What Would You Pay to Get Five Years Back? | (#106) 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 your host, David Tian.

So, you probably know what your investments are worth. You know roughly what your property is worth. If you own a company, you probably have a ballpark figure for how much that’s worth. You know what people in your company are paid, and if you’ve been successful for a while, you’ve probably thought about what an hour of your own time is worth. Successful people get used to thinking this way. When enough money is involved, you pay attention.

Now try a different set of questions. What’s your marriage worth, or your relationship? What’s your health worth? What’s your relationship with your children worth? What are five good years of your life worth? Those are harder, right? That’s strange because they may be worth far more to you than your company or your investments, or your property.

A financial decision involving millions of dollars usually gets serious scrutiny. A personal decision, though, can matter just as much to you or more, and still get made with surprisingly little thought about its actual value. [01:09.4]

By the end of this episode, you’ll have four questions that will make those comparisons a lot easier to see. They won’t tell you that your marriage is worth an exact number of dollars or that five years of your life has a market price. That would be silly. Money is useful here, though, because it gives you a measuring stick that you already understand.

Suppose someone offered you $50 million on one condition: you would lose your relationship with your child. Would you take it? If your answer is no, we haven’t thereby discovered that your relationship with your child is worth exactly $50 million. We’ve learned, though, that it matters more to you than $50 million.

We may find that the things that you value most are the things that you valued least clearly, and that really matters because some of the biggest decisions you’ll ever make are actually personal decisions. If their consequences are worth millions or billions to you, they deserve at least the seriousness that you would bring to a financial decision of that same scale. [02:10.4]

The numbers themselves aren’t sacred or anything. You’re not trying to turn your family into some kind of asset class. What they do, though, is that they force a comparison. You have to decide, at least approximately, roughly, whether something matters to you more than that amount of money or less than that amount of money, or so much more that the comparison just starts to feel absurd—and that’s already a lot more clarity than most of us bring to these decisions.

Once you start thinking in this way, one fact becomes much harder to avoid. It’s that you’re already making trades. We are already making trades every day. Refusing to put a price on something doesn’t stop you from exchanging it. It only makes the exchange harder to see and blinds you to it. [03:01.1]

We trade time for money, fitness for achievement, family time for professional opportunity, freedom for security, and sometimes, we exchange the years that we have now for a future that we hope will be better—and none of that is automatically a mistake. Sometimes a company deserves nearly everything you have for a while. Some projects are worth sacrificing for. Working longer, taking the risk, or accepting less freedom now may be exactly the right choice. The problem is in making the trade without understanding what you’re giving up.

Three evenings with your family may be a sensible price for an important opportunity. Three years would be a very different price for that opportunity, and three years can disappear through a long series of decisions that each looked small at the time and perfectly reasonable just in isolation. [03:57.2]

No one is going to ask you to sign a contract that says, “I agree to exchange three years of my family life for this business result.” No, it’s more like you agree to Tuesday night at the office, and then Thursday night at the office, and then the weekend at the office, and then the next trip for business. Only later do the small payments add up when you look back to a much larger price than you had anticipated and that you would have accepted if you could see the full thing before you did it.

Your calendar already contains prices. Every time one thing gets the hour, that means another thing doesn’t. Every sacrifice contains an exchange rate, whether you’ve calculated it or not, or whether you’re aware of it or not. This episode is not some argument for balance. The question is whether you understand the trade, the trade-offs. [04:50.1]

The company may really be worth those years you’re giving it. The security may be totally worth the freedom you’re giving up. The opportunity may deserve that family time that it costs for a while. If you saw both sides clearly, would you still make the trade? If your answer is yes, then the sacrifice may be exactly right. If your answer is no, you missed the price and you probably would have been much better off knowing that beforehand.

Okay, I’m going to walk you through four different value questions here to help you get clearer on what the sacrifice really is. “If this were lost, what would you pay to get it back?” Okay, this is the restoration question. “What would you pay to get it back?”

Take your health, for instance. Suppose your health collapsed and complete recovery was possible. What would that be worth to you? How much would you pay to get your health back? Would it be $100,000, $1 million, $10 million? The exact number is not as important as noticing that an amount which once seemed enormous will now look much smaller when it’s compared to getting your health, your life back. [06:04.8]

Notice what that question changes. Before this imagined loss, that money has dozens of possible uses. You could invest it, save it, spend it, or give it away. But once you picture the loss clearly, the comparison gets a lot simpler. You’re asking which you would rather have, that money or your health, let’s say your life, your physical life, back.

