Top Five Regrets of the Dying (Book Club with Frank Vasquez and Ginger) | Ep 574

24 Nov 2025 · 1 h 18 min

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In short

ChooseFI Podcast Episode 574: Top Five Regrets of the Dying

Episode Summary In this episode, hosts Ginger and Frank Vasquez explore the powerful concept of regret, drawing insights from Bronnie Ware's book, *The Top Five Regrets of the Dying*. They discuss how understanding these common regrets can influence a life filled with fulfillment and happiness. The conversation encourages listeners to reflect on their own lives and make intentional choices to avoid future regrets.

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Key Topics Discussed

  1. Introduction to Regret (00:00:00)
  2. The significance of understanding regret for personal fulfillment.
  1. Charlie Munger's Inversion Strategy (00:01:15)
  2. Using inversion to clarify what leads to a fulfilling life by considering what leads to regret.
  1. Overview of Bronnie Ware's Book (00:02:01)
  2. Discussion on *The Top Five Regrets of the Dying* and its impact on living better now.
  1. First Regret: Living Authentically (00:12:32)
  2. "I wish I had the courage to live a life true to myself, not the life others expected of me."
  3. Emphasizes the importance of self-expression.
  1. Second Regret: Courage to Express Feelings (00:20:52)
  2. "I wish I had the courage to express my feelings."
  3. Discusses the emotional toll of not sharing feelings.
  1. Third Regret: Maintaining Relationships (00:22:54)
  2. "I wish I had stayed in touch with my friends."
  3. Highlights the importance of nurturing friendships.
  1. Fourth Regret: Nurturing Friendships (00:23:07)
  2. The necessity of continually putting effort into maintaining connections.
  1. Fifth Regret: Allowing Happiness (01:40:22)
  2. "I wish that I'd let myself be happier."
  3. Discusses barriers to joy and the importance of prioritizing happiness.
  1. Conclusion (01:04:19)
  2. Encourages listeners to choose courage over complaint and take proactive steps towards authentic living.

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Key Quotes

  • "Live true to yourself, not others' expectations." (00:12:32)
  • "Rekindle your childhood passions beyond societal expectations." (00:16:30)
  • "Build friendships by starting with acquaintances and shared interests." (00:28:04)
  • "Choose courage over complaint." (01:04:19)

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Actionable Takeaways

  • Reflect on what makes you truly happy and take steps to pursue it.
  • Invest time and resources in nurturing meaningful relationships.
  • Practice sharing your emotions to deepen connections.
  • Engage in self-reflection to identify passions that may have been set aside.

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Related Resources

  • [The Top Five Regrets of the Dying by Bronnie Ware](https://www.amazon.com/Top-Five-Regrets-Dying-Transformed/dp/140194065X?tag=choosefi-20)
  • [Falling Upward by Richard Rohr](https://www.amazon.com/Falling-Upward-Spiritual-History-Creativity/dp/1118040973?tag=choosefi-20)
  • [The Soul of Wealth by Daniel Crosby](https://www.amazon.com/Soul-Wealth-Investing-Learning-Emotional-ebook/dp/B07X2FB2HC?tag=choosefi-20)

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Discussion Questions

  • What actions can you take today to align your life more closely with your authentic self?
  • How can you prioritize relationships in your daily life?
  • What does happiness mean to you, and how can you pursue it more actively?

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Transcript

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0:10Before we get started, I keep this podcast entirely ad-free for two reasons. First, this is a five podcast and I don't want to promote products that I don't want you to buy in the first place. And second, I really like the clean listening experience of a show where you don't have to fast forward ads. To keep it ad free, all I ask of you as a listener is the next time you open a travel rewards credit card, go to choosefi.com slash cards. And with that, onto the show. Hey everyone, it's Ginger and I am here today with Frank Vasquez of Risk Parody Radio. And we are here to talk about death. Or more specifically, we're going to talk about regret today.

0:52And I think regret is interesting for this community and for all humans for a couple reasons. One is it's a way for us to understand our lives. It helps us to say, here's why I feel this way. I did something and I should have done something else. And understanding that story helps me to reconcile my feelings that I have now. But of course, we can also understand regret kind of on the back end to say, what do I want to do now so that I can ensure I'll have more positive feelings in the future that I won't experience that regret? And I suppose that's a little bit why we would talk about that in this community, right?

1:33Because we're all about how can we optimize our lives? How can we live good lives? And part of that is, can I avoid the big regrets? Yeah. And what this is really an example of is what Charlie Munger talks about. If you want to really understand a question, what you should do is invert the question. And often that's the easier way to get to good answers. So instead of asking what would be a good life or what would make me happy, let's talk about what would be a bad life or what would I regret or what would make me unhappy. And oftentimes that is a much easier way to focus on if we just get rid of some of these things or get rid of some of these regrets, then it will elevate us to a higher level just by getting rid of the regrets, even if we don't have a clue as to what else is going to make us happy.

2:28Yeah, that makes sense. So for instance, if my question is, how can I retire as early as possible in the happiest way possible to invert it would be, how could I ensure that I can never retire and that I'm miserable throughout the entire process? Yes. So if I don't save any money and if I really make everybody around me really angry by saying mean things to them, you know, it sounds comical, but it actually does work extremely well to get to the meat of something. I like that exercise because I can see how even in that example that I gave, my question was easier. The reverse is easier to answer.

3:14Yes. All right. So what we're actually doing is we're talking about the book, which is called The Top Five Regrets of the Dying by Bronnie Ware. And okay, you guys, here's how I want to start. So Brad made the announcement or we talked about on the podcast a while ago. And then maybe you forgot about it, or maybe you didn't get that episode, right? But we got hardly any feedback. And Frank and I have different theories for why that is. But Frank is more interesting. So Frank, why don't you think people read this book or got back to us with feedback on the book? I tend to think that people who are interested in things like personal finance, fire, and things that involve planning are by their nature future oriented.

4:00And they really do not want to think about death or plan for the end of life other than wondering how much their long-term care insurance is going to cost. People who are better or are constantly future focused tend to try to avoid thinking about death, reading things about death, reflecting upon that. Because in a sense, by continuing to plan for the future, it's almost saying like, well, if I could just keep planning for the future, maybe I'll live forever. Or maybe my money will live forever. Some version of me will live forever. And that's what I'm really planning for. But unfortunately, life doesn't work that way.

4:41It's finite. And at some point, your future is now. I think it's now. I think it's happening. Yes. But I think that a book like this challenges the notion that just being a good saver or a good investor will just lead to happiness. because if you read personal finance books, they're all about building wealth and the procedures and the things. But there's an embedded assumption in there that if you do this and become wealthy, everything else will work out. You'll be happy and content and everything will be wonderful and your relationships will be wonderful. And that's the end. But as we know, that's not really the end and that many people who achieve great wealth and success in that part of their life still feel like failures at the end for various reasons.

5:35So I think that this is a challenge that many people don't want to address. But for some people, I mean, if you're young enough, it's sort of like, well, yeah, the chances are you won't need to address this in a very long time. Although, you know, most of us have probably had some experience with somebody who's died young. And depending on how meaningful that experience was also influences how you may view how important this topic is. We were talking a little bit before about this concept of some people being future oriented, some people being present oriented, some people being past oriented.

