I went from VP of Technology Integration for Derivatives at JPMorgan Chase to opening a $200 bottle of champagne for the first time in my life while a table watched me with the energy of people who knew exactly how much it cost if I dropped it.
I did not drop it. But my hands were shaking.
That was week one of my new life. Here’s everything that came after.
Job 1: Snowboard Instructor, Vail
This is the job I actually moved to Vail for. I’d applied online, gotten hired, and driven a packed Jeep across the country for $12 an hour and a ski pass. That was the deal and I took it without blinking.
I was also, to put it plainly, a bad snowboarder. Everyone else in training had been living in Vail for years, doing tricks and carving perfect turns on black diamonds. I had ridden in the Northeast maybe once or twice a year and I was still working on clean S-turns. I also didn’t know that chairlifts are called by numbers — that when someone says “meet me at Chair 4” there are roughly twenty chairs to choose from and nobody’s going to help you find it.
What saved me was the corporate skill set. When training got to communicating with parents and managing groups, I was suddenly the best in the room. They put me with the Little Rippers — five and six year olds on the magic carpet. Most instructors hated that assignment. I loved it. The goal was simple: get them standing, get them gliding, make sure they want to come back. I was good at that part.
The pay math only works if you’re getting privates, and privates go to the people with seniority. Two good bar shifts would have covered the cost of the pass with none of the stress. My coworkers pointed this out immediately and laughed kindly. I did it for two years anyway — and had anxiety going in more mornings than I didn’t, which eventually told me everything I needed to know.
What it taught me: Passion isn’t optional for the hard parts of a job. Skill you can build. Confidence you can fake for a while. But if you don’t love the thing at the center of the work, the hard days will eventually outweigh the good ones.
Job 2: High-End Restaurant Server, Vail
My last serving experience before this was a sports bar in college. Wings, beer, maybe a well cocktail if someone was feeling fancy. This restaurant was the opposite — a chef who had traveled the world, an Asian-inflected menu with short rib that people flew to Vail to eat, wine lists starting at $80 a bottle.
I was 32 or 33. My coworkers had been doing this for years. Some hadn’t gone to college. Some were stoners. All of them were better at this job than me, and I had to tuck my VP title in my back pocket and accept that.
High-end serving has a whole language. Seat numbers — every chair at every table has a number so food runners can drop dishes in front of the exact person who ordered without asking. Firing times — appetizers go in first, you watch them hit the table, then you fire the entrees so everything flows. Drinks go in immediately because your bar gets backed up. Water glasses stay full. Sauces are on the table before the food arrives. It’s ten thousand things happening in your head simultaneously and if you let one slip the whole table feels it.
I had a bad lunch shift early on. The head chef was working, I was the only server, we got slammed, I ran my own food, I made a lot of mistakes. When the night shift came in I was defeated. The sous chef came out and said — joking but not joking — “someone pissed off the chef today.”
That hit my core. I’m a people pleaser. My first reaction was defensive — I worked my ass off, I got set up for failure, screw all of you. But I took a breath. Looked over and saw the chef having a beer at the bar. Walked over.
“I’m really sorry. I messed up today. I know what I did wrong and it won’t happen again.”
He looked at me for a second — he was still pissed when he sat down — and then just said “okay, we’re cool.”
That was it. I don’t think he expected it. After that we were always on good terms.
What it taught me: Ego is the first thing you have to leave at the door. It doesn’t matter what your title was. Own your mistakes fast and without excuse and nine times out of ten you get to the other side. Also — respect the chef. It’s their name on the plate.
Job 3: Pizza Bar Bartender, Vail
This is the job that made me a bartender. Popular après-ski spot, slammed from 3pm on, service bar and walk-up customers hitting you simultaneously. I learned what it means to be weeded behind a bar — and that the regular martini is not actually complicated, But the infamous Espresso Martinis when ordered by 3 different tables and require 5 ingredients can 100% weed you!
What it taught me: Volume. Speed. How to organize chaos and not drop the ball on orders even when everything is happening at once.
