7 Money Decisions You’ll Regret in 10 Years (And How to Avoid Them)
Some money mistakes don’t show their true cost until years later—when you look back and wish you’d done things differently. Here are seven financial decisions that could cost you big in the next decade and the smarter moves to make instead.
1. Waiting Too Long to Start Investing
Time is your greatest asset. Start investing early—even small amounts—and you’ll benefit from decades of compounding. Consider this: Person A invests $500/month from age 25 to 40 ($90,000 total) and ends up with $2.2 million by age 65. Person B starts at 40 and invests the same amount until 65 ($150,000 total), but ends with just $650,000. The earlier you start, the less you need to invest. As Warren Buffett says, “Time in the market beats timing the market.”
2. Buying Cars You Can’t Afford
The average new car payment is $750/month. That’s $9,000 a year—or $90,000 over a decade—just for transportation. And that doesn’t include insurance, gas, or repairs. Worse, you’re paying interest on something that loses value the moment you drive it off the lot. Instead, buy a reliable used car with cash and invest that $750/month. Over 10 years, you could build over $150,000 in wealth.
3. Paying the “Stupid Tax” (a.k.a. Unnecessary Debt)
Financing vacations, clothes, or other non-essential purchases with high-interest debt is a trap. An $8,000 Cancun trip financed at 25% APR balloons to $25,000 over time. Credit cards and buy-now-pay-later services make it feel painless—until the interest piles up. One-third of Americans plan to put summer travel on credit cards. The smart move? Save first, spend second. Invest instead of paying banks to fund your lifestyle.
4. Skipping Emergency Savings
Life happens. A job loss, medical bill, or car repair can quickly become a crisis without a financial cushion. Having 3 to 12 months of expenses in an emergency fund gives you peace of mind and protects your investments. One example: the speaker’s AC broke unexpectedly, but their savings covered the repair—no stress, no debt. If you’re single, you might get by with three months. If you have a family or own a home, aim for more.
5. Buying More House Than You Can Afford
A house is not automatically an asset—it comes with a mortgage, taxes, maintenance, and repair costs. Follow the 75-15-10 rule: keep monthly housing costs below 75% of your income after taxes, save 15%, and use the rest for discretionary spending. Make sure you have a 20% down payment and plan for moving costs, updates, and emergencies. Buying too much house can delay your retirement, your savings goals, and your freedom.
6. Trying to Look Rich Instead of Being Rich
Spending money to impress others is a recipe for long-term regret. True wealth often looks boring. Jay-Z famously wore flashy jewelry when he was worth $100,000. Now worth over $1 billion, he dresses low-key. Why? Because wealth isn’t about what people see—it’s about what you own and control. Building wealth may mean skipping the designer bag or luxury SUV now to enjoy total financial freedom later.
7. Not Negotiating for Raises
A small raise now has a huge impact later. A 2% annual raise adds $17,000/year after 10 years. A 6% raise? You’ll be earning $73,000 more per year over that same timeframe. That’s a $130,000+ difference in a decade. Always negotiate. Show how your work drives results, how your role has expanded, and why your pay should reflect that. Don’t wait for your boss to notice—speak up and build your value.
Bonus: Building Investment Income So You Can Walk Away
Want to retire early? Replace your income with investments. If you make $80,000 a year, aim to generate that through rental income, dividends, or other passive streams. It takes time and consistency, but it’s the path to freedom. The key? Start now. Invest with every paycheck. Make your money work while you sleep, so one day, you don’t have to work at all.
Jaspreet Singh is not a licensed financial advisor. He is a licensed attorney, but he is not providing you with legal advice in this article. This article, the topics discussed, and ideas presented are Jaspreet’s opinions and presented for entertainment purposes only. The information presented should not be construed as financial or legal advice. Always do your own due diligence.
