What If Success Brings You the Wrong Life? | (#103) Beyond Success: Psychology & Philosophy for Achievers, with David Tian, Ph.D.

Welcome to the Beyond Success Podcast: Psychology and Philosophy for Achievers on the Bigger Questions Behind What You’re Building, and I’m David Tian, your host.

So, Ivan Ilyich is dead, and almost immediately, everyone starts thinking about what his death means for them. His colleagues aren’t unusually cruel people or anything. They worked with him. They respected him, and they knew him for years, but when they hear that he’s died, their thoughts turn almost immediately to their own promotions, vacancies, transfers, and the inconvenience of having to attend his funeral.

That’s where Leo Tolstoy, the author of War and Peace, begins his much shorter but very important book, The Death of Ivan Ilyich. Ivan had spent much of his life trying to become important inside an achiever’s system. He had risen through the ranks. He’d earned respect. His position mattered in society, and then he died. The institution carried on and his position became available, and you might think this is a pretty harsh way to begin a story about legacy. [01:06.4]

Successful people often start thinking about what will outlast them. Maybe it’s the company they created, maybe it’s the reputation they’ve built up, the wealth that they leave behind, or an idea or an institution, or a philanthropic project or a foundation. Those things can matter a great deal, but there’s a very important distinction that a lot of people miss—something you built can continue after you die and you can still have spent your life badly.

The fact that the company survives doesn’t tell us whether devoting 30 years to building it was actually a good use of your life. The fact that an institution keeps your name on the building doesn’t tell us whether that life that produced it was really worth living. [01:53.0]

There’s an uncomfortable irony here: the company may be one of the parts of your life that’s most capable of replacing you. Someone else can become CEO. Someone else can take that board seat. Someone else can handle the clients. Even if you founded the company yourself, a successful institution eventually has to become capable of carrying on without you, but your life does not get a replacement.

So, in this episode, I want to take the familiar idea of the deathbed test and make it even harder to get around. A common version of the deathbed test asks, “What will people say about me when I’m gone?” This is the famous “write your own eulogy at your funeral” kind of experiment, and this helps. There’s nothing wrong with it, but we’re going to go deeper than this, and that question of “What will people say about me when I’m gone?” sounds profound, until you notice that you’re still judging your life by other people’s approval or opinion of you. [02:53.1]

You spend decades caring what the right people think, then imagine your funeral and ask what those same people, roughly, will think when you’re dead. Another slightly deeper version asks, “What will I regret on my deathbed?” I really like this one. It’s generally more useful, but there’s still a problem here—the person imagining the future regret is the same person making the decisions now, so if I’m very good at explaining why I should keep postponing something today, I can probably imagine an older version of myself who agrees with me.

A stronger test starts by removing the conventional signals that currently tell you that you are succeeding. Take away the title, strip away the valuation, the promotion, the invitations, the praise, and the reputation, and then look at how you’re spending your time—very stoic, right?—and ask whether it still seems worthwhile, and don’t judge the life only from your own point of view. Include the people who have to live with your choices, your partner, wife, spouse, if you have one, your family, your kids, your friends, your parents. [04:03.0]

Then bring it down from the grand question of legacy to an ordinary week. Where does your time actually go? What keeps getting postponed? What do you keep telling yourself that you’ll make room for later? Tolstoy makes this especially uncomfortable because Ivan dies at 45. He isn’t 90 years old, looking back after decades of retirement.

He’s at an age when a successful person can easily assume there’s plenty of time left. He can still be building. He can still be healthy. He can still think of family mostly in the future tense, and those postponements can all sound reasonable at the time—“The company is in a demanding stage. The opportunity may never come back again. There’s one more geographic move that we have to make. A serious relationship can wait until all of this current push is done and over. Children can wait until life is more stable.” [05:01.4]

Most of those decisions taken one at a time in isolation may make perfect sense when viewed in isolation, but, actually, that’s what makes them dangerous. You don’t need to assume you’re going to die soon. You only need to admit that you don’t know how long you have left, and some of the things people care most about require years of participation, of investment. 

