Regret Minimization

Feb 27, 2023

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Considering regrets is a part of life. We wonder if we should have done something differently or not done something at all. We wonder what might have changed if we’d made another choice. Would things be better? Would they be worse?

Since I’ve been a coach, I’ve found the reality of evaluating past decisions and having regrets comes up a lot. And I have pondered and explored the possibility that there may be two ways of looking at regret. The first consideration is that regret is both a noun and a verb. The second consideration is whether or not indulging in regret can be avoided. Might we, instead, find a method for regret minimization? I think so. Let’s talk about it.

“Is there something that you regret not doing in the past that you could choose again for the future?” – Dr. Sara Dill

What You’ll Learn

  • Noticing regrets with intention
  • Projecting into the future
  • Themes from the terminally ill
  • Living your life true to yourself
  • Regret minimization framework (from Jeff Bezos)
  • 3 questions to evaluate decisions

Contact Info and Recommended Resources


Top Five Regrets of the Dying: A Life Transformed by the Dearly Departing by Bronnie Ware

Podcast Episodes that pair well with this one:

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I'm Dr. Sara Dill, and this is the Stressless Physician Podcast, episode number 55.

Welcome to the Stress Less Physician Podcast. I'm your host, Dr. Sara Dill, MD. Using my unique combination of coaching and mindfulness tools, I will teach you practical ways to reduce your stress level, feel happier at work, and create a better balance between your medical career and personal life. If you are a busy practicing physician who wants to design a life and medical career that feel good to you, you are in the right place.

Hey everyone, welcome back to the podcast. I hope you are well and having an amazing day. I am having a pretty good Monday, and now I'm hanging out with you, which is even better. So, I have a puppy who's 15 months old and I have to say little Teddy Winston has been very challenging for me. And so I was feeling super frustrated this morning and I've been considering whether it was just a mistake to have gotten him. Although I love him and he's super cute and he's a very sweet dog, but as anyone who has had a puppy, which I had never had before, knows puppies are a lot of work, and I was just thinking about would I regret re-homing him? Would I regret not keeping him? And what do I wanna do?

And I don't want to re-home him. I don't wanna get rid of little Teddy. I do wanna double down. I decided on my efforts to help him with barking, cuz that's one of the things that has been problematic for me, especially on the days that I work from home. And I've decided that I am going to enlist a private trainer. I've signed up for some additional training cuz as any everyone knows, I am really the one that needs to get trained.

But I was thinking a lot about regrets and in asking myself about did I regret getting him in the first place or not. And so I wanted to talk more about it. I don't think I've done a podcast on this before, but regret is something that I coach on a lot and I know I often talk to clients and also talk to myself in my head about the idea of not engaging in regret, not indulging in feeling regret.

I always like to first go to the dictionary and then I'm gonna come back to this idea about whether or not we are indulging in choosing to feel regret and whether we can opt out of that. But I found a few definitions of regret that I like and it's interesting, and that regret can be both a verb and a noun. And so one of the definitions that I liked is, as a verb, regret means to feel sad, repentant, or disappointed over something that has happened or been done, especially a loss or a missed opportunity. So it's about something that's happened in the past.

Regret as a noun, a definition of that is a feeling of sadness, repentance, or disappointment over something that has happened or been done. So it's either the feeling or it's the action of feeling regret, of feeling sad, and repentant. And a slightly different definition that I liked was a feeling of sadness about something sad or wrong, or about a mistake that you have made and a wish that it could have been different and better.

And another discussion point that I found that I really liked is actually in a research article looking at researching regret, and it's defined more scientifically or more tightly, as a self-focused negative emotion about something that has happened or been done to us. We feel bad because we did or didn't do something we believe we should or should not have done. And given that regret involves acknowledging our own role in our present circumstances, regret also often includes self-blame. And so I really like that definition because I think it highlights the sort of flavor of self blame that regret often carries with us or with it.

