People ask me sometimes if I’d go back. Friends call to tell me about their salary increases, their new titles, their latest trips booked on points from corporate cards. I have friends in New York City who spend more on a flight than I spend on monthly rent. And my answer is still no. I wouldn’t go back.
But there are things I wish someone had told me before I left. Not to talk me out of it — nothing would have — but because knowing them earlier would have saved me a few years of unnecessary confusion. Here are some truths I wished I’d known before leaving corporate for a simpler llfe.
The Identity Crisis Is Real and It Takes Longer Than You Think
Nobody warns you about this one adequately.
I spent ten years building a career. VP title, finance background, a résumé that meant something in a specific world. Then I moved to Vail and found myself being corrected on how to hold a serving tray by a twenty-two year old who was probably high for half the shift. And he was right to correct me. He had experience and I didn’t. I had to check my ego and I did — but checking your ego doesn’t mean the ego disappears.
For the first few years I always had a disclaimer ready. When people asked what I did I’d say I was bartending but I used to work in finance, I left corporate to figure out my own thing, I’m working on starting a business. I was never just a bartender. I always had the asterisk. Because I wasn’t ready to let go of the identity I’d spent a decade building and I wasn’t ready to fully own the one I was living.
Looking back I can say it plainly: I was taking a couple years off to enjoy my life with no real ambitions toward anything else. That was the truth. And it took me years to be able to say it without the disclaimer.
The Northeast culture makes this harder. A friend in Colorado said something to me early on that stuck. He said you East Coast people, when you meet someone the first question is always what do you do for a living. Out here we ask what’s your story. That reframing helped me more than I expected — the idea that your job and your identity don’t have to be the same thing, that what you’re passionate about might have nothing to do with how you make money. But it took living in Vail for three years, watching wealthy people be miserable, watching business owners with everything they wanted still be deeply unhappy, to really internalize it.
By year three I’d found clarity. Now when people ask what I do I tell them I bartend and I love it. No asterisk. No disclaimer. It took about three years to get there and I wish I’d known it would take that long so I could have been easier on myself in the meantime.
The “Poor Friend” Feeling Is Real Too
This is the one nobody admits to and I’m going to say it anyway.
When I’d come back to visit city friends — double income, no kids, six figures each, half-million dollar houses — I’d sit at the happy hour and feel like the fish out of water. Everyone was always fascinated by my life, always wanted to hear the stories, always said they envied the freedom. And I also felt, in those moments, like the poor friend. The one doing the crazy thing while everyone else was building something conventional and stable.
It’s not that anyone made me feel that way explicitly. It’s that the contrast was loud. And when you’ve spent a decade in that world and then stepped out of it, coming back even for a visit puts you face to face with the road not taken.
That feeling faded. It mostly doesn’t exist anymore. But it was real in the beginning and I think it’s worth naming because if you’re in that first year or two and you feel it — you’re not ungrateful, you’re not weak, you’re just human.
The Golden Handcuffs Are More Psychological Than Financial
One truth I wish I’d known before leaving corporate for a simpler life is that the golden handcuffs are more myth than reality if you’re ready to make changes. Everyone talks about the golden handcuffs like they’re purely about money. They’re not. They’re about lifestyle creep — and you don’t see it happening until you’re deep in it.
I remember sitting in an Uber after a couple years in Vail and the driver was working multiple jobs trying to get into corporate. I did some quick math for him on what my corporate life actually cost: $1,400 rent, $500 car payment, $100 utilities, $200-300 in Ubers, $500 a week going out to eat. Credit cards running $2,000-$3,000 a month easily. And I was barely saving anything beyond the 401k that came out automatically.
The more I made the less I thought about any individual purchase. New plates from HomeGoods? Fine, I want them. Another round? Sure. Upgrade the flight? Why not. You don’t notice it because each individual thing seems reasonable and you have the income to cover it. But collectively you have built a life that requires a specific paycheck to maintain, and that paycheck becomes the ceiling you can’t climb below without dismantling everything.