Try the same question with a genuinely good marriage. If you lost this good marriage, what would you pay to restore it? Or imagine losing your child. What would you pay to have your child back? For some losses, no amount of money would feel like an adequate substitute, and that doesn’t give that good a market price. Instead, it reveals the comparison that you can make a lot clearer once the loss feels concrete. [07:01.3]

Loss makes value easier to see. Health can feel ordinary while you have it. It’s easy to take it for granted. A good marriage can feel ordinary too, and again, easy to take for granted, and so can hearing your child in the next room who might be trying your patience that night. But if you imagine one of those things gone, then money that once seemed very important can become almost beside the point.

The thing itself doesn’t suddenly become more valuable. Instead, you become more aware of what it was actually worth to you. The problem, though, is timing. If you wait for the loss to teach you its value, you learn too late. So, the restoration question asks you to use that hindsight while you still have the thing. Imagine the loss now and ask what you would pay to reverse it. You don’t need a perfect number. A rough answer is enough to make that value less vague. [07:59.0]

Now let’s ask the question before the good has been lost. This is the preservation question. “What would you willingly pay today to know this would not be lost?” What would you pay to protect a good marriage, or to protect or preserve your health, or to keep strong relationships with your children and the people you love, or to avoid spending five years on a choice that you later regret?

Okay, so nothing’s gone wrong yet in this case, and that’s why this question is particularly useful. Someone may sincerely believe that his marriage is worth millions to him, while in fact giving it whatever time remains after everything else at work. That doesn’t necessarily make him a hypocrite. He may simply never have put those two valuations beside each other.

He says the marriage is worth millions, but his calendar says it just gets the leftovers. The calendar doesn’t have to mirror your rankings hour by hour. You may spend more hours on the company than with your spouse, and still actually value your marriage more. A job can simply require more hours. [09:06.8]

So, look instead at the choices where you have room to decide. When the extra meeting competes with dinner, which one keeps getting chosen? When the company asks for another weekend, how often does that weekend go to the company? Over months and years, those decisions end up telling a different story from the one that you would give if someone simply asked you what matters most early on or upfront.

Does the way that you allocate your time, your attention, and your money resemble the actual value that you believe something has? Most of the time, it won’t match perfectly. Life isn’t that neat, and this isn’t some argument for equal allocation. Your child can matter more to you than your company without, in fact, receiving more hours than the company every week. The comparison isn’t supposed to be just one hour for $1 or something. It’s whether the pattern of your choices makes sense to you, given what you say matters the most. [10:08.1]

A company may be in a very critical period, or there may be a professional opportunity that demands almost everything from you for a while, and you may decide with your eyes open and full awareness that it will deserve that cost, but if you would pay a fortune to preserve your life or your health, then that should matter when you go about deciding whether to neglect your health for another year.

If your family matters enormously to you, that should matter when you keep postponing time with them. You can knowingly make an expensive sacrifice. The real danger is discovering only 10 years later that it costs you much more than you thought it would. [10:50.7]

Okay, now we move to the third question out of the four. The third question reverses the transaction because the second question has a limit. When I asked you what you would pay to protect something, your answer is actually partly limited by what you can afford or what your assets are. So, ask instead this third question. This is what I call the indifference question: “How much would someone have to pay you before you would willingly give it up?”

Now, your bank balance no longer limits your answer. The test is whether money could compensate you for the loss at all. How much would someone have to give you to lose a marriage or a relationship that you value? How much would they have to pay you to never see your daughter or your son, or your sister or your mother or your father again? How much would it take to surrender 10 healthy years that you’ll never get back?

For some of these things, there may be a number, and for others, you can keep adding zeros onto it, and the answer will always stay no. That answer is stronger than saying something is worth a lot. It means money isn’t an acceptable substitute for it. You could become as rich as you want and still be worse off in your own estimation, because the thing that you gave up mattered more than all the money could replace. [12:10.3]

If there is no amount of money, then you have learned that this part of your life outranks your entire net worth. Most people have never gotten clear on this, and the things that they would never sell can still become cheap in your daily decisions. You see your child every morning, so just one morning feels ordinary and expendable. Your parents are still around, so another month can pass before you visit, maybe another year or years. Your health is just fine, so you take it for granted, so another busy week without exercise or eating unhealthy feels minor.