You can’t decide at 55 that you want 20 years of marriage behind you. You can’t decide later that you wished you had spent more ordinary years with your parents and then buy those years back. A friendship that lasts for decades requires decades. Time matters because some goods can only exist through time—which brings us to one of the most comforting beliefs that a successful person can have: “If I were wasting my life badly enough to matter, I would know. Surely, there would be obvious signs. My career would be falling apart, right? People around me would be worried. I’d feel like I was failing.” [06:02.2]

But Yvonne doesn’t look like that. He’s intelligent and capable. He’s climbing up the ladder. He becomes more successful and more respected over time. His choices look sensible to the people around him. Tolstoy’s challenge is that external approval can keep increasing, while the cost of your choices keeps increasing, too, without you noticing.

Three episodes back, I asked whether you’re measuring the right things. Two episodes back, I asked what deserves your finite time. In the last episode, I asked which “games,” quote-unquote, should prioritize your life. Tolstoy now forces the question that those episodes were leading toward. You can postpone answering for a long time. You may even be rewarded for postponing it, but you don’t get to postpone it forever. [06:52.7]

That’s one important reason why Tolstoy’s short masterpiece, The Death of Ivan Ilyich, is so instructive for us. Ivan doesn’t spend his life openly rejecting the things he cares about. He spends it learning what a respectable life is supposed to look like, and then getting pretty good at building that.

From fairly early on, Ivan pays close attention to people above him socially. He notices their manners, their tastes, what they admire, what they consider proper, and what kinds of ambition they respect, and he learns the rules well, and then the rules reward him for his performance and his career advances, by and large, steadily. He becomes more important. He earns more respect. His life begins to look increasingly like the kind of life a successful person in his world ought to have, and the same thing happens with his marriage.

Tolstoy doesn’t present Ivan as some cold calculator who marries purely for status. He’s genuinely attracted to the woman that he marries. Tolstoy tells us he enjoys being with her, but the fact that she’s also considered a suitable match in terms of status matters to him. Those two things can be true at the same time. He can want her and he can also like the fact that marrying her fits the life that he believes a successful man should have, from the outside looking in. [08:11.8]

Then the household starts to follow the same sort of logic. The home, the social life, the way he lives, all begin to match the picture of success in his mind that he has learned from the people whose judgment he respects. The important point is that Ivan never sits down and decides “I’m going to live a false life,” because that would make the story so much easier but simpler and almost dismissible then. Right? Instead, he accepts standards that were already there before he arrived, and he gets better and better at meeting them.

What he doesn’t do is examine very carefully whether those standards deserve the amount of life, amount of time and effort, and mental space that he gives them—and, of course, this is where social approval or living for social approval gets really tricky. [09:01.0]

Other people’s approval does tell us something. If intelligent people respect what you’re doing, that’s useful feedback. If customers want what your company sells, that really matters for your company. If investors are willing to put money behind you, that tells you something. If capable peers admire what you’ve built, there may be good reasons for that and you should know about those. But none of those people can answer the final question for you.

Money can tell you that the market values what you’re doing. Investors can tell you that they believe the company has potential. Customers can tell you that you’ve made something that they want. Employees, peers, media attention, invitations, your own history of success can all reinforce the same conclusion: “This is going well.” When enough signals point in the same direction, it becomes very easy to confuse “This is going well” with “This is a good way to spend my life.” Those aren’t actually the same question. [10:00.0]

Commercial success can tell you whether the company is succeeding, but it can’t tell you how much of your life the company ought to get, and I don’t think the answer is just to distrust society or just buck trends and reject convention and insist that only personal preference matters.

Other people can know things that we don’t. Customs can preserve lessons that took generations to learn. Our own desires don’t appear out of nowhere either. We learn what to want partly from families, friends, communities, our peers, the people we admire, our role models. The problem comes when we stop judging for ourselves.

