More Happier: How Regret Can Make You Happier [Revisited]

Summary

Podcast Summary: Happier with Gretchen Rubin – "More Happier: How Regret Can Make You Happier [Revisited]"

Release Date: May 3, 2025

In this insightful episode of "Happier with Gretchen Rubin," bestselling author Gretchen Rubin and her cohost, sister Elizabeth Craft, delve deep into the complex emotion of regret. Titled "More Happier: How Regret Can Make You Happier [Revisited]," the episode revisits previous discussions on regret, offering listeners a rich exploration of how this often-painful emotion can be harnessed to enhance happiness and personal growth.

Understanding Regret: A Dual Perspective

The episode opens with Gretchen Rubin emphasizing the constructive aspects of regret. At [01:12], she states:

“By anticipating future regret, we can make better choices in the present. And by reflecting on past regret, we can think about how to do better moving forward.”

Elizabeth Craft echoes this sentiment, sharing a personal anecdote about her experiences with past regrets concerning her puppy, Barnaby. She explains how anticipating similar regrets with her new puppy, Taffy, has shifted her approach to savoring these fleeting moments rather than rushing through them ([01:29]).

Personal Reflections: Gretchen’s Regret of Disconnection

Gretchen shares a heartfelt regret about losing touch with her college friends:

“I really regret how long it’s been since I’ve seen many of my friends from college who I love so much.” ([02:22])

This admission underscores the importance of maintaining meaningful relationships and serves as a catalyst for her commitment to reconnecting, despite geographical challenges.

The Role of Regret in Decision-Making

Sarah Fain joins the conversation to highlight how negative emotions, including regret, play a vital role in fostering a happier life. She points out that emotions like envy have previously guided her career choices, leading her to pursue writing over law ([04:36]).

Frameworks for Understanding Regret

The discussion shifts to established frameworks that categorize and explain different types of regret. Elizabeth references Dan Pink’s book, The Power of Regret, outlining two primary categories:

1. Regrets of Action – Regretting things you've done, such as losing your temper or making poor decisions ([10:57]).

2. Regrets of Inaction – Regretting things you didn't do, which Pink suggests are more prevalent and impactful ([10:58]).

Further expanding on this, they introduce four categories of regret as divided by Pink:

• Foundation Regret: Wishing you had done things like saving more or working harder.

• Boldness Regret: Regretting not taking risks or expressing feelings.

• Moral Regret: Feeling remorse for not doing the right thing.

• Connection Regret: Wishing you had reached out more to others.

Elizabeth emphasizes the universality of these categories, noting that everyone experiences different types of regrets at various life stages ([14:56]).

Personal and Listener Regrets: Learning and Growth

Both Gretchen and Elizabeth share their personal regrets, illustrating how these feelings have influenced their actions and decisions. For instance, Elizabeth discusses how her regret over not being more involved in extracurricular activities during college propelled her to engage actively in law school, leading to fulfilling experiences like becoming the editor-in-chief of the Yale Law Journal ([12:48], [12:56]).

Listeners contribute their own stories, ranging from missed weddings and not expressing love to not pursuing passions like playing the violin. These narratives, shared between [26:50] and [35:59], highlight the diverse nature of regret and its profound impact on individuals' lives.

Introducing New Dimensions: Setting the Stage and Wistful Regrets

Gretchen and Elizabeth introduce a new category of regret focused on “not setting the stage”—failing to establish traditions that could prevent future regrets. They encourage listeners to think proactively about creating meaningful rituals, such as annual meet-ups with friends or family celebrations ([21:37]).

Additionally, they explore wistful regrets, which are more about longing for what could have been rather than actionable regrets. These are characterized by feelings that something was desired but may not have been attainable given one’s circumstances or personality ([22:39], [23:02]).

Compassion and Moving Forward

As the episode draws to a close, the hosts stress the importance of self-compassion when dealing with regret. Elizabeth advises:

“We should show compassion for ourselves when we think about regrets... We can all learn from each other.” ([35:28])

They encourage listeners to use regret as a tool for learning and making positive changes, rather than dwelling on past mistakes. By reframing regrets as lessons learned, individuals can set themselves up for greater happiness and fulfillment in the future ([36:11], [36:16]).

Key Takeaways

• Regret as a Tool: Anticipating and reflecting on regrets can inform better decision-making and foster personal growth.

• Types of Regret: Differentiating between regrets of action and inaction helps in understanding the root causes of our feelings.

• Personal Stories: Sharing and hearing diverse experiences with regret can provide valuable insights and communal learning.

