Greg McKeown:
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Welcome back, everybody. I’m your host, Greg McKeown, and on this podcast, we are interested always in figuring out what’s essential, eliminating what is nonessential, and figuring out how to live a life that really matters. In fact, at the time of this recording, we just hit the ten-year anniversary of essentialism. And it’s, and there’s a special edition of Essentialism that has just been released. It has a new introduction; it has a new tool, a 21-day challenge for putting these ideas into practice.
And so it’s perfectly relevant to be able to have a conversation with Jodie Wellman, who is the author of You Only Die Once. It’s a combination of quite a poignant subject and approach but in a kind of darkly humorous way. Jodi is a founder, positive psychologist, and executive coach who spent 25 years doing leadership work and speaking, doing keynotes, workshops, and coaching programs you can imagine with the world’s top researchers on happiness and what makes life worth living.
I remember interviewing somebody on this podcast who – it was Eve Rodsky, and before she wrote Fair Play, her life was as an attorney, and she specifically worked with families that were a bit like the family in the movie Knives Out, where it’s like high net worth families with a patriarchal matriarch. And it’s trying to help them make a plan for what to do next. And she said that the number one response she would get when she would meet with the matriarch or patriarch was, “Well, why are we even doing this? I’m never going to die.”
And they seem to be saying it really literally. And, of course, that’s a form of self-deception, but it’s an interesting one, right? Like that. Somebody not only is avoiding the subject but, when faced with the subject, is saying, “No, that’s not going to happen. And therefore, what? I don’t have to think about it. Therefore, I don’t have to make any of these decisions. I don’t have to deal with any of this.”
That’s the reason self-deception is so useful to humans is that we can just not do anything, not change, avoid stuff, or at least in our minds we can. And so I think that’s the essence of what the title and the framing and the core message of your book is. Well, you are going to. So let’s start with that reality truth, and let’s work backward from that truth rather than to just constantly lie about that.
Jodi Wellman:
Yes, I noticed something else, too. Your summary there is super duper spot on. I love that. And there’s something else that occurs to me that joins with that for some people. Death awareness, death acceptance, it’s a spectrum, like everything, right? Some people are like, “I’m game, I’ll always talk about it. I’m really cool with it. I’ve got it all planned,” and all that good stuff. And then some people definitely, “Oh, what’s for dinner?” Change the subject completely. You’re going to have a variance there about who’s interested and who’s not. And that’s fine.
What I notice also, in addition to this thing about the delusional, I’ll push these dreams off till later. We introduce another variable, which is fear. And so whether someone is very conscious of the fact that they’re temporary or not, many people will push a dream out because they’re just afraid to get it started.
So whether it’s, “Well, I’m going to start that business,” or “I’m going to start my podcast,” or, “I’m going to pick up and find a way to move,” or “I’m going to start dating again,” or whatever the thing is that actually ends up having that sizzly feeling of, like, there are stakes here that is one of the biggest inhibitors. And I think that that is the thing that needs to be called out, is that we’re deferring our existence. Sometimes it’s not because we’re comfortably settling back into the idea that, “Well, I’m going to get to live forever, I’ll get to do it later.” But it’s a very convenient thing for me to say, “I’ll do it when I retire.”
But what we’re really doing is just punting the difficulty of “But if I start it and it doesn’t work, then I don’t want to deal with that emotional turmoil.”
Greg McKeown:
Yeah. And that very last thing that you said just puts me in mind. I remember when we were traveling as a family, and we were in a really lovely spot. We were in Spain, and we were at a really interesting hotel, and we were sitting down to eat lunch. I think just across from us there was a table, there’s two retired couples and there was like no movement the whole lunch, other than one of them kept checking the cricket scores every so often.
