In this episode, Adam Walker and I dig into Daniel Pink’s book “The Power of Regret“.
You can listen to the episode here:
For more on Adam, including his blog, newsletter, and podcasts, check him out at adamjwalker.com.
For more on the Monty Hall problem that we discussed, this video is a great place to start.
Mickey: [00:00:00] Regret is not dangerous or abnormal. A deviation from the steady path to happiness. It’s healthy and universal. An integral part of being human regret is also valuable. It clarifies, it instructs done right. It needn’t drag us down. It can lift us up. The purpose of this book is to reclaim regret as an indispensable emotion and to show you how to use its many strengths to make better decisions, perform better at work and school, and bring greater meaning to your life.
So that was from Daniel Pink’s book, the Power of Regret in joining me to discuss it today is Adam Walker. So Adam, welcome.
Adam: I, uh, I hope I don’t regret this
Mickey: No doubt. So, so who are you, Adam? Tell the folks a bit about yourself.
Adam: I’m still trying to figure out who I am. Let’s see, uh, Adam Walker known for, uh wearing fedoras and having a million kids, also known as five. And, uh, I do marketing and some podcasting and marketing content and just kind of all the things.
Mickey: All right, cool. Yeah, you’ve done this podcasting thing a lot more than I have, so yeah. This should be good. Yeah.
Adam: a several
Mickey: How many episodes of Tech Talk [00:01:00] Y’all do you have? Like
Adam: I think we’re at like two thirties or, or no, are we
Mickey: I thought you had 300 and some. Yeah.
Adam: we’re at like 300 something there. And then we’re at like Two 50 maybe for the Susan g Komen one. Uh,
Mickey: you’ve got a couple. Yeah.
Mickey: Yeah. So yeah, so today’s The Power of Regret, which yeah, was an interesting book. We’ll get into some of the surprises we found. And really the big one for me is that regret can be a positive thing. And he talks a lot about ways regret can be used for good. ’cause we always hear regret as no regrets.
Like you gotta just do it, avoid regrets at all costs. And maybe that’s not not the case. Um, he gets into to four main types of regret. I think it’s probably worth framing those to kind of get into the conversation, but . The four regrets he talks about in the book are foundation regrets, , focused on long-term efforts around like health or finance where you just didn’t stay healthy throughout your life or didn’t save money and just affect you in the long run.
Boldness, regrets, like failing to start that new business or learning to play new instrument. Um, I think you’re, that’s not when you have too much ’cause you seem to be starting a new business all the time, so that’s good.
Mickey: although, can you play guitar and piano? Like, yeah. Okay. Well there you go.
So you have none of that.
Adam: not good at it,
Adam: [00:02:00] I can do
Mickey: All right. Uh, the third one is moral regrets, where you wish you had done the right thing. You, you feel bad about something you’ve done before. And then connection regrets where you let relationships slide over time. So those are the four kinda regrets you talked about. And again, I think those are all kind of bad things, but again, it’s how you spin them for good.
Uh, what were kind of your overall thoughts on, on what you got outta the book?
Adam: I, I mean, so first of all, was kind of surprised that I enjoyed it as much as I did.
Adam: like when you, when you go into a book like called the Power of Regret, you just sort of expected like, this is probably not gonna be that great. Um, and it was fantastic. I mean, good enough to where I chose it to talk about
Mickey: There you go.
Adam: of the, of the many books that I’ve read recently.
And so, , I think what I really loved about it in particular is kind of this quote, uh, which is if we know what we truly regret, We know what we truly value.
Mickey: Yeah. I love that one.
Adam: being that like if you, if you go through something and you can reflectively look back on it and say, man, I really regret the way I behaved, or I really regret the actions that I took, or whatever, then it, it gives you this, in this interesting [00:03:00] and weird insight into yourself in a deeper way than you would otherwise have. And then you can go, oh, I, I really value this and therefore moving forward, I’m gonna make choices do not lead to that same
Adam: that’s, and that is ultimately the power of regret,
Mickey: Yeah, I like that. Yeah, he, another quote I think that ties into that, he said, uh, quote, a look at the research shows that regret handled correctly offers three broad benefits. It can sharpen our decision making skills, it can elevate our performance on a range of tasks, and it can strengthen our sense of meaning and connectedness.