• Proactive Strategies: Establishing traditions and setting clear intentions can mitigate future regrets.

• Self-Compassion: Approaching regret with kindness towards oneself enables constructive reflection and positive change.

Notable Quotes

• Gretchen Rubin ([01:12]): “By anticipating future regret, we can make better choices in the present. And by reflecting on past regret, we can think about how to do better moving forward.”

• Elizabeth Craft ([05:55]): “It could even be true that both things are true for the same person at different times in their lives.”

• Sarah Fain ([21:37]): “We're saying traditions. Years go by, and you realize you don't have a tradition for something.”

Conclusion

In "More Happier: How Regret Can Make You Happier [Revisited]," Gretchen Rubin and Elizabeth Craft offer a nuanced exploration of regret, transforming what is typically viewed as a negative emotion into a powerful catalyst for happiness and personal development. Through personal anecdotes, listener stories, and expert frameworks, the episode provides listeners with actionable insights on how to navigate their regrets constructively, ultimately steering their lives toward greater fulfillment and joy.

For more insights and to continue your own happiness project, visit happiercast.com.

Transcript

[Gretchen Rubin]

Gretch, May is just such a time of celebrations. And I know for us, when we're gonna host a celebration or take something to a celebration, I always go to Whole Foods Market.

[Elizabeth Craft]

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[Gretchen Rubin]

Lemonade.

[Elizabeth Craft]

Hello, we're here for more Happier, a podcast where we get happier. Today we are revisiting a fascinating discussion that we had about regret. And, Liz, I'm so glad we're revisiting this one, because I think regret is one of these emotions that can be really hard to talk about, but it can be very, very valuable to think about.

[Gretchen Rubin]

Yes. Many people actually don't want to use that word. But by anticipating future regret, we can make better choices in the present. And by reflecting on past regret, we can think about how to do better moving forward. So it can be very useful.

[Elizabeth Craft]

No. And I'll give you a perfect example from my own life. So we have our new puppy, Taffy, which is so exciting. And I remember how with Barnaby later on, I regretted that I didn't revel in his little tiny puppyhood more like, I was so concerned about, like, getting all of the training done and worrying about was this gonna happen or was that gonna happen? And I kind of wanted to rush through it. And now I am thinking with Taffy, like, yes, I'm sort of stressed out about getting all these things accomplished and getting used to her and her getting used to us, but I really want to enjoy this period. And I think because I regretted that about Barnaby later, like, when I would look back in pictures and I'm like, oh, I didn't take the time to really enjoy it when he was so little. I think that that is helping me to approach this time with a different frame of mind.

[Gretchen Rubin]

Yeah. And this. Just the fact that we're revisiting this has me thinking about regret. Of course. And I have to tell you, Gretch, I really regret how long it's been since I've seen many of my friends from college who I love so much.

[Sarah Fain]

Yeah.

[Gretchen Rubin]

And are such a valuable thing in my life, and yet I haven't seen them. So I need to really act on that. And I've talked about that on the podcast before. It's Hard because a lot of them are on the east coast and I'm on the west coast. But needs to happen.

[Elizabeth Craft]

But this is a good example of Elizabeth, how you revisit this regret. But it's important to revisit the regret because eventually you'll do it. I mean, I really, at some point it will happen. You kind of need the stars to align, but if you just let the regret go, then you might never think to do it and it might never happen. So it's valuable.

[Gretchen Rubin]

Yes. You could compartmentalize and just not look at something.

[Elizabeth Craft]

Yes.

[Gretchen Rubin]

But you need to look at it to deal with it.

[Elizabeth Craft]

Exactly.

[Gretchen Rubin]

Well, Gretchen, I want to note that this podcast was originally recorded in 2023, so you'll hear mention of things like the writers strike going on. And I will add, thankfully, I did make the most of my time during the writers strike to get work done on a novel with Sarah, my co host of Happier in Hollywood and writing partner. Although we're still working on it, which is needs to get done. That's another regret I have that we haven't finished yet. But we did work on it during.

[Elizabeth Craft]

The strike, even working on it.

[Sarah Fain]

Gretch, why is regret something that could actually make us happier?

[Elizabeth Craft]

So you think of regret as being a negative emotion, but negative emotions actually have a very important role to play in a happy life. Often they're a big flashing sign that something isn't right. And because they're unpleasant, they can sometimes help us take action, produce to make change when nothing else can. I know for me, for instance, the negative emotion of envy was really helpful when I was thinking about switching from law to writing because I thought, well, I feel sort of a mild interest when people get great law jobs. But when I thought of people who were writers, I was so envious. And that helped me see what it was that I really wanted. So reflecting on our regrets can help us to figure out how to set up our lives to be happier.

