Why Hitting Your Next Number Never Works | (#088) Beyond Success: Psychology & Philosophy for Achievers, with David Tian, Ph.D.

Let’s consider the case where your life looked at from the outside is the one your younger 25-year-old self was dreaming about when he was grinding it out all those years ago, telling himself it would all be worth it, but the pull is still there. You check the brokerage app before bed. You refresh the balance the morning the wire hits, just to make sure it’s still there. You compare yourself in the back of your head to the guy in the group chat who exited bigger than you did. The current deal hasn’t closed yet, and you’re already mapping the next one in your head.

You made a deal with yourself a long time ago. You were 25 or maybe 30. You picked a number, a specific number, and you told yourself, “When I crossed that line, this pull stops.” You crossed it, but the pull didn’t stop. You’re not poor. You’re not even close, but you still can’t sit still. You thought the money would do something that money cannot do. [00:58.5]

By the end of this episode, you’re going to see where that pull came from. Now, this isn’t a flaw in your character or some defect that you were born with. It’s the predictable output of a story that you were handed before you could read. It’s a story about three things, about money, about merit and about who you really are, and the cost of not seeing this story is substantial.

If you don’t see it for what it is, the next 20 years are going to feel exactly like the last 10. You’ll find yourself on the same Tuesday at 9:00 p.m. with the same feeling underneath it. The watch on your wrist will be maybe more expensive and maybe the view from your window will be better. The car in the driveway will be the one you wanted at 25, but the man sitting in the seat will be the same man that you are still right now, with the same pull haunting you and the same private weight that you’ve been carrying for years. That pull doesn’t get tired. You do. [01:55.1]

Now, the obvious story that you’ve been telling yourself about all this, the one you reach for when this comes up is probably something like, “I just haven’t made enough,” yet that if the number got bigger, the pull would loosen or disappear.

I want you to look at the evidence on this. The people who made twice what you’ve made feel exactly the way you still feel. The people ahead of you on the ladder are not at peace. They haven’t solved this. They’re caught in the same loop you’re caught in with a longer view from maybe a higher window. You’ve been working a subtraction problem this whole time and assuming it’s an addition problem. Addition says, “Keep adding to the pile until the hole is filled up.” Subtraction says, “Stop adding and remove what’s making that hole.” The hole is not in your bank account.

To see what I mean by that, I want to walk you through an idea from a Harvard philosopher named Michael Sandel. He won the Berggruen Prize recently—this is the sort of Nobel Prize for philosophy—and he wrote a book a few years back called The Tyranny of Merit, and there’s a part of his argument that I want to walk you through carefully. [03:02.8]

Sandel’s claim is this—the story that we have been telling ourselves about merit, the story that says the people who succeed earned it and the people who fail had it coming, that story sends two different messages. The losers heard one of them and the winners heard the other.

The message that the losers heard is the obvious one in our culture. It says, “You deserved what you got. You’re at the bottom because you belong at the bottom. If you were smarter, if you worked harder, if you had more discipline, then you would not be where you are.” That’s the message most of the critique of meritocracy focuses on, and it should. That’s a brutal message and it’s done a lot of damage.

But there’s a second message and the winners are the ones who heard that one. The second message says, “You earned this, and this is who you are, the income, the title, the recognition. That’s not a thing you have. That’s a thing you are,” and the second message is just as important as the first, but it almost never gets discussed. [04:06.5]

It almost never gets discussed because the people who heard it are doing well. They look fine. From the outside, they look better than fine, so nobody asks what the message did to them on the inside. But we’re going to ask, because if you believed the second message, and if you’re listening to this, you probably did, then your worth became your output. Your worth is your title. Your worth is your income. Your worth is your net worth. The number on the screen is not just a measurement of what you have. It becomes a measurement of what you are.

The second message did one more thing to you, and this one matters most for what’s coming next in this episode. It told you what to point your life at—“Just produce.” The production is the point. The story didn’t have a question in it about what the production was for. That question got dropped from the curriculum before you even showed up, so you’ve been producing for, let’s say, 20 years, without quite stopping to ask that earlier question: “What is any of this for beyond just more of the same?” [05:18.3]

Here’s what that does to your nervous system on a day-to-day basis. When the number moves, you move. Up days, you’re someone. Down days, you’re no one. A good quarter, and you can breathe. A bad quarter, and you can’t sleep. The belief structure that built your career is the same belief structure that runs your nervous system from the moment you wake up to the moment you finally stop checking your phone at night and pass out. [05:49.5]

T and there’s something else this belief does. It hollows out the work itself. You’ve climbed for maybe 20 years, and the climbing has been good, disciplined, willpower, hard, more than most men in their 40s have ever attempted. You’re high up the ladder now, and the climbing has its own rhythm. The numbers go up. The titles change. The deals close and the rhythm becomes its own reward day to day. What the rhythm has not been able to give you, though, is an answer to a deeper question that you do not take out very often. You’ve been climbing toward what?