Money behaves differently, though. Money sends statements. You can check every day what came in and what went out, and maybe you’ve got notifications in case you forget to remind you. Your children don’t send you a statement telling you how much of your son’s sixth year of life remains. Your health usually doesn’t send an invoice until something is really wrong. Time rarely tells you its price while you are spending it. [13:16.6]

A person can become extraordinarily wealthy while gradually spending the goods that he would never willingly have sold for almost any amount of money. He might refuse $50 million to lose his family, and still give away years of family time worth far less than $50 million in little pieces, because nobody asked him to make the trade all at once, and no one puts a highlight on it or no one highlights it for him. No one puts a magnifying glass on it for him.

The reversal may show that money is not a substitute that you would accept at all, but sometimes you would actually put a monetary value on it, and that’s really important information. [14:00.0]

Now here’s the fourth question. The fourth question deals with a different problem. It deals with the years you cannot recover, and this is what I call the time redemption question. Imagine yourself five years from now.

Okay, so you’re five years older, and you know with certainty that a choice that you’re making now was wrong. Maybe it was the company that you started or the person that you married, or the divorce that you chose to go through with, or the children, the quality time with the children that you kept postponing, or the actual children themselves, the birth of them that you postponed. Or this a city that you’re about to move to or this a project that took up the next five years of your life—so, in this thought experiment, there is no uncertainty. You now know because you’re looking back that the choice was wrong.

Now you’re offered something impossible, okay? You can return to today, like you get into a time machine and you’re back to today five years ago with everything that you know five years from now, and you get to choose differently. [15:02.0]

Okay, so that’s the setup. Now the question is, what would you pay? “What would you pay to go back and save yourself from making that bad decision?” Would it be $1 million? $5 million? $20 million? Half your net worth? For some choices, you might pay almost anything you had. That doesn’t prove the decision you’re making today is literally worth that amount. It’s worth your estimation five years from now, and five years from now you have information you don’t have today, but that number gives you a rough sense of how large the possible loss could be.

Right now, the decision is mixed up with immediate pressure, like the company needs an answer now or the relationship is on the verge, right? It feels urgent. That opportunity may disappear. Five years later, those pressures may be all gone, while the years that you spent on those choices are also still gone. It lets you compare today’s urgency with the price that you might only see later. [16:00.4]

A decision can look ordinary at the beginning, like you choose that company or you stay with this partner, or you leave that partner or you postpone children another year, and then five years pass, and only then do you see the full cost. Some choices become enormously expensive because time makes them irreversible.

Money can often be replaced. You can recover from a bad investment or sell one asset and buy another, but if you spend five years on the wrong choice, you don’t get those five years back. We don’t actually have time machines. You can make a better choice after five years, but you can’t make that choice five years ago. [16:39.2]

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.”

The wrong choice doesn’t always look like a disaster to other people. The company may grow. The move may improve your career. The project may succeed, and you can still look back and decide that you would gladly trade some large amount of money to have those years back again for something else. [17:46.1]

This isn’t an argument for indecision. Refusing to choose also spends time. You can lose five years refusing to commit just as easily as you can lose five years committed to the wrong thing, and maybe not just as easily, more easily. Not choosing itself is a choice, and every serious choice excludes other lives. Marriage excludes other partners. Building a company excludes other uses of those years or hours. Having children gives up some forms of freedom, and creates others. There’s no version of life in which you choose everything and lose nothing. It’s logically impossible.

You can’t eliminate regret or guarantee that the person that you become will approve of every choice that you make today, but you can notice when a decision may be far more expensive than it first appears. A company decision can consume five years of your life easily. A relationship decision can easily consume far more than five years. Postponing a choice also determines what happens to those years. You still have to choose without knowing the future, but you can at least ask what it might cost if you are wrong. [18:59.4]

There’s also another habit that makes these decisions harder to value. We’re used to measuring services by time, like lawyers charge by the hour, or a massage that lasts 60 versus 90 minutes would be different prices. Trainers sell sessions by time. So, longer service often feels like more value, because there’s more time attached to it, and that can make sense when what you’re buying is partly the time itself, but in business, the more important question is usually the outcome.

Suppose someone spends two hours helping you avoid a $10 million mistake. Does the advice become less valuable because it only took two hours? Would you prefer that they took 200 hours to get there? Of course, not. You would probably prefer the right answer in two hours instead of 20, or in two minutes, if you could. Hours tell you how long it took. They don’t tell you how valuable it was or what the result was worth. [19:58.0]

Time is easy to count, so we often use it as a kind of heuristic, a shortcut for value, but the easier number isn’t always the useful number. If the result of the advice is the same, making you sit through 10 times as many hours doesn’t thereby make the advice 10 times better or better at all. In fact, arguably, it makes it 10 times worse because it took so much longer to get there. If one advisor needs 20 hours to help you avoid the mistake, and another gets there in two, then the 20-hour answer isn’t obviously automatically worth 10 times more. It simply took longer and stole another 18 hours of your life.