Job 4: Sushi Restaurant Server, Vail
Higher-end, slower pace, older clientele, excellent tips. I learned ingredient knowledge the hard way — you cannot work at a sushi restaurant and not know your menu cold, especially when a seafood allergy walks in, which happens constantly in a way that will baffle you every single time. The restaurant ran a tip pool, which was new for me. You actually wanted your coworkers to do well because you were all in it together.
What it taught me: Know your product. And sometimes the team model works better than every person for themselves.
Job 5: Hotel Gym Attendant, Westin Vail
I thought this would be easy. Free gym membership, early morning shifts, calm environment. I was wrong.
I had to be there by 5:15am to open. In a cold Colorado winter. That alone nearly broke me.
But the real education was in dealing with people who genuinely cannot handle inconvenience. I had a woman ask if we could raise the heated outdoor pool two degrees. The problem: we had elite swimmers doing early morning training who specifically needed the temperature where it was. Two degrees would compromise their workout. This became a whole situation.
There were conflicts between hotel guests and monthly members over lane usage. Pilates classes that were full. Yoga studios that wouldn’t connect to the stereo. People who couldn’t find a clean mat. Complaints I could not have invented.
I am a gym addict. I work out constantly. I never once went back to that gym on my days off because the last thing I wanted was to be there voluntarily.
What it taught me: Resilience against entitlement. Some people genuinely believe the world should configure itself to their preferences at all times. Working in hospitality long enough either breaks you or gives you an almost zen-like ability to smile through the absurd. I’m somewhere in the middle. I still find it absurd. I’ve just gotten better at not showing it.
Job 6: Barbecue Joint Bartender, Minturn
One owner, local guy originally from Maryland, owned the actual building which in Vail is almost unheard of. Small menu. Maybe eight tables. And when you were on shift, you were everything — bartender, server, food runner, closer.
If things went wrong it was on you. No one else to blame, no one else to credit. The owner trusted me completely — he had cameras for closing safety but otherwise just let me run it. I loved that.
I also learned to tip out the kitchen. When you’re solo and things get crazy the kitchen is your only lifeline. If you take care of them, they take care of you on the next shift. That’s not just generosity — that’s strategy.
What it taught me: Self-management. When no one is watching and no one is there to bail you out, you figure out your own systems fast. I learned how I actually work best when I’m in control of the setup.
Job 7: Horse Tour Guide, Vail
I need to give you the backstory on this one.
I grew up middle class, fell in love with horses on a family vacation to Chincoteague Island, talked my parents into riding lessons, eventually bought a retired racehorse off the track. He was on the track from age five, lived in a field for two years, and I bought him at seven. He lived to 31. I had him for most of my adult life and I don’t regret a dollar I spent on him — but if you want one piece of financial advice: don’t buy a horse. It is a non-returning investment that eats money like a car payment that never ends.
That said, when I saw a job posting for horse tour guiding in the Vail mountains I knew I had a shot. English riding background, not Western, but horses are horses and she hired me.
I want to tell you about the tours because they were genuinely one of the most beautiful things I’ve ever done. You ride through hundreds of aspen trees — in fall when the leaves are turning it looks like a fairy tale. You come out to a lookout with Vail mountain directly in front of you. On the longer tour you climb to a higher peak where the views make you catch your breath. I was on horseback in the Rocky Mountains every day getting paid for it.
I also want to tell you about the stress.
You are responsible for human lives on top of animals you cannot verbally communicate with. Most tourists are scared and follow instructions. There is always one person who thinks kicking the horse is a good idea. The horses were bombproof — mostly — but they had days, and on a windy day when the trees are creaking you are watching every ear flick and every shift in weight and you are doing the math in your head constantly.
I had a woman fall off on a particularly windy day. Horse spooked, she lost her balance, she went down. She wasn’t seriously hurt. The protocol is to get them back on immediately — not because you’re being callous but because these people aren’t hikers and the fastest way to safety is back in the saddle. Then you write an incident report. Just in case.
The tours ran almost every hour. By September I had given my spiel about the aspen trees approximately ten thousand times and I could feel something loosening in my brain. The repetition of tour guiding is a specific kind of exhaustion that I wasn’t prepared for.
