What Success Can’t Tell You About Life | (#102) 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 Question Behind What You’re Building.

When the goal is clear, most of us know what to do. If you’re raising a financing round, you can define the amount. If you’re shipping a product, you can define the date. If you’re trying to reach profitability, you can look at the numbers and know whether you got there. The same is true in an election or an athletic contest. There are rules. There’s a result, and at some point you can say whether the attempt succeeded or not.

That kind of clarity is useful. It directs your attention. It helps you make trade-offs. It gives you a basis for strategy. It’s also one reason why competent people can become so effective. When the objective is clear and defined, they can organize effort around it. They can ignore distractions, accept short-term costs, and keep going when other people quit or lose interest, and in the right setting, that becomes a genuine strength, especially across many years. [01:03.7]

But try applying the same logic to a friendship. What’s the score? Or to a marriage. At what point have you succeeded? Or to being a parent. When do you know you’ve done enough? Or to learning. When are you ever finished? If you widen the question all the way out, what counts as success in a worthwhile life? That’s where the scorecard starts to fail us.

So, in this episode, I want to give you a way to separate the parts of life that really do need goals and scoreboards and clear results from the parts that get damaged or spoiled when you treat them the same way, because the habits that helped you succeed professionally can actually interfere with relationships or family, or enjoyment of life, and even with skilled performance itself. The answer isn’t to become less ambitious. You don’t have to choose between ambition and living well. The more useful question is how to keep finite goals without asking them to carry the weight of your entire life. [02:07.7]

In the previous episode, we looked at Oliver Burkeman’s argument that your weeks are finite. They disappear as you spend them. You don’t get to save them up and then use them later. This episode asks the next question—what should those weeks be spent for? You can become very good at allocating your time. You can get more efficient. You can hit one target after another.

You can still spend decades pursuing results that can’t give you what you expected or wanted from them, and that can actually show up in obvious ways, like a relationship that keeps getting postponed or children that get whatever time is left over after whatever your career demands, or friendships that thin out, or a partner who starts to become just part of the evidence that your personal life is going well, and the danger is hard to notice because professional success keeps rewarding the same way of thinking. [03:02.6]

So, the problem isn’t ambition or competition, or caring too much about the result. That would be the easy but lazy answer, and it’s not the right one. Some results matter enormously. Discipline matters. Competition can matter. Measurement can matter. Sacrifice can be appropriate. The problem begins when that logic that works so well in a finite contest gets carried into questions that it was never able to answer.

James Carse gives us a very useful way to see that difference. Carse makes an important distinction between finite games and infinite games. A finite game has boundaries. It has rules. It aims at a result, and at some point, the contest is decided. For example, a football match ends or an election produces a result, or a financing round either happens on acceptable terms or it doesn’t. An infinite game works differently. There’s no final victor whose success ends the activity. The rules and circumstances can change so that play can continue. [04:06.8]

Now, Carse isn’t saying that finite games are bad and infinite games are good. We need finite games. Their limits are part of what makes them useful. They remove ambiguity. You know what you’re trying to do. You can compare one result with another. You can tell whether you improved. You can point to evidence that something difficult was accomplished. That evidence might be a title, a valuation, an award, a rank, an exit, or an amount of money, and years of effort can be compressed into one result that everyone can recognize and there’s nothing wrong with that.

If you built a valuable company and sold it for a large amount of money, the sale tells us something important. You created something that other people valued enough to buy at that level. But notice how easy it is to ask that result to answer a different question—did the exit prove that every sacrifice required to get there was worth it? It can’t answer that by itself. That’s a different kind of question. [05:05.8]

The exit can tell you what happened in the game. It can tell you that you achieved the result you were trying to achieve. It might tell you something about skill or judgment, or persistence or timing, or luck. But whether the sacrifices were justified depends on more than the size of the result. You have to consider what you created, whom it helped, whom it harmed, what responsibilities you had while pursuing it, what you gave up, and whether you understood those costs while choosing them. You can’t settle those questions by simply adding more metrics.