[Sarah Fain]

Yeah. So we're talking about regret, which is when we feel sad, disappointed, or repentant about something that we did or didn't do in the past. Gretch it's interesting because from listeners comments, it's clear that some people choose not to use the word regret.

[Elizabeth Craft]

Yes.

[Sarah Fain]

They emphasize that they've done the best they could do at a certain time and they need to move on and not regret. We heard that from a bunch of people.

[Elizabeth Craft]

Yeah, right. So they don't like thinking about it in terms of regret. And look, vocabulary is really important. If you don't like Thinking about the past in terms of regret, maybe you want to frame it as, what are my insights from experience? Or what lessons have I learned the hard way. But it's just the idea that looking back on the past and thinking about what we did or didn't do, can we use that reflection to help us become happier by making better decisions? So one way it can help us make better choices is if we anticipate things that we might regret in the future. So we think about, okay, how is my future self going to feel about what I'm doing now? That can help us make better choices in the present. Or if we're thinking about past regret, which I think is more typical, we can think about, okay, given that I regret lessons that I learned from the past, what might I change or do differently moving forward?

[Sarah Fain]

And then we can also learn from other people's regrets.

[Elizabeth Craft]

Right? Like, we can think about our own regrets. But then when other people tell us their regrets, that can be very helpful. Just as a small example, Elizabeth, you know this because I talk about it all the is years ago, before I even was married, an older friend said to me, wow, you know, one thing I really regret is that I didn't have professional photographs taken when my children were really young. And for whatever reason, this made a huge impression on me. And I have really done that when I had newborns with Eliza and Eleanor. And then also throughout their childhood years, I've made sure to have regular professional photos taken. We feel like we're taking photographs all the time, but in the end, it's not the same as having, like, an actual good lighting and great paper and somebody who really knows it. And I'm quite confident it would never have occurred to me to anticipate my future self. And how I would think of it wouldn't just never even cross my mind as a consideration. But just her offhand comment really led to quite a significant effort on my part throughout the years that I'm really happy about.

[Sarah Fain]

Yeah, well, Gretch, I'm in a state of both reflecting on past regret in acting and anticipating future regrets. And acting. I'm sandwiched because, you know, Sarah, my writing partner and I and co host of Happier in Hollywood, we are on strike with the Writers Guild of America, and we've been through a strike before. In 2007, we were on strike, right. And we really regretted not using that time more thoughtfully, I guess I would say we just. We didn't do any of our own work during that time, and we really regretted it because, you know, that's five months down the day drain. So this time we decided, okay, let's looking at the strike that was impending. We said, let's make sure we use the time that we're on strike so that we're not. In addition to picketing, we're also doing something for ourselves, which is how we came to work on our novel, which we are writing. And if anyone's interested in our process or anything about our novel, we talk a lot about it on Happier in Hollywood. So that again, is a case where that regret then led to us now hopefully not having a regret and doing something good.

[Elizabeth Craft]

Right? I like the regret sandwich, where it's like I'm thinking about past regret and if you get to the end of the strike and nothing's happened, you're like, we know that we will feel that way. And so that's leading you to take action. So that's a perfect example of how the pain of regret actually is leading you to do something that's very positive. One thing that comes up over and over in our conversations about happiness is that we all have to figure it out for ourselves. There's no magic, one size fits all solution. And you can't think about your life in terms of, okay, what's the best way or what's the right way? And for regret, it's going to look different for different people. I could easily imagine someone thinking, wow, I really regret that I spent too much time hanging out with my friends, goofing off, messing around, and I just didn't work harder. And I can easily imagine someone thinking, wow, I really regret that I worked so hard, I put in so many hours, I was exhausted when I wasn't working and I really didn't make plans and I really regret that I didn't spend more time with my friends. Both things can be true. It could even be true that both things are true for the same person at different times in their lives. But whatever we realize now can help us set ourselves up for more happiness in the future by realizing lessons that we've learned from experience.

[Sarah Fain]

So, Gretch, before we jump into our regrets and listeners regrets, what are some frameworks by people who have thought a lot about this? Because that can be helpful.