And, you know, one has to be careful because I never even spoke to them. So it’s not like I really have any good data on it, but they seemed awfully bored. So this is my story for them. And I could be wrong, but they seemed like this is what we were saving up for his retirement. Now, we’ll get to relax and sit on the beach-type dream that’s sold to people. And I couldn’t really think of anything much worse than that. And I just. That’s the story I’m creating out of this as a narrative, but they didn’t seem engaged with each other or alive to use the term that you have. How alive are you? Quiz in the book. It’s like that. There’s got to be something better than that. Is this as good as it gets, this idea of sort of slowly relaxing to our demise?
Jodi Wellman:
Exactly. Yeah, yeah, yeah. I love how this, to me, is the makings of a really great movie. You know, your story about these couples, and you’re flagging something that I find so scary/amusing simultaneously. This idea that we have beliefs many times, like, I’m going to do this when I retire. So this is like, ooh, the big trip that we got to do. And we go and maybe it’s the thing you wanted, or maybe it isn’t, or who knows?
But the thing that I’m more concerned about, because for many of us, you might die before you get to that trip, or you might have gout so bad you’re not going to want to be walking around, or you might be in your, like, dementia phase too. Gosh, knows all the things that could happen. I don’t even care about that so much. I’m actually more of an advocate for “What about the life you’re living now? Doesn’t that deserve to get lived the crap out of?”
Again, all things considered to your level of preference, I’m not suggesting you need to go on trips every month. I mean, don’t not do that if that’s up your alley. But what about life now? So every time we say, “Oh, we’re going to save that trip,” did you say it was Spain where you were?
Greg McKeown:
Yeah.
Jodi Wellman:
“Well, we’re going to do it when work dies down, or we’re going to do it, you know when Reg retires.”
Yeah, but what about the next year of your life, you know, and I understand that resources aside, like, you may not literally have the money and that’s a very different situation. But most of us are just punting, and we’re deferring. And that’s the thing where who is standing up for your life now? No one else will do it for you.
We just need to be the ones to identify. And this is the exercise. Then it all comes back around to your first warm and glowy question of, like, what would I regret on my deathbed? It’s like, what would be the thing, or things, plural, that would make you feel those pangs that, oh, man, I always said I wanted to do that, and I never did it. For whatever reason, whether it was because I was scared, or whether it was because I was deliciously deluded into thinking I was going to evade the reaper, or whether it was just because I honestly believed that I would be healthy when I was 66 and retired.
Now. That’s the thing. Don’t wait. What is your calendar filled with now that brings you some degree of joy? And the good news is that, for the most part, it’s not a lot of stuff that takes a ton of time or money. So, this is not a conversation for the elite. Well, back to the aforementioned yachts. He’s the only one that gets to have fun. Or you can only have fun in Spain at a really cool hotel. Right?
Sometimes, it’s the simple, sweet things that deliver the essence of life between the big trips that we think that life is actually getting lived. No, it’s the simple stuff about having a coffee outside on the deck and looking at the birds when normally we might just be inside, rushing around. Those choices that we could make in moments just to save our life.
Greg McKeown:
There are two things in my mind about this. The first is a scriptural phrase, which deserves unpacking here, but the phrase is, do not procrastinate the day of your repentance. But the term repentance comes from. It was translated in the original Catholic Bible from the Greek word metanoia, which means to see yourself and others in the world with new eyes. And so it’s a really rich term. And within it, there is both conscience and calling. Right? There’s a conscience saying, don’t do that. That part of repentance that I think is most emphasized. But then there’s this calling side to it, which is, look, there’s more, there’s better, there’s different, there’s more joy ahead for you, there’s more love ahead for you. There’s more life ahead for you. And that, to me, seems to be one way of thinking about what you’re advocating for is: don’t procrastinate the day of your seeing with new eyes.
Jodi Wellman:
That is so beautiful. No nun ever taught me that when I was growing up in my school. So, thank you for that new twist on something that could be interpreted otherwise.
