I had $50,000 in savings when I left JPMorgan Chase after ten years in corporate finance.
I want to sit with that for a second because I know what you’re thinking — she worked in finance, she must have had it all figured out. I did not. Ten years of working, making good money, and I had $50,000 in savings. That number tells you everything about how I was living: well, fully, and without a lot of thought about what came next. I was investing in my 401k but beyond that I was spending what I made and enjoying it. No regrets — but also no illusions about being some financial genius who had a master plan.
Here’s what I actually did to get ready, with real numbers.
Step 1: Do a Financial Health Check — With Someone Else
The first thing I did was sit down with a coworker at JPMorgan who had an interest in financial advising. We took a lunch break, went into a conference room, and he looked at my actual numbers with me.
I want to be clear about something: working in finance does not mean you know finance. My title was VP of Technology Integration for Derivatives. I was working in Excel, doing data and analytics, trying to make numbers flow through systems. I was not a broker. I was not an investor. I did not inherently know where to put my money just because I worked at a bank. If anything the finance world is so specialized that you can spend ten years in it and still need someone to walk you through opening a Fidelity account — which is exactly what happened to me at 32.
He asked me one question: what are you doing in the next five years? Are you trying to buy a house? I told him I was packing my bags for Colorado and had no idea what the next five years looked like. He said then let’s get this money making money and put my savings into a mutual fund.
That one conversation made me approximately $20,000 over the next five to six years as the market ran. I did nothing. I just didn’t leave it in a savings account.
The lesson: Don’t sit your savings in a savings account. A regular savings account gives you almost nothing. A high-yield savings account gives you 4% or more. A mutual fund, if you won’t need the money for five or more years, can do significantly better. I’m not a financial advisor and your situation is your own — but please, get your money out of a standard savings account before you do anything else.
Step 2: Max Out Your 401k Before You Leave
If you’re still working a corporate job and you know you’re leaving, this is the move.
I knew I was leaving in November 2019. The 401k contribution limit at the time was $18,000 and I was not going to have an employer-sponsored retirement plan once I left. So I maxed it out. I made sure every dollar of available contribution went in before I walked out the door.
Here’s the thing about 401ks that I think people underestimate: it’s the easiest money you’ll ever save because you never see it. It comes out of your paycheck before it hits your bank account so you never learn to live on it. My dad drilled this into me early — it’s free money, it lowers your taxable income, and most companies match up to a percentage which is literally free money sitting on the table.
I’ll tell you my favorite accidental money story. When I was at my consulting firm I had to elect my 401k contribution percentage. I meant to put in 6% and I accidentally typed 16%. I never noticed. For five years I was putting 16% of my paycheck into retirement without realizing it. To this day I am grateful to my idiot past self for that typo. Some of the best financial decisions aren’t the strategic ones — they’re the ones you set and forget and never touch.
Max it out the year you leave. You won’t regret it.
Step 3: Deal With Health Insurance Before You Need It
This is the one people skip and it’s the one that can absolutely wreck you.
I made sure to stay at JPMorgan through the end of November so I had that month covered. Then I had to figure out what came next. I was going to be working at a ski mountain — no employer plan. I called a friend of a friend who worked in insurance and he set me up with a high-deductible catastrophic coverage plan for about $70 a month. Was it perfect coverage? No. Did it cover hospital emergencies? Yes. Was it better than nothing? Absolutely.
I’ve seen people in Vail lose $20,000 on a broken wrist because they had no insurance. That’s not the lifestyle change you’re planning for.
Look into your options: your employer’s COBRA coverage, marketplace plans, Medicaid if you qualify, or a high-deductible catastrophic plan as a minimum. The Affordable Care Act marketplace is worth checking — I’ve used it. It varies a lot by income and state but it exists for exactly this situation. Don’t skip this step because the premium feels like an unnecessary expense. One emergency without coverage will cost you more than years of premiums.
Step 4: Pay Off What You Can Before You Go
I had about a year or two left on my car payment when I moved to Vail. The day that payment disappeared was one of the best feelings of my whole first year there. $600 a month just gone from my expenses. When you’re making inconsistent income, fixed monthly obligations become really stressful really fast.
If you can pay off your car before you leave, do it. If you have high-interest credit card debt, attack that first — it’s costing you money every month you carry it. Student loans and other fixed debt you may not be able to eliminate but know exactly what your minimum monthly obligations are before you go, because that number is your floor. That’s what you have to make every single month no matter what.
Step 5: Know Your Real Monthly Number
When I got to Vail and started making consistent money, I sat down and actually looked at my monthly expenses:
Rent: $1,200 Car payment: $590 (until it was paid off) Cell phone: $100 Utilities: $100 Horse retirement barn: $300 (yes, I had a retired racehorse — long story) Gas: $50 (Vail has a free bus system, I barely drove) Groceries and going out: $400–500
Total: roughly $2,500–$3,000 a month out the door.
Once I knew that number I knew what I needed to make. My goal was double that for security — so $5,000 to $6,000 a month. At $300 to $400 a night bartending four to five nights a week I was hitting that. When I was comfortable I was putting $4,000 a month into savings.
Know your number before you go. It sounds simple but most people don’t actually sit down and add it up. Add up every fixed obligation, add a realistic estimate for food and gas and the basics, and then figure out what you need to make to cover it with room to save. That’s your target.
What I Do Now With the Money I Make
This is what’s evolved after a few years of doing this:
When I’m bartending I keep my cash sorted by denomination. My ones go in a jar — that’s my treat myself fund. My fives and tens I live off of for day to day spending. My twenties and hundreds go straight to the bank. When I accumulate $5,000 to $10,000 I put it into a short-term CD — usually three months, which lines up with my season length. When the CD matures at the end of the season I move that money into an ETF or another longer-term investment.
It’s not complicated. It’s not genius. It’s just a system that makes sure the money doesn’t sit idle and doesn’t get spent.
The Honest Truth About Money and This Lifestyle
I cut my salary in half when I left corporate. I save more now than I did then. That’s not a flex — it’s just what happens when you stop spending money to compensate for a life that isn’t quite right.
I don’t get massages the same way I used to unless I’m in Mexico where they’re a quarter of the price. I bought my mountain bike three years into living in Vail, used, for $1,200. I still buy the healthy food I like because my body is how I make my living. I’m not couponing and suffering — I’m just intentional in a way I wasn’t when I had money to throw at anything that would make a bad week feel better.
You don’t need to be financially perfect to make this change. You need to be honest about your numbers, get your money working instead of sitting, protect yourself with health insurance, and know what you need to make every month before you go.
The rest you figure out as you go.
