The Role of Regret in Personal Finances: Constructive or Draining?

  • DH = Dear husband
  • DD3 = Dear third daughter

At our church, we were challenged to give up something for the season of lent – 46 days – leading up to Easter. Some people have given up chocolate. DH gave up coffee. I have given up TV and movies – with the proviso that I can watch Christian content. There are some great YouTube resources out there, and I’ve discovered, among others, the teachings of Andy Stanley. Over the last few weeks, I haven’t been pining for my Netflix series.*

Andy and Sandra Stanley

Last night, I watched “Me and the Mrs.” – a segment from Stanley’s sermon series “Guardrails” in which he and his wife talk about the boundaries – or guardrails – that they established early on in their relationship to protect their marriage, their finances, their family, and their work-life balance. I have written before about how envy has sometimes reared its ugly head as DH and I have walked our journey out of debt, but I’m happy to say I felt no envy as I watched the Stanleys speak their wisdom and describe their life.

I did feel regret though.

As I told DH about the segment afterwards, I was caught off guard by my voice cracking  – and tears. DH was even more caught off guard. He asked me what was wrong, and I did my best to capture it. I was overcome by a sense that we had – not exactly wasted, but compromised so many years. We had lacked intention in building our lives – we had just gone with the flow in the absence of a plan. We hadn’t communicated well with each other, and we hadn’t been solidly rooted or united in values to guide our choices. We had been all over the map in terms of competing priorities. Our financial stress of a few years ago was certainly one major result of that fragmented approach to life.

Regret: a constructive role

“Live without regret,” is a popular piece of advice. It’s true that we can do nothing about the past, so there is no point in devoting too much energy to it. It’s so much better to channel that energy towards building the future we want – and starting from where we are right now. But it’s also true that regret about the past can serve a purpose. It emphasizes what it is we don’t want, so that we can recognize it and turn away. It’s not a bad thing to know what to avoid. I, for instance, know that I don’t want to be a passive bystander in my own life. I don’t want life to happen to me. I want to be proactive – intentional.

Starting from where you are

The regret that surfaced in particular for me was the fact that I had to give up being a stay-at-home mom – which I had been for a couple of years after the birth of our third daughter – because of the financial mess we had blindly set up for ourselves. And having to go back to work full-time – after having previously worked part-time – when I knew I wanted to be at home, resulted in my depression for several years. And I mean clinical.

DH eventually got on his feet with his business, and inspired to take down our debt after reading Dave Ramsey’s The Total Money Makeover, we started from where we were – and moved forward. Almost four years later, we’re in a much, much better place financially. The positive ripple effects have impacted our marriage for the better, and we’ve been heartened to see that they’ve impacted our children as well. We weren’t too late to make a difference for them. There’s a lot to be encouraged by.

So why the regret? Maybe it’s this time of year – the long winter still holding on in these parts, bringing on the winter blahs. Maybe it’s a need for rest- which DD3 and I  will have next week with the March Break. Or maybe it’s that regret serves a purpose, and the timing was right for me to be reminded. I didn’t stay in it too long, and I’m harnessing that energy for a future of more intentional living. Of asserting healthy boundaries – or “guardrails” – to protect all that is important to me. So that I can live without regret.


Do you think that regret can play a positive role. Do you have any regrets that you have a hard time overcoming? Your comments are welcome.


*(Full disclosure with regards to my having given up TV: DH peer pressured me into watching one episode of the new House of Cards season with him when it came out. I was tired – and capitulated.)

*Photo courtesy of Simon Wright

24 comments on “The Role of Regret in Personal Finances: Constructive or Draining?

  1. Thanks for sharing Ruth. As much as I like to stay positive and move forward, I do regret that we did not start our money makeover sooner too. It does feel like we wasted time, lots of it. We are on a great path now, and have seem similar results, a better relationship for my wife and I, less stress, and children who are in much better shape to start their financial lives. The regret serves as a reminder of a time and place we wish to never return.

    1. I’m with you on never wanting to return to that place. And like you, I’m grateful that huge changes are possible even for those of us who start later than we could have. Thanks, Brian.

  2. Regret can certainly show you what you missed, but on the flip side it can show you what you’ve learned. As you move forward, that’s the part that will guide you to better opportunities and more financial freedom.

    1. That’s true. There is evidence of plenty of learning in this regret – as well of plenty of motivation to apply that learning. Thank you, Mr. Money Beagle.

  3. As long s you don’t ruminate too long in the past, it can teach us lessons. I totally understand where you are coming from, if not in a slightly different way, but when I was working full time before my layoff, I had such an opportunity to build up more savings. And even when I did start freelancing, I could have done SO much better with money to not be in such a financial pinch for 7 years. But I have taken the experiences and have applied it to my new full time job, where I’m going out of my way not to make the same mistakes. Enjoy your upcoming break!