[Elizabeth Craft]

Yeah, no, it's good to just think of different categories people have set out. Well, one and this every once in a while goes all over the Internet. So I'm sure many, many people have seen this. It started out as a blog post and then it turned out as a book by Bronnie Ware. It's called Regrets of the Dying, and it was inspired by her work in palliative care. So, according to Bronnie Ware, the most common regrets of the dying were, I wish I'd had the courage to live a life true to myself, not the life others expected of me. I wish I hadn't worked so hard. I wish I'd had the courage to express my feelings. I wish I'd stayed in touch with my friends. And I'd wish that I let myself be happier. Interesting.

[Sarah Fain]

Yeah, really interesting. It's interesting. You have to let yourself be happy. I can relate to that.

[Elizabeth Craft]

There's a lot in there and these ideas. It's interesting. Dan Pink, who's a very thoughtful writer who wrote a really excellent book that, if you're interested in regret, I highly recommend called the Power of Regret, where he talks all about different aspects of regret. He makes a few points that are helpful if you're just trying to sort of, in your mind, figure out how to think about it. And I think that one of the most useful things that he points out is that there are regrets of action and regrets of inaction.

[Sarah Fain]

So what are examples?

[Elizabeth Craft]

Well, so regrets of action are something like, you lost your temper, you blew up at somebody, you did something. Or there are regrets of inaction, which is something like, I didn't work very hard in college. And what he points out is that we tend to have more regret for the things we don't do. Which reminds me, you know, I love a proverb, and one of my favorite traditional proverbs is that it is more painful to do nothing than to do something. And that's what Dan Pink's research suggests.

[Sarah Fain]

Well, and that makes sense, Gretch, because we learn from mistakes. So if you did something and it was a mistake, at least you can learn from it. Whereas I think if you didn't do something, it's harder to feel like you've learn from it.

[Elizabeth Craft]

Right.

[Sarah Fain]

And it's more of just a regret.

[Elizabeth Craft]

Yeah. Inaction can kind of haunt us. The road not taken. And here's an example of how I benefited from this in my own life, my own regrets. So when I was in college, I did no extracurricular activities. None. And by the time college was over, I really wish that I had been more involved. And after college, I felt like I missed opportunities to do fun things and to engage more deeply with people and with the school and to learn about something. So that was something that I really, really regretted. So a couple years go by when I did this and that, and then I Went to law school. And the regret that I had acknowledged to myself that I felt about college really fueled me to push myself to do activities in law school like Barristers Union and the Law Journal, which, by the way, especially the Law Journal, ended up being huge engines of happiness for me. But I think if I had not consciously acknowledged my regret for what I did in college, I wouldn't have known to do something different in law school, because the things that made not want to do the things in college were still true for me in law school. I had to really be like, hey, Gretchen, learn the lesson from experience, do things differently. Yes.

[Sarah Fain]

And I have to point out, as your sister, that you ended up being the editor in chief of the Yale Law Journal. Gold star for that, which was one.

[Elizabeth Craft]

Of the best experiences of my life. So it ended up being very, very important. This is a place, side note, in terms of regrets, I think this is a place where parents can play a bad role. Out of love. Out of love. As parents, we don't wanna see our children struggle or fail or be disappointed or be at risk in any way. So we may urge them not to pursue something that to us feels like a risky path, but then they wonder about it forever. Right. I remember switching to writing back to my own experience. I remember at a certain point I was like, well, now I'd rather fail as a writer than succeed as a lawyer. And so I need to take my shot. Our parents were very supportive of that. But I could imagine some parents being like, don't do it, don't do it, don't do it. And then I might have always thought, like, what? This was like, my road not taken. This is where let people decide their own roads. If you intervene too much in that, you might set the stage for regret.

[Sarah Fain]

Absolutely. And then, Gretch, before we get to our regrets, Dan Pink divides major regrets into four categories. So there's foundation regret, which is like, if only I'd done the work to quit smoking, to study harder, had saved more, things would have been different.

[Elizabeth Craft]

This is the kind of thing that, when I was writing better than before, I saw often, because often foundation regrets.

[Sarah Fain]

Are regrets related to habits and then boldness. If only I'd taken the risk.

[Elizabeth Craft]

Right. This is like, I wish I'd said how I felt to somebody or taking chances. This is something that's very pertinent to me. I think, as an upholder. I often have regrets of boldness. So this is something that I'm gonna focus on more in the future, making sure that I'm not hanging back from taking risks or making mistakes.

[Sarah Fain]

And then moral, which is, if only I'd done the right thing.

[Elizabeth Craft]

Very, very painful kind of regret looking back and realizing that we did not make the moral choice.

[Sarah Fain]

And then finally, connection. If only I'd reached out.

[Elizabeth Craft]

I bet that's one of the most common ones, right?

[Sarah Fain]

Yes, for sure. Although I think all of these. We probably all have regrets in all of these categories.

