The Four Biggest Financial Regrets People Have


Sunday was a lovely day for me and my husband. We took an hour drive down the coast to our favorite restaurant on the Tampa Bay for brunch (Oystercatchers…if you’ve never been, go) with two of our favorite couples. It was a belated 11th wedding anniversary celebration for us, a birthday celebration for another couple and an early anniversary celebration for the other. Basically, it was an excuse to overindulge in amazing food, bottomless mimosas and a few hours without the kids. We had a beautiful morning, and our conversation was flowing as beautifully as the bottomless cocktails.

At one point, we were surprised to hear one of our friends mention he was going back to school. He has a great job with an amazing company, and he does very well. He left college a semester or so short of his graduation because he’d worked his way up this company into his dream position. Fast forward 13 years and he would like to pursue a new career, but that means going back to school. It led us to begin talking about any regrets we might have from way back when. He regrets the fact that he did not take college more seriously back in the day, especially when he was living at home with his parents, they were footing the bill and he was basically living the kind of life we all dream of living.

Now he is paying his own classes and books, and he’s setting a new example for his daughter. We talked for a while about things like this, and it led me to thinking that many of our past regrets come in the form of financial choices we wish we’d had more clue about in the day. Saving earlier for retirement, for example. Creating a bigger emergency fund sooner in life was another. I got to thinking that we have a group of successful men and women sitting here, and even we have regrets that go along with our money matters from when we were younger.

It turns out that even when you are in a wonderful position, you might have a few regrets. For us, it seems that simply getting older and learning more about life has changed our way of thinking. We look back now and think that if we’d only known better we could have made different, or better, decisions earlier that would have been useful at the time – even if they don’t really impact us now. That said, I thought perhaps sharing people’s biggest money regrets might inspire others not to make the same mistakes.

Not saving for retirement

For me, this is an easy one. Not saving for retirement when I first began working as an adult is something I wish I would have done. It simply didn’t seem like that big a deal 15 years go. Now I think that had I started then, I’d be even further ahead than I am now; and I like that idea. I can add more now and make up for it, but I do wish I would have saved for retirement even when I was 18. You don’t think so at that age, but you will when you get older.

Not saving for emergencies

When I was first an adult, I didn’t put any thought into an emergency fund. I didn’t need one; I had no emergencies. However, I wish I would have started one then and added to it over the years to really grow it before we had any emergencies. Again, it’s not the biggest deal in the world, but it’s something that I could have done sooner and that would have been beneficial.

Not saving for kids

Now that I have four kids, I get it. I wasn’t able to imagine before kids why I’d want to save for kids; but now I get it. I wish I would have started a college fund or a new car fund or a first down payment fund (whatever my responsible children will use this for as they grow up) for them long before they were born. It’s a hindsight thing, but it’s something that you should consider if you do want kids and you would like to help with things like this sooner.

Not buying a house sooner  

This is not a problem that we have, but I know people do regret this. My husband and I built our first house when we were 20 and 21. Now we are 32 and 33 and we still own that house plus our dream house. Our friends all bought their first homes at the same time we bought ours, and now we are all building or buying our dream homes while other people our age are buying their first homes – their starter homes. It’s a completely different feeling to be out of that starter home and into one much larger, much more luxurious and much more dream-home-like. For us, this is not a regret, but I do hear people mention they wish they would have purchased far sooner.

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