6:15And Frank had said, oh, well, fire people are future oriented people. And of course, right? Because we were thinking so much about like, how can I take care of that future self? And I'm making a lot of decisions that are all about what's going to happen in the future. But part of me is like thinking everybody is future oriented. The human is future oriented, right? Because if I were to say to you, Frank, you're going to have the greatest week of your life. And it can be next week or it can be last week, right? Which one are you going to choose? This week?

6:55Well, with a conceit, Frank, you're going to choose next week, right? Because there is this way where we do value, I think, this experience that we can have more than the one that we did have. I don't know. Well, the research you're talking about comes from Philip Zimbardo, who's a famous Stanford psychologist who passed away last year. did all kinds of other interesting research, but this comes from a book called The Time Paradox that I read like 15 years ago. But it gives you a good model for understanding various people in society. And the truth is most of the people in society, consumerist society, YOLO, that is present focused people.

7:37And when I'm talking about present focus, it's the near future, like tomorrow, next week. So that is actually the dominant culture is what Zimbardo would call present hedonist people that, yes, I do want to buy the boat or go on the trip and I don't care what it costs. I'll figure that out later. The second probably largest group are people that are future focused. And in modern society, that is a much better thing to be if you want to be at least hourly successful because you're the ones that, you know, go through and go to medical school or get all the degrees or climb the corporate ladders, do all those things that in our modern society will help you a lot that wouldn't have necessarily helped you in a hunter-gatherer society.

8:27Being present focused is probably the safest way to be because you're not going to get eaten and you're going to find food. So I think when you're thinking about present focused. That's basically consumer society. The other kind of present focused are what they call present fatalist. And these are the people who are self-destructive. They do a lot of drugs. They're like, I'm going to die anyway. I might as well go out with a bang sooner rather than later. Sure. And that focus, that's obviously self-destructive. It's interesting, the author of this book, Bronnie Ware, is very present focused and seems to have alternated, if you read through the lines in her life between kind of present hedonist and present fatalistic that she would work a job and then, you know, I just hate my life.

9:10I'm just going to go off and live in a different country for a period of time. Really important that helped me understand the present focus of where you said, okay, it's actually not about this moment. It's about the very near future. That is really different to say, oh, you only live once. And so I'm going to buy this dumb car today, right? That's very different from I am fully in the present and okay with reality exactly as it is. Yeah. Yeah. The present is the near present as opposed to 10 years away. And that's what personal finance people are always thinking about is 10 years plus away. Yeah, absolutely.

9:53All right. So Adley wrote in and she said, our society has shut death out almost as a denial of its existence. We are all going to die. But rather than acknowledge the existence of death, we try to hide it. We carry on trying to validate ourselves through our material life and associated fearful behavior instead. So, yeah, we're here today. We're going to look at it a little bit. Yeah. Maybe it would be helpful. So Frank, how do you feel about like giving a brief, very brief summary of the book for us? Okay. So this book is written as a memoir. So it is about somebody's personal experiences. It's not like reading a typical personal finance book or a self-help book where the chapters are lined out.

10:37Sort of here are the questions, here are the answers, do these things and you'll have good results. It is more a reflection on the experiences of the author, Bronnie Ware, who was a palliative care nurse. So she was assigned to work with people who were dying as their nurse and kind of the last person or one of the last people who would be around. And so I had many experiences. and through that process she observed kind of patterns of what they had to say about whether they enjoyed their life whether they regretted their life and oftentimes it is towards death that people start saying i wish i would have done this or i wish i would have done that and so i think that that led to her categorizing regrets which became the five regrets of the dying i i keep wondering whether she's the one that categorized these things into five things or whether some editor told her, you need to make this more structured.

11:35Because if you are not used to reading memoirs or books like this, this can be frustrating for people who are looking for the self-help books or some kind of double blind study of 10 ,000 people or die or a Framingham longevity study. This is not that. This is one person's personal experiences and then a reflection on that. But because people are very similar, particularly towards death. We're so similar when we're born and then we get more similar again when we get close to death. Since these are common experiences. I think that she did hit on some themes. And in my experience, this book is written over 10 years ago.

12:21I think it came out in 2013. there is a reason why it continues to have currency and has been picked up by other people who have looked at other aspects of this in more of that analytical framework, like somebody like Daniel Crosby has done in like the soul of wealth recently. But the same themes are there. And I think this is very useful for giving you examples. Do you want me to read the five regrets of the dying? So people sure give us the five regrets, or do you want me to keep it a secret? you'll know once you reach a certain age there'll be a quiz at the end okay so the first regret of the dying is i wish i had the courage to live a life true to myself not the life others expected of me and this pertains largely to people following expectations from their families in particular from people who are have a history of lawyers or doctors in the family and they're expected to do certain things at certain times or take on certain professions or things like that, which is, it's a very common story.

13:30Maybe we should pause there and kind of talk about them a little bit as we go. Okay. Okay. So the first one is about expectations, living the life that you want to live. And I think there is so much for us to take from that. Like partly there's those stories we've all heard about. I really wish that I had been a baker, but instead I became a dentist, right? Yeah. I mean, I'll read you the, or give you the outline of one of the patients here. There was a patient named John she's talking about. He spent his life working in a job as a lawyer because of his father's expectations, but his true passion was art.

14:07I mean, he expressed a deep regret for not pursuing creative dreams and doing those sorts of things. And he wished he had found the courage to defy expectations and follow his heart. Yeah, it does require courage. And I think it's something like it is something we talk about a lot in this community. You know, like I'm even thinking of I just finished Jillian Johnsrud book, Retire Often. Yes. And to me, one of the greatest things about reading that book. It's such a helpful book in terms of, here's how you can take a sabbatical. Here's how you can talk to your family. Here's how you can talk to your employer.

14:45Here's what you can do about health insurance. All of that is great. But the really great thing is that she's making something normal that we don't often think of as normal. And so as you read story after story, you start to see, hey, I could also do this thing that is outside of this box that I feel like I'm in, right? Like I could also look at those expectations that people have of me and here's how I could kind of get around that, right? Like how could I live this life that is more exciting and more in line with what I want to do? And partly what we need is we just need other people to make it normal or other people to show us, right?

15:25Same thing with early retirement. Yeah. Well, it does require you to have a little courage. I mean, all of these regrets, you could term them as kind of a lack of courage and maybe it's fair or not fair, depending on the story involved. But what we can learn out of this from fire, whether you do these things as retire often and take sabbaticals and do them, or this can be one of the purposes of getting to fire and sort of, well, then what do you want to do? Because is this person, you know, I'm a lawyer. I've retired from that or mostly retired from that. But then what do you want to do? And particularly on a sort of creative non-paid side, what would you do?

16:10This is that question. What would you do if you could just do anything and whether you got paid for it was not relevant to the conversation? And that's what you should be asking. And usually these things are, they're oftentimes creative endeavors. Some people fixate on travel, but I think that only goes so far for most people. But there's usually some kind of, in this case, art. And in some cases, you just want to throw parties or you, I'm trying to remember what her name is. She's from St. Louis, the person who was the weather broadcaster. I'll think of her name as we go. But she's now coordinating trips.