What it taught me: That the most beautiful job and the most stressful job can be the same job. That repetition is its own form of burnout. That when people’s safety is in your hands on top of an animal’s unpredictability, you earn every dollar. I did it for two years and I’m glad I’ll never do it again.
Job 8: Ranch Banquet Bartender, Wolcott
About thirty minutes outside Vail there’s a ranch called Four Eagle. It’s a non-profit — the money goes toward veterans’ programs and getting people back on their feet — and it sits on a massive property with a banquet hall, small cabins, zip lines, four-wheeling, horse guides, and views that make you understand why people move to Colorado and never leave.
They hosted weddings, corporate retreats, employee parties, and weekly events — country line dancing nights, Thursday happy hours, live music. A rotating calendar of things people needed bartenders for. The way it worked: the manager sent out a spreadsheet, you signed up for the shifts that fit your schedule. You wanted Thursday off? Don’t sign up for Thursday. You had a slow week at the restaurant? Pick up a Friday wedding. It was the most flexible gig I’ve ever had.
The bartending itself was makeshift in the best possible way. No soda gun. No dump sink. You’re working with ice coolers, soda cans, and buckets — ad hoc everything. Someone orders an Old Fashioned and you’re looking at your setup thinking okay, I have the ingredients, just not the ideal version of this. No shaker because you have nowhere to rinse it, so you’re improvising with two cups when someone wants something shaken. Gin and tonics? Easy. Tito sodas? Done. Martinis? We’re doing our best.
You’d be amazed how many people still try to order an espresso martini at an outdoor ranch wedding with no electricity running to your bar cart. I learned to work with what I had and give people as close to what they wanted as the situation allowed. Weddings especially — people want fancier things and you’re playing bartender MacGyver in a flannel shirt and a cowboy hat, which honestly is its own kind of fun.
The tips were unpredictable — some events tipped out as a team, some were tip-optional depending on who booked — but the hourly was higher than a standard bar shift to make up for it, somewhere around $20. You were done before 11pm every night. The management was excellent. And the setting was genuinely beautiful — aspen trees, mountain views, the kind of place where you look up between orders and remember why you moved here.
The other thing nobody mentions about banquet work: shoulder season is wedding season. When the ski bars slow down in spring, the ranch is fully booked. When October hits and the mountain’s not quite open, someone’s getting married with fall foliage behind them and they need someone to pour champagne. The two seasons almost perfectly offset each other, which means banquet work is one of the few gigs that actually fills the gap when your main job goes quiet.
What it taught me: Flexibility is a skill. Knowing how to work with limited equipment and still give people a good experience — that’s not a lesser version of bartending. It’s a different version. And pick-up work that fits around your main schedule isn’t a side hustle in the hustle-culture sense. It’s just good time management. The spreadsheet sign-up model is something I wish every job had.
Also — you get to bartend in a cowboy hat. Some jobs have a uniform. Some jobs have a vibe. This one had both.
Job 8: Golf Course, Vail
Three shifts — clubhouse bartender, hole 11 grill, and cart girl. The cart girl shift is designed for a 22-year-old who enjoys playful banter with older men who’ve been drinking since the third hole. I am not that person. My favorite shift was Sunday night men’s league — local guys, industry people, the best tippers in a town full of billionaires. Bartenders tip bartenders. I gave them a heavy pour and they kept me well and everyone had a good time. Best part you cannot golf at night so I was home by 9pm most nights.
What it taught me: Know your crowd. The locals will always take care of you better than the tourists if you take care of them first.
Job 9: Marina Bar Bartender, New Jersey
The ski bar and the marina bar are the same job the way New Jersey and Colorado are the same place — technically both in America, genuinely different worlds.
I work at two restaurants now, both owned by the same people, both marina bars, both on the water. One is smaller and more intimate, one is high volume with a full service bar that runs constantly. The setups differ, the pace differs, but the vibe is consistent: boats pulling in, sun on the water, people in a genuinely good mood because they chose to be somewhere beautiful today.