Ivan becomes very good at asking, “Is this what a successful person does?” based on other people’s approval. He becomes much less practiced, if at all, at asking whether the successful person he is becoming is living in a way that he would actually want if viewed from the end, and once Ivan is married, that question gets much harder. His marriage becomes difficult. [11:05.2]

His wife becomes pregnant and she’s having a rough time with it. They have children and she’s having a rough time with that. There are arguments, emotional demands, resentment, and all the ordinary complications that come when two people build a life together with a lot of children and discover that neither person behaves exactly as the other hoped.

During all of this conflict at home and the stalemate that they’re in as a result of the pregnancy and the children and varying priorities here, Ivan discovers that he’s really good at his career. How convenient. There are rules in his career. There are procedures. He likes that. There’s certainty and there’s significance there. He knows what his authority is. He knows what competence looks like, and other people recognize that competence that he’s got. When a problem appears, there’s usually some formal way of handling it.

For him, though, home is different. His wife has needs that can’t be settled by applying the rational procedure. There’s no rule book that tells him exactly what to do when she’s angry or disappointed, or sad or frightened, or demanding something from him that he doesn’t know how to give or want to give. [12:09.2]

Children create their own demands. Family life depends on people who need things from one another, sometimes at inconvenient times, and for reasons that don’t fit neatly into any rational system, and Ivan can’t control that world, and the way he can control his professional world. So, he spends more and more of himself in the place where he feels competent.

His career becomes increasingly central to his life, and he keeps giving more and more of his life to it, and the more he gives to it, the better he does with it, and that’s actually what makes this kind of avoidance so hard to detect at the time. If you avoid a difficult conversation by, let’s say, getting drunk every night, eventually, somebody is probably going to point out that you got a problem. [12:59.2]

If you avoid a difficult conversation by becoming excellent at your job, people will congratulate you. You may get promoted. You may earn more money. You may become more respected, and every reward gives you yet another reason to believe that spending more time, investing more time there, must have been the right decision.

For a founder, the same company can end up serving two purposes at once. It can be a mission that you genuinely cared about. You may love the product, the problem, the people, the act or activity of building, creating, and the possibility of creating something that didn’t exist before that’s necessary or needed—and it can also give you somewhere to go when the rest of life becomes too hard for you to understand. Those two don’t cancel each other out.

A person can genuinely love creating a company and building a company and still find it much easier to stay immersed in that company than to have the necessary but difficult conversation with his partner that he doesn’t know how to handle and has hardly any experience or training to do so, and has been avoiding for a very long time. [14:06.8]

He can be intensely ambitious and still find commitment frightening. He can be very good at deciding between two business strategies, yet have no idea how to decide whom to marry. He can manage enormous uncertainty in a market and still hate the uncertainty involved in loving another person.

He can spend years solving complicated problems for customers and employees, while avoiding the fact that making room for small children would force him to change how he uses his time and which part of his brain he uses during that time, and some needs simply cannot be optimized away—a partner, wife, spouse may need time when it’s inconvenient for you. A child doesn’t care that the company is at an important stage. A difficult conversation doesn’t become easier just because you’ve had a strong quarter. Professional competence actually offers very little protection in those more intimate, personal moments. [15:11.8]

Now, that doesn’t mean that extreme ambition is evidence that someone is avoiding his private life. Some people really do love building at an extraordinary level of intensity for a long time, and they may look back and decide that the sacrifice was totally worth it to them. The more useful question is whether the intensity is doing another job as well. What does spending this much time on the company allow you not to have to confront? Maybe the real answer is nothing. Maybe you’ve looked at the trade-offs carefully and still believe this is exactly how you want to spend those years.

But Ivan never really makes that examination. The career keeps rewarding him, while his family life keeps becoming more difficult, so one world keeps inviting him further in and the other keeps giving him more reasons to stay away. Eventually, the place where he feels most competent, significant and certain becomes the place where he spends most of his life. [16:11.1]

Once career becomes that central, another question usually appears, sooner or later: “What is all of this going to amount to?” After enough success, people often start thinking about legacy. They think about impact, institutions, philanthropy, reputation, contribution. They start asking what will still exist after they’re gone, and that can be a serious and worthwhile question, no doubt.