So yeah, same kind of thing where if you look at the regret and use it in a positive way, it can, it can do some great things for you.
Adam: Yeah. the other thing I loved is He talks a lot about or a bit, I mean, regret is kind of this feeling, right? It’s this emotion that we have, And he sort of ties in, he goes to this argument that I’ve never heard anybody go through before. It’s a little philosophical, but he basically said, like, asked the question like, what are, what’s the purpose of feelings?
Adam: do we have them? Because like we, you cannot, you can think about like, what’s the purpose of thought and the purpose of thought’s pretty clear. The purpose [00:04:00] of thought is so that you take action. So you do something
Adam: think about something, you make a plan, you make a strategy, you do it.
Thoughts lead to doing. what are feelings for? And you know, do, do feelings. Should feelings be directly tied to doing. Probably not. ’cause I feel like we make very bad decisions based on
Adam: Um, should, do we feel feelings just for the sake of feeling them? Probably not. Because what’s the point in that particular case?
And so his, his quote here is when FE is that the premise is feeling is for thinking. So the quote is when feeling is for thinking and thinking is for doing. is for making us better. And so the,
Adam: point being that regret’s a feeling, it, it’s a feeling that is for thinking to make us think more clearly about something. And that thinking is that for doing so, that we do something based on that, that clear
Mickey: Gotcha. Yeah. I think you see when people use feeling straight into doing it usually results in bad things where they, yeah, get married hastily, or punch the guy in the face, or just, yeah, do something just without that thinking. Step in between, which is
Adam: Listen, [00:05:00] most of my regrets related to my children are, are feelings to action with no thought in between. Like, and, and honestly, if you think about it like too, like almost every time you as a, a spouse have said something that’s just profoundly stupid there, you’re missing thought
Adam: So I, you know, if you can add that thought in between, I feel like we’re all probably better people.
Mickey: Yeah, the thought kinda leads to another quote he talked about with, uh, the no regrets philosophy and how, how that’s a bad thing. I love this one. This is kind of a longer quote. I’ll read the whole thing here, but,
Mickey: so however, one group didn’t feel any worse when they discovered that a different choice would’ve produced a better outcome.
People with lesions on a part of the brain called the orbital frontal cortex quote, they seemed to experience no regret whatsoever. In neuroscientist Nale Camil and her colleagues wrote in this journal of Science, the patients. These patients fail to grasp the concept. In other words, the inability to feel regret in some sense, the hypothesis of what the no regrets philosophy encourages, wasn’t an advantage.
It was a sign of brain damage. So people that don’t [00:06:00] feel regret and have no regret are because they have lesions on their brain and yeah. So
Adam: I, I did in particular though, like the, the story of the person with the no regrets tattoo, where regret is
Mickey: no regrets. Yeah.
Adam: like that, like I could almost see myself getting that tattoo, like that feels like so on point to me and so hilarious. Like I, I’m half tempted,
Mickey: Do you have any tattoos?
Adam: I do not.
Mickey: Okay, I don’t either.
Adam: specifically I do not have any tattoos. Because I, I can look forward and go, I will almost definitely regret that. And so like,
Adam: think there are situations where people get tattoos that they absolutely will never regret. I’ve got a friend that’s got like, uh, I think arrows on his arm, one for each kid.
Adam: gonna regret that, right? Um, but I think you have to be very thoughtful about it. And I find that, know, I, I tend, I have this tendency to look back on myself five years ago and go, man, what an idiot. Like, I was such an idiot five years ago, and then, you know,
Mickey: That’s a good sign though.
Adam: And so I feel like I’m gonna do, if, if there’s a tattoo involved, I’m probably gonna do that, and I don’t want to regret
Mickey: [00:07:00] I can see that. That’s kinda where I’m, I don’t have any, but I could see for the right reason maybe. Yeah,
Mickey: Um, I thought another interesting thing, it brought up a few other things I’ll get into, but was about people that . Regret making changes. So he’s the quote from the book I like to hear.