The ski bar is darker — literally. You’re inside warming up, coming in off the mountain at 3pm with your edges still cold, and the culture is apre-ski which means shots happen immediately and often. It’s vacation drinking with mountain energy: aggressive, celebratory, fast. I poured more shots in a single Vail shift than I pour in a full season here.
The marina bar is Jimmy Buffett energy. People sip. They eat. Families come in. The bar closes by 10, food stops at 9, I’m out by 11. I haven’t dealt with a late-night crowd since I left Colorado and I don’t miss it. The busyness isn’t about shots and chaos — it’s about the service bar volume running alongside a full dinner rush, both happening at the same time, both needing your attention simultaneously. That’s the skill this job has sharpened: managing multiple streams of demand at once without letting either one feel neglected.
I also get to meet the boat world every shift, which for someone living on a boat is just endlessly good. Boaters tip their bartenders. They know what it’s like to have people depending on you. They’re usually in the best mood of their week. It’s a crowd that matches my life right now in a way that still feels a little lucky every time I show up.
What it taught me: The same title means different things in different contexts. Bartending in a ski town and bartending at a marina bar require completely different emotional registers. One is high-intensity crisis management. The other is high-volume hospitality. Both are hard. Both are worth knowing. I’m a better bartender for having done both.
Job 10: Surf Shop, New Jersey
One day a week. Checking people out, answering questions, handling whatever the shop needs. On paper it’s a retail job and I won’t pretend otherwise.
What it actually is: an education in an industry I love from people who know it completely. I came in knowing almost nothing about equipment — boards, fins, leashes, stingers, float factors, how a board’s shape changes what it does in the water. At the surf shop if they need me to do something I do it, and they explain why, and I’ve accumulated more working knowledge of surfboards in one season here than I would have picked up in years of just renting and paddling out.
The owners have been genuinely good to me. They let me work around my bar schedule, they’ve included me when it mattered, and at the end of last season they discounted three boards that are currently in Mexico with me. Sometimes a job isn’t about the hourly rate. Sometimes a job is about who you’re around and what they’re willing to teach you.
I can now put fins in, rig a leash, identify what board fits what kind of surfer, and have an actual conversation with someone buying their first shortboard instead of just pointing at the wall. That’s worth more to me than the paycheck and I knew it going in.
What it taught me: There’s no such thing as a job below you if it puts you closer to something you love. I spent ten years in a title-first culture where what you did and what you were called were the same thing. Checking people out at a surf shop while learning everything I can about an industry I care about is not a step backward. It’s exactly the kind of thing I left corporate to be able to do.
The Side Hustles
In between all of this I picked up woodworking. Vail has a constant churn of wealthy people redecorating and leaving perfectly good furniture on the curb. I started collecting it, bought a sander, started building. Colorado flags made from pallet wood were my best sellers — $60 to $80 each. I turned a coffee table into a Colorado flag piece I was genuinely proud of. Probably not profitable once you count the tools. Genuinely fun.
I helped a friend who owned a water detection system business — changing batteries, learning how to strip wires, making sure sensors were active. Three to five hours, good hourly pay, weirdly interesting. You learn something about electrical systems you didn’t know you’d ever need and then it turns out it helps you with your boat wiring three years later. Some skills don’t show their value until they do.
What All of It Actually Taught Me
There’s a quote I love: a jack of all trades, a master of none — but better than a master of one. Everyone cuts it off before the last part. The last part is the whole point.
I am not a master of anything I’ve listed here. But if you need help I have baseline knowledge in more areas than I can count. I’m currently building a surfboard rack out of PVC pipe because I’ve worked with hose clamps and wire strippers and weird materials enough that it doesn’t intimidate me. My boat has more wiring than you’d think and I’m not afraid of it because I once spent three hours changing batteries in a water detection system and learned how to strip a wire.
If I had stayed at JPMorgan I would know how to make derivatives flow through an Excel model. I would be very good at it. I would also know nothing else.
I don’t know if knowing what a derivative is has ever helped me since I left. But knowing how to open a $200 bottle of champagne without panicking, apologize to a chef and meaning it, guide twelve people on horseback through aspen trees, and manage a full bar by myself on a Saturday night? That’s helped me every single day.