[Elizabeth Craft]

Yes, absolutely. Yeah.

[Sarah Fain]

All right, Gretch. Well, coming up, we're going to share some of our regrets and listener regrets. But first, this break.

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[Gretchen Rubin]

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[Sarah Fain]

Well, one regret I have, Gretchen, which is funny, you mentioned extracurriculars in college. One of my regrets relates to Jack's grade school, which is I regret that I didn't participate more. I volunteered in the volunteer slots, but I didn't do committees or get to know other parents through working at school. And I think it would have connected me to a lot more parents. I mean, as you know, I have a lot of connections with parents. You do, but then I would have met the different grades. I know everyone in our grade. I think I just. I would have enjoyed that. I love meetings and talking to people.

[Elizabeth Craft]

Yeah.

[Sarah Fain]

Felt shy about it. And then, of course, there's always work to deal with as well. But that's just kind of a regret that I have right now. Like a current regret.

[Elizabeth Craft]

Well, I have sort of a related regret. And this is because now that Eliza and Eleanor are both graduated from high school, I realized that I regret that I didn't think about their school years in terms of my experience, because I saw them as like, this is their experience, this is their thing, and I'm a supporting bit player in their drama. Instead of saying, I have a role, my role is as a parent who has a child in grade school or high school or whatever. And I don't know why I think that would have made a difference in how I approached it, but I think I would have felt like it should play a more central role, and maybe it would have led me to do the kind of thing that you're saying, which is volunteer for a committee or something. Because I just saw it as very much their thing that I was hanging onto rather than something that was central.

[Sarah Fain]

To me and Gretch. There are those small regrets, but that just nag at you.

[Elizabeth Craft]

Yeah.

[Sarah Fain]

For instance, I regret that I haven't gone to more concerts in life, but specifically Adam and I almost went to see Tom Petty at the Hollywood Bowl. I saw, oh, Tom Petty's playing tonight. There's still tickets. We could go. We both love Tom Petty, and then we just. Inertia got the best of us. And we just didn't deal with it. And he died, like two days later. It was his last concert, and I Never ended up seeing him live. And it just. Still to this day, I'm like, why didn't we go to that Tom Petty concert? And it just bothers me on a regular basis, so I should use that to go to concerts rather than just regret that I haven't. I should say, okay, let me go see Paul McCartney. Let me go see these people. But it's just funny how a little thing like that can stay with you.

[Elizabeth Craft]

Yes, Right. But it's like, okay, if I feel that inertia kicking in and dissuading me to get something, get the anticipatory regret, think about the future self and be like, okay, you don't want to be in that situation again. That's a really thing. I have a regret that we didn't get a dog sooner. Both Eliza and Eleanor really wanted to get a dog, and I was the holdout. Jamie was very amenable to it. He wasn't pro. Particularly, though now he is the biggest proponent of having dogs. He was like, sure, fine. It was a whole process, which I talked about on the podcast for a long time. And then the minute we got a dog, I was like, oh, we should have gotten a dog long ago. It added so much happiness to our family. So I do wish that I. And the thing is, all the happiness research said that. So I was like, of all people, I should have known better. And we loved our dog growing up, so I had every reason to. To do it anyway. Oh, speaking of small regrets, here's another regret that I have, and this is a regret I'm telling Eliza and Eleanor, because this is like a young person regret, which is, I have messy systems. The way I do my passwords, the way accounts are set up, the way I've named my word documents. It's just messy. I wish I had a clean system. But now, you know, I've been doing it for so long, it feels like it's one of these things. You're like, I wish you started out thoughtfully. So I'm just like, you know what? Come out with a convention and stick to it or whatever. Again, that's a small thing, but yes.

[Sarah Fain]

And, Gretch, there's a new category of regret that you and I are coming up with, which is regrets about not setting the stage.

[Elizabeth Craft]

Yes.

[Sarah Fain]

We're saying traditions. Years go by, and you realize you don't have a tradition for something.

[Elizabeth Craft]

Yeah.

[Sarah Fain]

So we're suggesting people think about what traditions they'll regret not having. For instance, I regret that I didn't start an annual tradition of a Weekend with my college friends.

[Elizabeth Craft]

Yes.

[Sarah Fain]

Because years go by and I don't see them and I miss them and it really bothers me that I don't see them. But we don't have this set thing in place.

[Elizabeth Craft]

Right.

[Sarah Fain]

But if we'd always seen each other every October, a certain day, then we'd still be doing it.