Yeah, you’re catching me thinking about something now that I find myself tamping down the message so that it doesn’t intimidate people. And I think I need to stop doing that because I want to get ahead of someone’s criticism of. Yeah, but back to the idea of astonishingly alive. Right? Like, the idea, you know, carpe the f out of this diem. In fact, I have those socks. They’re lovely. But the idea, like, within reason, you know, that a lot of people will say, I’m really busy. You know, you’ve got kids, or you got stuff going on. I can’t fit all this stuff in. And I’m not trying to say that you have to, or that needs to be, this grandiose life that looks good on social media. Right? Or I’m trying to let people know who are still a little scared. Well, don’t worry. Even the small things count. And I believe all of this is true, and I think that’s a really crucial message. And yet, I do believe that I might be selling short.
Back to the earlier opening discussion about playing it small versus not. It’s like, let’s also make room for the big dreamers where there is this thing, like, I do want to start a nonprofit, right? Or I do want to do the thing, which is breaking up my long term marriage because I know that it’s lifeless and loveless, or I do want to do the big, grand gestures that.
Greg McKeown:
You know, or I want to get married, or I want to have children.
Jodi Wellman:
Thank you. Find love.
Greg McKeown:
Yeah. And I say that because the statistics are increasingly showing that people are opting out of that in a very fast change in the human condition and for a lot of complex reasons. But I just had Marshall Goldsmith on the podcast, and I was saying, “Okay, so what advice would you give to yourself, and what would you learn? And what advice of all the different things you’ve written have had the biggest impact?”
That question, he said, “Well, literally, the most impactful advice I’ve given to people has been to have children.” He said, “This week, I’ve had two emails from totally different people saying, when you said that, I was like, ‘Oh, my goodness, that’s not on my agenda right now. But that really has been where the meaning has been and the vitality has been.’
So, I just think it deserves to be mentioned. When we talk about big things, it doesn’t have to be things out there. Big and grand. I think having a family is the grandest thing, the most challenging thing, the funnest, most playful thing that, you know, I often think about it as the absolute ultimate entrepreneurial startup because you never get out of the startup phase, because the moment when they turn two, that’s a new phase. You don’t know what you’re doing. Then they turn seven; you don’t know what you’re doing. Teenagers and so on. As soon as you think you know what’s going on, the marketplace of your relationships has changed again, and you have no choice, I think, to some extent; anyway, you have no choice but to experience metanoia in a perpetual way because you can’t hide from yourself. They can’t hide who you are. They’re seeing it, they’re feeling it, they’re responding to it. And so I suppose I’m just making the case for that. When we think of carpe diem, it’s very easy to sort of pratize our carpe diem or holiday our Carpe diem. And sometimes the magic of the meaning and the joy is available closer to home.
Jodi Wellman:
Yeah, you’re aligned with a lot of the regret research about people who look back and say, and like I said, something like 83% of people do agree that “Hey, you know what? I do look back and wish I could do a do over again.”
I’m not concerned about regrets of commission that we did and wish we hadn’t – water under the bridge. But family regrets do chunk in, and that could be about wishing that they had family, wishing that they made up with some sort of a fissure in a relationship, and spending more time with family.
At the end of the day, yeah, there’s a lot of a link to belonging there that super duper matters. And I mean, you’re tracking nicely to so much of the research around. You know, positive psychology validates that having even just social relationships, of which family is the ultimate of that having social relationships is the most sort of validated aspect of if you want to find enduring happiness; what would that look like? And they study the difference between happy people and super happy people, and that is the differentiator. You know, it’s their relationships in a sense.
Greg McKeown:
It’s so obvious. You know, it’s easy not to say it, but it seems like it’s been a whole generation of not saying it. So now it’s not obvious. I think that well-intended people have advocated unintentionally for corporatism. You know, give everything up for, go get that job. You can do it. You can be it. You can do anything you want. And then what they mean when you get the details, like, go get that job, go be that doctor, go be that dentist, go be that.