Most people in your position can’t answer this. They have answers that sound like those sort of B.S. answers, building the business, grow in the firm, scaling the platform, maybe providing for the family they don’t yet have. None of these is wrong technically. They simply don’t address what the deeper question is asking. The question is asking what your life is for. The answers are about what your life is doing. [06:54.3]

If your worth is your output, the question of what the output is for never quite forms. The output becomes its own justification. The climb stops needing a destination, so by your 40s, the climbing is the most stable thing in your life, but it’s also one of the lonelier things you do, because nothing in it points beyond itself.

There’s a pattern that I’ve seen in people at every level of success. They build something substantial, and years in, they discover two things at the same time, that they are more alone than they wanted to admit and the thing they’ve built has no mission inside it that connects them to anyone, including to themselves, and what they do next decides the rest of their life. [07:44.9]

Some go looking for the next deal, because the next deal is the only language they have. Some discover that the missing piece is not only a partner. The missing piece is a sense of what their work is actually for, beyond the production of more of it, and the people who do find it in contribution, in mission, in something that they are building that points beyond themselves, they end up discovering that the work itself begins to clarify in ways it never did when the work was its own purpose, and that clarity is its own form of compounding return. [08:22.1]

A person who knows what their next 20 years are for makes different decisions every day than a person who’s still climbing for the sake of climbing. The decisions get clearer. The work naturally pulls in a meaningful direction instead of just pulling. You do not have that clarity. Yet the world around you is busy congratulating you for the climb.

Nobody hands you the question, the deeper question, because the climb is producing exactly what it was supposed to produce. That deeper question only forms in private on a Tuesday at 9:00 p.m., and even then, you will usually push it down. Then, having hollowed the work out, that belief follows you home. It doesn’t stay in the office. It sits in the chair beside you at every dinner you’ve ever been on. [09:15.1]

You’ve measured yourself by output for over 20 years, so naturally, the people you choose to date have measured you by output, too, not because they’re shallow, but because that’s what you keep showing them. You walk in and you lead with, unconsciously, the résumé, the deal you just closed, the exit, the thing you’re building, the future you’re building, maybe the optionality, and it worked.

The polished résumé can get that second date almost every time, but the person behind the résumé, the actual person, not the polished version, the True Self, rarely makes it to the third date, because that person has barely been introduced, not to her—and here’s the harder part—sometimes, not even to you, and it’s important to say this, you do not know you are doing this. You’re not aware of it. [10:10.1]

You think the women keep being wrong. You think they don’t get it. You think the next one will be different, but the next one will not be different, because the next one is going to meet the same résumé. So, I want to ask you something and it’s important that you actually try to answer it, not just listen to it. When was the last time someone you cared about asked you what you wanted, what you actually wanted, and you knew the answer without first running it through the filter of what would be most impressive to the person you’re with?

Take a second with that one. In fact, it was kind of a mouthful, so let me repeat it. When was the last time someone you cared about asked you what you actually wanted and you knew the answer without first having to run it through the filter of what would be most impressive to the person you’re with? [11:01.5]

If you have to reach for it, that’s the diagnosis, and this diagnosis goes back further than your dating life. It goes back to a deal you made with yourself a long time ago and probably forgot you made. Years ago, maybe in your teens or your 20s, you picked a number, a specific number, and you told yourself in so many words, “When I make x, then I will know I’m okay,” and that number was probably honest at that time. You meant it. You weren’t bluffing.

Maybe it was a million dollars. Maybe it was 10. Maybe it was a specific exit at a specific multiple. Maybe it was a title partner, founder, principal. Whatever it was, it was the line, and you believed if you cross that line, then the inner question gets answered, and then you get to leave that question aside. You crossed it, and maybe you didn’t just cross it, maybe you doubled it. Maybe you’re sitting at five times that number right now, and the question the number was supposed to answer, did that question get answered? [12:09.8]

No, right? You crossed the line and the question you crossed it to answer was still sitting there, waiting for you on the other side, like it hadn’t even noticed you’d moved. There’s a story I think about when I sit with people in this position. The mouse finally caught the cheese and the mouse discovered the hunger was never about the cheese. The mouse, having found this out, did the only thing the mouse knew how to do. The mouse went looking for more cheese.

