Regret: A Treatise

July 27, 2023

I listened to a Happier episode today about regret. I found the topic fascinating, in part because . . . regret isn’t logical, in a way!

You can do X and regret not doing Y.

You can do Y and regret not doing X.

But truthfully, you often can’t do two things at once! You have to choose. I feel like it might be very natural to feel like we made the wrong choice, because of the grass-is-greener phenomenon. You might not see the downside of the choice you didn’t choose.

I think this was sooooooo applicable (and mind-bendingly difficult) in the COVID era — it was so easy to regret doing something or regret NOT doing something. I think at some point, I personally had some regret fatigue. And that can be pretty paralyzing actually – it makes it hard to make any choice at all because OMG-WHAT-IF-I-GET-IT-WRONG-AND-REGRET-SOMETHING?

Let’s take Taylor Swift.

I really wanted to go, and I didn’t buy tickets.

Do I regret it? MAYBE

If I had bought tickets, would I have regretted spending thousands of dollars on (probably) bad seats with kids who may not have the concert endurance that Taylor does? MAYBE

I guess in some way my choice was made more by balancing regret probabilities than anything else.

There are also areas of life in which I feel like TINY regrets are very helpful.

I regret that I didn’t do piano with G last night. I’m trying to build this routine with her (for ~10 min, nothing crazy) but I was tired (and a bit moody – riding the hormone roller coaster right now!) and this takes a LOT of energy because even getting her to try for that length of time is very challenging for both of us.

But when I put her to bed I didn’t feel like we really spent any quality time and I felt both guilty and regretful. That feeling is helping me put piano higher on the priority list tonight even though I still don’t feel amazing.

I guess my takeaway is that I think regret is an incredibly powerful and interesting emotion and I’m glad the episode made me think about it! I do NOT regret listening to the ep 🙂


  • My college choice
  • Med school / residency / fellowship choice
  • Leaving my PhD
  • Starting this blog!!
  • My husband choice 🙂
  • Stopping running in 2010-11 to focus on fertility (I mean from this vantage point it seems like nothing but back then it felt like A Decision)
  • All 3 kids!!!!
  • Hiring our nanny nearly 10 yrs ago
  • Going part time in my clinical role + focusing on writing/creating/podcasting
  • Basically every vacation (except maybe this one lol)
turns out being up all night with a toddler EVEN LESS FUN at the Ritz


  • Not starting my newsletter list earlier
  • Not staring a podcast earlier!
  • Not discovering the library + the hold system until I was old!
  • Not seeking therapy at certain times in my life when it would have been helpful (or waiting too long to do so)
  • Hours spent on social media ( + not quitting sooner!)
  • . . . honestly, I had to dig pretty deep to come up with regrets! I guess that’s a good thing. (I’m not even THAT broken up about Taylor. If the stars align, I’ll see her eventually.)


  • Reply Gwinne July 27, 2023 at 7:32 am

    Interesting. I was just reading Brene brown on regret. She ssays its important because it teaches us. I really don’t use that word to describe my experiences in general. Certainly not major life choices….you make a choice and you make another choice and… I learn from.poor choices without “regret

    Certainly I’m aware of many things I wish I’d handled differently in hindsight, but I think regret can only apply to an active choice made with knowledge. Like if I had known X, I would have chosen to do Y instead.

  • Reply Suzanne July 27, 2023 at 7:51 am

    Regret is such an interesting topic and I love your thoughts on it — the “tiny regrets” is such an intriguing idea, and I am going to think about that. I can definitely relate it to things like spending too much time scrolling or being snappy when I could have chosen a different way of responding.

    When it comes to big regrets… I don’t know how to evaluate them. I try to make choices based on the best information I have, and sometimes it just doesn’t work out, I guess. I think my biggest regrets are things that there is no opportunity to re-do, so I don’t know if the “lessons” I’ve learned make that much of an impact going forward, if that makes sense. For example, I regret that I didn’t stop working when my daughter was an infant. At the time, I didn’t want to stop working for many reasons, plus at the time my income was helpful to our financial situation, so it made sense to keep working. But now I look back and see all this lost time, all this untapped potential for bonding and relationships etc. I’m not sure what to extract from that that I can put to work in my life going forward, except to make the best of the time we have together. It seems to me that regret is so painful because often you *couldn’t* have made a different choice, because you simply didn’t have the experience/wisdom/hindsight you have now.