    1. 7 years is a long time to be in a financial pinch. What a relief to be out of it! It’s great that you’re not letting your lifestyle rise to meet your income, and that you’re letting your savings rise to meet your goals instead. Thanks for the good wishes for the March Break : )

  4. Wow – I feel like you described my frustration with where my husband and I are right now! We recently had a big and very tense money talk, and I’m feeling a lot of the things you described – regretful that we didn’t stop our debt accumulation and develop a plan sooner, as well as feeling like we’re not being very intentional with our finances, and life, in general. We have basic priorities and somewhat nebulous goals (“save more for retirement”), but my husband feels that structures and specific goals are confining and limiting, whereas I love structure and feel confident that we need more of it. I’m well aware that we’re a good match because we balance each other out in a lot of ways, especially emotionally, but this is one area where we’re having more frustration than balance.

    (I’m planning to write a post about the big talk, but it was so stressful, I’ve been dragging my feet on getting it down “on paper”…)

    1. I hope that you will write about your conversation with your husband, Amy. It’s a delicate dance to get on the same page as your spouse financially. It sounds like your husband wants to have the chance to be spontaneous with money every once in a while. The thing is, that can be built into the structure you choose. We each have a discretionary allowance, and it acts as a bit of a buffer for our differences. I wish you very, very well in facing this issue with your husband and in working out, with some compromise and some flexibility on both parts, a workable system.

  5. Wonderful post as usual. We used to fall into a lot of regret – and still do on occasion. But we try hard to move forward and just focus on the future while, like you said, being sure we allow that regret to keep us from falling back into past patterns.

    1. Thank you, Laurie. I was truly surprised to have been overcome with regret at that point. I thought I had moved past regret and onto building the future. I think now that the two work in tandem.

    1. Thank you, Mackenzie. I will follow your advice and have a lovely weekend. It’s going to be an extra long one of 9 days with the March Break : )

  6. I don’t spend a lot of time on regret. With respect to personal finance/money management, as Brian noted earlier, I wish that I had started down my road to financial freedom earlier. However, I recognize that I can’t spend too much time and energy lamenting the fact that I did not. Generally, that is time and energy wasted. As you astutely note, ultimately, you have to start from from where you are. Learn lessons from the past, but don’t get mired down there.

    1. Thanks, James. I don’t spend a lot of time on regret either. This one just snuck up on me – I thought I had done with regret long ago. I’m with you on not getting mired in it. I’ll just take it as a reminder of where I don’t want to go.

  7. Great post Prudence!
    I agree that regret is a useful tool, like a compass showing us which way to head now. I think we also have to learn to accept who we were in the past as the total of our experience, knowledge, and biological make-up at that time. Accumulted life learnings and a willingless to act on those aha moments can lead us to living more congruently and with greater purposeful passion.

    1. Thank you, Shirley. Your comment makes me realize that I don’t accept who I was in the past. I think that I could have made wiser choices then, and I have some resentment towards my former self for not having done so. Perhaps a little former-self-compassion is needed here? Hmmm… Good food for thought.

  8. You’ve been through a LOT Ruth. But you’ve proven yourself to be a strong woman. I am in awe of that strength and I’ll bet a lot of others are too, including your dear family. Enjoy your time off. Sounds like it’s coming at the perfect time. 🙂

    1. I think that there are many people out there who have been through job loss and a time of lower income. For some, it’s not as difficult simply because they’re set up to absorb the difference – they aren’t maxed out. The additional stress we suffered was partly self-imposed. I will definitely enjoy the break : ) Thanks, Kay!

  9. Great post, and yes–I think regret can play a constructive role. I regret that I didn’t really understand investing when I started my first job. I made a mistake as a result; luckily it was a small mistake in the grand scheme. But it definitely motivated me to learn more about investing!

    1. How great that you learned from a mistake early on in the game! Some of us seem to have a more stubborn resistance to admitting to mistakes, and it takes us longer to learn. Another positive thing about regret is that it often serves as evidence that a real change for the better has taken place.

  10. As a depressive, I don’t find regret to be very constructive for me; but it definitely has possibilities. And it also helps you remember where you were. I now regret that we didn’t prioritize retirement more when we were getting out of debt (the fact that we’re still not prioritizing it will rear its ugly head I’m sure). But then I remind myself that we were living on disability, a contract job (that might, at any point, not get renewed) and unemployment. We had no idea how long the last two would continue. So we had to put every cent possible at our debt. If things had run out, we’d have been living on $730 a month.

    In the end, things worked out better than we could have hoped for, so I look at the wasted years through that lens. But at the time, it was probably the logical thing to do.

    1. I don’t think regret has any place in your decision to make getting out of debt a priority! Given your circumstances, it was the wisest thing to do, In fact, debt-reduction is wise for ANY set of circumstances. Now that things have worked out well, you are able to save more aggressively for both the short-term and the long-term. If short-term savings are of greater importance right now, that’s OK. You are on a good financial path. Abigail.

  11. There are really regrets I am dealing with. But, sometimes I realize that my attention shouldn’t be on that because it consumes my time and energy. I just consider that regrets should have a positive effect on me, making me a better person.

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