A person may build a company that improves millions of lives. He may give away most of his wealth. He may create an institution that keeps serving people for generations. There’s absolutely nothing trivial about that and it’s pretty awesome when it happens, but legacy can also become one more immortality vehicle. It can become one more achievement project. [17:00.6]

Human beings know they’re going to die, and one very understandable response is to create something that seems capable of carrying part of us forward into time after death. The company keeps going. The foundation keeps giving. The ideas keep circulating. The name stays on the building. In one sense, all of that’s true. Things we create can continue after we’re gone, but there’s a temptation to ask those things to do more than they actually can.

If you’ve spent most of your life using achievement to answer the question, “Am I important” or “Am I enough?” then legacy can simply become yet another attempt to keep answering that same question with that same answer after death. “Will I still matter then? Will people still remember me? Will my name still mean something? Will I still be enough?” and Tolstoy is actually pretty ruthless about this. Ivan gets the obituary. [18:00.0]

People in his professional circle hear about his death. They think about him. His name appears where it’s supposed to appear, and then the institutions keep going. The position that mattered so much to Ivan during his life simply becomes another vacancy. His colleagues start thinking, scheming, planning already about what that vacancy means for their own careers. The prestige that carried so much weight while he was alive turns out to be surprisingly thin, non-existent, once he’s gone.

That doesn’t mean that Ivan’s career was worthless and it doesn’t mean that reputation itself is meaningless or that nobody should ever care whether their efforts continue helping people after they die. Instead, what I’m getting at is that legacy or continuation itself cannot bring the meaning that you’re hoping for to your life now, to your life as you are living it. [18:53.7]

Sometimes, the real problem isn’t more effort or more motivation. It’s knowing the right direction. A lot of people listening to this podcast are capable and driven. Things still look fine on paper, but life still feels strangely flat. When that happens, more advice usually isn’t the answer. Clarity is.

I’ve put together a short assessment that takes about two minutes. It’s simply a way to see which area deserves your attention most right now, whether that’s relationships, decision-making, or how pressure is being handled day to day. Based on your responses, you’ll be sent a short set of master classes related to that area.

If that sounds useful, you can find it at DTPhD.com/quiz. That’s “dtphd.com/quiz.”

Suppose you spend decades building something substantial, enormous, let’s say, and it survives you. That still can’t give you a marriage that you never lived. It can’t give you children that you never had, that you never got to fall in love with. It can’t restore friendships that you stopped maintaining. It can’t give you the years with your parents back that you kept assuming would be available later—and it can’t create the ordinary history that exists only because two people spent a really long time living alongside each other, contributing to each other’s lives. [20:13.7]

That last point really matters because some of the things that people value most depend on an extended duration. You can make money very quickly. You can sell a company and become wealthy in a single transaction. You can receive a title in a day. You can be famous almost overnight. It’s all possible, but you can’t decide at 60 that you would now like 30 years of friendship with someone. You would have to have done that 30 years ago. You can’t decide that you’d like to have known your children throughout their childhood, after their childhood is finished. You can’t finally clear your calendar and then purchase 15 more years with a parent who is no longer alive.

Some goods simply require time passing while you are actually there, and that’s one of the reasons the question of legacy can mislead us if we’re not careful. It points our attention toward what remains later, when a big part of the problem may be what never happened earlier. [21:11.3]

A monument can survive for centuries and still tell us very little about the life of the person whose name is carved into it. The same is true of a company or an institution, or an enduring reputation—they may represent genuine contribution. They may represent service. They may be worth building, but they can’t go backwards and supply the years that were put elsewhere.