Suppose one founder made $10 million and another made $100 million. That may tell us who produced the larger financial result, but it doesn’t tell us who made the better use of those same 10 years. That same confusion appears with titles and awards and rank and money. A result can become evidence not only that you succeeded at a particular game, but that your life is going well or that your choices were justified, or even that you are the kind of person that you hoped you would be after all that time. [06:13.8]

At that point, the scoreboard has taken on a job that it was never actually capable of doing, and once the result becomes personally loaded in that way, it can begin changing how you perform while you’re still trying to get it. The goal is no longer merely just a goal. It begins carrying questions about identity and value that that finite contest simply can’t answer, and that creates a real problem—the more the result has to prove about you, the harder it can become to pursue it well, or even to choose your sacrifices wisely.

The ancient Daoist philosopher Zhuangzi gives us a wonderfully simple example of this. In Chapter 19 of the Zhuangzi, there’s a story about an archer. When he shoots without much at stake, he can use his skill freely. As the prize becomes more valuable to him, though, his performance actually ends up getting worse. [07:10.4]

The passage goes like this in the Zhuangzi: “When you’re betting for tiles in an archery contest, you shoot with skill. When you’re betting for fancy belt buckles, you worry about your aim. And when you’re betting for real gold, you’re a nervous wreck. Your skill is the same in all three cases—but because one prize means more to you than another, you let outside considerations weigh on your mind. He who looks too hard at the outside gets clumsy on the inside.”

His ability hasn’t disappeared. He hasn’t forgotten how to shoot. What’s changed is how much the result matters to him. Part of his attention is on the shot, but another part is on the prize, and that second concern interferes with an ability he already has. [07:57.0]

You can see the same thing in much more ordinary situations. Suppose you’re giving a presentation. You want it to go well. Of course, you do. You prepared for it. You have a point that you want to communicate. You want the people in the room to understand it. But now suppose their response also has to prove that you’re intelligent. Now you’re no longer just giving a presentation. Part of your attention is watching the people in the room and trying to determine what their reactions say about you.

The same thing can happen with a whole company. There’s a difference between wanting the company to succeed and needing its success to justify who you are—and this happens with attraction, too. There’s a difference between wanting someone to be attracted to you and needing that attraction to establish that you are indeed desirable. In each case, the activity has now acquired a second task. You’re trying to do something well while also monitoring what the results will mean about you. [08:53.7]

Professor Philip J. Ivanhoe develops a related idea in his excellent essay on unselfconsciousness in the Liezi, which is another ancient Daoist text. Unselfconsciousness here doesn’t mean ignorance. It doesn’t mean laziness or lack of skill, or refusing to think about what you’re doing. The archer still has to learn archery, right? So, preparation does matter. Training matters. Reflection matters. The problem comes when reflection continues the same moment when you need to act.

Sometimes you can search for something so hard that the searching makes it harder to notice what’s there. Sometimes you can monitor your performance so closely that the monitoring makes you perform worse, and sometimes you can become so preoccupied with whether you’re meeting a standard that an ordinary activity becomes much harder than it needs to be.

Anyone who’s become skilled at anything has probably experienced some version of this. You practice. You correct mistakes. You think carefully about what you’re doing, and then at some point, you just have to do it. If part of your attention remains occupied with evaluating yourself while you’re doing it, you’re asking your mind to perform two very different tasks at the same time. [10:09.6]

That brings us to another assumption that sounds sensible but isn’t always true. If an outcome matters more, then caring more and trying harder should improve the result, right? Sometimes it does. If you haven’t prepared enough, more preparation may help. If you’re distracted, more attention may help. If you’ve been careless, greater effort may help. But increased stakes can also divide your attention and make you worse at something that you already know how to do, and the problem becomes much stronger when the result has to establish more than whether you succeeded at the task. Now it has to establish your intelligence, your desirability, your worth, or the value of the life that you’ve been living.