He said, the conventional wisdom is plain. Stick with your first instinct and don’t change the answer. So talking about like taking tests,
Adam: Yeah. That’s,
Mickey: you know,
Adam: the typical
Mickey: that’s what they say, and the conventional wisdom is also wrong. Nearly every study conducted on the topic has shown that when students change answers on tests, they’re significantly more likely to change from a wrong answer to a right answer than they are to switch from right answer to a wrong one.
Students who change their answers usually improve their scores. So I think, I think the issue is, again, it comes to regrets. People will worry that if I had the right answer and change it, I’ll feel so bad ’cause I had it and I couldn’t let it go.
Mickey: I think this, this sort of reminded me of the Monty Hall problem.
I dunno if you’re familiar with the, the behind all that. I won’t get into too much, but it’s from, let’s make a deal where they, they give you, pick one of three doors and you pick door number one, and then he opens up, door number three says there’s a goat behind there. Do you know, do you wanna switch or do you wanna change?
And the math says change [00:08:00] every time. If you change doors when he says two, you double your odds of winning. But people don’t want to ’cause they’re worried like . I might’ve picked the car and then changed away from it. So even though they can double their chances of winning. People just don’t wanna change.
And it’s complicated to get the grasp behind it. ’cause it doesn’t make sense. There’s two doors left, it feels like 50 50. I’ll post a video in the show notes that kinda walk through the logic there. But it’s, it’s fascinating just to see that logic too. But it’s, even when people understand it, they’re still like, I, but if I have the car there, they change.
I’ll regret it so much. Even though you’re odds double ’cause your odds double, but you still could lose the car that you had. And so people aren’t willing to take that risk and then you have more regrets. So yeah, people do . Dumb things to avoid. Potential regrets, like changing answers on tests, you know,
Adam: mean, or, or, or even like, you know, like there, I think there was an example in the book too where it said like, I imagine that you’re, there’s two kids and they have to ride around a lake to go to school, and one kid rides around the right of the lake every day, and one kid rides around the left of the lake every day.
And one day, you know, they’re riding the school and the kid rides around the right of the lake and it’s blocked. And, you know, and he has to go all the way back around the other way. [00:09:00] But the kid that normally rides to the left of the lake for whatever reason, he decided to ride to the right that day as well. And it’s blocked. And then he has to ride all the way back around. And he, and they, they posed the question, which one feels more regret?
Adam: more regret, of course, is the one that randomly chose to ride the different way that day and was then blocked. And he is like, oh my gosh, should’ve just done what I normally do.
And so Like that, that avoidance of regret sometimes makes us make poor decisions, whereas, you know, it might’ve been a, normally a fine decision to ride around that
Adam: whatever reason.
Adam: it’s kind of interesting example.
Mickey: It is. Yeah, it’s, it’s easy. Yeah. A lot of books talk about hindsight and how it’s so easy to look back and say, of course I shouldn’t have made that decision because I can see all the warning signs there. But at the time, those three warning signs were buried among 57 other signs and you couldn’t pick ’em out.
And yeah, it makes it so tough to make those kind of decisions. In this case, there were no warning signs. He just, yeah, happened to make a bad choice and didn’t work out. But he’s gonna regret it more than, more than maybe he should.
Adam: Exactly. Yeah. One, one thing I was gonna mention, uh, so you mentioned the four core regrets earlier, uh, foundation regrets, which like not saving [00:10:00] for retirement early enough, I. Uh, boldness, regrets. We already mentioned you should start with the moral regrets, which are obvious connection regrets. So that’s an interesting one to me.
So there’s this big long story in the book about this woman that fell outta touch with this, this, you know, best friend from college. And they didn’t talk for 20 years, and she felt really weird about reaching out to her and they found, she reached out to her. It was such a blessing and such a wonderful thing, and blah, blah, blah. And I, I, I gotta, I gotta be honest, of struggle with that one because To some degree, like relation, like connections happen and they fail and they happen and they fail, and relationships come and they go and they come, they go and like to, so like there’s, there’s the regret of, you know, I was very close to this friend 15 years ago, and now we don’t really talk anymore. Now it’s weird if I call ’em up, like that’s a legit regret. But the other side of it is you could also regret being the person that’s constantly pursuing that relationship that’s not going anywhere.
