MW How to move past your biggest money mistakes

By Genna Contino

Plus: Ways to keep 'lifestyle creep' from wrecking your finances

You sent in your biggest financial regrets. Here's how you can learn from them and still thrive.

Welcome back to Don't Short Yourself, where we cut through the noise and share practical ways to help you take control of your money.

Last week, we asked you to tell us about your biggest money mistakes - and you opened up about everything from dicey stock-market bets to spending habits that got out of control. Some of these mistakes cost thousands of dollars. Others were harder to quantify.

So here's what we can learn from those setbacks - and how we can get better at managing our money.

- Genna Contino

Big money tip of the week

How to learn from your money mistakes

If you've made a big money mistake or two, you're not alone. Nearly three out of four Americans have a financial regret, according to an August 2025 Bankrate survey. And I recently shared my own embarrassing secret - that I didn't have a budget, and my spending was getting out of control.

Experts say framing mistakes as a learning experience can actually strengthen your financial literacy and set you up to make smarter decisions. "Failure is just an outcome. It's not the end game," said investment adviser Jay Sharifi, founder of Legacy Wealth Management in Virginia. "Don't let one or two small failures in life derail you from your bigger goals."

Here are some of the most common money mistakes we heard about - and what to learn from them.

Investing with your gut - and without a plan

Investing mistakes were the most common regrets you shared. One person wrote in to say they regretted "buying stocks because of FOMO." Another shared that they "sold stocks feeling the market was too hot. Missed future bullish months," while another said, "Selling stocks during COVID. Should've stuck with them."

We're human, and leaving our emotions out of investing can be incredibly hard. Fear might push you to panic sell - or buy - even when it's not logical. Acting on emotions creates what analysts call a "behavior gap," which is the difference between strong returns and poor returns that tend to be associated with reactionary decision-making. Or as the well-known economist and investor Benjamin Graham put it: Investors are often their own worst enemy.

One way to remove emotions from the equation is to automate your investing strategy. You can set your own account rules in apps like Robinhood (HOOD) or Fidelity $(FNF)$ to automatically trim holdings during gains or buy more during dips, said David Johnston, a certified financial planner at OnePoint BFG Wealth Partners in New Jersey. This helps you stick to a plan, rather than relying on gut feelings if the market swings dramatically - the way it's been doing lately.

Lending money to a friend or family member - who didn't pay it back

Many of us can relate to the reader who said they lent all their savings "to a close friend without a written agreement, only to lose both the money and the relationship."

This is a difficult situation to be in, because it's hard to say no to someone you care about. And if they're coming to you for money, it's possible they're going through enough hardship that even a bank won't lend to them - but that also means they might struggle to pay you back.

Even with written agreements, your options may be limited: accept the loss or take legal action. Small-claims court can help, but winning may come at the expense of the friendship, and legal victory still requires time and filing fees (ranging from $30 to $200).

Experts say it's best to avoid lending money to friends and family if possible. But if you feel that you must, make sure you don't lend more than you can afford to part with. "The only money I lend is money I'm willing to lose 100%," said Legacy Wealth's Sharifi.

Waiting 'too long' to start investing

One user on the social platform X told us they waited until age 34 to start investing, losing out on over a decade's worth of potential gains. "Thought I had time," they said. "The math on what that [will] actually cost me by retirement is a number I don't like saying out loud."

We can't go back in time - but we can make smarter decisions moving forward. And that doesn't mean throwing all your extra cash into risky investments to make up for lost time. There are savvier tactics.

Johnston recommends increasing your 401(k) contributions to as much as 17% to 20% of your salary, but he notes that "you're going to have to make sacrifices somewhere else to free up that capital to invest." If you earn $100,000 and contribute 6% of your annual income to your 401(k), then you would need to find about $800 to $1,100 in your monthly budget to reach that recommended contribution range. That's not chump change - and it could require pulling back on discretionary spending such as dining out or travel, or redirecting any future raises, bonuses or tax refunds toward your retirement fund.

And don't forget that people over 50 qualify for additional "catch-up" contributions. MarketWatch retirement reporter Jessica Hall has a helpful retirement-checkup checklist that spells out these additional contributions, and Fix My Portfolio columnist Beth Pinsker dug into the IRS rules around catch-ups for high earners. Beth also hosted our last Don't Short Yourself Live Q&A on Roth IRAs: You can watch it here.

One long-held piece of financial wisdom is that the best time to invest was yesterday - and the second-best time is today.

It's never too late to start.

Getting a car loan when you have bad credit

One reader said they paid $60,000 for a car worth $20,000 due to their low credit score.

Bad credit significantly increases borrowing costs, which can add up to thousands of dollars over the life of a loan compared with someone who has a strong credit score. And when it comes to vehicles, remember that a car also depreciates in value. So you could end up "underwater" on your loan, which means you owe more than the car is worth.

This can be an especially tough situation if you need a car ASAP, because it's impossible to increase your credit score 100 points overnight. So what do you do?

If carpooling, borrowing a car or taking public transit won't work, then seek out a used car that costs $4,000 to $5,000, even if it's "a car that you would never, perhaps, want to be seen in ever again," Sharifi said. MarketWatch's Kat Borgerding recently got a used car for $8,000. In the meantime, get your credit in shape and start saving for what you want.

Already stuck with an unfavorable auto loan? Our personal-finance team has you covered. Here's how to know if you should refinance your car loan. My colleague Venessa Wong has also laid out a simple "order of operations" for getting your credit in shape (some of these actions could improve your credit score in as little as 30 to 45 days).

Join Don't Short Yourself Live to ask MarketWatch's Christine Ji your AI and investing questions on Wednesday, April 3, at 1:30 p.m. Eastern time.

Join the Don't Short Yourself Live Q&A

What's the smartest way to use artificial intelligence to lower your costs and be more productive - and is the tech's promise living up to the hype? Join our next Don't Short Yourself Live on Wednesday, April 8, at 1:30 p.m. ET to ask MarketWatch's Christine Ji and IBM's vice president of AI Foundations, David Cox, your AI questions in real time.

In case you missed our last live Q&A on Roth IRAs - or you just want to hear the advice again - you can watch it here.

Definition of the week: Lifestyle creep

Lifestyle creep is when your discretionary spending (what you lay out for your fun or unessential "wants") rises along with your income. It's a subtle shift where "treat yourself" moments - like frequent dinners out or luxury upgrades - slowly morph into consistent, insidious monthly expenses. The result: You're making more money than ever, but you suddenly have less left over at the end of the month.

Left unchecked, this "can lead to setbacks on your way to future goals like homeownership, a child's education, and retirement," according to Fidelity.

Here's how I outsmarted lifestyle creep: I knew I couldn't trust myself with extra income when I landed my first job out of graduate school. After two years of scraping by on internships and part-time gigs, my take-home pay essentially doubled overnight. So to resist temptation, I hiked my 401(k) contributions from 3% to 12% and set up an automatic $1,000 monthly transfer to a brokerage account. By hiding that money from myself before I could even see it in my checking account, I forced myself to keep living like a grad student - while my future self got a massive head start.

Key money reads

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The hottest job perk right now isn't unlimited paid time off or oat milk in the office kitchen - it's job security, period.

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Share your favorite money tip

Send us your favorite way to save money - or to make your money work for you - and we'll share it with our readers. Send it to dontshortyourself@marketwatch.com.

-Genna Contino

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April 07, 2026 09:44 ET (13:44 GMT)

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