Common Business Regrets

After looking the research about regret and the biggest life regrets, I thought we covered it. (“WHAT?! More regret? Get over it Maggie!”) But then I came across an article published in 2012 the Harvard Business Review blog network about the top five career regrets. Since we’re still mid-career and this is still primarily a personal finance blog, I had to talk about it. (Last in the series of regret, I promise.) So, what do 30 professionals say are their biggest career regrets? I’ll tell you (along with additions as to how I think Mr. T and are doing on these potential regrets):

  1. I wish I hadn’t taken the job for the money. Mr. T and I are happy to report that this is not something we have done. Mr. T did take his current job because it was the only one available, but when the Great Recession started winding down, Mr. T and I had a few good conversations about how he could be making so much money elsewhere. But we consciously made the choice to stay because Mr. T’s flexible schedule and six weeks of vacation can only be improved if Mr. T left any job entirely. I also have a Master’s degree and could definitely choose to work full time, but it was important to us to have someone at home for the kids, especially These are decisions we have not regretted. Yes, it will take us longer to get to early retirement, but we get to enjoy the journey a lot more. For some early retirement people, taking a job for the money is part of the plan and I would argue they probably don’t regret that decision. But for Mr. T and I, we’ll take the slower pace and time with family now.
  2. I wish I had quit earlier. We may very well face these regrets. It’s so hard to say when the perfect time to leave actually is.
  3. I wish I had the confidence to start my own business. This is in our eventual plan. We have ideas brewing, but in sticking to the goals of being more present and maintaining a good balance, we’ll probably not get anything started this year. But we definitely plan to try some things. Otherwise we’ll regret we never did.
  4. I wish I had used my time at school more productively. We generally don’t have this regret. Though we both wish we had taken more classes outside our specific majors.
  5. I wish I had acted on my career hunches. So far so good here as well, but we’ll keep it in mind for the future. Act on career hunches. Noted.

So where do you stand on your business regrets? Do any of these resonate with you?

Business Regrets


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  1. Thank you — this was just what I needed to read today! 🙂 Sometimes we get in our heads and wonder if we’ll regret quitting one day, if we ever start to feel irrelevant (we have jobs now that make us feel very “plugged in,” so this is a risk we sometimes worry about). But it’s so heartening to read that people regret that they didn’t quit sooner. Phew! And as you definitely know, we stay in our jobs for the money, even though they are quite fulfilling as far as these things go, and make us feel like we’re helping people, for which we’re grateful. But that money comes with a price — an unsustainable pace, too much stress, effects on our health. I love that you guys have a much healthier, happier arrangement!

    • MaggieBanks

      I am grateful for that too (though we always might face that regret of not just leaving and doing our own thing… but that comes with a price as well and we’re not willing to pay it quite yet.)

  2. Although I worked my butt off in college, in some ways I do which that I had used my time more productively. I wish that I had taken more classes, because during college I paid full tuition and could therefore take as many classes as I wanted for one price. I really came to appreciate the benefits of this during my MBA, when I paid per credit. I no longer had the luxury of taking extra classes just for fun, and I regret not taking advantage of that when I had the chance.

    • MaggieBanks

      Interesting on the per credit tuition. Yeah, I paid full tuition both in undergrad and graduate school. And I did take some interesting classes that weren’t part of my major (we took sailing together one spring!), I could have done more to graduate as a more well-rounded skilled student. I’ve also heard that college is the one purchase most people actually want less for their money. They celebrate when class is canceled! 🙂

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