That’s the part nobody tells you about crossing the line. The anxiety that had been pointing at that number, I don’t know, for 15 years, that anxiety had nowhere to go. The thing it had been reaching for had been caught, so it ended up turning inward, and the engine in your head that was built to chase that number, the part of you that wakes you up at 5:30 a.m., the part that runs the calculations in the shower, the part that never stops scanning, that engine kept running, but there was nothing left to chase. But the engine still runs. [13:11.2]

I want you to think back to the morning after your share is finally turned into money. Pick whichever moment that was for you, the big win—the day the acquisition closed, or the morning the lock up lifted and you could actually sell. The day a big tranche vested and the number on the screen became something you could spend. Pick the one that was supposed to fix it, the win.

The night before you slept, you actually slept, and you woke up. You checked the account to make sure it was still there, and it was still there, and you had about 45 minutes, 45 minutes where you walked around the kitchen, made coffee, looked out the window and felt the thing you had been promised you would feel. “Ah.” But then the next number started forming in your head, the next round, the next vehicle, the next multiple. They all started showing up, and the engine that was supposed to retire that morning started up again before the coffee was even cold. [14:09.6]

That’s the moment I want you to hold, not the morning itself, but the 45 minutes, and what came right after the 45 minutes when the engine started looking for the next number, because the 45 minutes is the entire dividend the number paid out. That’s what the line you crossed was actually worth in the currency you wanted to be paid in. You spent 15 years earning 45 minutes of relief. [14:37.5]

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.”

That accounting is going to keep coming back. Before we look at what to do about it, I’m going to slow down and walk you through a story you’ve almost certainly heard before but have probably read wrong. It’s a parable of the talents from the Bible, from the Gospel of Matthew. If you grew up in any version of the Western world, you must have heard some version of this, even if you have never set foot in a church.

The setup is simple. The master is going on a long journey. Before he leaves, he calls in three of his servants and gives each of them a different amount of money. To one, he gives 10 talents. Talent was a unit of money back in the ancient world. To another, he gives five talents, and to the third, he gives one. [16:08.0]

Okay, so now the master leaves, goes on his journey. Time passes, and the first two servants, they put their money to work. They trade with it and they end up doubling it. The third servant takes his one talent, digs a hole in the ground and buries it.

Now the master comes back from his journey and he calls the servants in for an accounting. The first two, one at a time, come forward and show him what they’ve done. They’ve doubled what they were given, and the master says to each of them in the King James, “Well done, thou, good and faithful servant. Enter thou into the joy of thy lord.”

But then the third servant comes forward. He digs up his one talent, brushes the dirt off and hands it back to the master, and the master is furious. He takes that talent away from him, the one talent, and he gives it to the servant who already has the most, the one with 10 and now 20, and now 21. [16:58.5]

Now, the standard reading of this parable in churches, in business books and motivational seminars is usually straightforward, something like, “Be aggressive. Take risks with what you’ve been given. Do not sit on your capital. Burying the talent is cowardly. Putting it to work is faithful,” and that standard reading isn’t wrong, but it’s shallow.

I want you to think about that story again more carefully this time. Why did the third servant bury his talent? Actually, in the Bible, it says so. It tells us, in the text itself, he says, “I was afraid of you. I knew you were a hard man. I was afraid, so I hid what you gave to me to make sure I wouldn’t lose it.” So, this one talent servant wasn’t lazy. He took the trouble to dig the hole. He wasn’t stupid either. He was trying to preserve what he’d been given. He thought he was being careful, but his error was fear. Fear preserves, but trust multiplies. [18:00.0]

The two servants who doubled what they were given, go back and look at how they were described. The text doesn’t call them aggressive or ambitious, or driven or hungry. They simply went and put the money to work. They were not afraid of the master, and they were not afraid of losing what they had been given, so they used it. They didn’t multiply because they were aggressive. They multiplied because, actually, they were courageous.