16:47She's found this sort of second creative life of organizing trips for people to go on. And of course, if she would have thought to that, what I really want to do is organize parties. Maybe that is what you want to do. But the point of it is, it's sort of what is that thing that you really liked doing? And oftentimes, it's a thing you were interested in as a child that you liked playing music or painting. I know several people in Firespace who have gone off the Mad Fiendist, for example, he decided he wanted to make music and make a little, I don't know if you call it an album anymore, but he did that.

17:26And that's an example of oftentimes this being FIRE gives you that opportunity that, yes, it is time to just go do something and stop trying to monetize everything. I think that is often a sticking point that people go, and you hear this, it's like, you know, I'd really like to go sailing. And then often the response is, you know, you could have this business where you take people out. And it's sort of like, no, let's take the money out of it. What are you going to do that is fulfilling to you that may cost you money rather than make you money and stop trying to connect it with, it needs to have this productivity categorization or factor to it.

18:09I think people are still afraid to do things like that, that, no, I really wanted to ride a unicycle and be a clown. Okay, go do it. Yeah. So this one is about how can you, our takeaway here is like, how can you express yourself. Yeah. How can you not let everyone else's expectations sort of squash that for you? Yeah. Yeah. And oftentimes it does require kind of reflecting on what were those fun things you liked doing as a child, as a first starting point, or just something that had come up along the way where people just find little interest even through their job. It's like, you know, I'd rather be doing that job or I'd rather be doing something with children.

18:55There's sort of myriad things, but the courage you need to have is to be able to tell the people around you that, no, I really want to spend time on this endeavor because oftentimes the people who are closest to you are the least helpful about this. They'll say things, oh, why would you want to do that? That sounds dumb. You'll shoot your eye out. I love that you bring up the courage piece there because you know something I see in my practice a lot, I'm a counselor, is that people will be really scared to share this kind of thing with their spouse or their friend, but then they do and their spouse is like, great, I don't care.

19:38We are the ones putting these huge expectations, or we assume that other people have these expectations of us. And if we can have the courage to actually voice them, that you might find, in fact, that people are easily on board. Yeah. I think the other stumbling block that people often have is like, well, if I say I'm going to do this, then I need to do it for, I don't know, a period of years at a very high level. Otherwise, it's not worth doing. And, you know, maybe you'd like to run or experience running. And the next thing you're thinking, well, then I got to run marathons and maybe ultra marathons.

20:18And it's like, no, you don't.

20:23I like to ride a bicycle, but I don't go very fast and I can't keep up with people. But the joy has to be in the doing and also in the doing, not necessarily at a highly proficient level where it turns into another game that, you know, I need to be the best at this in my age group or something like that. Yeah, I love that, that we can say, OK, so again, you guys, it's important to express yourself and we're not bringing your optimization game into this, right? Yes. This is not to win the prize or to make the money or to get the most clicks because you end up back in what are called the four idols, which are power, fame, money, and pleasure seeking.

21:11That goes back to Aristotle. But once you shove your activities into trying to get at those things, you're on the wrong path. Well, I feel like what we're talking about, we're talking about like, oh, we don't have to monetize everything. This leads into one of the other regrets, which was I worked too much. Yeah. Let's kind of jump to that one. Yeah. The second one is I wish I hadn't worked so hard. this tends to be the regret of people that you know had involved careers the example in the book was a woman named grace she was an elderly woman she spent much of her life prioritizing her family's needs but her regret centered on her husband's absence due to his relentless work you know this is that song the cats in the cradle her husband a breadwinner worked long hours missing out on family moments.

22:04And Grace shared how his absence strained their relationship. And he later died regretting the time spent working. This is a very common story in the great scheme of things in our society, because we're taught to love careers. It's interesting that that is more characteristic of baby boomers than people who are younger. Yeah. You know, one thing that I've heard about lawyers is that they work all the time. They do. We do. That's what we did. I worked like 80 hours a week for decades. Oh my God. Do you have any regrets about it? Yeah. Some of the time I missed, but I can tell you it's why I don't have a travel bug anymore.

22:45I was traveling all over the world doing that kind of work. I was lucky. I had very interesting work that involved a lot of travel, meeting a lot of interesting people and doing a lot of interesting things in international arbitration in particular. So there were a lot of nice aspects to my job that I liked, but you do feel like the rest of your life goes on hold. And that's, I think that's the common thing for careerists like that. I mean, it leads to high rates of divorce with lawyers and doctors in particular, and other people who are, you know, essentially more married to their career. I think people are more recognized that this is a problem now than they did in the past.

23:30Hence, there are things like books about retiring often. Yes. Like taking breaks. Because this was an expectation that was particularly put on men to go out there and have that career. And it was very, you know, gender role from the 1950s or before that. There was almost a different spheres of, well, this is where the men go and do this. And this is where the women go and do this. That is all broken down, fortunately, but it still does affect a lot of people. And I knew a lot of people in my profession, you know, at my firm who just kept coming to the office until they died. Because it was sort of like that was the whole life and there wasn't going to be any afterlife.

24:14And they got into the habit of that. And typically you do end up with these kind of regrets because this really affects relationships. Yeah. Your primary relationship, but also with your children. This is why so many people, careerists, are essentially estranged from their children. And it causes a lot of resentment there. Because basically, what you're really choosing is that idol of power when you are a careerist. Because that's what's attractive about the career. You have power. You've got minions. You have a task, an important task that needs to be done. And you're all working out on this team.

24:54But since the relationship is just around the career project or whatever, that's not a real friendship kind of relationship. Your real friendships and relationships are back with people that you are not working with and you need to choose or be able to say, no, I'm going home. For me, the way I dealt with it in the last 10 years of my career was I made sure that when we got the schedules for all what the kids were doing and all their sports or activities and things, I put that on my work calendar. So it was already blocked out. Yeah. So when it was time to schedule whatever else, I could legitimately say, no, I can't do it then.

25:41Let's do it the next week or something like that. There are ways of doing this, but again, it does take some kind of conscious effort because what I saw mostly was people were so driven by the career and what everything going on in there, they just prioritize that schedule and then there wasn't any room left for anything else. Yeah. I like that you gave something kind of specific there because the problem that I have with this discussion of like, oh, you want to be really careful to balance. Sure. We know we're supposed to balance work and family. And that might be useful for someone like me who is self-employed and I get to decide how many people I'm going to see a week, right?

26:27Yeah. But most people, or at least the people that I know I'm hanging out with, they don't get to decide that. They're like, this is my shift. It's from 7 to 7.30, right? And if I don't come for this many hours a week. I'm not going to have this job anymore. And so it also seems like really tricky to be saying, hey, we have to really be prioritizing relationships and we can't have it all be about work. And it's like, well, how do I do that if I also have to have a job that is structured? Yeah. And to a certain extent, yeah, you are at the whim of your employer. But I mean, this is really addressing people who are in the same job or career for a long time.

27:10But what you need the courage here for is to decide. At some point, I had to decide, you know, I could keep trying to climb the ladder, becoming more important in my profession, start writing papers, going to conferences, doing all this other extra stuff to make my career even bigger and bigger and bigger. But I consciously decided, no, I'm not going to do that. I'm going to do the work that needs to be done to be proficient and professional. But a lot of this other extraneous stuff designed to become even bigger and more. Yeah, I'm not going to do that anymore. Oh, I love that. I love that because it's one of the things you hear about like in the fire movement of like, okay, well, you can only save so much, you can only like be so frugal.

