Financial Mistakes You’d Make All Over Again

I think it’s fair to say that every single one of us has made some financial mistakes.

There are several that I regret — getting into debt, buying gifts I couldn’t afford to try to make someone happy, and cashing out a retirement fund.

Then there are a few that could have ended up disastrously but didn’t — mistakes that I made but miraculously escaped from by the skin of my teeth without huge negative effects. (Buying a duplex on an interest-only loan when I didn’t even have an official job being one of those.)

But then, there are the financial “mistakes” that I’d make all over again.

What I’d do again

One of those was quitting my full time job with benefits and a 100% 401k match to….go work in West Germany for 3 three months. I worked in a tourist information office, staying with a host family and receiving a VERY small monthly stipend that basically paid for lunch and bus fare.

From the financial perspective, it was kind of a dumb thing to do. I did at least speak German, but I remember landing at the airport and wondering what the heck I was thinking.

Things were by no means perfect while I lived in Germany. Some of them were far from perfect, in fact, but I learned a lot about myself, and I would do it again even in hindsight. (I might do a few things differently while there if I had to do it over again, but I would still quit my job and go.)

Sure, my bank account suffered, and my old job was not immediately available again when I returned.

Benefiting from your mistakes

Sometimes though, we need to make mistakes to grow. And sometimes the things that appear to be mistakes from the conventional perspective actually set us on a positive path that we would never have otherwise gone down.

So, are there any financial mistakes that you’d make all over again? What were they, and how did they turn out?


  • Actually, I’ve been sitting here for 10 minutes and I can’t think of a single one. I just keep thinking about all the Monday-morning quarterbacking I’ve done… but nothing worthy of repeating, unfortunately.

    No, wait, I’ve got one. I went to a very pricy, very well-reputed university for undergrad. I had a lot of student loan debt when I graduated, but it was WORTH EVERY PENNY. For one thing, I met my husband there – and if I hadn’t met him, my entire life would be different and I wouldn’t have my kids. That alone makes it worth it!

  • I am so happy for making my mistakes as otherwise I would have not learn’t a ting about the real world. I want to make one like your Germany adventure, I work in IT and jobs with German speakers get a considerably higher salary. So if I did lose some money in the short term the risk would be worth it if I managed to come back into employment with a new skill and new pay packet!