[Elizabeth Craft]

Well. And this is like my family in the fourth of July. Like growing up, our mother's birthday is the fourth of July, so it was always like, birthday, fourth of July. It was sort of like this thing. But then with my family, the 4th of July is a great minor holiday. There's so much fun that you could do. And I always, like, we should come up with a tradition. But now it seems like, oh, okay, maybe we just missed that. Everyone's.

[Sarah Fain]

Yeah.

[Elizabeth Craft]

So one thing to think about is, in terms of anticipatory regret, especially if you're going through a transition, is to think about what will you wish that you have had. Ah, yes.

[Sarah Fain]

And then glitch. It seems like there's a slightly different kind of regret. Like a wistful regret.

[Elizabeth Craft]

Yeah.

[Sarah Fain]

So maybe it's something that's not really realistic given the kind of person you were. But still you wish it could have been a reality. That's the road not taken.

[Elizabeth Craft]

Yeah. Like my wistful regret is that I wish I'd known that I wanted to be a writer in college. If I'd known that I was going to end up a writer, there's so many things I would have done differently. But looking back on college, I understand why I didn't at that time, understand it. And I'm really glad that I went to law school. So. But it is one of these things, like, sometimes wistfully, I think, oh, wow. I really wish I'd gone through college thinking of myself as a writer in training. How about you, Elizabeth? Do you have a wistful regret?

[Sarah Fain]

Well, yes, I do. And it's kind of the opposite, but not. Which is as a TV writer, I always say that I wish I'd gone to business school, not to be a business person, but to understand the entertainment business. I feel like I'd be so much better off if I had a solid understanding of business. However, it's probably the case that if I did go to business school, I wouldn't have ended up being a TV writer, so I probably would have gone into business. So it's a wistful regret. It's like, you know, I wish both things could be true, that I was a TV writer and that I'd gone to business school.

[Elizabeth Craft]

Right. Well, it's interesting.

[Sarah Fain]

Okay, Gretch. Coming up, we are going to hear from our listeners about their regrets. But first, this break.

[Gretchen Rubin]

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[Elizabeth Craft]

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[Gretchen Rubin]

Big month for me. Not only is it my birthday, but it's Mother's Day. Graduations are happening. It is just such a time of celebrations. And I know for us when we're gonna host a celebration or take something to a celebration, I always go to Whole Foods Market.

[Elizabeth Craft]

Yes, Whole Foods Market helps you save on everything you need with the quality and ingredient standards that we expect. They have hundreds of yellow low price signs that make it easy to save without compromising the quality that you expect from Whole Foods Market. One thing we love to do in the summer is grill. Jamie loves to grill. And the house brand of Whole Foods Market, 365By Whole Foods Market has all the essential at daily low prices that you need for the summer. Things like organic burger and hot dog condiments, chips, salsa, organic ice cream, refreshing sparkling waters. Save on May celebrations with great everyday prices. At Whole Foods Market. We heard from so many listeners. It was absolutely fascinating to read about people's different experiences and reflections. We will try to go through as many as we can because we can all learn from each other. Often we really can learn from learning about other people's regrets.

[Sarah Fain]

Jen said, I didn't go to my best friend's wedding. It was a destination wedding right after the holidays. At the time, I'd started a new job, didn't have the time off and didn't really have the money. Of course she understood. If I had somehow known she would only live three and a half more years, I would have figured out a way to make it happen. It was a hard way to learn the importance of showing up for the people you love. Yeah, that's a painful one.

[Elizabeth Craft]

That's. Yeah. Sherry said, I regret every single time I worried about the opinions of others and allowed a lot of my decision making to be based on them. Sadly, I didn't break free of this people pleasing until I was in my 50s. So the list of wondering what could have been is huge. Right. So that's the regret of inaction.

[Sarah Fain]

Kristin says, I regret moving away from my home state, Nebraska. Life happens and you get married, buy a house, have a kid, et cetera, and before you know it, you're rooted and it's impossible to move back. I miss the people the most. I'm not unhappy in where I live now or our situation, but I certainly regret thinking there was something better out there because I do miss my extended family and cornfields are calming to me. Us, too.

[Elizabeth Craft]

Yeah.

[Sarah Fain]

Definitely a learned lesson in appreciation. It's interesting, Gretch, because you could see someone having the opposite regret as well. They regret that they didn't move away from their home state. So again, the individual.