We looked at this earlier in the series when we talked about finite time. Some things become valuable partly because they have a history, and history, of course, logically, takes time, so if the plan is to devote most of your life to the career now and then purchase the rest of your life later, there’s obviously a big logical problem here. By the time the career finally gives you that freedom, some of these things that you hoped to use that freedom for may require years that are no longer available to you. [22:07.6]

Legacy may tell us what continues after us, but it cannot tell us the quality of the life that was happening before we died—and when Ivan becomes seriously ill, most of what gave him his place in the world starts to fall away before his very eyes. His competence doesn’t help much anymore. His status doesn’t help much. The rules that he understood so well can’t tell him what to do with the fact that he might be dying.

The doctors approach his illness the way professionals usually approach a problem, especially back then. They examine him, discuss possible causes, prescribe treatments, and focus on what can be done next. Ivan goes along with this because he wants to believe there is a solution. If the doctors can identify the problem correctly, perhaps they can fix it and normal life can resume for him. But as his conditions get worse, Ivan becomes increasingly certain about something that the people around him don’t want to say out loud—that he is dying. [23:01.4]

His family keeps talking about ordinary things. Visitors come and behave as though this is a mere illness that will eventually pass. Doctors keep discussing treatments in a detached way. Everyone acts as though the proper medical procedure might restore things to the way they were before, and Ivan comes to hate this. It isn’t simply that people are being optimistic. What isolates him is that everyone seems to be cooperating in a story that he knows is false.

He knows what’s happening to him and he can’t get the people around him to admit it. There’s one person who behaves very differently. Gerasim is a servant in Ivan’s household, and he doesn’t pretend that Ivan isn’t dying. He helps Ivan physically. He stays with him, and when Ivan is in pain, Gerasim holds his legs because it gives him some relief. He doesn’t act as though death is this strange event that has somehow singled Ivan out. People die. Gerasim accepts that. [24:00.5]

That plain acceptance gives Ivan something that he isn’t getting from the doctors or the visitors, or most of his family. Gerasim can be with him without pretending that the basic fact of the situation is different from what it is. There’s no great theory involved here. He sees a person who is suffering and he takes care of them.

Ivan’s son responds to him in a similar way. The boy is genuinely upset by his father’s suffering. He isn’t interested in preserving appearances or pretending that life is normal. He responds to Ivan as his father and as a person who is in pain.

By this point, almost everything that once established Ivan’s place in society has become now irrelevant. His title can’t comfort him. His professional skills can’t solve what’s happening. His social position can’t protect him, and that raises a question that’s easy to avoid. While all of those things are going well, who knows you apart from what you can do for them? Who knows you when your competence stops being useful to them and your status doesn’t matter anymore? And just as important, whom do you know that way? [25:04.7]

Think about the people who get your time when there’s no transaction involved—your partner, spouse, girlfriend, if you have one, your children, your closest friends, your parents, your brothers or sisters. How much of your life do those people actually get? That’s a different question from whether you care about them.

Most people care about the people they care about, and that might be their families. Most people would say their closest friends matter to them. They may genuinely love their parents. But Ivan’s illness strips away all the usual ways of measuring importance and status and significance, and leaves him face to face with the people who are actually there.

Gerasim doesn’t care about Ivan because Ivan holds an important position. His son isn’t grieving the loss of a respected official. They’re responding to the person they care about, and once competence and status no longer have much value, that distinction becomes impossible for Ivan to ignore. [26:06.0]

For most of his life, he’d learned how to succeed in settings where there were clear standards and recognizable rewards. Now none of that can help him. What matters instead is actually much more personal. Who can sit with him? Who can admit what’s really happening? Who cares that he’s frightened and in pain? Who has known enough of him, apart from his professional role, to care about losing him?

That question leads Ivan into a much harder one. If the things that mattered so much during most of his adult life now don’t matter much at all, what does that say about the life he spent pursuing all of that? As he looks back, his childhood memories feel different from the rest. There was a lot more spontaneity then, more friendship, more intimacy, more hope. He remembers times when he was simply living, before so much of his life became focused on advancement and respectability. [27:06.7]

Then he looks at what came later. He became more successful. He rose up professionally. Other people respected him more. From the outside, it looks like his life improved, but his experience of living it actually did not improve, and that’s the reversal Tolstoy forces us and him to see. The further Ivan advanced according to the standards around him, the less satisfying his life actually became, and Ivan does not want to accept that conclusion.

