12 Money Failures Americans Say They Regret the Most

Tobias Funke crying in the shower after realizing he has poor financial planning and personal finance skills -- and failing at becoming an actor
Tobias Funke cries in the shower after realizing he has poor financial planning and personal finance skills — and he’s failing at becoming an actor. | Fox/Netflix

We all have regrets. Perhaps you wish you wouldn’t have dropped out of college, or that you would have been more on top of your financial planning when you were younger. It’s easy to look back and point out the things we could have done better. That’s why they say that hindsight is 20/20 — when you’re in the moment, you don’t generally have a bird’s-eye view of what’s going on.
This holds true when it comes to personal finance as well. You never know if you should invest in this, or refrain from spending on that. What if you had spent all your money on Beanie Babies, expecting a big return? That may have seemed like a good idea a the time. But what about now?
Naturally, those chances we didn’t take, or the gambles we did, turn to regret. With time, these regrets can gnaw at us. Keep us up at night. Or, we might just consider them sunk costs of sorts, and move on with our lives. Still, we all have regrets.
But what are the most common regrets Americans cite, particularly when it comes to money? A new survey gives us some insight.
That survey, conducted by Claris Financial, asked more than 2,000 people about their personal finance training and education. It also asked what those people considered to be their biggest financial successes and regrets. The resulting list isn’t all that surprising, but does give us a glimpse as to what people truly hold dear when they look back at their financial decisions.
Here are the 12 specific money regrets Claris Financial was able to dig up as a result of its survey.

12. Not being able to support their kids

A family has dinner at home
A family has dinner at home. | Sean Gallup/Getty Images

For most people, the ability to take care of their family is a top priority. But if you can’t manage to make ends meet? That’s as big of a failure as it comes, and 6% of respondents said that not being able to fully financially support their kids was their biggest financial planning failure.

11. Not being able to put their kids through college

Graduates holding college degrees
Graduates hold college degrees. | iStock.com/michaeljung

Spring-boarding right into the next item, having the inability to pay for their children’s college education came in next. With college costs rising sharply over the past couple of decades, this one probably hits home for many families. About 7% of respondents said this was their biggest financial regret.

10. Not having enough to retire on time

A retirement savings plan and some coffee
A retirement savings plan is important. | iStock.com/c-George

We generally peg retirement age as 65 or so. But for a lot of people, especially these days, it’s simply unachievable. Around 11% of those polled said not being able to retire on time was their biggest personal finance shortcoming.

9. Not investing in business

Business investment and growth
Business investments can change your life. | iStock.com

We all wish we would have bought some Amazon stock back in the ’90s or some Google stock in the early 2000s. But we didn’t, and we have to live with it. Evidently, a lot of people regret not having invested in businesses — 12% of poll respondents named it as one of their top regrets.

8. Not being able to purchase a second home

Real estate for sale signs are seen in front of homes for sale
Homeownership is seen as a sign of success. | Saul Loeb/AFP/Getty Images

About 12% of respondents said they regret not being able to buy a second home. Those folks must be doing fairly well if buying a second home was even an option on their radar.

7. Not being able to support aging parents

An elderly couple have coffee
Health care is expensive as you age. | iStock.com

We know that people struggle with not being able to support their kids. But what about not being able to support your parents? That’s a top personal finance regret as well, with 16% of those polled naming it in survey.

6. Not investing in the stock market

A broker follows the stock market
A broker follows the stock market. | iStock.com

We know that people regret not investing in businesses directly. But that also goes for not throwing some money into the stock market. Even some modest investments in index funds would have paid off handsomely over the years. Around 17% of people list this among their top regrets.

5. Not being able to retire early

Early retirement
This is only a dream for some people. | iStock.com

Forget retiring on time. What about retiring early? Roughly 19% of people surveyed said this was one of their top personal finance regrets.

4. Not having enough money for college

A UC Berkeley student works on her laptop while sitting on the UC Berkeley campus
A UC-Berkeley student works on her laptop. | Justin Sullivan/Getty Images

This one is for the (relative) youngsters out there. Not having the funds to pay for college means tapping credit lines and taking out loans. That can bury you if you’re not careful. An estimated 20% of respondents said not having money for school was one of their top regrets.

3. Never starting a business

A young entrepreneur at work
A young entrepreneur is at work. | Sean Gallup/Getty Images

Starting a business is a huge undertaking. It requires capital, time, and patience. There’s a high barrier to entry, and for that reason, a lot of people never take the leap. But a lot of people also regret never doing it, and 23% of respondents said never starting a business is one of their top regrets.

2. Never taking a big trip

Loading up the RV for the trip of a lifetime
Load up the RV for the trip of a lifetime. | iStock.com

Always wanted to take the trip of a lifetime? We all think about it, but many of us never actually do it. Even if our financial planning was on point, we forgo taking that big trip. And 29% of us regret it — that’s tied for the top spot.

1. Not being able to buy a house

House for sale
This is the biggest financial regret for Americans. | iStock.com

Along with never taking a big vacation, not being able to purchase a house is the biggest financial regret Americans named, according to this survey. Though owning a home builds equity and has numerous advantages, but some people never manage to pull it off. According to the Claris survey, this is America’s top financial regret.
Follow Sam on Twitter @SliceOfGinger.