Zhuangzi’s archer is dealing with one shot and one prize. The larger danger appears when the same relationship to the prize spreads across an entire life, and one result after another becomes the next thing that has to prove that you’re doing life correctly. [11:10.0]

Now, this is where Alan Watts becomes useful because he points to a mistake that’s much larger than caring too much about just one prize. In a speech that’s often called Life Is Not a Journey, Watts compares a journey with music and dance. If you’re traveling somewhere, the destination matters, like if you book a flight to Toronto, but the plane lands in Vancouver, something has gone wrong. The trip is partly judged by whether you arrived where you meant to go.

But music is different. A piece of music has a beginning and an ending. It has direction. It may build toward a final chord, but the value of the piece does not come from reaching that final chord. If it did, then the best musicians would just be the ones who got to the final chord the fastest. Dance works the same way. You can finish a dance, but the purpose is not to get yourself to the final position as quickly as possible. So, a piece of music is actually finite. A dance is actually finite, but their value is in what happens while they are being played or danced. [12:08.2]

Okay, Watts applies this idea to a whole human life. We start very early by preparing for the next thing. Childhood prepares you for school, and then school prepares you for university, and then university prepares you for a career, and then the early years of the career prepare you for more senior positions as you go up the ladder. One company prepares you for a bigger company. Your current wealth prepares you for financial freedom, and financial freedom is supposed to prepare you for the life that you will finally have afterwards.

Every individual step can make sense, and that’s what makes this problem so hard to notice. The mistake is not that any one goal is foolish. The mistake appears when each present moment becomes valuable, mainly or only because of what it’s supposed to produce later. [12:54.8]

Carse helps explain why this can feel so natural. Inside a finite game, present effort really does serve a later result. Training serves the race. Negotiation serves the final agreement. Investment serves the return. Preparation serves the presentation, so there’s nothing strange about that. The trouble is when the same relationship spreads across time itself, like if you were to say Monday serves Friday, or this year serves next year, or this job serves the promotion, or this company serves the exit, or this period of intense effort serves the freedom that’s supposed to come after it, and when that freedom arrives, it becomes the starting point for yet another future. [13:37.6]

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 last episode, drawing on Oliver Burkeman, focused on the fact that your weeks disappear as you spend them. You can’t just put them aside and keep them pristinely preserved and then come back for them later. Watts adds another point to that. Those deferred years were not merely years spent waiting for life to begin. They were the life. If every present is sacrificed to a future, then the arrangement can never pay off. When the future arrives, it becomes the present, and if you treat that new present the same way, you sacrifice it yet again. [14:56.5]

Still, there is an obvious objection—substantial achievement requires sacrifice. A medical degree requires years of training. Building a company can require periods of intense effort. Raising children may require giving up things that you would otherwise enjoy. Saving money often means not spending it now. Some future goods are important enough to justify present costs.

So, “live now” can’t mean “do whatever you feel like that feels good today.” That would just be childish. The better distinction is between having destinations inside your life versus treating your life itself as transportation towards some destination. You can spend years preparing for something that matters without deciding that those years have no value except as the price of getting there. You can delay gratification without treating the present as disposable. You can make a sacrifice without pretending that sacrifice has no cost.

Once you see that distinction clearly in career and achievement, the same mistake becomes much easier to notice in the part of life where another person that you care about is involved—so, relationships. [16:04.6]

Relationships make this especially tricky because they contain both kinds of logic at once. There are decisions with clear outcomes. “Do we start seeing each other? Do we commit? Do we get married? Do we have children? Do we live together? Do we stay together?” Okay, so, all of those questions matter. Some relationships should end. Continuing a relationship itself does not prove that the relationship is good.

So, it would be too simple to say that relationships are just infinite games, and therefore, we should never think in terms of decisions or outcomes. The trouble begins, though, when the relationship starts carrying another meaning. A partner can become evidence that you’re desirable or successful, or finally a man, or finally an adult in the way you think an adult should be.