27:57So you really have to be thinking about like, how can you make more income? And I think what you're saying is kind of the flip side of that of like, also think about the value of the opportunities that you turn down. right like that there's there's something on the other end of that as well and so that it's not just like you say can we therefore then monetize every fun thing that we do can we therefore think about every hour that i'm not working is an hour that i'm you know not meeting my goals yeah or i mean what a careers gets into is the continually climbing up some ladder that if i'm going to be in this career.

28:33Oh, I want to be the best. I want to have the top sales or the top receipts or some superlative. Yeah. The award. I knew a number of people in my profession that were involved in all these things and they became presidents of bar associations and did all these sorts of things. And their offices were strewn with awards and things like that. But they did sacrifice other things in their life for doing that. Yeah. Spoiler alert. None of the top five regrets were I didn't make top sales. That's correct. People tend to overvalue that at the time. And a lot of it is because if you get caught up in the social environment of these professions, whether it's sales law or whatever else, they're sort of like you look around and you say, oh, well, they just kind of liked to do this or they just sold the big thing or they're meeting with the important client or, Or, you know, there's sort of this, I'm behind.

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29:31I need to do this other thing. And it really just takes some reflection and the courage word to decide. It's funny, they call this quiet quitting now. I just call it limiting, self-limiting my career so that I could do other things. But the expectation always that you have in most careers, most competitive careers, is that you're just going to keep going and getting bigger and better, and you need to decide how valuable that really is. Yeah, and like you were saying at the beginning, how there's some connection to that. There's a denial of sort of death there. Yeah. Well, ultimately, you know, if you're really serious about your whatever profession, you're looking for that Nobel Prize, aren't you?

30:17Whatever it is that's going to go on that plaque somewhere that makes you immortal. Yeah. People try to cheat death by becoming immortal in some way, and it generally doesn't work. And as a proposition for whether it will work or not, it probably isn't because life is random as to who actually gets remembered. If you go back 60 years and look at who was being talked about in the popular press or whatever, you're probably like, I don't even know who that is. I mean, and go forward a little more in 200 years. It doesn't matter what prize you won. The people get remembered for all kinds of things that they never intended.

31:02Sometimes books that they wrote before they died and nobody heard about it until somebody published it 50 years later, then all of a sudden they become famous. Okay. So I think this leads into what we both agree is maybe the big one, which is about the people one, right? So read us the one about relationships. Well, there's two. Yeah. Three is I wish I had the courage to express my feelings. Okay. Which the example is a woman named Margaret who hit her pain and kept her emotions all bottle up to maintain peace in her family. It's interesting. This one is almost the female version of this role-based expectation that particularly these people who are older would have been baby boomers or silent generation or something like that, who did live in that world of men need to have careers, women need to take care of the family and be the backstop and make sure everybody's happy except for themselves.

32:05And so it's kind of an old story, but it still goes on that some people, particularly if you are introverted and you live in an environment where you feel like you have to take care of everybody else, or maybe you were a parentified child or there's some other history going on there, that you do feel like you didn't actually live your life. You lived a life for other people that was never fulfilled in some way. I think this is much less likely to be something that is experienced by people in the fire movement. Oh, say more. Because people who are listening to things like Choose FI have already decided that they want to do something different or more, or they're not completely sort of bottled up or restrained in that way.

32:58Yeah. That I think people who have these regrets probably would not be listening to podcasts like this one or reaching out. You've already expressed some bold emotions. I think this is a common thing that therapists run into, particularly with female clients who are older. Okay, well, let's jump to one then that you might think is more relevant. So the one about maintaining relationships. Yes. It's entitled, I Wish I Stayed in Touch with My Friends. But I think more broadly, it is, I wish I would have pursued my relationships better or more, regardless of whether they were particular friends or family or anything of that nature.

33:39The example was this woman named Rosemary, who was an isolated widow. She had had friendships earlier on, but she had let them lapse as sort of marriage, children and work took over. And she was regretting that she missed these people, that she spoke fondly of them, but kind of realized, well, she doesn't have everybody to talk to or she would really have wanted to talk to those sorts of people. But I think it goes to a more broader perspective of maintaining those old friendships, but also how do you make new friends as an adult? This is so important. And so it covers a big spectrum because people who feel successful at the end of their life, and this comes not only from Bronnie Ware, but from people like Daniel Crosby and others, generally have good relationships.

34:34Yeah. That regardless of whether they're old friends or some other friend they met along the way or some combination thereof, the people who report sort of having the best experience of life, it's always based on relationships. Yeah. And so if you're wondering what to do when you reach FI, what should I prioritize? One of the things you need to prioritize is your relationships. And that includes spending money on relationships. Okay. We're going to go in, going to see those old friends, looking them up, finding them. You're the one that's financially independent. They may be working. You need to get out there and renew those sorts of things, or at least invite that to happen.

35:22And that is also the way you're going to make new friends is to join some kind of club organization, go to Camp Fi or other things like that. Whatever your interests are, that is where you're going to find new friends. Yeah. Okay. I'm going to read from an email that we got about this, this part of the book. And this one just really touched me because I think so many people can relate to this. Okay. This is Susan. And she said, I just finished this book and it really resonated with me both as a retired RN and as someone starting my retirement while my husband continues to work. I struggle with the differences my husband and I have with nurturing friendships.

36:08To me, people in relationships are the things that really matter. I'm the one who generally makes or accepts invitations to nurture our relationships. My husband is more of a loner, and it is not as important to him to spend his time in this way. I struggle with balancing this for us as a couple, and I really hope that I don't regret not spending more time with the people who are important to me. I hope that this dynamic changes once he retires as well. And my thought to this is, yeah, you're going to regret it. So you've got to do something now, right? Today. And just like you were saying, oh, well, once you reach fire, you have to really work on those relationships.

36:46Even better, start now, right? Before you get that, right? Because this is the most important thing. That was my takeaway from the book and from life. Yeah. Yeah. I think the, um, I think these five things do ultimately boil down into two, one being self-expression in its various forms and the other one being maintaining positive relationships or growing them over time. And the person who just wrote in, that's a very common situation. And again, it does attach to some of these general kind of things that women are often maintaining the relationships of the family with other people and organizations.

37:28And the person whose relationships are tied up in work, often those are not actually what I would call real relationships in terms of a friendship, because what you really have in common with that person is you work with them. And oftentimes what people find is that when they stop working, those relationships fall off relatively quickly, because they were based on being both happened to be involved in this organization or this project. And a real positive relationship tends to form on somebody having a problem and somebody else helping them with it. Interesting theory. That is, in my experience, so, and this is the difference between acquaintances and friends.

38:14You need to start with acquaintances. You need to go and suppose you want to build new friendships. You don't like the ones you had before, or they're not there anymore, or you can't rekindle them or whatever. And I think this applies to most people that even if you do have old relationships that are good, you probably still want some new ones, particularly if you're retired early and you have half of your life left. So the first thing you do is you go and join organizations that do things that you're interested in and you get acquaintances through that, find people you do things with. But in my experience, a real friendship does not form there until somebody has some kind of a problem and somebody else reaches out to them or helps them with it.