  • Reply Lisa of Lisa’s Yarns July 27, 2023 at 8:26 am

    I haven’t had a chance to listen to this episode but will on one of my runs this week. I don’t have many regrets either. I do regret buying my first condo back in 2005. I worked in the mortgage industry so kind of felt like everyone was buying a house. I should have waited. It was an educational experience, though. But I was very stuck with that condo for quite some time due to the 2008 market collapse. I was so happy when I was able to sell it in 2018. It was still well below what I paid for it but I didn’t have to bring money to the closing table. I also regret not having a better attitude about my unwanted relocation to Charlotte in 2013. The timing was terrible as I had just met the man who is now my husband. I should have gone to therapy but I really don’t know how I could have with the number of hours I was expected to work. I got permission to leave at 5 each day – so 10 hours after I started my work day – to study for the CFA exam; I studied 20 hours/week. I use that as an example to show how very unhealthy that company/team was. I was so intensely miserable, though, and that’s when I got dx’d with RA (I feel like the stress of that move was a major contributing factor in trigger the onset of my disease). But I could have handled the move better than I did. I am glad I traveled as much as I did while I lived there, though!

  • Reply Think I'm going to stay anonymous for this one July 27, 2023 at 8:27 am

    The only real regret I have is about my college experience. I think I would have benefitted from going to a smaller school, but – because of the Bright Futures Scholarship – a large public university was the only thing in my family’s budget. There was this vibe at UF at the time that there were “too many” students who wanted to be engineers, doctors, lawyers, etc. and that a lot of students needed to be flunked out of classes so that they would have to change their major to something “for dumb people”. So even though I was a strong student and made great grades, I spent my entire college career feeling stupid and worthless, which led to – what I now see was – a mental health crisis, which no one noticed because I was one of 40,000 students.

    While I have a few fond memories of college, other than my husband, who I met there, I didn’t form the kinds of special friendships that many people do. And I had almost 0 fun. I think if I had been able to go to a smaller school where I could have had positive relationships with my professors (instead of hostile relationships), I would have had a more positive experience and might have gone on to have a “big job”.

    But OTOH, things have worked out okay for me. Would I be happier with a big job? Probably not happier, but happy in a different way… I do think it’s made me much more conscious about how I talk to my own kids about setbacks. I feel like – to my parents – any time I did anything less than “perfect” in their eyes, it was a sign of a huge personal failing. But instead of making me want to work harder, it made me brittle and paranoid. As much as I love them and am glad of our relationship today, I live in fear of their judgement. I guess maybe the lesson I learned from my regret is the importance of resilience, and that sometimes bad things just happen…

  • Reply Omdg July 27, 2023 at 8:35 am

    I have no regrets about letting Dylan quit piano. I would have had to force her to practice every day, sit with her the whole time, and deal with constant complaining, and I don’t consider that quality time in any way. I was sort of surprised you put it in that category! I do make her do advanced math, which she complains about also, but to me that seems like a more worthwhile investment, and I actually enjoy helping her with math whereas piano… not so much. I suppose if I were a good mother we’d have done both, but oh well.

    Thinking about anticipated regret (no GR did not invent this idea) now is totally paralyzing. I absolutely despise about 50% of my job, but what if doing something else is worse. I am not sure whether I regret going to medical school, but I might. I do absolutely regret my choice of where I did residency.