Now, I believe careers matter. I believe you can make a tremendous contribution. I’ve invested a lot in my own career. I’m not saying it’s nothing, but if you emphasize it entirely, it’s like these dual virtues that go together where you need them, both the yin and the yang. And if you only have one, they cease to be virtues anymore. And that seems to be consistent with what you’re saying in the breadth and depth. It’s like you need both. And if you do one and not the other. Let me ask you this. Have you seen the movie About Time?
Jodi Wellman:
Remind me which one that is.
Greg McKeown:
About time is the story. Well, I mean, it’s an old movie, so I suppose nobody can complain about, you know, movie spoilers now. It’s been out for a dozen years. Don’t tell me you were going to watch it tonight.
Jodi Wellman:
You ruined it.
Greg McKeown:
It is the story of a family, particularly the protagonist is the son of a man who, when his son turns, I think, 18 or 21, some key age point, he says to him, okay, it’s my turn to tell you that the men in this family can time travel but in a very particular way. You can go back in your life and relive something, redo it, but you can’t go back to any place that you haven’t been. It’s only within your own life and these limitations.
Have you seen this movie? Are you familiar with this?
Jodi Wellman:
It’s possible. I saw it. I might have been. So just wait. I think I might have been so distracted by the bad acting that I couldn’t get into the premise. But I’m loving what you’re saying.
Greg McKeown:
This is superb acting in this movie. I don’t think this is likely.
Jodi Wellman:
Okay. I’m thinking of something different.
Greg McKeown:
Yeah. This is a beautifully done movie, I would say. Well, look, I thought we could riff on something here because I was imagining you may have seen it, but there is a point at the end of the movie, a discovery that he makes that fits so well with, I think, the aspiration that you have for people, this idea of living fully alive, not in the past, not in your death either, ironically, but living fully now and not getting to the end of life, as Thoreau said, and discover that I have not lived. It’s how do we utilize the reality of our death to drive life into us now and taking responsibility for that life right now so that we can do with it, you know, do we pay attention to it so that we’re alive in it and not sleepwalking through it?
Jodi Wellman:
You have summarized that so perfectly. I like to think of myself as, you know, a representative of the Grim Reaper, and I think he may be coming after you in a good way to also represent him the way that you just summarized that because it can be used to our advantage. Right. It’s a tool. It’s an awareness. I mean, memento mori, this idea of, remember, we must die. People have been doing it for centuries, and, yeah, there’s more power in it than what we initially think. Oh, it’s morbid. And I don’t want to touch it with a ten-foot pole.
Greg McKeown:
Well, I have, to some extent, struggled with this because, I don’t know, death is quite present for me. That doesn’t seem strange to me. I once read about somebody who I admired who, when he would travel around the world, made a point of going, you know, into tombstones,
Jodi Wellman:
Cemetery, Mausoleum.
Greg McKeown:
Wherever they would go, they would go into a cemetery and just spend time there. And that seemed surprising to me. Not that I couldn’t get my head around why someone would do it, but I just didn’t imagine that they would have enough time to do this. And the fact they did it really taught me something. And the person I’m talking about is no longer alive now, which reinforces the point. It’s like when I read about this, he seemed very much alive. He seemed like he had lots of time ahead. And the whole point of him going there is to remember this is coming for you. You have precious time left. What are you going to do with it? What will you do with that responsibility?
Jodi Wellman:
Yes, well, we need that urgency. It’s like this is the power of a deadline. And that word is so appropriate that we need manuscripts don’t get submitted unless there’s a deadline. We don’t put reports in at work until we have a deadline. We know we need a line in the Sandheen, and yet we lose touch. And we intentionally plug our noses and don’t want to talk about this idea. But pay attention to the deadline, because that’s the very thing that can animate you to go on and choose.
These are the things that I want to have stuffed into my life, and we need to. This goes back to the disciplined pursuit of less, Mr.McKeown. Like, this is about you ain’t gonna fit it all in if you’re ambitious, you know, the bucket list will. You will die with things on that list. But what do you want to emerge and bubble up to the top as you every now and then, recalibrate it every quarter, which is just like a life practice about saying, what now?