Marriage can become a milestone that proves this part of your life has been handled, too. Children can become another stage in the plan. You built the career or you made the money, or you found the right person and you got married and you had children, and now the picture is complete, but gradually, the person you’re with becomes just part of the score. [17:07.2]

So, yes, a wedding is an event—it has a date. It starts and ends—but marriage is mostly what happens afterwards. You wake up the next morning, and then there’s another morning, and then another one after that. Having a child is an event, too. There’s a day before the child is born and a day after, but parenting is what happens in all the ordinary days that follow.

Family life doesn’t mainly exist at some future point when the company is more stable or when you’ve made enough money, or when the travel slows down or when your schedule finally opens up. Your family experiences the life that you’re living with them right now. Ferris Bueller put it better than most philosophers: “Life moves pretty fast. If you don’t stop and look around once in a while, you could miss it.” [17:50.7]

This gets uncomfortable because the usual defense from achievers may be completely sincere. You may be working this hard for your family. The money matters. Security matters. Opportunity matters. Freedom matters. If your effort gives your spouse and children a safer home, better choices, more freedom, a fewer financial worries, those are substantial benefits, but the future benefit doesn’t erase the present absence, and the present absence doesn’t automatically make the future benefit a bad trade.

That’s why “career bad, family good” is also useless advice. The harder question is “How much present absence is justified by what you’re trying to provide later?” There isn’t one answer for everyone, but there is a trade-off, even when the career effort is noble and the intentions are good. Zhuangzi’s archer appears again here in a different form, though. You can become so concerned with succeeding as a husband or a father or a partner that you start paying more attention to whether the family fits your idea of success than to the actual people in it. [18:55.3]

You want to create the ideal family, or you want to be a good father, or you want the marriage to succeed. Those are all understandable desires. But now, part of your attention is on the person in front of you, but part is checking whether the relationship is turning out the way you think it should. You can end up responding to the marriage you think you ought to have instead of the marriage you actually have.

There’s a moral problem here, too. Another person that you care about in that relationship cannot merely be part of “your” life plan, as though they were an accessory or a sidekick. Your partner has desires and purposes of their own. Your children don’t exist just to justify the life you chose before they arrived. Your friends don’t exist merely to make sure you have enough connection or support in your life.

The more another person becomes useful, mainly because of what they contribute to your result, the less room you leave for that person to be independent of your plan, and the less authentic connection you actually experience. This is why another common assumption fails. “Once the right external pieces are in place”—so goes this assumption—“the private life will largely just take care of itself.” But it won’t. [20:05.6]

Getting married doesn’t complete marriage. Having children doesn’t complete family, and becoming financially free doesn’t automatically teach you how to spend your freedom well. Success can create excellent conditions for a good private life, but the conditions are not the life itself—and none of this requires you to become less ambitious. You can still want the company. You can still want the breakthrough, the wealth, the mastery, or the public success. There’s no necessary conflict between achievement and presence, or ambition and love, or discipline and enjoyment.

Think again about the example of music. A good musician doesn’t become good by avoiding effort. A concert pianist may spend thousands of hours practicing. There is repetition, correction, discipline, standards. The musician has to notice mistakes and improve. But the point of all that practice isn’t to get through the music faster, to get to the end. The practice allows the musician to participate more fully in the music while it’s being played. [21:09.2]

That gives us another way to think about finite goals. Suppose the company succeeds. What does that success allow you to create or contribute then? Suppose you make more money. What freedom does the money give you? What responsibilities come with it? Suppose you finally have more control over your time. What deserves that time once you have it? Suppose you have the family you wanted. How do you want to live with these people now that they’re actually here? The result matters, but what the result serves matters, too, and arguably more.