This matters because “How many hours do I get?” is an easy question to ask. We’re biased towards that. It’s sort of a lazy way of thinking. “What decision am I trying to get right?” however is a much harder question to ask. But when the decision can affect years of your life, that latter question matters much more than the former. “How many hours do I get?” versus “What decision am I actually trying to get right? What is the outcome worth?” [21:04.7]

We understand this when the subject’s business, like if a decision affects millions of dollars, getting it right matters far more than how many hours someone spent helping you think it through, but then we become oddly reluctant to apply that same logic when the decision is personal. The same question applies when you’re deciding whom to marry or whether to divorce, or whether to have children or whether to spend another decade building another company, or whether to sacrifice your health for another stage of achievement.

Those decisions can carry consequences as large as the business decisions that we take so seriously and that are so easily trackable in terms of the payoff or the cost, but we often evaluate help around those personal decisions or individual decisions as if the main thing that’s being purchased were the hours, the time that it takes to think about it. [22:00.0]

If one discussion prevents a decision that would have cost you five years, then the number of minutes tells you almost nothing about what that conversation was actually worth. Some discussions can have seven- or eight-figure consequences, even though they never appear on any balance sheet. There’s no line item for marrying the right person. There’s no line item for losing 10 healthy years or spending five years on a choice that you later regret. The absence of a line item doesn’t make the consequence itself smaller.

These questions become even more weighty when we remember one fact that none of us can get around: we will die. Mortality matters because death makes time much more scarce. If you had infinite years, five wasted years would matter much less. You could try again until eventually you get it right, but you have a limited number of years, and we don’t know how many. You can earn another dollar, but you can’t earn another 2025. [23:03.8]

Money and time behave differently. Money can accumulate, disappear, and sometimes accumulate again. But time moves in only one direction. Every year you spend becomes part of the life that you’ve actually lived, whether you would choose it again or not. You can make more money later. You can build another business later, but you can’t go back in time and live that year again.

The same is true of your children, maybe more true because of how quickly they grow when they’re young. If your child is three now, you can spend more time together when they’re seven or 10, or 20, but you can’t get three back or six back, or any earlier year back when you weren’t around. [23:46.6]

Some of the things that we value most depend on accumulated time, like you can’t be single today and then have a 20-year marriage next year. A 20-year marriage takes 20 years. The years are part of what makes it valuable. Relationships also depend on accumulated time, like you can meet new people later, but you can’t instantly create years of dinners and arguments, and holidays and illnesses, and jokes and getting back together, reconciliations and ordinary fun afternoons together. Part of the value is that shared history.

So, postponing these things isn’t actually free when the years, intrinsically, are part of the thing itself. You may still build the friendship or marriage later, but the five years of shared history that you could have had are not sitting in some reserve for you waiting. Those specific years will never become part of that relationship—so, every serious choice contains a loss. Choosing one life means not living several others. [24:49.8]

If you spend 10 years building this one company, those are 10 years that you didn’t spend focused on something else. If you choose this one partner, you’re not choosing these other partners. You don’t get to keep every alternative available and return for it later. If you choose all the other partners, then you don’t get to choose that one partner and go all in and commit. You don’t get to have that experience either. Every serious choice forecloses other options.

This is where successful people can get trapped. Failure is the obvious danger. You can choose badly or the company could collapse. The relationship could fail or the project could go nowhere. The more dangerous possibility is actually that you succeed. You spend 10 years building exactly what you set out to build and you make the money, and you get the status and you accomplish the goal, and only then do you realize that the thing you succeeded at was never actually worth that much of your life. [25:46.3]

Achievement can be worth the years. The mistake is spending them without asking beforehand what they’re actually worth. Success can hide the real cost, because the result keeps telling you, or society keeps telling you, that the choice is working. The revenue is rising. The company is growing. The project is succeeding. So, you continue, but a plan succeeding doesn’t tell you whether the life required to succeed at it is one that you would have chosen if you had seen the price clearly.

The cost is especially easy to miss when the rewards arrive on schedule. You’re making progress. You get this promotion or another funding round, or a larger exit or a bigger opportunity that confirms that you’re succeeding by the measures that you chose back then. None of those results can tell you whether those measures deserved those five years or 10 years, or more.