Well, that feels less resonant. You know what? I don’t think I need to learn Italian right now, but I do want to go and volunteer at the cat shelter, like, whatever the thing is, but paying attention to it, or else the months fly by, we get into the habits form. I have a very uncomfortable attitude towards habits because I think that they, as many philosophers have said, they dull the edges of our lives. We go through the motions, and next thing you know, we’re these highly functioning zombies, and we don’t know how all of a sudden it got to be the month of September.
You know, we gotta like wake up to it with that deadline. It’s the only thing I have found that has been this effective. And we need consistent reminders. This is the thing. Cause every single person listening knows that you’re terminal like, this ain’t like a newsflash, but we need the reminders. We just have to keep coming back to it. Which is why, of course, I’m a fan of counting Mondays and carrying small skulls around with you everywhere you go.
Greg McKeown:
Yeah, the carrying the skulls is like. I just can’t get my head around to that.
Jodi Wellman:
I might send you one, and we’ll see if you’re converted.
Greg McKeown:
Yeah, you should try that. You should send it, and I’m going to see what the effect of it is. You might be right. I mean, you know, you’ve got that classic Hamlet moment, right? Where he’s always represented as holding the skull as he’s thinking about his life. To be or not to be. You know, his great soliloquy is often portrayed with him holding a skull while he’s doing it. I mean, I suppose that’s the essence of the question, isn’t it? To live or not to live.
You have a whole variety of practical things that you think people can do with these questions that we’re talking about, beyond the 68 questions, beyond the quiz, to assess which quadrant that you’re in one of them. And it’s like, it’s not a new idea, but probably most people still haven’t done it, which is to write an obituary draft. Why don’t you talk us through the process for writing an obituary draft?
Jodi Wellman:
Yeah, I’m a fan of the double obituary. Okay, so there’s the version, and we could trade eulogy, obituary, whatever one, for whatever reason, calls you. You know, the obituary is usually the one that goes in the newspaper, which is usually a little bit less. So if you’re feeling more frisky, go for the eulogy, but go for version one, which is, how do you think people would write it for you right now?
What would be the things they would say? And then the real juices in; what about the version that you want people to say about you the way you want to be described? And I have a whole program I do on legacy and the research there, just as an aside, because I cannot go there. It’s fascinating. You ask people, how do you want to be remembered? And we can usually cobble some words together, and that’s good.
What is more important for people, or more results-oriented, is how do you not want to be described? So write the version that you want, that you would just feel tickled in your grave to hear people read about you and then compare and contrast, say, well, what’s the difference between the real one today and the one that I. How do I earn the right to be described this way, when I’m dead and gone, either in my obituary or not?
Greg McKeown:
But I’m just slightly confused by that. So I understand write, the version that would happen right now, and I understand the idea of writing the version that you would want people to say and the difference. And I like that idea. But then, when you say writing down the things you would not want somebody to say about you, where does that fit into your…
Jodi Wellman:
Where does that go? Yeah, great question. That would be on the rough notes about. Then you flip it. So, for example, if you’d say it would horrify me to be described as cheap, with my resources, with my money, well, then that would probably mean you’d like to be described as generous and giving, right? So then that’s just fodder for, like, how to find the words that actually you do want. So it’s usually just the reverse being true.
Good question.
Greg McKeown:
But it’s an interesting way of writing the whole obituary. The whole second obituary is literally just writing down what you would hate for somebody to say about you when it was all done. The people that matter most to you, anyway.
Jodi Wellman:
Yeah, I have a recent blog post which is like, what would make you roll over in your grave? And it’s the stuff that you would not want at your funeral for people to be saying about you, the whispering, and they’re like, oh, my gosh, the guy was such a dick. Like, if that would really bother you, note that and then say, well, how am I actually behaving in order to be described as the opposite, which is somebody who is perhaps, maybe your interpretation of the opposite could be that you’re empathetic or that you are caring or that you are thoughtful or whatnot, and say, well, what would be two ways I could actually demonstrate that this week?