Mickey: Yeah. Huh.
Adam: And so like, so it’s kind of a weird, it, it, like, now, now I also wanna juxtapose this, this comment. another quote in there, and it’s a very long one, and I won’t, I won’t read the whole thing, but the, the whole quote, the premise [00:11:00] of that is, the ties to people, the relationships in our lives. That give us the happiness. And it’s not based on iq, it’s not based on income, it’s not based on social class, it’s not based on genes.
It proves true across every study from every type of person, it’s always the relationships and the connectedness in our lives that lead to happier lives, less, less dementia, better health all
Adam: So like, so then there’s this, this, this, uh, these ju these juxtaposition of, of forces within me that say, well, should I call that friend that I, that I talk to once a year more often? Or not, you know what
Adam: a tough, that’s a tough call, so I, I don’t
Mickey: Yeah, I think it depends on who the, who the friend is. I mean, certainly you can reach out to people over and over again and they don’t want to, and that’s fine. You don’t wanna be that annoying person. But I also think back, there’s, I think back to a friend I had in elementary school named Tommy Simpson.
Um, and I haven’t talked to, I moved away in sixth grade and haven’t talked to him since. I. I think it’s kind of on him to find me. ’cause I cannot find a person named Tommy Simpson on Facebook ’cause there’s millions of them. But I do feel kind of bad ’cause we were, we were good buddies who played a lot of baseball and had a good time.
And I just [00:12:00] moved away and there was no real way to keep in touch at that point. And so we just drifted like, I don’t think we’d be good friends anymore. But like, he was a good dude. He is part of my life. You know, he’d be cool to, to touch base, but again, I’m not sure how to, how to even find him. So I, I blame him for that.
’cause I’m easier to find with my name than, than he is with his, but it’s totally his fault. But I can think of
Adam: I’ve got an old roommate named Jimmy Hill. Same
Adam: So there’s a lot of Jimmy Hill
Mickey: yeah. So I can think of like three or four people that I think probably I have connection regrets with, just, not that we’d be good friends today, but just I wanna see what their life is like and I care about ’em and hope they’re doing well and have no real way to even know if that’s true or not.
But yeah, I don’t think I have too many there. I tend to be pretty good about staying in touch with folks and you know, but there, there are a few out there for sure.
Mickey: And I’m trying to think, yeah, I think, I’m not even sure which regret probably hits me the hardest that that could be an interesting question.
I mean, I think . I’m not a particularly bold guy, but I did start a new business and you know, I, I think, I don’t have any boldness, regrets there, moral regrets. I’m probably almost too far the other way where I’ve been taken enough risks, you know, , so I, I think maybe foundation regrets are probably the most, yeah, I need to [00:13:00] get in better shape.
I could probably stand to have more money in the bank, that sort of thing,
Adam: I think for me it’s definitely foundation regrets, and oddly enough, you know, you made the joke that like, don’t have Boldness regrets. But like I, I’m constantly looking at my world and going like, could I start that I would regret not
Adam: a year from now or like, or like, what moves could I have made three years ago that would’ve been bolder that I wished I had made?
Adam: And there’s a, there’s a bunch. so, so I kind of, it’s, it’s almost like it’s, it’s, it’s like I’m willing to be bold, but I’m almost afraid I’m gonna miss the opportunity to be bold sometimes,
Mickey: that’s fair. It’s, it’s, it’s hard to see that too. I remember you and Sanjay talking once in your podcast about, man, I wish I knew all this stuff 10 years ago. ’cause all these Uber and all these companies that came up that we missed. But looking ahead, those, those, those kinds of companies are coming in the next 10 years too.
Like we just don’t know what they are.
Mickey: And it’s
Mickey: frustrating to know that there’s someone out there with a new of an idea right now that’s gonna be a billionaire. And I have no idea what that idea is, and I won’t know until he is already a billionaire. We will have missed out on that, but,[00:14:00]
Mickey: You know, so it’s not
Adam: that, and, and that’s, that’s what I want, that’s what I’m constantly trying to think through is like what, like I’m always asking myself like, what am I
Adam: missing, I’m missing something that 10 years from now on ago that was so
Mickey: Oh yeah.