So I wanna go back to this idea about, what if we could not indulge in regret? Is this an emotion that we should catch ourselves in the middle of? And, because our thoughts are the ones creating our emotions, if we're telling ourselves, "Oh, I should have done something differently", or "I could have done something differently, and then I would be in a different situation", those are thoughts that we could work on not believing, on not indulging in. And so if regret is an emotion caused by how we're thinking about something we did or didn't do in the past, and labeling what we did as a mistake, is that optional?

And I don't think that feeling regret is very useful. I think when you stay in it, I think that if you notice, you're feeling regret, you're in that state of sadness, repentance, or disappointment in labeling something, a mistake, and blaming yourself for it. I think that's helpful to catch as quickly as possible, because I do think there's information for you in that. I think there's information for me in thinking about why I chose to get a puppy when I did and do I like my reasons for it still.

So I think noticing what we regret can be very useful when we do it intentionally. It provides good information. As you know, I always believe, and this is sort of logical actually, that when we tell ourselves, "Oh, I wish I could go back and make a different decision", that's not something that's possible to us. We can't go back and make another decision. So the reason we feel negative emotion is that it's a thought that doesn't even really make sense. And yet, you could go back and decide, "Why did I make that decision? What were those reasons? Do I still like those reasons? Would I choose that?" That's useful I think in having regret highlight that and then moving into those questions.

I also think, and this is what I wanna talk about today, I think projecting into the future and asking yourself what you might regret doing or not doing, what you might regret experiencing or not experiencing, can be very instructive in helping us live a life that is meaningful to ourselves and that feels like our life. This is a process that I really like to go through when I'm making a decision and I'd like to offer to you.

This is the idea of regret minimization. And the reason this also came to me is that I came across an article and a book called the Top Five Regrets of the Dying. And so this is a book that was written by an Australian nurse, and interestingly enough, she's also a songwriter, but by a woman named Bronny Ware. She spent several years working in palliative care, caring for terminally ill patients in the last couple months of their lives.

And she initially posted on her blog about this, about the themes that she came across and the themes that she found in working with the terminally ill, and so she then put her observations into a book called The Top Five Regrets of the Dying. And the top five regrets of the dying, according to Bronny Ware, the number one top regret was: I wish I'd had the courage to live a life true to myself, not the life others expected of me. Number two: I wish I didn't work so hard. The number three most common or top regret of the dying was: I wish I'd had the courage to express my feelings. The fourth one is: I wish I had stayed in touch with my friends. And number five is: I wish that I had let myself be happier.

I think we could talk about all of these. I think this is so interesting and it resonates so deeply with me, but what I wanna go back is talk about that first one: I wish I'd had the courage to live a life true to myself, not the life others expected of me. And I think so many of us, certainly myself, this is what drove me into coaching and personal growth, was this feeling that I was living a life that others expected me to do and that I had taken on expectations, consciously or unconsciously. And I felt like I was living a life that was close to what I wanted to be doing, but sort of in parallel.

And some people, might be living lives that feel very distant from what they want to be doing. What feels true to yourself? So this idea, of really reflecting on this possible regret of the dying then ties into this idea or this technique of regret minimization.This is sort of a long , a long beginning to this. So the regret minimization framework, I love that title because it sounds so nerdy. It's actually based on a technique that is, popularized by Jeff Bezos from Amazon. And so he labeled this framework or this idea of regret minimization framework as how he initially made the decision to leave his job and start Amazon. And I again like it, and you can see different versions of this, but I wanna give him credit for this particular title, but so it's pretty easy.

What I'd like to offer you is if you are faced with a difficult decision, really any sort of decision, but certainly one that you find difficult or that seems to have a big impact potentially, there are four steps that you can do. So I just want you to think about if you have a decision that you've been thinking about, just try it on. All right?

I want you to pick one. The first step is to imagine yourself much older, like 80 years old. So you're gonna project yourself forward into the future to whatever ripe old age you wanna pick. Eighty is a nice round number. The second step is to look back on the decision that you're contemplating making. So you as an old person, whatever age that is, maybe a hundred, look back on the decision that you're contemplating now and ask yourself, this is step three, will I regret not having done this or tried this?

