Why More Money Won’t Fix This: The Steward Posture vs. The Dictator Posture | (#090) Beyond Success: Psychology & Philosophy for Achievers, with David Tian, Ph.D.

Here’s a question that decides how the rest of your life goes. Do you own your money or does your money own you? Most successful people don’t know the answer and they don’t know that they don’t know. They feel disciplined and sharp, and on top of it, when what’s actually happening is that they’re being owned, and the ownership is invisible to them because it looks like the very thing they’re proud of.

By the end of this episode, you’ll see what it actually means to own what you have instead of being owned by it. The change is in how you view the money, and from there, the returns show up in the decisions that you make at work, in the people you let close to you, and in the next 10 or 20 or 30 years of your life. This isn’t supposed to be some moral upgrade.

I’m not telling you to give your money away or feel bad about having it. The job is to see what you actually have in a certain and, I think, better way, and that seeing changes the relationship to the money, and the relationship is what determines everything downstream from there. [00:58.6]

You probably think the way out is more money, that if you just had a little more, the money would stop having its hold on you and you’d be free of it. But there is no such line. I’ve worked with people across every income bracket who crossed the lines that they thought would dissolve the grip. They got the promotion they’d been chasing for years or closed the deal that was supposed to change things, or hit that compensation number or paid off the mortgage, or set up the kids’ education or sold the company, or bought the place in that other country. But the control that money had over them didn’t relax. They aren’t less owned by their money than they were before, and in some cases they’re more owned.

The person at the celebratory dinner sits there with a thought that he doesn’t dare say out loud, not even to himself, and it’s that he thought this moment would feel different, but it doesn’t. You can see your bank balance, but you can’t see how you view your money, so you keep working on the part that you can see, because it feels like progress, while the part that you can’t see is the part that actually has control over you. [02:00.7]

Add another zero to the number, and that control over you comes with it. The next promotion, the next bonus, the next exit, whichever version is next in your life, the new money will own you the way the current money does. You aren’t going to buy your way out. The way you view the money is where the way out lives, and that’s what we’re attending to for the next 20-something minutes, the part that actually changes things, instead of the part that has already failed.

What actually changes things is an irony at the heart of the inner game of money. The more you treat what you have as yours, as something you possess and direct and defend, the more it possesses and directs and defends itself through you. You think you’re the one holding the money, but look at your week from the outside. Your attention goes to it first. Your calendar bends around it, and the first thing you check in the morning is some version of that number, the portfolio screen or the banking app, or the inbox where the next number lives, whichever one tells you where you are in relation to that number. [03:02.1]

You didn’t sit down one Saturday and decide to live this way. The arrangement decided for you and it happened gradually over years. You think you’re managing your wealth, but the wealth is managing your hours and your mind. Some part of your attention is on it, even when you’re doing something else. You can be at dinner with people you care about, but a piece of you is still inside that spreadsheet.

By any sensible accounting, you’ve made enough, or are making enough, but your morning is still obsessed and organized around what the number did overnight, and your attention is bent toward the money far more than the actual management of it actually requires.

The way out is to stop thinking of the money as yours to begin with. That’s going to sound really weird at first and maybe even wrong. You earned that money, right? You put in the years. You took the risks. The money is legally yours, and I’m not saying otherwise. [03:53.0]

But if you view yourself as merely holding the money as a resource passing through you, owed to important people and deeper purposes beyond yourself, if you view it that way, then the grip and control over you that that money has loosens and relaxes, and then that frees up the space for all the good stuff, all the good emotions you’ve been waiting to feel and the next level of your work and legacy. The asset register can stay where it is and nothing in the financial picture has to change. What changes is where you stand in terms of it.