You can understand why, right? He followed the rules. He did what respectable people did. He built a career. He performed his duties. He climbed up the ladder. He married. He created the kind of household that someone in his respectable status and position was expected to have. Other people looked at his life and envied him, and they saw a man who was doing well. So, how could the life itself have been mistaken? [28:01.0]

That question becomes especially difficult for successful people because success gives you so much evidence that your earlier judgment was right, right? You learn to ask very practical questions: “What works? What has upside? What scales? What’s most likely to succeed given the market? What do other capable people usually choose in this situation?” Those are useful questions. If you’re building a company, you need to be good at them, but Tolstoy is asking Ivan to consider a very different kind of question: “Was it worth the cost?”

That question doesn’t always give the same answer. Something can work extremely well and still cost far too much of your life. An opportunity can have enormous upside and still not deserve the next five years. A decision can be completely rational according to the standards of your career and still be a bad decision about how to spend your time, and some of the things that make a life worth living don’t produce much that can be measured. [29:06.4]

Spending an evening with your children definitely doesn’t scale. Calling an old friend doesn’t produce any obvious return. Sitting with a parent who is getting older may not improve anything that you can put on a spreadsheet or measure. Even the word “productive” starts to sound really strange when you apply it to those personal parts of your life. Productive toward what? That’s the question Ivan never really asked while things were going well.

He knew how to recognize advancement. He knew how to recognize professional success. He knew what counted as moving upward in the eyes of the people around him—but a life can contain things that look like interruptions, from the point of view of achievement and advancement and getting ahead, and still be some of the most important parts of that life. [29:57.4]

Time with your loved ones can look inefficient. Friendship can look inefficient. Being there for someone you care about can look inefficient. None of that means those things are always more important than the career. It means the career can’t decide the question for you, and that’s the part Ivan begins to see far too late. He had a reliable way of measuring whether he was rising, but he had a lot less practice asking whether rising was actually making his life better.

For most of us, those two things are easy to confuse because they often happen together at first. You work hard, become more capable. You earn more money. You gain more freedom. You meet more people and you have more choices. Success, especially at the beginning, can genuinely improve life, but it does not follow that every further increase will improve it again. At some point, you may be giving more of your time to the thing that already has plenty of it, while continuing to postpone the parts that have received very little. [31:00.6]

From the outside, you can still appear to be doing better. That’s the frightening possibility that Tolstoy puts in front of us: public assent and private diminishment can happen at the same time. You can become more respected while enjoying your life less. You can become more successful while giving less time to the people who really matter to you.

You can keep receiving evidence that you’re doing well, while the parts of your life that don’t produce those signals gradually become smaller, and because the approval keeps coming, there may be no obvious moment when you’re forced to admit what’s happening or even to notice what’s happening.

Ivan only has to face it when almost everything else has been taken away from him, and this is where Tolstoy’s conclusion gets harder than the usual advice of “Live authentically.” The shallow version is that Ivan realizes he should have followed his heart, enjoyed life more, YOLO, carpe diem, and then done what he had personally wanted, but that’s not where Tolstoy leaves him. [32:03.7]

Near the end, Ivan’s attention turns toward his son and his wife. He sees that they’re suffering, too, and for the first time, the question is no longer only about whether he has lived the life he wanted. He starts thinking about what his life has meant for them, and that gives us a much stronger version of the deathbed test. It’s actually relatively easy to ask, “Did I get enough from life?” or “Did I do what I really wanted?” Those questions matter, but they’re incomplete.