38:56I want to frame that another way and see what you think about that. I hadn't thought of it that way. That makes a lot of sense to me. I always think about the place of that friendship is when one person risks being vulnerable and that the other person can respond to that with care. That bid and acceptance from God. Yeah, I agree with you. I agree that that's a better, a broader definition. I mean, the example I'll give you is how I became friends with Diana Merriam, who runs the Economy Conference. Tell us. So I got to know her because she had been on podcasts talking about hiking the Camino. And that's something that me and my wife had talked about doing.

39:37And so I reached out to her and said, tell me about that and give me some books or some materials I can read and look at that. So I did that. So, you know, we were kind of aware of each other and were acquaintances in that respect. After she ran her first economy conference, I mean, the conference itself, she felt went well for a first go, but she lost a lot of money,$40 ,000, which was like a year's worth of living for her. and so she was wondering can I still do this and she reached out to a few random people including me oddly enough she reached out to me because she thought I was good at social media which I'm not

40:19so but I did help her you know sort of look at her numbers she says do you think I can keep doing this and I said well you can't lose$40 ,000 a year she says no no I can fix that I can break even. I know I could break even if I just fix a few things. And I said, yeah, and I'll help you. I can't do social media, but I know you need to fill these slots for people doing little workshops and things. I can teach. So I will come and do one of those for you. Yeah. She made herself vulnerable by saying, I need help. Yeah. And you said, I can help. Yeah. And that's how we became friends. And so I'm driving to Chicago in a few weeks and And I'll stop and see her then.

41:00Yeah. And, you know, we went to our wedding one and a half years ago and things like, I mean, it's just that process in order for that to happen. First, you need to get yourself out there to getting acquaintances on the things you may have mutual interest in. And then when that bid comes, you have to take it or you need to make some bids. Yeah. Knowing that, you know, some will be rejected, but the only, the only way you really get to a friendship is if there is this vulnerability and acceptance of it and help with it. Courage. Yeah, again. I'll tell you why I framed it the way that I did, why I think it's important to talk about it in terms of vulnerability, because I see so many people who, guess what?

41:40Everybody wants more friends. Everybody wants to have more love in their life. Yeah. And what can happen is that people think, well, if I'm just perfect, right? Like if I'm just like this super amazing person, then this other person will want to be friends with me. And then I have to be like, no, no one wants to be friends with the perfect person. What are you talking about? Right. It's the moment where you actually reveal that you're not perfect. That brings people to us that allows us to feel like, oh, this person's like me. You know, like I could tell this person something. Yeah. Yeah. I think people often confuse fame for friendship, particularly in the era we live in when, you know, you can put up stuff on social media and get lots of clicks.

42:25It's like the more clicks I have, the more, you know, friendliness I have in my life. It's like, no, that is not actually how it works. There's no real relationship there at all. If somebody just sort of likes what you do or admires you from afar or anything like that is not, there's not a two-way street going on there. Yeah. And so just becoming famous or notorious or whatever in some activity is not, if you're joining groups, that your goal should not be to be the best performer of the activity. And in fact, you're more likely to make friends if you're a bad performer and reach out to somebody and say, can you help me with this?

43:09I can't figure out how to get into this yoga position or whatever. Because that exchange of the bid or the problem and the person solving it, that's how friendships are formed. Yeah. I want to talk a little bit more about the idea of bids because one thing that you said that I think a lot of people say is like, okay, well, if you're looking for friends, then go join a club, you know, a group of people who like to do what you like to do. And most people who are my age who hear that are like, what are you talking about? I have a job. I have my families. Like, where am I going to find this weird club?

43:45And how am I going to have time to do that? So, I mean, it's great if you can join a bunch of clubs, but it's not essential, I think, to go find a pre-made sort of network that you're going to fit into perfectly. And what you were saying about the bids, I think, is so essential. You said, well, you're going to have to increase your bids, right? Which can be so simple in terms of just like looking for one little way that you can connect with someone, right? Right. So I'll give you an example. Before we press record, Frank and I were talking really briefly about books because I had said, oh, yeah, I have that book you mentioned.

44:24I have that on my bookshelf. Right. And I think maybe Frank and I like to read some of the same books. So later, what I'm going to do is I'm going to make a list of some books that I think Frank will like, and I'm going to send it to him. Right. Like that's a bit that's like me noticing, hey, here's one thing that we have in common. So I can take a little bit of time to do this thing, right, to show him that we have this thing in common. And there's so many ways that we can do that in our lives. Yeah, that's correct. You know, when I was talking about joining clubs and things, who I was addressing that to is people who had reached fire, and they're not working anymore, they have the time to do things like that.

45:03I agree with you. I had no time whatsoever to do that when I was working and our family was growing and our kids were still in school and doing all their things. I only had time for work and the family and maintaining some old friendships. That was about it. But that changes over time. And when you're talking about somebody who's retired and that space between retired and then dead, that is where you need to get out there. So for me, one of the things I joined, I'm a board member for a charity. And I've met a lot of interesting new friends that way. Yeah. But it's sort of like you don't know where you're going to find them or who you're going to connect with.

45:51Yeah. And what I was, I was probably just anticipating the usual question or the usual things like, yeah, well, I'm just kind of content with my life. And it's just, it's fine. It's like, well, would you like to make some new friends? No, not really. you know, just this sort of, I don't want to try very hard because I might get rejected or something negative might happen. But the problem with that thought process is no, but you're more likely to regret later on that you didn't make an effort to develop new relationships or deepen older relationships or do something in that, that had to do with, I'm just doing this for relationship purposes.

46:30Frank, I've got a great title for your book, which is The Space Between Retirement and Death.

46:41Okay, before we back away from the relationship regret, I want to go back to something you said about like, hey, you might have to spend some money on this. Because I think that, yeah, like, let's talk about that. Like, what are things that are good to spend money on? Your relationships. and I think it's not super intuitive that that might be a useful connection. So maybe can you talk about that a little bit more? Yeah, I think, and I've tried to prioritize this more now in my life, that there's one of the questions I'm always asking myself in whether to choose to do an activity or not is, is this going to further a relationship or is there a relationship component to this activity?

47:25So recently, we took a trip to South Africa. And we took it with some new friends of ours. This was with Bill Young and his wife, Karen. So I had met Bill at like FinCon in 2019. And his wife was there and I talked to her. And so we kind of bounced around and had this, we saw each other in various places. But over the past, say, year and a half, we become closer friends and friends as couples now. But part of that was over the summertime, they wanted to take a little trip and they decided to drive up to Tennessee and see us in the D.C. area and stay with us and did things. But there had to be a bid and acceptance there.

48:09And then we had also planned this trip to South Africa that, again, we were talking about doing the Camino and they were wondering if they wanted to do that. they found this trip to South Africa that they wanted to do. And then they asked us if we wanted to go on it. And we said, yes. And it costs a lot of money and it was great. But the point of it is, for me, I will not travel anymore unless there is a relationship component to what I'm doing. And it might just be with my wife because I traveled so much. So I only go to one Phi conference, Iconomy. And Mary comes with me. And I won't go to any other ones because I spent so much time away from her that I want her to be part of my life and whatever we're doing with that.

48:56Yeah. But that's different for each person as to how that plays out. But the point of what I'm saying is you want to make relationships a component of what you are doing or planning on doing, whether it's joining this club or going on this trip or taking on this job or giving to a particular charity or whatever it is, see if you can, and never use the excuse when you're fi that it costs too much. You shouldn't be having that problem anymore for most things in most people. And I think that that gets oftentimes used as, as an excuse or the first priority is minimizing costs of something. Yeah. And if somebody else plans a trip or something and you think it's costing too much and you'd rather stay in a cheaper hotel.

