Should You Quit Your Corporate Job?
I took a phone call in the JPMorgan Chase cafeteria and found out I’d been hired as a snowboard instructor at Vail for $12 an hour. Coming off a six-figure salary as a VP. And I was genuinely, embarrassingly ecstatic.
That moment probably tells you everything you need to know about where I was at.
My Background — Because Context Matters
I didn’t have some dramatic moment where I threw my laptop across the room and walked out. My story is quieter than that, and honestly I think that makes it more relatable.
I spent ten years in finance. Three years at a Big Four accounting firm right out of college, then a small internal audit role that had me traveling constantly in a way that wasn’t sustainable, then five years consulting — which I actually loved because the work changed every six to eight months and I’m not someone who does well with complacency. That consulting work eventually led me to JPMorgan Chase, where I first came on as a contractor.
I fought taking a full-time role with them for a while. But eventually they sat me down and told me they were getting rid of contractors and wanted to keep me. My boss laid it out: a VP title, a small team to manage, a real seat at the table. I remember sitting across from him and being completely transparent — I told him I was a bit of a free bird and could see myself leaving in two years. He laughed it off. Then, I have no idea how we got there, but somehow he started showing me Instagram photos of his nephew who was surfing in Hawaii and living this rogue life.
I can’t explain why that moment stuck with me. But it did.
I took the job. It was November 2017. I left exactly two years later, in November 2019. I packed my Jeep and drove to Colorado.
Why I Actually Left
Here’s the thing I want to be clear about: I didn’t leave because I hated my boss or hated my job. My bosses were great. My team was great. I had a two-story one-bedroom apartment in Old City Philadelphia that I loved. My weekends were stacked — sports leagues, dinners out, happy hours, a really good core group of friends. Philly’s food scene is incredible and we took full advantage. On paper everything was great.
But internally, something had been off for a while.
I started noticing it in small ways. I was envious of the tour guides on my vacations — the ones who seemed carefree and happy, living simply. I’d catch myself watching a bartender or a river guide and feeling something I couldn’t name. My dad used to tell me when work was rough to get a massage, go out to a nice dinner, treat yourself — you’re making good money. And I did. I had the disposable income to reward myself. But at some point the retail therapy stopped working. The massages, the nice dinners, the new bike — none of it was hitting the way it used to.
In February 2019 I remember just knowing. I can’t point to a specific day or a specific event. I just knew something in my life wasn’t aligned with who I was. The life I had wasn’t fulfilling me and I was ready to chase one that would.
I want to be honest about something else too: I was not married. I didn’t have kids. That gave me a flexibility that not everyone has and I don’t want to gloss over that. If you have a family, this decision looks very different. It’s not that you can’t make a change — but you’re not going to pack your car and move to Colorado on a whim. The point is that you can still look for ways to move toward a better fit, whatever that looks like for your situation.
The Pros of Leaving
Freedom — real freedom Not just the Instagram version. I mean the freedom to choose where you live, how you spend your time, and what you actually work on. When I left I went from a city apartment to a ski town where I didn’t know a single person. I bartended, I served, I instructed snowboarding. I learned things about myself I never would have sitting at a desk. I’m more comfortable with who I am now than I have ever been in my life. The anxiety I carried in corporate — where the wrong phone call could set me off — is just gone.
Clarity on what actually matters When you stop making six figures and have to think about every dollar, you realize very quickly what you actually need versus what you were buying to feel better about a life that wasn’t quite right. I cut my salary in half and I save more now than I did in corporate. Not because I’m some financial genius — because I stopped spending money to compensate for something else.
You find out what you’re actually capable of I went from VP at a bank to learning how to hold a serving tray at 32 while a line cook yelled at me. It was humbling. It was also one of the best things that ever happened to me. I’ve worked as a bartender, a horse tour guide, a golf course attendant, a snowboard instructor, a contract worker. Each one taught me something. Each one made me more capable.
You find your people The people I’ve met since leaving corporate are some of the most interesting humans I’ve ever encountered. Not because everyone in corporate was boring — but because seasonal work and unconventional living attract people who made a choice to do it differently. That changes a room.
The Cons — Being Honest
Financial uncertainty is real This isn’t something to minimize. Seasonal income is irregular. Some weeks are great, some are slow, and you have to save aggressively during the good weeks to cover the gaps. If you have debt, dependents, or a mortgage, the math gets complicated quickly.
You might have to start over Not forever, and not completely — but there’s a real adjustment period where you’re learning new things from scratch, building new networks, and yes, making less money than you used to. Some people find that energizing. Some people find it destabilizing. Know which one you are before you jump.
The fear is real — and it doesn’t go away until you just do it This is the thing nobody tells you. I spent six months before I moved being more scared than I’ve ever been in my life. The fear lives in the hypotheticals — all the what-ifs your brain runs through at 2am. The day I actually got in the car and drove to Colorado? Easy. The doing is almost always easier than the anticipating. But you have to get there first.
The One Thing I’d Tell Anyone Considering This
Keep your relationships.
I gave six months notice at JPMorgan. I was honest with my boss, helped with the transition, and left on genuinely good terms. To this day I still check in with my main boss — he’s more entertained than anything by the photos of my life. That door was left open and that matters, whether you ever walk back through it or not.
Don’t let the excitement of leaving make you sloppy about how you leave. The f*** you walk out the door moment might feel good for an hour. The professional exit you’ll be glad about for years.
So Should You Quit?
I can’t answer that for you. I have a friend who’s still in finance, just bought a home in Philly, and is genuinely happy. He loves hearing my stories but he loves his life. There is no right answer here — there’s only what’s right for you.
What I can tell you is this: if you’re reading this article and something in you recognized itself in what I wrote — the complacency, the envy of the tour guides, the retail therapy that stopped working — that’s probably not nothing. That’s your gut talking.
I believe in the gut. It’s what got me in that car.