“What was it like to be married to me? What kind of parent was I? What did the people I loved have to absorb because of the choices I kept making? Who paid part of the price for my ambition? If I looked at those sacrifices from their point of view, would I still think the end justified the cost?” That matters because personal fulfillment isn’t enough as a moral standard. [33:05.4]

You can understand yourself very well and still make a bad decision. You can know exactly what you want and still want something that asks too much from others that you care about. So, judgment has to include responsibilities, consequences, and the interests of people affected by what you do, and the more successful you become, the more important that becomes, because your choices often affect more people.

Now, none of this means Tolstoy has proved that you should quit the company or stop striving, or treat ambition as some kind of pathology. Okay, it doesn’t mean any of that. It doesn’t mean family always outweighs vocation. It doesn’t mean sacrifice is automatically a mistake. Some things are really worth sacrificing for. The harder question is whether you actually know what you’re sacrificing and whether you know who else is carrying part of that cost. [34:02.3]

If you do, then you can ask yourself whether the thing you’re pursuing really deserves it. That’s very different from drifting into the sacrifice because the career keeps rewarding you for making it. Ivan’s mistake isn’t simply that he wanted the wrong things. It’s that he kept accepting the standards around him. He kept receiving reinforcement for meeting those standards and he never examined the total price closely enough while he still had the time to choose differently.

That’s the warning Tolstoy leaves us with—a life can look respectable, successful, even enviable, and still be badly chosen, and it doesn’t require one reckless decision. Reasonable choices can pile up for years until they produce a life that you never meant to build. [34:52.6]

I’ve seen this so many times with clients. One client, let’s take him as an example, was professionally successful and single, and he had always intended to marry and have children, he says. He wasn’t opposed to family at all. He wasn’t making some grand decision to stay single forever. He kept thinking the time would come after the next professional milestone, and each postponement made sense on its own. There was another goal worth pursuing. Another opportunity appeared.

The career kept rewarding him for putting more into it, and each success seemed to promise that eventually he’d have enough freedom to make room for the rest of his life, but every achievement created another opportunity. That finish line kept moving, and eventually, he had to reckon with a fact that had not been obvious when he made any one of those decisions—time had changed the decision itself.

He was much older now. The pool of potential partners had shrunk and changed significantly. The timeline for having children had changed, and even if he eventually built the family he wanted, there was less shared history available than there would have been if he had started earlier. [36:02.8]

That doesn’t mean his career was a mistake. He still valued what he had built. The mistake was failing to count the total cost of a long series of individually responsible, reasonable decisions when looked at in isolation. That’s the version I’d be much more concerned about than some dramatic collapse.

Imagine the next 10 years go very well. Professionally, you keep succeeding. Every sacrifice remains defensible. There’s no crisis that forces you to reconsider anything. You keep telling yourself the relationship can come after this stage of the company. Children can come when circumstances are better. You’ll see your parents on the next trip. You’ll reconnect with those old friends when things calm back down at work. You’ll make room for a fuller life after the next financial or professional target—and then 10 years pass. Nobody ruined your life. There’s no villain. There may not have even been a clearly bad decision. You simply arrived at a life created by the priorities that you kept choosing. [37:04.3]

That’s what mortality can help with now, while you still have choices. It doesn’t have to make you less ambitious. You can still build something difficult and important. You can still sacrifice for it, but the sacrifice should be deliberate. The career no longer gets first claim on your time simply because it produces the clearest reward.

A good relationship gets actual quality years instead of just good intentions later. Family becomes part of the life that you’re building now, rather than simply the prize that you hope to collect once all that building in your career is finished. Friendships get enough time to become old friendships. You know your parents while they’re still here, and success no longer has to prove that your life mattered. [37:52.7]

Tolstoy takes away one simple idea of legacy. The office, the title, the obituary, the institution, the reputation may all continue, but none of them can determine or settle whether the life itself was well lived. Still, that doesn’t mean nothing continues after us. Some part of us remains in the people who knew us. What did they absorb from being around us? What do they carry into their own choices and relationships? What good continues through them, and what harm does?

That’s where I want to go in the next episode. I’ll see you there. Thanks so much for listening, David Tian, signing out. [38:30.0]