49:44You'd rather do this. It's like, no, pay the money, stay in the hotel, do the thing. One of my friends, my old friends is a big Cubs fan and he likes to go to a different city every year and watch the Cubs play whoever is there. And so last year it was the New York Yankees. And so it was in New York and it's like, I've been in New York a million times for work. I don't need to go to New York again. New York's expensive. It's crowded. There's all kinds of things that are undesirable about going to New York. But I went. I didn't go there to go see the Cubs play the Yankees. I went there for the friendship and for the relationship.

50:21And that is the way you need to start thinking about these things. If somebody invites you to do something or you're organizing something, the cost of it or what it is in particular should not necessarily be the biggest priority anymore. It should be, Who do I get to hang out with for some period of time doing something fun? And that should be the priority, not some other thing that might have been a priority at some other point in your life. Right. So recognizing the thing you're buying is not a ticket to a game. The thing that you're buying is a life experience with the people that you love.

50:59Yeah. Because that's how you made friends when you were children. Yeah. You just went and did things with other kids and eventually you became friends because you were doing things together for so long. I love how this gets back to what we were talking about at the very beginning about sort of being future oriented and how that's wonderful in some seasons and in some ways. And yet you can see in the example that Frank's giving how it just wouldn't make sense to say, no, I need to really save this money. Right. Yeah. You can imagine a situation where you had planned out a vacation budget for the year, and then you would plan the events for that.

51:40And then something comes up where a friend or acquaintance of you says, hey, this thing came up and I want to go to this thing. And your reaction should not be, it's not in my budget. It should be, yes, I don't know, assuming you like this person. and it's like, take it out of next year's budget or do something else. Don't spend money on something else. You need to make sure you are not making decisions about money and budgets and finances and things when you could choose relationship over this magical plan that you have about how much you're gonna spend on vacation this year. Now, obviously I'm talking about people who are fire close to it.

52:24I'm not talking about people or at the beginning of their jury who do need to say no to the eighth wedding or some destination thing that their friends want to do. That's a different story. I'm really talking to people who are at a point where they do have the wherewithal to say yes, but the reason they're saying no has to do with some other priority that they've created over relationships. Yeah. I think you have some awareness of your audience, right? That this audience isn't the one who's going to blow their yearly income on eight weddings, right? They're more at risk of sort of making that mistake of...

53:04Yeah, I'm talking about people particularly in the second halves of their lives. All right, let's move on to our next regret. Number five is, I wish that I'd let myself be happier. And the example is Harold, the man stuck in routine. He's an older man that lived a comfortable but unfulfilling life, stayed in a job and a marriage that no longer brought him joy out of fear of change. In his final weeks, he reflected on how he could have pursued happiness by leaving his unfulfilling situation, but chose familiarity instead. His regret was not about specific actions, but in failing to allow himself to seek joy, showing that happiness often requires courageous choices.

53:46And to me, this is what Emerson was talking about when he's talking about a foolish consistency is the hobgoblin of little minds that oftentimes people fall into consistencies about the way they are and that prevents them from changing. And I'm sure this person was like, well, I, you know, it's a good enough marriage. It's a good enough job. It's good enough I'm, quote, content, unquote. I read that in a, there was a post on the Choose That Buy board where somebody was saying, we have this money, we've saved a bunch of money in our account. We're also going to get a pension of$135 ,000 a year, but we only spend$75 ,000 a year and we're content with that.

54:35And the sort of conversation, well, what do you want to do? And they're like, well, we'd like to spend more money on our kids and help them and work with our church and do these other things. And my reaction is like, well, why aren't you doing that right now? To me, the minimum you should be spending is the$135 ,000 minus taxes. Because if you're content with 75, what happiness or relationships or other things can you buy, essentially buy with the excess that you know you can spend anyway? You're not going to have any financial problems. But it's kind of this weird idea that because I'm content with this amount or this situation, that's enough.

55:20I was also reading Morgan Housel's new book, The Art of Spending. And he talks about some of the most dangerous words in his chapter about identity are, I am a saver. Because putting that as, and he was saying that if you're a saver your whole life, when do you spend the money? you're just saving and saving to max wealth at death. Right. And that doesn't mean die with zero. It just means be more thoughtful about it. But he was saying that attaching identity to those sorts of things is not where your identity should be because it's just as bad as saying, I am an attorney and that's my identity.

56:00I think where you really want your identity to be is that it has something to do with either relationships or creativity or both. And I imagine you're saying that because if your whole identity is being an attorney, well, one reason you might be saying that, right? There's a time when you're not going to be an attorney. If your whole identity is being a saver, what do you do when it no longer makes sense to save, right? Like we are sort of ripe for crisis. Yeah, that eventually tends to cause, it actually, it not only does not develop relationships, it detracts from relationships. This fixation on always being efficient and saving money.

56:43People notice that and they don't want to be around you. And those people may be your kids. there is a lot of work done by, his last name is Grubman, and he counsels very wealthy families. And they all have these ideas. It's like, well, I need to toughen my kids up by showing them, by not giving them too much early on and making them work for it and all that sort of stuff. And some of these kids get to be age 40. They don't realize how wealthy their family was. They find out and they're not happy about it. it's huge resentment time. Yeah. Because you were basically just setting up a dishonest situation.

57:24Actually, Morgan Housel has a story about this in his book. One of the funniest things was he was talking about there was this family that had a grandpa who would tell the grandchildren, it's like, I'll buy you a lift ticket if you walk up the mountain at least once. And he thought that he was like teaching them a lesson and they would think, oh, grandpa's so tough and cool and macho and whatever. And Morgan writes, what they were really learning is that grandpa was an asshole. And that is likely what people are going to start thinking about you if your identity is a saver to the point of irrationality and there's no real reason for it other than you thinking it elevates you in some way.

58:09And so choosing your identities can be very important. It's funny, I actually talked about this a little bit in the last twos fi episode i was on number 508 it all comes back around it does but that that has to do with the idea of narrative psychology and picking your story or the stories you want to have now and you want your identity i think to be connected with some kind of relationship at least some of your identity that you know i'm i'm a good friend i'm a good father. I'm, you know, the organizer of our family. I, you have a natural profession that you're a counselor. You know, me being on the board of a charity is another identity that helps me feel elevated.

58:55But that has to do with the relationships with other people. But I think these kind of inchoate saver, trader, butcher, baker, candlestick maker are probably not really good identities to adopt or keep. Yeah. You want to think of what identity do I want in terms of relationships? Another good way of thinking about this, about spending money in relationships is making a down payment on your eulogy.

59:29People say, you should write your eulogy. That's maybe a good exercise. But I also think is like, what generous or kind or nice thing can you do with money today that is a down payment on your eulogy so that when somebody gets up to give you a eulogy, they will say, yeah, they really knocked it out of the park with this. Oh, all right. I want to read another email from a listener that's about this. So this is from Adley. And she said, if I had to guess, the regret I'm most at risk of having is I wish I had let myself be happier. I come from generations of women who didn't have the space or freedom to be guided by what their hearts truly wanted.