  • Reply Florence July 27, 2023 at 8:37 am

    I find regret difficult to evaluate… sometimes I regret choices, but think I would also have regretted making the opposite choice. I regretted only taking 6 months of mat leave per baby for my two older kids (I’m Canadian, so this is considered short here) but I definitely would have regretted not splitting the 12 months with my husband as he would have been done residency a year earlier and it would have delayed post-residency life by a year. And there are some choices I initially regret that I later am happy about (when I was pregnant with my third, I regretted having only 3 years between my second and my third because my second was a crazy two year old…by the time he was born, three years seemed like a perfect age gap). There are somethings I didn’t do that are clear regrets…like not getting a Toyota Sienna in 2020/2021 hah! And also not better celebrating certain milestones like my oldest’s first birthday (we invited no one and did a quick cake smash with no decor because I was on call and I reasoned my son didn’t care…now I realize it was a milestone for us parents not the baby and my kids want to see their cake smash videos on repeat and our second has a much nicer homemade cake and pretty decor haha) and the end of med school and residency (we basically did nothing to celebrate except enjoy our time off…still nice but now I look back and realize that I’ll never hit that big of a career milestone again!). I do not regret quitting the research masters I was starting prepandemic… turns out it would not have been useful at all at my current job!

  • Reply AW July 27, 2023 at 11:38 am

    To be fair, G also looks like she regrets agreeing to the trip ;).

    • Reply Sarah Hart-Unger July 27, 2023 at 12:26 pm


  • Reply Jessica July 27, 2023 at 2:53 pm

    I haven’t listened to this podcast yet but have it queued up. I personally hate the philosophy of “No Regrets” I think it’s similar to mistakes, we all make them and it’s a part of life. How we move forward is what matters. One of my biggest regrets is my college choice and overall experience. I didn’t take it seriously at all. It was basically 4 years of social time and parties. Maybe because my parents paid for it and my mom was very opinionated about where I went I just wasn’t as invested. But part of me feels I wasted those precious years. But the impact it’s had on me now is that I take advantage of opportunities and don’t waste time, so I’ve learned.

    • Reply Sarah Hart-Unger July 27, 2023 at 3:09 pm

      Love that Jessica!

  • Reply Name withheld this time July 27, 2023 at 3:38 pm

    I probably won’t listen to this podcast. I’m 62 years old and in the past few years I’ve done lots of reflection on my life. I’ve decided for me no regrets means I’m done reviewing the things in my past that make me feel shame, self criticism and perfectionism. Are there things I could have done differently- yes. Can I change that now- no. I am looking forward now to make the most of the time I have left on this earth.

    • Reply Sarah Hart-Unger July 27, 2023 at 3:43 pm

      Totally makes sense!!!

    • Reply Gwinne July 27, 2023 at 5:14 pm

      Yes!!! I know i have made mistakes and learned from them. I do not “regret” making the choices i did. They have defined me. I feel like it’s more than a rhetorical distinction…your comment about shame and self criticism is clarifying for me about why. And “REGRET” is way too weighted a word for small things like eating one too many pieces of pizza.

  • Reply Lizzy July 28, 2023 at 5:18 pm

    Only sort of related, but the quitting running/fertility “non-regret” gave me a lightbulb moment! I had been training for a marathon and trying to get pregnant last year when I quit training for other reasons and got pregnant that month! Obviously could be due to a variety of factors but this is one I hadn’t connected the dots on. I really appreciate you sharing.

  • Reply San July 28, 2023 at 7:35 pm

    Regret is an interesting topic. You’re right – there’s often a choice and we can’t do both. I am often paralyzed by these kinds of choices (unless it’s a decision about dinner or what colored shirt to wear).
    But I guess we’ll have small regrets in our lives (out of necessity) and it’s always a good learning experience.

  • Reply Daria August 3, 2023 at 5:43 am

    Regret: not having a mentor in younger years/college, being homeschooled (not my decision), not standing up for myself enough, overpaying for my first condo in 2008 then not making any profit off the sale 10 years later.

    Not regret: everything else :))

  • Reply Jessica August 8, 2023 at 12:26 pm

    Just FYI in case you missed it – Taylor has added new dates in October in Miami. Maybe there will be cheaper tickets on resale when the tickets go on sale tomorrow 🙂

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