Top 5 Money Mistakes I Made

Now that I’m 55 years old, I’ve spent a lot of time thinking about the financial decisions I got right and the ones I wish I could do over.

The truth is, a lot of personal finance advice online comes from people who either want to sell you something or act as if they’ve never made mistakes themselves.

I’ve made plenty.

Some of them cost me a lot of money over time.

So I thought I’d share the five biggest money mistakes I made in my 20s, 30s, and early 40s in the hope that maybe someone can avoid some of the same ones.

#1. I Didn’t Start a Roth IRA Early Enough

This is probably the biggest financial regret I have.

If I could go back to my 20s, I would start investing in a Roth IRA immediately, even if it was only $200 or $300 per month.

People underestimate how powerful time and compounding really are.

Historically, the stock market has returned around 8–10% annually over long periods of time. That means money invested early has decades to grow.

A person who consistently invests in a Roth IRA in their 20s could potentially end up with well over $1 million by retirement age, even without massive contributions.

I didn’t do that.

Now, because of income limits and where I am financially, Roth investing looks very different for me. I’ll likely need to do Roth conversions later in life, which is a much less ideal path than simply starting early.

The lesson: start investing earlier than you think you need to.

Even small amounts matter and you will be happy you did when you are looking at retirement.  

#2. I Bought Too Many Cars

When I was younger, I constantly rotated through vehicles.

Every few years I’d buy another car — sometimes new, sometimes only a year old and then after a few years I’d get bored and do it again. It doesn’t matter if you buy or lease in this situation.  

And every time, I lost money.

Monthly payments.

Money down.

Depreciation.

Taxes.

Registration.

Insurance.

It all adds up.

I never bought anything outrageously expensive, but even average car payments over long periods of time quietly drain wealth.

Eventually, around age 35, I finally stopped the cycle. I bought a very dependable car and drove it for over 20 years.

Honestly, it ended up being one of the best financial decisions I ever made.

Cars are one of the easiest ways to slowly destroy your ability to build wealth without even realizing it.

The longer you can drive a reliable vehicle, the better the math usually works in your favor.

#3. I Waited Too Long to Buy a Home

I rented for a very long time.

Part of the reason was that renting allowed me to live in nicer places in urban areas than I probably could have afforded to buy at the time.

But looking back, I waited too long.

I didn’t buy my first home until I was 41 years old.

That meant decades of rent payments that built zero equity for me.

Now that I’ve owned the same home for over 14 years, I finally understand why real estate becomes such an important wealth-building tool for many families.

Part of every mortgage payment goes toward principal - more to the principal the longer into the loan you are.  

Meanwhile, over time, the home itself may appreciate in value.

That combination slowly builds equity.

It doesn’t happen overnight, but over long periods of time it can become significant.

I can now see that in my own home.

#4. I Didn’t Always Max Out My 401(k) — Or Even Get the Full Match

This is another mistake I think about often.

I worked for large companies for most of my career, and many of them offered 401(k) matching.

Yet there were years where I either didn’t contribute enough or didn’t contribute consistently.

That was a mistake.

If your company offers a match — even something like 4% you should do everything reasonably possible to get it.

That’s free money.

And when you combine that with decades of compounding, those contributions can become substantial later in life.

The biggest advantage younger people have is time.

Money invested in your 20s and 30s simply has more years to grow.

#5. I Let Credit Card Debt Get Away From Me at Times

This is one I feel strongly about.

Credit card debt is brutal.

Today, many credit cards charge 20–25% interest rates. Even 15% is extremely high and that is a great interest rate for a credit card.

That’s not good debt(we’ll talk about good debt at another time).

That’s money working against you every single month.

It’s a terrible cycle.

I’m generally fine with low-interest debt tied to appreciating assets or long-term value — things like mortgages under reasonable rates.

But high-interest credit card debt is different.

If I could go back, I would have treated paying off credit card balances as an absolute top priority every single month.

Final Thoughts

The interesting thing about money mistakes is that most of them don’t feel huge in the moment.

It’s the repetition over the years that matters.

A few hundred dollars not invested.

A car payment that never goes away.

Skipping a 401(k) contribution.

Carrying a credit card balance.

Those decisions compound — positively or negatively.

The good news is you don’t need to be perfect financially to improve your future.

You just need to make a few better decisions consistently over time.

Hopefully some of my mistakes can help you avoid making the same ones.