1:00:10At 36, I recently found myself telling my daughter's swim instructor, who was heading off to start her freshman year of college, do what makes your heart sing. It will never lead you wrong. It's amazing how easily I can cheer on others, care for others, as Bronnie did, and yet still wrestle with fully allowing myself to be happy and at peace with who I am. Yeah, that's interesting. I mean, that's also part of Bronnie Ware's story herself. Yeah. That, you know, after multiple different sort of careers and bouncing around and relationships that didn't work, she finally found a few things that did and then did find a relationship and have a daughter she valued.

1:00:53She thought at one point that wasn't for me. I'm not cut out for it. I'm not allowed in some way to be happy. I think that's still a common cultural restriction that many women face, depending on what kind of family or group they grow up in, that it goes both to that kind of expectation kind of thing that your purpose is to make other people happy, not to be happy yourself. Okay. One thing I loved about this comment was how Adley had the wisdom of like knowing where the solution to this is, right? Where she was saying, I can do this for other people, but it's hard to do it for myself. And that can be such a good starting place for people in terms of like, how can I care for myself?

1:01:43Oh, I have those skills, right? Like I'm so great at doing that for my family and my friends and people who are basically strangers. I can give us some confidence around. I really want happiness for those people. I really want to cheer them on. And so we can kind of start to work to do that for ourselves. Yeah. Yeah. I mean, I think some people think, well, if I assert myself in a, you know, I want to do this or this would make me happy that other people are going to think bad of me in some way that, you know, I'm selfish or, or many other negative emotions associated with not taking care of the other person in favor of taking care of myself.

1:02:23And, you know, I think that's, that's still a relatively common problem. Societally, it's still probably more with women than it is with men, but. Society. Yeah. Okay. Well, I want to read one more listener email because this is kind of along the same lines. And it also kind of gives us a way in to that solution. So this is from Charlotte and she said about the book. She said, I haven't read it yet, but my mom died from cancer when I was 20. And I've always carried with me the treasured gift that this gave me, that I know I was deeply and unconditionally loved. And it's people that matter. Tell your children and the people who matter that you love them all the time.

1:03:03It is also important to appreciate the ordinary so that it becomes extraordinary. the autumn leaves on the trees, the hot cup of tea, the walk to the park with my toddlers, chocolatey faces and marshmallows after cold swims, torrential rain, Sunday roasts, being grateful for every day to stop looking externally and to start looking internally to feel like I have and I am enough. And this is part of that thing about allowing yourself to be happy, allowing yourself to choose happiness. And I love how she has chose those small things. And that's also about being present focused. Yeah. You know, for me, you know, I enjoy humor and I try to laugh every day and I give myself extra points for making somebody else laugh.

1:03:47But that to me encapsulates those moments that occur or that you live in. You can either appreciate them or miss them, depending on what your focus is. And if you are too future focused or focused on something else, you will miss life. Isn't that what Ferris Bueller told us?

1:04:13We were going somewhere more profound. I got you to laugh though. I mean, and the other point this raises is how, how death that you've experienced the death of another person oftentimes does help people focus. And I think that's always been one of the purposes of being exposed to death helps us appreciate life more. But the fact that we are not as exposed to death in our modern society than we used to be, because there used to be whole protocols about how to die, about how to have the family come. Because most of most people died at home and it was sort of like so-and-so's dying. So everybody would come and they would express their, their thanks, regrets, whatever they had to talk about.

1:05:06And this might go on for weeks. And we just don't do that in our society anymore. That oftentimes many people I think are not exposed. They haven't been around somebody who's died. Yeah. And that gives us this great luxury of pretending it won't happen to us. Yeah. Yeah. Yeah. And all of the things we do to avoid it or think it's not going to happen or prepare for it in weird ways. I think one of the weirdest things that goes on in personal finance is the fixation with long-term care. Because most people aren't going to have long-term care. You're just going to die. but you know i i can tell you that my personal experiences with people who have died or are dying have been some of the most meaningful experiences of my life i don't know how many you want to hear about but i can tell you about a couple tell us okay well the one that's common to charlotte i had a good friend who was like my first friend outside the family was the next door neighbor who I was friends with since I was like four.

1:06:11He died when he was 16 of leukemia. And he was, he was a special person. I mean, he, he was really smart. He was really gifted athletically and he was also extremely charismatic. So it was like, he was the last person you would think, you know, is going to have a problem in life, let alone be dead at age 16. But I can tell you that what the effect that had on me was this kind of urgency. It gives you an urgency to life if you've known people who have died, that you are more likely to really pursue something, whatever it is you think is important at the time, with a lot more vigor and gusto. And for me at the time, it was going to Caltech or MIT.

1:07:01And so I really, you know, I wasn't that greatest student up through junior high school, but I really kind of buckled down and made that my goal. And part of that was this urgency I kind of felt is like, well, if Stevie can die when he's 16, I could be next. I mean, I might only live 10 years. Yeah, I got no time to waste. And I think that that's, it's actually a healthy thing to happen. I mean, it's not healthy for people to die and it's sad, but that experience of somebody else dying close to you, I think does give, give people more urgency in life and meaning. Yeah. But then I've spent time with, with people on the end of their life who lived a long life.

1:07:46And, you know, I had a, and this has turned into one of my most important friendships in adulthood. So my friend was a woman named Mamie, Mamie McCoy. And I was friends with her for about the last 10 years of her life. She died at age 90. I became friends with her through a pro bono case. Her house got seized by the federal government and there was a shooting in it and there was all kinds of crazy stuff that happened. But, you know, we were able to not fix that, but get her to a better place and get her into senior housing. But we really, I wouldn't say we became friends until the end. of that segment, because it was at the end of that segment, there was some money that we had gotten.

1:08:32And I said, well, what do you want me to do with the money that we got from the government for this? And she says, I want you to take care of it. And that was a bid. And I took her up on that. And so she was poor. I mean, this was only about$20 ,000. She lived entirely on social security and Medicaid. She was in, you know, senior housing for poor people in Washington, DC. And you're familiar with Washington, DC. I'm talking about across the Anacostia River in Ward 8. But I would go and see her every month to talk about, you know, what she wanted to do in the rest of her life. Now, Mamie was born in 1915 in rural South Carolina and had come up to D.C.

1:09:22with the African-American migrations that occurred in the 20s and 30s seeking work in the cities. And so for most of her life, have you ever seen the movie The Help? I have read the book. Okay. She was the help. Oh, sure. And so all through like the, I guess, the 40s, 50s and in 60s, that was kind of her job. And it left her with this kind of interesting legacy. I'll tell you what I'm telling you. She was a connoisseur of baked goods. And she found out that my wife knew how to bake. So every month she would ask me for various things. Can your wife make me a sweet potato pie? How can you say no?

1:10:08A red velvet cake? Sometimes you'd want me to bring her a honey ham. Or she'd ask me for something like, can you get me some housecoats? And I'd be like, Mary, where do we get housecoats? She wanted the ones with the pockets in them. For her, she felt wealthy, not by having money, but by the fact that she could ask people to go and get her things and bring her things. That was what made her feel wealthy. She also used those baked goods that we gave her to develop relationships. She would, you know, take them down to the little beating rooms with all the other old folks in the home there. And she was like, my lawyer's wife brought me.