Adam: am I, what am I missing right now?
I’m missing something. What is it? I don’t know.
Mickey: But I think there’s the other side of that too, though. You can spin your wheels too much for a while back in the like 2005 kinda range, I was making pretty good money from content and Google ad sense and stuff. So I was spinning up new blogs all the time. And anytime I had a new idea, I’d start another blog, start another site.
And I ended up with dozens of sites that were just crap because I had too many, I couldn’t just focus on getting one on, ’cause I’d like, Ooh, this is a great idea, I don’t wanna miss it. Ooh, this is a great idea. I don’t wanna miss it in
Mickey: Being bold for all of them did not work out well. So there’s, there’s an advantage too, to being focused on, on what you wanna do, and it’s a tough line.
Adam: I, I will tell you like I have gotten better about like having ideas. Then like, you know what, it kinda just with purchases too, like, I want to do this or I want to buy this. I’m like, I need that to sit on the shelf for two weeks. Like, I [00:15:00] can’t touch that for two weeks. And if it still feels like a brilliant idea in two weeks, it’s probably worth considering
Mickey: Hmm. I like that.
Adam: But otherwise, like, it’s, if it, if the, if the fizzle dies in two weeks, it’s not that interesting,
Mickey: Yeah, I’ve had a lot of ideas over the years too that I’m glad I didn’t pursue. ’cause the advent of the cell phone and the app store destroyed all of them pretty quickly. So, you know, I’m like, we’d have an app that would, you could text sports scores to people and me and a buddy would like set up this thing like, but then ESPN’s like, oh yeah, we’ll just do push notification.
Like, we couldn’t have competed with that, even if we had done anything, you know? So,
Mickey: yeah, so many like that.
Adam: So, so something we probably need to talk about, uh, in this is, uh, I think chapter 11, which is the antidote, the antidote of regret, uh, which is forgiveness, right? And so I think like his point there being that I. We can feel regret, and that can, that can share, tell us what our values are.
It can help us make better decisions moving into the future. It can, and I mean it can enable us to be bolder as we live. It can enable us to connect more deeply with people around us so that we don’t have those connection regrets. But [00:16:00] at the same time, for the things in the past where we did screw up for those moments where I colossally stuck my foot in my mouth or treated my children in a way that I wish I hadn’t or whatever else. The, the antidote is just to forgive ourselves and to recognize what we can learn from those things and move forward.
Mickey: Yeah, and it’s tricky ’cause yeah, we wanna get forgiveness from other people too, if we’ve made a mistake with them. And almost every time when you bring something up that happened years ago and you’re so sorry for like . I forgot that even happened. Like, yeah,
Mickey: people aren’t carrying around too much unless you were just a horrible bully to lots of people and, you know, but I mean, the, the mistakes you’ve made, yeah, really other people don’t remember and aren’t holding it against you, but holding it against yourself is, again, there’s a little advantage to it in terms of regret and making you a better person, but holding onto it and worrying yourself sick is not helping anyone.
Adam: No, no, it’s, it’s not helpful at all, for
Mickey: So I think, yeah. The one other piece I wanted to hit too was the at least stuff. Um,
Adam: Oh yeah. Oh yeah. I love
Mickey: The, at least, so the, the quote here, he said, so well, you might try to find a, a future facing lesson from the regret. Next time check the consumer guides a little more carefully about purchasing the vehicle. You [00:17:00] should also at least it think about how it could have turned out worse.
At least I got a good deal. At least I didn’t buy that other make and model which had less trunk space. At least it’s paid off. At least can turn regret into relief. The problem is, I, I’m good at this. I’m pretty good at the, at least game. I worry I take it too far though, and it’s gonna burn me someday.
’cause I can say things like . Ooh, I, I had to go to the doctor and say, I wasn’t feeling good. I had this thing. At least it wasn’t cancer like, okay, so that’s good for now, but what happens when it is cancer? Like, you have to keep, go. Yeah,
Adam: not, it. At least it’s not the worst version
Mickey: right. But then what happens if you get that, like, eventually the at least could run out if the right situation hits.