This is where I want to bring the parable back to you, because if you read it the standard way, you’re just going to nod and say, “Yeah, I’ve been aggressive with my capital. I’ve not buried anything. I’ve done exactly what the master, quote-unquote, ‘asked of me,’” and you would be right about the first part. You, let’s say, have been aggressive with capital for whatever, 20 years, but that’s never been the issue. The fear is the issue. [18:52.3]

A frightened person, driven by fear, cannot steward anything, not their capital, even when the capital is multiplying a bit, not their career, and not the most important thing they’ve ever been given, which is themselves. The fear built the engine, and that fear is still running the engine, long after the engine is no longer needed.

Let’s set aside the philosophy for a minute and just talk directly to you. I’m not trying to corner you here. I’m not trying to win some argument about who you are. I’ve sat with too many people in your position to think any of this has to do with character. It doesn’t actually, so if a part of you is already getting ready to say, “No, that’s not me,” hear me out for a minute. I’m not describing a flaw. I’m simply describing a toxic pattern.

Here’s the pattern. Neediness towards money is rarely about money. It’s neediness for worth in a form that you can count. That’s what you’ve been doing for 20 years. You’ve been trying to settle the question of your own worth in a form that can be counted. [19:59.7]

The countable form is what made it work as a career, but the countable form is also the trap, because worth that cannot be counted feels like nothing to someone who has spent 20 years counting. You’ve trained yourself every day for two decades, let’s say, to know that you are okay by checking a number. So, now when there’s no number to check, you feel nothing, or worse than nothing.

I want you to look at how this shows up in your actual life. Maybe you recalculate your net worth more than once a day. Maybe you check the portfolio. You run the income forward. You watch the markets. You watch the currency. You watch the asset class that you happen to be in this year. Sometimes you do this without quite noticing you’re even doing it, right? You cannot sit still with whatever is actually present in front of you. Stillness feels like falling behind. [20:56.7]

A quiet afternoon at home with no calls, no fires to put out, nothing to push against, doesn’t feel like rest. It feels like loss, like the meter is running and you are not earning. You need to be producing something every waking hour. If you’re not producing, you’re reading something that will help you produce later. If you’re not doing that, you’re watching someone on a YouTube video or a podcast tell you how to produce more efficiently.

The phone is the leash, and that leash is short, and rest, when it comes, doesn’t feel like rest. It feels like discomfort pretending to be ambition. You tell yourself you’re recharging so you can hit it harder next week, but you are not recharging. You are managing the discomfort of not producing by promising yourself you will produce more really soon. That’s the first blade of the diagnosis. [21:47.9]

Now I want you to slow down for the second one, because this one is the one that will matter more, and notice that the same need shows up in your relationships or your dating life. You’ve been giving the people that you date, the version of you that the market rewards, the accomplishments, the frame, the optionality, the future you’re building and how she could be a part of it.

That’s what walks in the door of the bar or restaurant, and you’ve been wondering why no one stays for very long, why she seems interested for a few months and then drifts away, why you can’t tell sometimes whether she actually likes you or whether she likes the picture of the life she thinks she would get with you.

She drifts because there’s no one truly there to stay with. There’s just a kind of résumé on a date. You’ve been showing her the most marketable version of you for so long that the marketable version is the only version you know how to bring. You may not even be sure anymore what any other version would say if she asked. We touched on this earlier in the episode and now it comes home, and so that’s the second blade. [23:01.2]

Beneath both of these is the third thing I want you to see, because it’s what gives the others their grip. You don’t have a frame that tells you what your life is for beyond producing more output. The frame your generation was handed had the production in it. It didn’t have the question of what the production was for and that missing frame is what makes the daily output panic feel justified. It’s what makes the polished résumé on a date feel like the right thing to lead with.

Both are the results downstream of the same “blank,” the place where a sense of mission or purpose or contribution of what a life is building toward is supposed to sit. Earlier generations carried this around without thinking about it. Cultures that have not yet handed that question over to the market still do. Yours—ours—has not had it for a long time. The career pattern, the relationship pattern and the missing larger frame, they’re all the same pattern, just three expressions of one engine, so I want you to see that, because until you see that, none of this resolves. [24:16.1]

Let me pull back from the diagnosis for a minute and put the whole picture in front of you. The problem is not that you haven’t made enough money. I want to be really careful here because I’m sure almost every part of you is going to want to argue with that sentence. The part of you that has been running this engine for 20 some odd years is going to say, “Yes, but if I just made a little more, if I just got the next round done, if I just hit the next number, then I would have the room to actually look at this.”