1:10:56How do you use your resources? Tell me all about these things. But then there was another thing that I helped her with that really, because she was really a present focused person. she lived this crazy life she had survived three husbands she had a glass eye there was there's a one story after another uh because she was always a present focused person she never knew what was gonna happen next but when it came to the end of her life it's like well what what was important to her that she needed to do and this is what you might want to be thinking about before you get really old. So what was, she was religious and believed in the afterlife.

1:11:42So what was important to her is what she called her homegoing, which we would call death, but she viewed it as the next step. And in her view, in order for this to be done the right way, essentially. She wanted the cemetery plot, the casket, all of the things that in her mind made the right kind of home going. And she asked me to help her with that. It's emotional to think about. So I was driving Miss Mamie and we'd go casket shopping. We went shopping for cemetery plots. This is what she wanted to spend that money on. The point of this and what I learned from that is that at some point you need to be really focused on what's important to you.

1:12:33And it may not be something that other people think is important. And you need to have the courage to pursue it and to ask for the help you need to get there if you need help. Because I can tell you, once we had made these arrangements for her home going, and had seen the cemetery plot, she knew exactly where it was, had picked out the casket. It was a blue-gray metallic.

1:13:00She was content. I mean, she was happy with feeling like, I have done the thing that I needed to do at this point. And I don't know how many people get to their death and feel like, I have done the thing I needed to do. Some people do. I think it's fewer. But in order to do that, The first thing is you have to be conscious about the fact you're going to die. You don't know when it's going to be. For most people, it's probably later than sooner, but it may be sooner than you think. And I mean, there's no time like the present to be thinking of, you know, what are those things that I want to have done or be done before that happens?

1:13:45And, you know, maybe I need to be working on some of them today or something like that. That's why I'm often very critical of people who have reached fire or they have a lot of money and they're like, I just don't know if I have enough to retire. And then there's this, how am I going to pay for long term care and how? There's this litany of whiny things. But I can tell you there are people in the world like Mamie who were perfectly happy with next to nothing because they were very intentional about what they really thought was important and made sure that they focused on that, that her relationships with people were very important for her.

1:14:27she used the things that we brought Mamie's fruitcake is a whole other story that I can tell you about but what I learned so much from her and my experience with her about living and dying I mean it's a gift and you know I hope I can do as well as she did okay so our conclusion here today folks is be courageous and not whiny okay when we started today i had shared frank's theory for why people not a lot of people wrote in right that frank said all people in the fire community don't want to think about death i didn't tell you my theory my theory was that people don't want to do homework and i'm always assigning them homework so i get it maybe you don't want to read books but if you have made it this far into this episode then maybe this topic is of interest to you.

1:15:25And so we would encourage you to read the book, but maybe we could close by Frank and I each giving a recommendation for a similar type book that people might enjoy whether or not they read Bronnie's book. What do you think? Yeah, I think so. I actually, I will also tell you, I have a podcast episode where I list several of these books. It's number 436 of Risk Parity Radio that you can listen to. Yeah. So give us a sneak peek. Give us one of them. Yeah. I think some of the best books about this are not specifically about death, but transitioning to the second half of life or the next stage of life.

1:16:04One of them is called Falling Upward by Richard Rohr. Another one's called Second Mountain by David Brooks. Another one's called Strength to Strength by Arthur Brooks. No relation. I always get those two confused. Yeah. You need to have a different name. And both great books. But any of those three, just talking about how do I get to my next stage of life? Because that's really what this is about, is not worrying about what happens at death, but what are you doing between now and death? And you need to sort of focus on being done with career one or that first, whatever stage you were in, getting to fire, and then where are you going next?

1:16:48And all three of those, I think, are very useful ways to look at it. Because this book is, what do I not want to be regretting? And those books are more like, well, now what do I do? How do I approach this? Yeah. I'll throw in Midlife, a Philosophical Guide. I'm not going to try to say his name because I'm a screwed up. But I just finished it. And it's not about death, but it is about regret. And it's about how once you hit midlife, you're actually able to kind of see some of the losses of like paths that you didn't take where you couldn't kind of see those before. And I think it's a really interesting exploration and it gives some clear like ways to reframe it.

1:17:35Like, what do we do with that regret or how do we think about it? So if regret is of particular interest to you, then you might enjoy that book. Frank, thank you so much for your willingness to come on and to share with us today. I'm very happy. You're much better than Brad. Brad, did you make it to the end of this episode? This will be your test. Made you laugh. There you go. You got many points today.

1:18:07And thank you everyone also for listening today and we'll catch you next time. Thank you.

From the publisher

Join Ginger and Frank as they dive into the impactful concept of regret, exploring insights from Bronnie Ware's The Top Five Regrets of the Dying. Discover how these regrets can shape a life of fulfillment and happiness, and learn how to embrace self-expression and relationships to achieve true satisfaction.

Episode Summary:
In this episode, the hosts explore the concept of regret and its role in shaping meaningful lives. Inspired by Bronnie Ware's work, they discuss the common regrets of those at the end of their lives and provide insights on living authentically, nurturing relationships, and prioritizing happiness. Listeners are encouraged to reflect on their lives and make intentional choices to avoid future regrets.

Key Topics Discussed:

  1. Introduction to Regret (00:00:00)

    • Understanding the concept of regret and its implications for personal fulfillment.
  2. Charlie Munger's Inversion Strategy (00:01:15)

    • Utilizing inversion as a technique to clarify what leads to a fulfilling life by considering what leads to regret.
  3. Overview of Bronnie Ware's Book (00:02:01)

    • Discussion on The Top Five Regrets of the Dying and the importance of reflecting on these regrets to live better now.
  4. First Regret: Living Authentically (00:12:32)

    • "I wish I had the courage to live a life true to myself, not the life others expected of me."
    • Importance of self-expression and the courage to defy societal expectations.
  5. Second Regret: Courage to Express Feelings (00:20:52)

    • "I wish I had the courage to express my feelings."
    • The emotional costs of not sharing our feelings and the impact on personal relationships.
  6. Third Regret: Maintaining Relationships (00:22:54)

    • "I wish I had stayed in touch with my friends."
    • The significance of nurturing friendships and relationships.
  7. Fourth Regret: Nurturing Friendships (00:23:07)

    • The necessity of continual effort in maintaining connections as life evolves.
  8. Fifth Regret: Allowing Happiness (01:40:22)

    • "I wish that I'd let myself be happier."
    • The barriers to joy and the importance of allowing oneself to seek happiness.
  9. Conclusion (01:04:19)

    • Encouraging listeners to choose courage over complaint and to take proactive steps toward authentic living.

Key Quotes:

  • "Live true to yourself, not others' expectations." (00:12:32)
  • "Rekindle your childhood passions beyond societal expectations." (00:16:30)
  • "Build friendships by starting with acquaintances and shared interests." (00:28:04)
  • "Choose courage over complaint." (01:04:19)

Actionable Takeaways:

  • Reflect on what makes you truly happy and take steps to pursue it.
  • Invest time and resources in fostering meaningful relationships.
  • Practice sharing your emotions to deepen connections.
  • Engage in self-reflection to identify passions that were set aside.

Related Resources:

Discussion Questions:

  • What actions can you take today to align your life more closely with your authentic self?
  • How can you prioritize relationships in your daily life?
  • What does happiness mean to you, and how can you pursue it more actively?

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