15 Money Mistakes I’d Gladly Make Again

Making mistakes with money is part of the learning process. We all make choices we later regret, but not every mistake is a setback. Some of the best lessons I’ve learned in life came from my poor financial choices. In fact, there are some money mistakes I’d gladly make again, because they shaped my financial growth in ways I didn’t expect. Here are fifteen money mistakes I’d gladly make again, and why they ultimately helped me grow.

Buying the Expensive Laptop That Lasted 10 Years

I once bought a high-end laptop that was well beyond my budget. At the time, I felt guilty for spending so much on tech, but it ended up being one of the best purchases I ever made. The laptop lasted for over a decade, and it continued to perform at a high level, saving me from needing to replace it every few years.

The initial investment paid off because I didn’t have to worry about upgrading every couple of years, and the long-term value far outweighed the guilt I felt at the time.

Going on an “Overpriced” Vacation

I almost skipped the vacation of a lifetime because I thought it was too expensive. But I decided to go anyway, and it turned out to be one of the best experiences I’ve ever had.

The memories, personal growth, and experiences I gained far outweighed the cost. Sometimes, spending money on experiences, especially ones that push you out of your comfort zone, is worth every penny.

Investing in an Expensive Course

I once spent a significant amount of money on an online course that promised to teach me a new skill. The course was a bit more expensive than others, but I still signed up. While it didn’t offer everything I expected, it gave me the foundation I needed to take my career to the next level.

The knowledge I gained opened doors for new opportunities. Sometimes, paying more for quality education can be worth it, even if it doesn’t meet every expectation.

Taking a Risky Investment That Paid Off

There was a time when I made a risky investment that most people would have advised against. It was a high-stakes decision, and I nearly backed out. But it paid off in ways I never imagined, and the returns helped me build wealth in a way that more conservative choices wouldn’t have. While taking risks is never easy, sometimes they can lead to significant rewards.

Paying Off Debt More Slowly Than I Should Have

In my early years of debt repayment, I chose to pay off smaller debts first for psychological reasons, even though it wasn’t the most cost-effective strategy. While it took longer to clear my debt, I ended up feeling more motivated and accomplished with each small victory.

Though I now understand the importance of tackling high-interest debt first, those smaller wins kept me going through tough times, and the emotional payoff was well worth it.

Spending Money on Experiences Over Material Things

There was a period where I chose to spend money on travel, events, and experiences instead of buying material things. In hindsight, I’m glad I did. While it might not have seemed practical at the time, those experiences enriched my life in ways possessions never could. I learned new things, met interesting people, and built lasting memories. Choosing experiences over material goods has been one of the best financial decisions I’ve ever made.

Borrowing Money to Start a Business

Starting a business can be costly, and I once borrowed money to fund a business venture that seemed risky. Looking back, I don’t regret the decision. The business didn’t succeed in the way I’d hoped, but it taught me valuable lessons about entrepreneurship, risk management, and resilience.

The experience gave me the confidence to try again with better preparation. Sometimes, investing in yourself—even through borrowing—can teach you more than a guaranteed return.

Choosing the “Wrong” Career Path at First

Early in my career, I jumped into a field that didn’t align with my passions, simply for financial security. While I eventually moved to a different path, the time I spent in that role taught me invaluable skills, built my confidence, and allowed me to make key connections that helped me later on.

Even when you feel like you’re not on the perfect track, every experience adds value to your personal and professional growth.

Not Having Health Insurance for a Short Period

There was a short period in my life when I didn’t have health insurance because I thought I couldn’t afford it. During that time, I ended up facing an unexpected health issue that led to expensive medical bills.

While this mistake was costly, it reinforced the importance of having insurance and the need to plan for the unexpected. I’ve since made sure to have coverage at all times, even if it means tightening other areas of my budget.

Overpaying for a Rental Property

I once rented an apartment that I thought was overpriced at the time. However, it turned out to be a great location, and the experience of living there was worth the extra cost. It provided me with convenience, comfort, and a sense of stability that helped me during a transitional phase in my life. Sometimes, paying a little more for the right living situation can give you peace of mind that is priceless.

Paying for Convenience When I Was Busy

There were times when I opted to pay for services that made my life easier, like food delivery or a cleaning service, even though I could have done it myself. At first, I felt guilty for spending money on these things, but they gave me the time and energy to focus on more important tasks. It taught me that sometimes spending money for convenience is an investment in your well-being, especially when you’re juggling multiple responsibilities.

Giving Family and Friends Financial Help When They Needed it

There were moments when I helped family and friends financially, even though I wasn’t in the best position to do so. While it was a difficult decision, I don’t regret it. Helping others when they need it most is a deeply rewarding experience, and I’ve learned how to better manage my finances so I can give back in meaningful ways. It’s important to balance your own financial health with the desire to support others.

Letting My Savings Sit Idle for Too Long

There was a period when I kept my savings in a low-interest account, thinking I was being responsible. However, that money wasn’t working for me as it could have been. Once I learned about different investment opportunities, I made sure my savings were in places that offered better returns.

While the lesson was a costly one in terms of missed opportunity, it ultimately taught me the importance of investing my money wisely.

Not Planning for Long-Term Goals Earlier

I spent a lot of time focusing on short-term goals, like paying off debt and managing everyday expenses, without considering long-term objectives like retirement. While I did okay, I wish I had started planning for retirement earlier.

The earlier you start saving and investing for the future, the better off you’ll be in the long run. I now prioritize long-term savings and work it into my monthly budget from the start.

Letting Money Decisions Be Based on Fear

In the past, I made money decisions based on fear—fear of running out of money, fear of missing opportunities, or fear of taking risks. Although these choices sometimes paid off, I’ve learned that making decisions based on fear rarely leads to the best outcome.

Now, I focus on making informed, balanced decisions instead of letting fear drive my financial choices. Learning to manage fear and uncertainty has been one of the best lessons in my financial journey.

Valuable Lessons

Every money mistake I made taught me something valuable. These mistakes weren’t easy, but they shaped my financial habits and gave me a deeper understanding of how to approach money. Sometimes, those lessons are the ones that lead to the most growth, and while I wouldn’t want to repeat every mistake, I wouldn’t trade the lessons for anything.

9 Money Mistakes You’re Likely To Make at Some Point in Your Life

We all make mistakes when it comes to money, and that’s totally normal! Whether you’re just starting to manage your finances or you’ve been doing it for years, there are common blunders that many of us will encounter. Here are nine money mistakes you’ll likely make at some point in your life, along with tips on how to avoid them or bounce back. 9 Money Mistakes You’re Likely To Make at Some Point in Your Life