But that part is wrong, and it’s been wrong for a long time, and the reason it’s been wrong is the part I want you to take with you out of this episode—the story connecting your money to your worth was rigged before you got here. It was rigged before you were old enough to understand what was being handed to you. [25:07.8]

By the time you were a teenager, you were already inside it. By the time you started your career, you were driven by it, and the story is constructed such that no matter how much you make, the grip doesn’t let go. The race doesn’t have a finish line in it. It was never designed to.

That’s why the next number doesn’t work. That’s why the one after that will not work either. That’s why the people ahead of you on the ladder, the ones you sometimes look up to and assume have everything figured out, they haven’t figured this out. They’re running the same race you’re running with no finish line, but just on a higher floor. [25:50.7]

In the next couple episodes, I’m going to take you deeper into this. The next episode is going to reveal what’s actually behind the story, the part doing the gripping and where it comes from. The episode after that I’m planning anyway is going to be about what becomes possible when the part that’s gripping lets go—in other words, what your work clarifies into, what your life points toward, what becomes possible in the part of your life, the domain of your life you’ve been least willing to look at, but is the most fulfilling potentially.

For now, I want you to sit with one thing—it is not the number. That’s the thing I want you to take with you out of this episode. It is not the number. The pull you have been carrying for 20 something years is not a flaw in you. It’s the output of a story. The story told you that your worth was something that you could count, and then it gave you nothing larger to point your life at. The story is wrong on both counts. It’s been running your career and your dating life on one engine the whole time. [26:53.7]

I want to step out of the frame for a minute and tell you something about my own life, because I would not be sitting here saying any of this if I hadn’t lived inside it myself. Almost two decades ago, I was living in Singapore, and it was the first Formula 1 race in Singapore, the famous night race.

At that time, I had a five-star condo atop the center of all the action, directly above Turn 18 of the circuit, right in the middle of the whole Formula 1 festivities, and from my window, you could watch the cars coming around the bend. In fact, in my view, it covered three turns of the circuit, and from my window, you saw the city the way the people who run the city see it, except the moment I’m thinking about, I was not at my window.

I was at the Paddock Club, watching the race with all these cool people, and then straight to the VIP table at the after party at the Amber Lounge. Back then, general entry, remember, this was two decades ago, was just to get in $1,000. I was surrounded by beautiful women, models. I was surrounded by what I considered back then the coolest people, the celebrities, the drivers, and it was free-flow champagne, and the feeling that came in while I was standing in the VIP, drink in hand halfway through the night, a night and lifestyle that my pimply-faced pubescent self would never have dreamed possible for me. [28:12.2]

I felt emptiness, meaninglessness. There was no zest in any of it for me. No part of me was on fire about being there. No part of me wanted to remember any of it the next morning. I didn’t care. The thought I had at that table, and I remember it precisely the way you remember the ones that make a difference, was, “If this isn’t it, what is?” I had no answer that night. I sat with that deeper question. The night went on. I partied, or tried to. I went home.

I want you to picture something. Picture the version of yourself at 65 still running this program, this race with no finish line, this story, still on the engine, still chasing the next number. The house is larger. The art on the walls is better. The car you wanted at 30 is now parked in the garage, maybe several of them, finally bought without thinking about the price. [29:08.0]

The work has gone on. The deals have gone on, but you cannot tell yourself what any of this has been for. You’ve stopped asking because asking doesn’t change the answer, and you’re alone in it, or, and this is the version that scares me more for you, you’re with someone who fell for the résumé you 20 years ago and never met the true you.

That grip hasn’t loosened in those 20 years. It’s just gotten more sophisticated. It’s learned to dress itself up in things that you call wisdom or discipline or standards. That dread used to sit in the corner of the room, but by 65 years old, it is now the room you are sitting in. [29:55.6]

Now, picture the other version of yourself at 65. You walk into, let’s say, the second half of your life without the grip. The number stops being the question. You still work, you still create, but the work is no longer the answer to who you are. The number is just a number, and the work itself has clarified. Somewhere along the way, you found out what it was for and you turned the rest of your life toward it.You could tell yourself on a Tuesday afternoon what your next 10 years are for, and the answer would not be simply “more,” and with you, besides you, there’s someone who chose your True Self, not just the practiced persona that you used to walk into bars and restaurants with on dates 20 years ago. A morning coffee, the phone is across the room. You’re not checking anything, not the markets, not the messages, not the line. That version is actually available to you, but you can’t get to it from where you are right now on the engine you’re running on right now. [31:02.2]