[Elizabeth Craft]

But then I will say that our parents, one of their pieces of advice is like, get where you're going. As young people, you often move, move, move, but then at a certain point, you stop moving. And so I remember when Jamie and I were in dc, they were like, just think about the fact if you want to end up in New York City, remember to move there. Which felt very obvious. But, yeah, you do get stuck. Marlene said, my one regret is that I didn't follow my heart and mind and prepare myself for a career I believe I would have enjoyed and learn skills that I would have been good at. So this is also the inaction. Yeah.

[Sarah Fain]

Danielle said, I regret not making that phone call. I wanted to when I sensed something was not right. It probably would not have changed the outcome, or maybe it would have just delayed it. But I could have maybe had one more conversation. I regret not saying I love you more to people or how much they mean slash meant to me. That's something I can and have changed.

[Elizabeth Craft]

Daniel says, I regret not flying home sooner. When my dad was sick, he passed a few hours before I arrived and I haven't been able to forgive myself, especially since the same thing happened when my mom passed. That's hard.

[Sarah Fain]

Those are hard. Ireland says, I regret not asking about anxiety medications sooner. I white knuckled my way through years of panic attacks because I was afraid. And I distinctly remember articulating my fear to myself. This way, if I had to tell my doctor what I was feeling, I'd start crying and never stop. As soon as the medication kicked in, it was like the sun came up in my brain. All those years I thought I was high strung when I'm actually super laid back.

[Elizabeth Craft]

On the subject of the term regret, Joanne wrote, I like to think of regret as I wish I had. It sounds less harsh. And when I say that I wish I had, I like to add, okay, so what now is the plan? It may not look like the original plan from oh, so many years ago, but it can be exactly what I need now. That's helpful.

[Sarah Fain]

Yes. Jennifer said, I regret working one minute over 40 hours in a week at a corporate job or any job that isn't my own business. The only reward for hard work is more work in that culture. A lot of people are feeling that right now.

[Elizabeth Craft]

Abby said, I have one regret. In 1997, Garth Brooks gave a free concert in Central park, now iconic 1 million people attended. EPIC. I did not attempt to go because the logistics were challenging. I was living in New York City. Why, oh why? What was I thinking? I'm disappointed in myself. Well, this sounds very much like you're Tom Petty. Maybe it's good to know you're not the only one.

[Sarah Fain]

Yeah. Carolyn says, most of my regrets center around raising my son, but he grew up to be a fine man. The one that lingers is not getting to know my mother better. She was 65 when she died and I was 31. We never got to have those long talks that usually come when parents are elderly. P.S. i am now elderly, so I know whereof I speak.

[Elizabeth Craft]

Kelly said, I regret I wasn't braver when I was young. It kept me from going places, speaking up, trying things, traveling, etc. I wish I had more courage to.

[Sarah Fain]

Just do and be Bren said, marrying a man I and everyone else knew was wrong for me. I bet there are a lot of regrets in that category.

[Elizabeth Craft]

Yeah, yeah, well. And something on a not quite such a deep note, Tracy said, I regret not wearing sunscreen in my 20s. Mind you, the range in quality back in the 80s was nothing compared to what it is today.

[Sarah Fain]

Janice said, I regret quitting the violin when I was a teenager. I have started to learn to play again 20 years later. So she did something about it.

[Elizabeth Craft]

Alyssa said, I regret every time I chose not to speak up for the week. So this is the moral regret that we were talking about in the Framework.

[Sarah Fain]

Elizabeth says, I regret not being there more for my sons when they were growing up. I regret not finishing college when I was young so I had to go back to school. When my youngest son was in high school, I was a single mom, so he spent way too many evenings home alone and ended up getting in with the wrong crowd. He finally got his act together in his late 20s, but I always wonder how it would have been if I had been home at night when he was a teen. That's hard. Yeah.

[Elizabeth Craft]

Lori writes, I regret not going to my senior prom. I was asked by a friend, but because it wasn't the boy I had a crush on, I said no. Had I gone with my friend, we would probably gone with a big group of friends and had a great time again. This is a good one to learn from the future.

[Sarah Fain]

Rebecca Ann says, I regret not pursuing my professional career starting with taking it more seriously as a college student. I went to art school. Regret number one, married a Marine, zero regrets and was very happy to follow him around the world. I've done a lot that I wouldn't have been able to do, not well anyway, if I had been working through it all. But now that he is retired, I feel I have very little to offer. The kids are growing up and won't need me much soon. And now I have been out of the professional world so long that I'm really intimidated by how much things have changed. It's affecting my self esteem in ways I never anticipated.

[Elizabeth Craft]

Well, this is. This is complex. There's a lot of good, there's a lot of bad. There's consequences you didn't anticipate. I mean, thought provoking.

