The 7 Financial Choices You’ll Regret 5 Years From Now

Published June 30, 2025

Speaking as a thirty-something, I feel like there’s a certain magic (and pressure) that comes with being in your thirties. You're likely earning more than you did a decade ago, maybe climbing the ladder at work, starting a family, or dreaming bigger about what your life could be. But these years can also be financially tricky.

You’re old enough to know better, young enough to still feel behind, and right in the middle of life’s most expensive chapter – not to mention the external pressures of what’s happening with high interest rates and impacts from inflation.

But here’s the truth: when it comes to finances, you have to be future-oriented. As much as we all want to live in the moment, the fact is that the financial decisions you make now will either cost you or support you in the future.

So before you swipe the credit card, sign that lease, or ignore your 401(k), consider these seven financial choices that could come back to haunt you.

If I could turn back time to five years ago, here are seven financial decisions I would do over.

1. Prioritizing Lifestyle Over Financial Security

You deserve nice things. But you also deserve peace of mind. The temptation to match your friends’ Instagram is real. At this moment in time, you might be earning more than you ever have, and some of those larger items might feel attainable. You’re finally buying a new car from the dealer instead of a used car on a sketchy Facebook Marketplace listing. You’re springing for the extra leg room in the Comfort+ seat instead of crouched over in Economy. I get it.

In five years, you may wish you’d skipped the “treat yourself” mindset more often and built a solid emergency fund, invested consistently, or paid down your student loans instead. Security may not be as Instagrammable, but it’s far more valuable.

2. Ignoring Retirement Contributions

It’s easy to put off saving for retirement. After all, retirement feels decades away, and right now you might be juggling rent or a mortgage, a car payment, and maybe even childcare.

But compound interest doesn’t wait. A dollar invested today has way more growth potential than a dollar invested five years from now. Maximize your 401(k) match if your employer offers one, and consider opening an IRA (Roth if you’re eligible).

The you of 2030 will wish you’d started now—even if it’s just $100 a month.

3. Not Having a Plan for Debt

Credit cards, student loans, car loans—it adds up fast. And if you’re making minimum payments without a strategy, you could be paying thousands in interest without making real progress.

Five years from now, you’ll regret not tackling your highest-interest debt first. Consider using the avalanche method (highest interest rate first) or the snowball method (smallest balance first) to stay motivated. Whichever path you choose, just don’t go into autopilot. Your debt needs a plan.

4. Not Building a Relationship with Investing

If you’re keeping your money in a savings account and calling it a day, you’re losing money to inflation. Investing feels intimidating—especially if no one taught you how—but getting started is easier than you think.

A 401(k) or an IRA are both great places to start. If you’re feeling more comfortable, consider reaching out to an accredited financial advisor to see what other investment opportunities make sense for your goals and timelines. (Always go with an accredited professional).

5. Letting Fear Hold You Back from Negotiating

This might be the decade where you plateau—or where you make massive moves. If you’re staying quiet at work, not asking for raises, or underpricing yourself as a freelancer, you’re leaving tens of thousands on the table over time.

But your future lifestyle, career, and even retirement depend on your income now. Learn to advocate for yourself—you’ll regret the money you didn’t ask for far more than any awkwardness you felt while asking.

6. Buying a Home Without a Long-Term Plan

Owning property is a major milestone, but it’s not always the smartest financial move. Rushing into homeownership because it feels like the “adult” thing to do—or because you’re tired of renting—can backfire.

In five years, you might find yourself stuck with a mortgage in a city you no longer want to live in, paying for repairs you didn’t budget for, or trying to sell in a bad market. Buy when you’re ready, not just when you’re emotionally fed up with rent.

7. Not Understanding Credit

It’s pretty easy to forget about your credit. It’s this thing that you don’t have much control over that you don’t typically need on a day-to-day basis. But there are so many things that require you to have a good credit score and a good credit report (there’s a difference), especially in your twenties and thirties. Things like purchasing a car, renting an apartment and even qualifying for some jobs.

Understanding your credit and how your score is calculated is paramount to building a solid score, protecting a good score and fixing your credit if something happens to it.

Considering how long it can take to build a good credit score, having a thorough understanding of credit is better to develop earlier rather than later.

If you’re looking to understand your credit, you can sign up for a free credit report card here at Credit.com to see your credit score and how it’s being impacted.

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