When I left corporate and my spending got forced down, something surprising happened: I was fine. My friend who helped me look at my finances before I left said something I think about often. He said Sarah, you have no debt and you have savings — do you know how many people here are $40,000 into a car loan or $400,000 into a mortgage and calling it an asset? The golden handcuffs disappear faster than you think once you stop needing the things you were buying to make the life feel worth it.
Nobody Tells You About Health Insurance
Corporate hands you health insurance and you never think about it. You pay your portion, you show your card, you don’t think about what it actually costs or how it works because you don’t have to.
When you leave, you have to. And it’s complicated in a way that genuinely surprised me given that I have a finance background.
COBRA — extending your corporate coverage after leaving — is real and expensive. Often $400 a month or more. The ACA marketplace exists and is worth investigating, especially if your income is low enough to qualify for subsidies, but the brackets change, the rules change, what you owe at tax time can change. I went two years in Vail without a real retirement account because nobody told me I needed to set one up myself and I owed money on my taxes before my dad finally said — do you have an IRA? Shelter some income.
For a person with a finance background I was remarkably slow to figure this out. So I’ll say it plainly for everyone else: when you leave corporate you need to immediately research health insurance options for your state and income level, and you need to open an IRA or Roth IRA because the 401k that came out of your paycheck automatically is gone. Nobody is going to do it for you now. It takes ten minutes to set up and costs you years if you don’t.
The Physical Reality of Hospitality
If you’re quitting corporate and going into hospitality — bartending, serving, hotel work, any of it — be ready for the physical adjustment.
In corporate I had lull time. I’m not saying everyone sits around, but there were stretches where I was at my desk, work was done, and I was planning events or researching things or having full conversations on my phone while appearing to work. I was getting paid very well per hour for some hours where I was doing almost nothing.
Bartending doesn’t have lull time. I don’t check my phone during a shift. I’m lifting heavy things, on my feet for ten hours, moving constantly, running on tip income which means every interaction is also a small performance. When I go home I am physically tired in a way desk work never made me.
That’s not a complaint — I sleep better, I’m healthier, my body is stronger than it was in corporate. But if you’re making the switch, know it’s coming. Give your body a few months to adapt and don’t be surprised when the first season leaves you exhausted in ways you didn’t expect.
The Fear You Don’t Talk About
There’s a fear that lives in the back of my head that I don’t hear other people in my situation talk about much, so I’ll say it.
I’m afraid of losing my skill set.
Excel, data analytics, financial modeling — I was good at those things. The tech world moves fast. AI is changing what those skills even mean. And every year that passes I get a little further from being able to walk back into that world at the level I left it. I’d be taking significant steps back if I went back now and I know it.
I also have moments of wondering about the long game of bartending. It’s hard on the body. It’s a young person’s game in certain environments. I’m good at it now and I enjoy it but I’m not naive about the fact that at some point the physical demands or the environment or just my own tolerance for it will change.
None of this keeps me up at night. If the fear of losing my corporate skill set was strong enough I’d be taking courses to stay current and I’m not — which tells me that fear is theoretical, not real. And the bartending fear is what keeps me working on side hustles, building the blog, thinking about what comes next.
But I want to say it because people in corporate have the same fears — getting fired, becoming obsolete, the company changing — and pretending that leaving corporate means leaving fear behind is not accurate. You trade one set of fears for another. The difference is the fears you’re living with now feel like yours, chosen, part of a life you actually want. That makes them easier to carry.
What I Know Now That I Didn’t Then
I don’t miss feeling important. I don’t need a title right now. I don’t need to prove I can hit a salary point or manage a team. I’m good with my money, I save it, I invest it quietly, and I don’t need to tell anyone about it.
It took me three years to get here and i still am working on it. Society has a very loud opinion about what success looks like and what the right timeline is — a title by 30, a mortgage by 35, a retirement plan that looks like everyone else’s. That version of me, the one who needed the title, who always had the asterisk, who felt like the poor friend at the happy hour, she was still figuring out what she actually wanted versus what she’d been told to want.
There is no right way. There’s just the way that actually fits your life when you’re honest about what you need. If I could go back and tell her one thing it would be this: the disclaimer isn’t necessary. Own the life you’re actually living. The blueprint was never yours to begin with — and the story is better without the asterisk anyway.