This also helps separate wanting an outcome from needing that outcome to establish who you are. You can want something intensely without making it your identity or making your identity depend on getting it. The difference often becomes easiest to see when the circumstances change. [22:05.2]

Can you change direction without experiencing the change as a personal collapse? Can one good become more important than another? Can you lose a title without losing your sense of who you are? Can one game end without immediately needing another game to replace it? Those are difficult questions precisely because achievement can become so closely tied to identity that ending the activity feels like losing the person who was doing it.

This is also where Carse can be easily misunderstood. Infinite play doesn’t mean never retiring. It doesn’t mean founding company after company forever. It doesn’t mean maintaining the same level of ambition for the rest of your life, and it certainly doesn’t mean keeping every relationship going simply because continuing sounds more infinite. That would just turn Carse to some argument for endless striving, which would leave us right back where we started. [23:02.3]

A finite game can end. A company can be sold. A career can change. A relationship can end. One good can give way to another. The larger question is whether you’ve mistaken any of those finite contests for the final measure of the life that contains it. You can care deeply about the result without asking it to tell you everything about yourself, and once you stop demanding that much from the result, ambition doesn’t have to disappear. It just has less to prove.

So, Carse gives us a way to separate the games that need a scoreboard from the larger life that those games are part of. Finite games need results. They need rules, boundaries, and some way of knowing whether you have succeeded. But the results can only tell you so much. It can tell you how the game went, but it cannot settle every question about whether the game was even worth the time you gave it. [23:54.7]

Zhuangzi’s archer parable shows what happens when the prize starts carrying too much weight for you. The skill may still be there, but concern with the result begins to interfere with the activity or action, or performance itself.

Ivanhoe helps us to see why unselfconsciousness matters so much here. At some point, you have to stop monitoring yourself and simply do the thing, and the point from Alan Watts takes it even further that the bigger mistake is treating life itself as a preparation for some arrival. That becomes especially costly when the people you love become part of the destination that you’re trying to get to.

Let me illustrate all this by telling you about a client. Okay, this is a composite of several clients I’ve worked with. This person had done very well professionally. The company had grown and his income had grown along with it, and he’d made choices that were completely understandable at each stage. One more demanding year was needed because the business needed him. One more stretch of heavy travel because, of course, the opportunity was important. [24:58.4]

One more delay in making room for a serious relationship that he really wanted was understandable because things were unusually busy then—and each decision made sense on its own, but that was really precisely the problem. There was never one obviously disastrous decision to point to. There was just a sequence of smaller, reasonable choices, each of which pushed the personal life a little further into the future.

Meanwhile, the professional side kept rewarding him, and this is why failure itself isn’t the only danger. Continued success can protect your unconscious strategy from further reflection or scrutiny. A result produces another opportunity, and then the new opportunity makes another sacrifice look reasonable, and then the sacrifice buys more success, which creates another reason to delay.

While all of that continues, your children get older. You miss those years you can’t get back. Your partners get older or your parents get older, and your friendships thin out and weaken, and you get older. Nothing dramatic has to happen in any particular moment, and from the outside, the whole period can look like uninterrupted success. [26:06.2]

The alternative doesn’t require giving up ambition. You can still commit yourself seriously to a finite game. You can still care about the company, the result, the money, the skill, the public success, but the purpose becomes clearer. Professional success no longer has to establish your self-worth. Your partner no longer has to complete the picture of your successful life. Your children no longer have to justify sacrifices made in their supposed interest. An ordinary time with people that you care about can matter even when it produces nothing later. You can prepare for the future without treating the present as merely the price you pay for that future.

Carse helps us distinguish those games. Zhuangzi and Ivanhoe show what attachment to the prize can do to you while you’re playing, and Watts has brought up the mistake of postponing life until this mystical arrival of something. [26:59.3]

But there’s still one more problem here. We’re very good at explaining why the sacrifice we’re making right now deserves another year, and then another and another. In the next episode, I’m going to remove the assumption that yet another year will always be available.

Thanks so much for listening. I’ll see you in the next episode. [27:16.5]