Like literal behaviors, well, I could check in with Carrie on my team, or I could listen for a change, you know so that it provides us with tools to be able to say, well, how do you actually bring that to life, this ideal version of you? So that obituary exercises one and two, or eulogy one and two, could be instructive.
Greg McKeown:
You give a few specific suggestions. You say, aim for about 200 words. You can be short and sweet at around 50 words, and if you’re a little long-winded, you can blow up to about 500 words. Surely referencing your loquaciousness, skip the details and date of your death in this draft unless you want to jinx your life forever. Hit the highlights of your life story, which may or may not include your date and place of birth, your hometown, places you’ve lived, schooling details, employment details, and any special interests.
Ask yourself if the obituary captures the essence of your “youness” so that readers would say, “Yes, that sounds like Sophie. Late for her own funeral.” And then obituaries usually include shoutouts to key people in one’s life, surviving and already dead, family members, friends, and pets, who might make the cut. In this brief encapsulation of your life, do you want to include charity details for donations to a cause you care about?
What photo would you select? That’s a really fun point. You don’t normally have control over that. And they’re going to go through all those photos, all that stuff, and they’re picking one or maybe just five or ten at most of your entire life. That’s pretty wild.
Jodi Wellman:
Yeah. Back to the difference between obituary and eulogy. The obituary is a nice exercise because it just encapsulates so much at once, right? It’s like, how would people succinctly capture my life? And in many ways, it’s like a miniature life review, right? Well, this is what I did, quote-unquote, in terms of accomplishments, and back to the idea about charity. So it covers, like, well, what matters to you, if anything does in that regard.
So it is a really nice, succinct exercise, and I like the eulogy to come next because that’s where you can get a little more flowy with the stories that people might tell about you, the anecdotes, the ways in which you passed on your values or didn’t. And that can be, for many people, insightful.
I did a workshop once where one gentleman, the exercise was like a 20 minutes draft, you know, eulogy time, go. Drinks were served. And he sat there, and it was this moment where he was like, “I am afraid to put pen to paper because I realize I have not been living the best version of myself.”
And he was pretty clear on how he didn’t want to be described, that he felt like that is exactly what people would say. And everything someone wrote about me would be because they were trying to be polite, and it was an important exercise to be like, “Hey, this is your starting point. So what would be one thing that would matter maybe the most that you’d like to be described as?”
And then that’s all we can do, is just pick one small thing. And in fact, that’s a big theme that I have in this book, and in anything I’ll talk about, is that at the risk of overwhelming back to this idea about all of our hopes and our dreams and our goals and all the things that we want to fit into this limited time, we’re very much rattling the cage of possible anxiety that I don’t have enough time to do these things, or how am I going to somehow tackle it all? And first step, we’ll acknowledge you won’t get to do all of it. And so you just have to pick the things one at a time that might be good for you.
So this gentleman wanted to be described. He really was very clear as kind, and for him, it was all right, Operation kindness. And so for the next month, and it’s funny, his team was all around him, and they could acknowledge in a really professional and caring way. Yeah, right now, that wouldn’t be our first description for you. We would say that you’re brilliant, you know, and he is brilliant, and he had all these great strategies, and he was doing good work, but he also was void of, you know, the human touch that he knew might maybe matter at the end, because that’s the stuff at the end that people really care more about. Right? It’s not that it might be interesting that you invented a rocket ship, but how were you with the people while you were making the rocket ship? That matters more.
The end.
Greg McKeown:
Jodi Wellman, the author of You Only Die Once, how to make it to the end with no regrets. Thank you so much for being on the podcast.
Jodi Wellman:
Oh, thank you for having me here.
Greg McKeown:
For everybody listening, what is one thing that stood out to you? What’s the news of this episode? And now, what can you do about it immediately, within the next few minutes, a tiny action? To be able to as much just make things in your life a little bit better. Thank you for listening.