Okay, so at 80 years of age, when I'm reflecting back, is this something I'm gonna regret not having tried to do? If the answer is no, "No, I'm not gonna regret not having tried this." Sorry for the double negative. " No, I won't really care." Basically then don't bother, right? Your decision's made. Don't do it. Done.

But if the answer is yes, I would regret not having tried this. When 40 years in the future, 50 years in the future, 60 years in the future, wherever you are. So if the answer's yes, I will have regretted not trying this, then you can ask yourself a follow up question. If I fail, if I try this or I do this, if I fail, will I still be glad I gave it a go?

That could look like travel. It could look like quitting your job could look like starting a new job, a new career. Could look like getting married, getting divorced. So many different things. For me, looks like keeping Teddy or not keeping Teddy. So if your answer is yes, "I will regret not having tried this in the future", and you ask yourself, "If I fail, will I still be glad I gave it a go?" If your answer is yes, done. Your decision's done. That's a yes and a yes. And then the fourth step is to take action. That's where we often find it difficult. Some of us who spend a lot of time thinking and less time acting.

So those are the four steps, regret minimization framework. When faced with a difficult decision, number one, you're gonna imagine yourself much older. Maybe lying on your deathbed or an elderly person reflecting back. Number two, you're gonna look back on the decision. Number three, you're gonna first ask, will I regret not doing this, not having tried this. If the answer's no, then done, you don't need to even do it. If you aren't gonna regret it, then don't do it.

If the answer is yes, I think I would regret not having done this, then you can ask, if I fail, will I still be glad I gave it a go? And if that answers yes, then full steam ahead. Number four, take action.

And the goal of this is to minimize the decisions you make that could lead to regret in the future. Yes, you can decide not to feel regret, but how much better to act in your own integrity, to take the actions that you wanna do, to go after what you want in spite of the fear, right? This is really about helping you move beyond the fear and worry that you might have in the short term about the failure of it about not achieving your goals.

If you weren't afraid to fail, what might you be trying? And I came up with the second exercise cuz I love exercises. And this may resonate with some of you that don't like the previous one, or this is a slightly different flavor or version of it, but this is another way to ask yourself some questions, especially if you're feeling dissatisfied or unhappy or not sure about whether to make a decision that you're wrestling with.

How long have you been spending on making decisions? What if you just made decisions more quickly? So another exercise, again, starts with projecting yourself into some future older age. Again, I like 80. It's a nice round number or 90, but whatever you want. And then you're gonna ask yourself three questions. So you older you, you're gonna ask yourself: I spent too much time in my life worried about blank. What is it? Second question: I spent too little time in my life, blank. That could be, I spent too little time doing this or experiencing this. And the third question is if I could live my life over again, or you could ask yourself: if I could make a specific decision over again, I would blank.

So ask yourself, what did I spend too much time worried about in my life? Ask yourself, what did I spend too little time on or doing in my life? And if I could live my life over again, what would I do differently? Are there decisions I would make that would be different? And so this also is another way to get at that regret minimization.

Yes. We don't have to feel regret. We can work on our thoughts and disbelieve them and understand our reasons for why we made choices. And how amazing is it to live a life where you don't have to do that. You don't have very many regrets that naturally arise. What would a life that's full of meaning look like for you? Is there something that you regret not doing in the past that you could choose again for the future?

All right, I'm gonna leave you with that. If you want help with this, I would love to talk to you more. Feel free to email me at [email protected]. And look out for an announcement. I'm going to open up a new group coaching session. Or maybe two. And if this is something that resonates with you, I'd love to work with you, either one-on-one or in a group. So stand by.

I hope you have a wonderful week, and really just try doing this exercise next time you're making a decision. Let's not waste time on decision making. Let's not make decisions that we already know we might regret. Yes. We can work on the regret, but let's just make a different decision to start with. Okay. Love hanging out with you. I will talk to you next week. Bye.

If you are a busy practicing physician, ready to start feeling less stressed, enjoy work more and learn how to create a more balanced and sustainable medical practice and life, sign up for a consult call with me at It would be my privilege and pleasure to work with you.

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