What Is Your Biggest Financial Regret?


We all have financial regrets that we look back on from time to time. This is perfectly normal and not something to be ashamed of.

In fact, it can do us good to think about these regrets now and then. Instead of trying to sweep them under the carpet we can then try and learn from them to avoid making similar mistakes in the future.

Not Going to College

For a long time not going on to take some sort of further education was a big regret of mine. I felt that with some sort of additional qualification would have helped me get further at work and earn more money as well. In the end, my life took a different route in which qualifications don’t matter and for a long time I haven’t even thought about the subject. However, from this experience I think I have learned to value education more and I’m definitely going to try and encourage my daughter to carry on studying for a few extra years. Heck, I might even pay for it.

Not Buying a House When Prices Were Low

Do you remember the days when houses seemed incredibly cheap but you never bought one? Property is one of those investments that tend to always do well over the long term. For example, I remember a beautiful rural property near where my parents lived when I was a kid. It is probably worth a fortune now but when I first started working it was within my price range if I had taken the risk on a big mortgage. Thankfully, this experience has stood me in good stead in recent years. I now live in a developing country in South America and when I first got here I made it my priority to buy some real estate. Prices have started going up now and I’m delighted that I didn’t miss the boat for a second time.

Not Being Adventurous Enough

Do you sometimes regret not being adventurous enough with your money? Maybe you once considered buying shares in a new company called Apple or perhaps a young guy called Donald Trump once asked you to lend him a few bucks and go into business with him. Ok, maybe not but you get the point. There are opportunities that pass us by time and again and the important point is to learn from any missed opportunities.

Being Too Adventurous

On the other hand, maybe you have lost money through being too adventurous in the past. Taking risks occasionally can be a good thing but it could be that you have learned not to be quite so bold in your decision making. We all need to find the level of financial risk that we are comfortable with and sometimes the only way of doing this is to make some mistakes and learn from them.

Not Paying Enough Attention to Your Finances

Finally, is it possible that you have simply not paid enough attention to your finances in the past? This is easy to do if you are earning good money and don’t feel much need to check out interest rates or investment possibilities. However, if you don’t take the time to find out how to make your money work harder for you then at some point you are sure to regret it. Sometimes all it takes is a couple of hours a week to put your finances in order and get a better return on your money. It might not seem like a big deal at the moment but at some point in the future you will be able to look back and be grateful for what you did in the past.

So what is your biggest financial regret?

20 Responses to What Is Your Biggest Financial Regret?

  1. Dave Lalonde says:

    Without a doubt, I wish I paid more attention to my finances when I was younger. If I only knew how to budget then, I would’ve been well prepared to retire sooner than expected. Also, I am more on the minimal side, so I wish I could’ve spent my money more on experiences.

    • Robert Bell says:

      Thanks Dave. I wonder how many other people have the same regret about not paying more attention to money issues when they were younger

      • Dave Lalonde says:

        Yes, it’s definitely not something that many young adults are not aware of yet. They need to save for retirement as soon as they can! It’s one of the best things you can do for your future!

  2. Right after I graduated college, I felt the need to leave the nest and entered into an expensive lease agreement. At the time, I did not monitor my expenses as closely as I do now which aided my decision in this mistake. While it was great to live out on my own (I learned a lot about myself and it helped me grow as a person), I should have lived at home a little longer and found a more reasonable place to live. This would have allowed me to save a lot more money and achieve my investing goals sooner. This may be rationalizing this mistake, but sometimes you need a kick in the mouth to help you grow going forward.

    Thank you for posting this article. It is a great conversation topic that will allow all of your followers to learn from others mistakes. Keep up the great work and I am looking forward to reading your future articles.

    • Robert Bell says:

      I guess that’s a common enough regret, DD. I did something similar myself at one point. Thanks for the comment

  3. I too regret not buying a house when prices were so cheap. I didn’t have tons of money then- but the government was offering the $8k tax break for first time home buyers. Now I’m finally ready and looking but there isn’t tons available. I have to remind myself there is always another boat coming.

    • Robert Bell says:

      You’re right Julie, something good is often just around the corner. The key is in using any regrets to not miss the boat again I think

  4. kammi says:

    I honestly don’t really have any. I’m happy with where I am right now and am a work in progress. I’m actually really happy that I’m also able to manage my own brokerage accounts, also, and I perpetually strive to learn more each day. With that in mind, this is a sort-of-regret. When I was younger (probably about 13 years old), I had already saved a good chunk of money (about $2000). I was into saving because that’s what EVERYONE in my household did and encouraged. My parents had some relatives over and one of them, who had a history of financial issues, was also invited. At the end of the evening, even though well hidden, my entire stash was GONE. I can’t even begin to describe how crushed I felt. I was able to recover it (of course) and learned better about just stashing that in a bank account or brokerage account, but that one really hurt. Lesson learned!

    • Robert Bell says:

      That’s an interesting story Kammi. Good to see that you learned something useful from it as well

  5. I don’t have financial regret yet. The story goes like this. I swapped my phone with iPhone, my family get angry to me because they thought I wasted my money for it. It is not true, I just swapped my phone with iPhone because it is my birthday wish and they never can’t buy one for me. They regret it so much but me? I never regretted it. I am very happy I got my wish with my own way.

    • Robert Bell says:

      Sometimes spending a bit more on what we really want doesn’t lead to any regrets at all Hannah. Glad to hear you made a good choice

  6. jim says:

    My biggest financial regret was never saying no to mine and my wife’s “mandatory” get togethers – that took place several miles away from us and occurred at least 4 times a year. We were young, had a little kid and were broke and we actually went in debt to attend those “mandatory” get togethers. Looking back, we should have just said “no” and saved that money for our kids’ education/down payment for a house/school loans etc. I don’t regret all of them, but I do regret the vast majority of them and when we finally put our foot down and started politely declining – Good Lord you should have heard the back lash – “what’s you’re problem” “you too good for us” “don’t you love us anymore” “oh sure, you’re young, you can afford it” blah, blah, blah. Really wish we would have learned to say no many, many years before we did.

    • Robert Bell says:

      It sounds like you got to the right deicision in the end Jim. Sometimes it can take a long time to be able to look back see things so clearly

  7. My biggest financial regret was turning down an opportunity to buy Apple Stock when the company was first starting! Maybe this falls into your “Not adventurous enough” category. It can be difficult to know when to make your move and when not to. But if you keep playing the investing game, you have a better chance of making some excellent choices.

    • Robert Bell says:

      That would have been very nice WD. You are right, if you keep on plugging away you have more chances of success

  8. When my wife and I built our home 10 years ago, we maxed out on what the bank said we could afford – which led us to being “house poor” for quite a few years. If I could go back, we would have done things differently so we wouldn’t have had to struggle for that period of time.

    • Robert Bell says:

      Thanks for that Brock. It’s a tough balancing act between borrowing a lot to get on the property ladder while it is affordable and borrowing so much that you face a real struggle to pay it off

  9. dojo says:

    Not starting out with my business earlier. I never took it seriously until I lost my job. It’s been 5 great years since then, but I can only imagine my success if it was 10 years for instance.

    • Robert Bell says:

      That’s probably a common regret Dojo. It can be frustrating to think about the time spend before you founnd something you love and are good at

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