out the door and signed up for three surf lessons at a beach nearby. My instructor is still one of my closest friends here — the kind of calm, meditation-grounded person the universe puts in your path at exactly the right moment. He taught me how to actually surf and then told me what every surf instructor eventually tells you: now you just have to sit in the lineup and figure it out yourself.
So I did. I fell constantly. I was a kook. I paddled into waves wrong and got worked and came up sputtering and went back out. I rode a longboard that was forgiving of my mistakes. And then one day the timing clicked — the paddle, the pop-up, the feeling of the board catching the water — and I understood what all of it was about.
There is no high like catching a wave. I don’t know how to explain it to someone who hasn’t done it except to say it uses your whole body and your whole brain simultaneously and when it works there’s a half second of pure presence where nothing else exists. I was hooked completely.
What Mexico Actually Did For Me
I’m a people pleaser. I’ve said it before. I spent my corporate years performing, my city years maintaining ten friend groups and being the life of the party, my Vail years smiling through difficult customers and being endlessly available. I had never in my adult life had a sustained period where my agenda was entirely my own.
Mexico gave me that.
When I’m here I’m selfish in the best sense. If I want to surf I surf. If I want to sit on the beach for four hours I do that. If I want to cook a weird dinner and watch something on my laptop and talk to no one I do that too. I’m not performing for anyone. I’m not managing anyone’s experience of me. I’m just myself, quietly, in a place that has come to feel like a reset button.
I also learned something about myself here that I hadn’t fully understood before: the ocean is where I heal. The mountains are beautiful — I still love Vail, still visit, still have friends there who are my people — but there’s a loneliness to mountains that got to me by the end. The altitude, the insulation, the party culture that never sleeps. The ocean moves. It’s never the same twice. It matches something in me that the mountains eventually stopped matching.
I spend my summers in New Jersey working hard — six days a week, two restaurants and a surf shop, building the financial foundation for the rest of the year. Then I come here. I surf every morning. I cook. I work on the blog, on business ideas, on whatever creative project has been waiting. My brain comes alive in a different way than it does when I’m constantly on, constantly talking to people, constantly giving my energy away.
Then I go back refreshed and actually excited to bartend again instead of dreading it. That cycle — grind, reset, grind, reset — is the rhythm I’ve built and it works.
Where This Goes
I have no idea.
I say that without anxiety, which is new for me. Vail was supposed to be a chapter and became three years. Mexico was supposed to be an experiment and became an annual anchor. New Jersey was supposed to be one summer and is now my third season back.
I don’t know if Mexico is forever or if something else comes next. I don’t know if I’ll always do summers in Jersey or if the boat chapter leads somewhere unexpected. I don’t know if I’ll open a business next year or in five years or what form it takes.
What I do know is that I can always go back to Vail and it will welcome me with open arms. That’s what I love about that place — judgment free, no questions asked, understanding that it might be a stopover or a transition but never anything less than a warm welcome. Some places are just like that. Vail is one of them.
I left corporate because complacency was killing me quietly. I left Vail because it was happening again. And I got on a plane to a country where I knew nobody and didn’t speak the language and found out that the thing I’d been running toward my whole life was something I had to get very quiet and very alone to finally hear.
The ocean helped. It still does.