Mickey: I, I think about that a lot. Like with my kids and stuff at hey, at least they’re healthy and grown and like what happens if they aren’t? Like there’s no, at least to fall back on there. But I think for so many things, day to day at least, really can help.
Adam: know though, but I think there always
Adam: I mean, so like, let’s take your cancer example. So, so as you, as you, as you mentioned earlier, like one of my podcasts is real pink for Susan g Komen and I interview. Uh, women about breast
Adam: and interview a lot of women that have stage four breast cancer, which most people would say is like the most terrible.
Like the, the worst.
Mickey: right? For sure.
Adam: know, the most advanced. And, [00:18:00] uh, and I would say like most of them would say, you get to a point where it’s like, well, at least, at least it’s not stage. At least it’s not stage two. At least it’s not whatever. You get to the point where it’s like, at, at least I have today.
Adam: know, at least I have this moment. At least I have whatever it is, you know? And, and, and I think we can always get to that point where it’s like, well, okay, here. At least I have this time,
Mickey: That’s a good point. I mean, yeah, if you can, if you are able to summon the words, at least I have this time, you’re in a better place than some. So yeah, that’s, that’s a good way to put it. Okay, I like that. Very cool.
Adam: it’s a very stoic
Mickey: It is. Yes. That’s very stoic on that one, so, yeah.
Adam: that’s a different set of books
Mickey: they do kind of tie together a bit though.
I could see that in some ways. Yeah.
Adam: Yeah, I know. I mean, I think, I think stoic philosophy and, and the power of regret are actually very similar. Yeah. I think, and I think there’s like some philosophical or some regret kind of philosophies built into stoicism as
Mickey: Daniel Pink that, yeah. Wrote this book and then Ryan Holiday that writes a lot of stoke books. I do kind of almost get ’em confused at times ’cause they do kind of cross paths a good bit. And really anything from either of ’em is worth reading. So, yeah.
Adam: Oh my gosh. [00:19:00] Their books are so good. I’ve read I don’t know, four or five, probably five of Ryan Holiday’s, books so far, probably just this year.
Adam: I, I haven’t read, read as many Daniel Pinks, so I’ll have to
Mickey: Yeah. Anything of his is good. So anything else? Any other quotes you wanna share from this one?
Adam: Uh, let’s see if there’s anything. did, I did like this one. It’s not necessarily related to this, but related to like putting your finger around that said, uh, he said, perhaps you’re familiar with the first law of holes
Mickey: Oh yeah.
Adam: yourself in a hole. Stop
Mickey: Yep. I did like that.
Adam: Like, I was like, oh, I, I find myself in holes all the time. I wish I, I wish I could go back and tell my 20 something
Mickey: Oh my gosh, I could have such a great conversation. Yes,
Adam: like please just, just stop. Just don’t say every thought that that’s, you know, anyway, so
Mickey: Nice. Yeah. So yeah. But yeah, for me, this book though, yeah, the whole thing was just, yeah, I, I always saw regret as regret is bad period. And it’s not, I mean, there’s ways to see regret is good. And again, I like some of the things you came up with again, at least we have today. That’s kinda my main.
I’ll take outta that, I think is that piece. But yeah, this is [00:20:00] one, like we said, anything from from Daniel Pink is worth reading. I mean, I’ve read some of his other books too and they’re fantastic. But this one probably is top of the list for me of, of what he has and it’s fantastic.
Adam: I do have one final quote
Adam: final quote’s pretty good. So, uh, the quote is one of the most robust findings in the academic research and my own is that over time we are much more likely to regret the chances we didn’t take than the chances we did.
Mickey: There you go. Well said. So Adam, where can people find more about you?
Adam: I’ve got a firstname.lastname@example.org. It’s got links to site that I’m willing to be found on and uh, it has got some old blog posts. I’ll hopefully have some updated one soon and you can sign up for my newsletter there
Mickey: Awesome. Very cool. And we’ll have a link to that in the show notes. So yeah. Thanks Adam. See ya.