11 Financial Regrets I Have (And What I’d Do Differently)
Looking back, I made some pretty bad money mistakes—here’s what I wish I had done instead.
- Sophia Zapanta
- 6 min read
I still remember sitting on the front porch one quiet evening, looking back on all the financial choices I’d made over the years. Some brought peace of mind, others—well, they kept me up at night. One regret that stung the most was how long I waited to start saving for retirement. Back when I was in my twenties and thirties, it felt like there was always something more urgent—a car repair, a family expense, a weekend out. But as I got older, I realized that some of those decisions came with a cost far greater than I anticipated. Those moments taught me lessons I wish I’d learned sooner.
If you’ve ever looked back and wished you’d handled your money differently, trust me, I’ve been there. Today, I’m sharing eleven financial regrets I’ve carried—and the five key changes I’d make if I could go back.
1. Blowing My First Paychecks Like I Was a Millionaire
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The moment I got my first real paycheck, I acted like I was Elon Musk on a shopping spree. I bought expensive dinners, gadgets I didn’t need, and clothes that looked good but wrecked my bank account. I thought I deserved it after years of being broke, but I was just setting myself up for more financial struggles. If I could go back, I’d start saving at least 30% of every paycheck before touching a single dollar.
2. Not Learning About Investing Sooner
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For way too long, I thought investing was for rich people in suits. I left my money sitting in a sad little savings account, earning basically nothing. By the time I realized compound interest was my best friend, I had already wasted years of potential growth. If I could start over, I’d put my money in index funds the moment I turned 18.
3. Relying on Credit Cards Like Free Money
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Credit cards felt like magic when I first got them—swipe now, worry later. The “worry later” part hit hard when I was drowning in interest payments. I paid for things I didn’t need and ended up paying double because of interest. If I had another shot, I’d use credit cards wisely, paying them off in full every month.
4. Not Building an Emergency Fund
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I used to think saving for an “emergency” was unnecessary because, well, what could go wrong? Turns out, life enjoys throwing expensive surprises—car repairs, medical bills, sudden job loss. When those hit, I had nothing to fall back on and had to rely on loans, making everything worse. If I could do it again, I’d build at least six months’ worth of expenses before splurging on anything.
5. Renting for Too Long Without a Plan
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I rented apartments for years without ever considering buying a home. I told myself I was “paying for flexibility,” but in reality, I was just paying someone else’s mortgage. By the time I realized I could’ve been building equity, I had already wasted thousands. If I could rewind, I’d at least start planning for homeownership much earlier.
6. Ignoring Retirement Savings in My 20s
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Retirement felt a million years away, so I figured I could start saving “later.” Later, I realized I had wasted precious years when my money could’ve been growing. The difference between starting at 25 vs. 35 is massive, and I learned that the hard way. If I had a do-over, I’d max out my retirement accounts from day one.
7. Falling for Lifestyle Inflation
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Every time I got a raise, I upgraded my lifestyle instead of my savings. New job? Time for a nicer car. Bigger paycheck? Let’s move to a fancier apartment. I didn’t realize I was sabotaging my future by constantly increasing my expenses. If I had another chance, I’d keep my expenses low and invest the extra money.
8. Not Negotiating My Salary
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I used to think whatever salary I was offered was the final deal. Turns out, companies expect you to negotiate, and I left thousands on the table over the years. When I finally started asking for more, I was shocked at how often I got it. If I could go back, I’d negotiate every single job offer like my future depended on it—because it did.
9. Lending Money I Couldn’t Afford to Lose
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I wanted to be generous, so I lent money to friends and family, assuming they’d pay me back. Some did, most didn’t, and it put me in financial stress I couldn’t afford. I learned that if you can’t give it as a gift, you probably shouldn’t lend it. If I had a redo, I’d only lend money I was 100% okay never seeing again.
10. Not Having Multiple Income Streams
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For years, I depended on a single paycheck, thinking it was enough. Then came job cuts, unexpected expenses, and the realization that one income source is risky. I wish I had started a side hustle earlier or invested in passive income streams. If I could go back, I’d always have at least two ways to make money.
11. Avoiding Financial Advice Out of Fear
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For the longest time, I avoided looking at my finances because I was scared of what I’d find. I thought ignorance was bliss, but it was really just a slow-motion disaster. When I finally faced my money situation head-on, I realized it wasn’t as bad as I feared—and fixing it was actually empowering. If I had another shot, I’d get financial advice sooner and take control instead of avoiding reality.
The truth is, no one’s financial journey is perfect. We all make mistakes, and it’s easy to beat yourself up over them. But every regret became a stepping stone that taught me how to do better moving forward. It’s not about dwelling on the past—it’s about using those lessons to create a stronger future. Here’s what I’d recommend based on my experience:
Start saving for retirement earlyI delayed contributing to my 401(k) far longer than I should have. Even small contributions in my twenties would’ve grown significantly by retirement.
Avoid unnecessary debtI relied too heavily on credit cards in my younger years. If I had focused more on living within my means, I would’ve saved thousands in interest.
Build an emergency fund soonerI didn’t prioritize emergency savings until a major car repair wiped out our checking account. Having even a small fund earlier would’ve saved a lot of stress.
Invest consistently instead of trying to time the marketThere were years I hesitated to invest, worried about market conditions. Looking back, steady contributions would’ve served me far better than waiting for “perfect” timing.
Have more open conversations about money with familyFor too long, Mary and I avoided discussing money goals openly. When we finally started regular check-ins, it strengthened both our finances and our relationship.
Mistakes happen, but it’s never too late to take control and move forward. Learn from the past, stay focused, and you’ll set yourself up for a more secure tomorrow.