Mortality makes the price impossible to avoid forever. We don’t get infinite attempts. You can’t live every possible life, and you can’t recover the years after you finally understand what they were actually worth. So, the question isn’t only whether this choice will succeed. It’s whether success is worth the time, the years that you’re about to spend getting there. [27:05.3]

This is where the Stoics become really helpful, especially for successful people. Success rarely asks you to give up something important all at once or upfront. It usually asks for just one more trade that seems reasonable, like you spend another late week on the quarter, or you take another business trip for a meeting, and you put off making more room in your life for your relationship, or your marriage, or your health, or your friends, or your loved ones until next year, and each decision can make sense on its own at that time. That’s what makes the accumulation so hard to see.

The Stoics had a practice that might sound gloomy until you understand what it’s really for, and this practice is to deliberately imagine the loss of something that you still have. This is a practice, okay? [27:54.1]

Imagine that your spouse is gone, or that your children are all grown up and no longer living with you, or that your health has declined severely, or that a friend that you care about is no longer alive, or that you’re already 10 years older than you are now. You don’t have to stay with these thoughts for long. The point is to borrow the perspective that that loss would otherwise force on you. It’s easy to take these goods for granted because familiarity dulls our attention to value.

Missing another dinner can seem really small when your spouse is there every day. Another Saturday can feel easy to make up when your child is six years old, and when your body is working just fine, postponing fitness or a better diet until after this yet another busy period can seem very reasonable in the moment. Success gives you a good reason every time. [28:46.5]

The deadline matters or the opportunity has some clear upside, and things are supposed to calm down after this period. The people in the years that you’re trading away don’t send you some flashing warning that you’ve now done this for four years, so for a moment, remove the assumption that these things will still be waiting when the next quarter or the next deal or the next project is finally over, and then look at that next actual decision on your calendar. [29:15.2]

Maybe you’re thinking of missing dinner or adding yet another business trip, or postponing some medical appointment or giving another weekend to some other deadline. You don’t have to choose the personal option every time, but you do need to see what that choice costs if it becomes the normal choice for a year or more.

Ask yourself, “If this disappeared tomorrow, would I discover that I had been valuing it far too cheaply today?” Maybe the answer is no, and this really is the period when the sacrifice makes total sense. Then you would choose it again, knowing the cost clearly, but perhaps you notice that just for now, it has gone on for five years or more. [30:02.5]

Failure eventually interrupts you. Success can keep supplying good reasons to continue. You can hit every target, but still discover later that you kept extending a trade that you would never have accepted if you had gone in with your eyes open, if you had seen the total price at the beginning. The Stoic practice gives you a chance to seize some of that price while you can still choose differently and do something about it.

At this point, you don’t need four separate accounting exercises. The four questions are different ways of testing the same thing. What would loss reveal about the value that you have? What would you pay now to preserve it? Is there any amount that could compensate you for giving it up? If a choice cost you years that you later wish you had back, how much would you pay to get those back? How expensive was that choice? [30:57.5]

Choose three or four things that matter most to you in your life right now. Maybe it’s your relationship or your children, or your health, your family, the relationships that matter most, or what you’re giving the next five or 10 years to. You don’t need exact numbers. An answer could be no amount of money. Then compare those answers with the life that you’re actually living or actually trying to live.

I’ve seen this problem with successful clients in many different forms. Someone can care deeply about a marriage or his family, or his health or the years ahead of him, and still make a series of decisions that price those goods far too cheaply.

Usually, he knows what he cares about. He can tell you immediately that his family matters more than any increment of money or that his health matters more than another professional milestone. The mismatch appears in the sequence of decisions, not in what he says he values, and it rarely happens through one dramatic choice. Each sacrifice looks reasonable at the time, but then enough years pass that the total price becomes visible. [32:02.5]

Your children are all grown up and you miss those years you’ll never get back, where your body has aged a lot and you didn’t notice until now when it’s creaky, where your relationships end suddenly to you—it seems sudden to you—or people that you value die suddenly, or opportunities that you thought would be there forever disappear.

Five years, 10 years, 20 years means something different at 50 than it did at 30, and eventually, you may know exactly what something was worth, but knowledge acquired after the possibility has disappeared has very limited use.

The aim isn’t to become afraid of loss or to abandon ambition, or to preserve every option. You can still sacrifice heavily when you have deemed the goal to deserve it, and you can keep building when the goal deserves those years, and you have decided that and you have calculated it, and you’re ready to pay the cost, but see the price as clearly as you can. Know what you’re spending and what you’re spending it on. [33:07.0]

Then ask the question that matters most: “What actually deserves the life that you have left?” Some things are far too valuable to discover their price only after they’re gone. [33:21.1]