[Sarah Fain]

Yeah. And this is where you can make changes now that will. Ten years from now things may look very different.

[Elizabeth Craft]

Exactly. Exactly. Elizabeth said, I wish I had taken the basketball course in college taught by the legendary IU coach Bob Knight. I was on the school paper and would have had a hell of an article. Amazing stories to tell decades later and more knowledge of a game I love.

[Sarah Fain]

Robin said, I regret allowing people to think I was a doormat for too long. I wasn't. I just did not have the tools to set boundaries or know how to speak up for myself if effectively.

[Elizabeth Craft]

Amber says the only regret Smoking every other action or decision led to places where there has been at least one positive along the way.

[Sarah Fain]

Betsy said, not writing a journal. My whole life I've forgotten too many memories. Well, Gretchen, she should get the one sentence journal and start keeping a journal.

[Elizabeth Craft]

If it's hard to keep a whole one, one sentence is enough. Yeah, I'll post a link in the show notes to the shop. Or you can go to happiercast.com shop of course Judy said, I regret not applying for funding for my PhD after I wasn't successful the first time. I still got my PhD but had to work part time and was never part of the academic community. Friends of mine applied three years in a row before they got funding in the humanities.

[Sarah Fain]

Lou said, I only really have two that irk me. Giving up dance and watching someone be bullied at school and being too scared to speak up. A lot of people regret not standing up to bullies.

[Elizabeth Craft]

Amy says not buying a sequin pillow of Danny DeVito's face at the Goodwill when I saw it.

[Sarah Fain]

Okay, that's hilarious.

[Elizabeth Craft]

The next time you see that sequin pillow you will jump.

[Sarah Fain]

Yes, Kim said not finding cute and comfortable shoes earlier in life.

[Elizabeth Craft]

Court says not getting a therapist at age 2025 years ago and Dominique says.

[Sarah Fain]

The way I treated people in high school, I was so focused on being a cool kid.

[Elizabeth Craft]

Well, it's fascinating to hear about people's regrets. I think we can all learn from each other. One thing that is really worth keeping in mind is that we want to show compassion for ourselves when we think about regrets. Partly it's so that we can stay open to the lessons of regret. It's too painful. You're not going to think about it. And you know, the thing is, most of us are doing the best that we can at the time, so it means we should be compassionate. But then can we learn also to do things in a different way in the future?

[Sarah Fain]

Yeah. And then also remind yourself of the but like I regret my bad marriage. Somebody might say but I have my children or I regret taking that job, but I met my sweetheart there.

[Elizabeth Craft]

So a lot of times good things are part of things that we regret and so there's value there.

[Sarah Fain]

Yeah.

[Elizabeth Craft]

So let us know how reflecting on regret helps you think of ways to make your life happier. This is such a thought provoking conversation. We just poured over what listeners wrote in. Let us know on Instagram, TikTok, Facebook threads. Drop us an email at podcastretchenrubin.com or as always, you can go to the show notes. This is happiercast.com 440 for everything related to this episode. And Elizabeth, what are we reading?

[Sarah Fain]

I am still reading the Lying Game by Ruth Ware and I am still.

[Elizabeth Craft]

Rereading Story of a Soul by Saint Therese of Lisieux. Well, we hope you're feeling happier after this episode. Whatever you choose to call it, the emotion of regret can be a very useful tool in creating a happier life. And remember, the best time to start a happiness project is 20 years ago. The second best time is now. Elizabeth, There's a regret I forgot to mention about my book Better Than Before.

[Sarah Fain]

What is it?

[Elizabeth Craft]

So I like the title Better than Before. But when I was working on it and trying to come up with the title, mom said, why don't you call it the Habit of Habits? And the minute she said it, I was like, oh, my gosh, that is the greatest title. And I thought that it was right. And kind of along the way, people dissuaded me from it. And they were like, it's not the Habit of Habits, it's the habits of Habit. And it just got lost in a shuffle. And I really do think that would have been a stronger title. Cause people would have just known what the book was about just from the title alone. Better Than before is like, it's a good thing to be better than before, but it's a little bit.

[Sarah Fain]

It doesn't tell you.

[Elizabeth Craft]

Right. It could be a novel. I think it was because Mom. Mom just said it. I was like, could it be this easy? I just counted it. And I should have trusted that feeling that I got of rightness when she said, I remember exactly where we were sitting in the kitchen. I can see her sitting there and saying it.

[Sarah Fain]

But I learned your next book about habits can be called that.

[Elizabeth Craft]

Yes, exactly. From the Onward Project.