This is the irony of the inner game of money. The person who treats it as his own ends up being owned by it, while the person who treats it as held in trust ends up free. There are two main postures that sit behind that contrast. The legal ownership is identical in both. The bank balance is identical, but the relationship to the money is completely different. Okay, let’s call them the dictator posture and the steward posture. [04:57.2]

The dictator says the money is mine. I decide I answer to no one. This is the default posture of nearly everyone who has accumulated anything and it’s the posture that the previous two episodes traced the damage from. He isn’t just claiming that he earned it, which is usually true, or that he’s entitled to make decisions about it, which, of course, most of us would grant. He’s claiming something further, that what he does with what he has is no one else’s business but his own.

Ask the dictator what his money is for, and that question barely registers for him. It’s for him, for what he wants, of course. The dictator’s question, “What do I want to do with what I have?” shows up in every choice he makes with it, from which apartment to buy to which cause to support this year, and so on. The scale changes from one decision to the next, but the question is the same one.

The steward, however, asks a different question. He asks who and what the money is for, beyond himself, and he holds what he has in trust for the people who depend on him, for the work he has bound himself to, for the contribution he’s making while he’s here, for the deeper meaning or purpose or legacy that he’s committed to. [06:10.6]

The question he’s asking when he opens the bank statement isn’t the dictator’s question. It’s not “What do I want to do with this?” but instead “What does this owe, and to whom?” What makes this stewardship rather than mere generosity is the commitment. Generosity moves with mood, and mood is a strange thing to build a life on. It comes and goes for reasons of its own. Half of them you’re not even aware of, like you give because you feel like it on a Tuesday and then on the Wednesday you feel like something else.

Okay, so the steward is not operating from mood. The steward gave his word to specific people and to specific work, or he committed internally to those people, so the check goes out. The time gets put in. The attention shows up on days when he doesn’t feel like any of it. Stewardship holds up even when the mood doesn’t. [07:00.4]

You may be listening to all this and thinking that sounds fine. The dictator gets to do what he wants with his own money, which is what most people in his position do, and which is by most measures the reward for having built what he built. So, what’s wrong with that? Okay, two things, and they cost more than the dictator is aware of. The first is that the dictator’s posture is self-centered at its root.

The main question he’s asking in every choice that his money is involved in is, “What do I want?” In a life organized around “what I want,” however large that “I,” the scale of that “I” gets, is a small life, not small in dollars, but small in the sense that only one person is inside it. The dictator doesn’t feel the smallness directly, because from where he’s sitting, the view might be large, properties or deals and options, the next thing, but the person taking in the view is one person asking what he wants, getting it, and then asking again. [07:56.3]

There’s a certain fulfillment available to a child who’s given everything he points at, but there’s no version of that fulfillment available to a grown person. The grown-up knows this somewhere, which is why the satisfaction keeps thinning out the more he gets.

The second cost is relational and this isn’t the cost a dictator would describe if you asked him. He would say he’s busy or that he hasn’t found the right person yet, or that the people he meets aren’t at his level, and what’s actually happening is that his money has made it very difficult for him to know who is with him for reasons that have nothing to do with the money.

The room might be full. The calendar might be full, and invitations coming in faster than he can answer them, but somewhere in the back of every interaction is the question of what the other person really wants from him, and whether the warmth that he’s being offered would still be on offer if the bank account weren’t. [08:53.1]

The dictator can’t fully answer that question about anyone because he’s never let anyone close enough to a part of his life, to a vulnerability that has nothing to do with his money. He has trusted nothing that is vulnerable to anyone, so no one has had the chance to show him what they do with that trust.

The relationships in his life, however many of them there are, all live on the side of him that the money built, while the other side of him, the side that would be there if the money weren’t there, has no witnesses. That door is locked. This is the cost the dictator pays without knowing he’s paying it. The problem isn’t that he’s questioned too little. He’s questioned all day long by lawyers and accountants, and family and the board. The cost is that he’s loved, if he’s loved at all, on terms that he can’t verify. He’s living a life whose central question is what he wants, which he will keep answering for the rest of his life, and never in a way that satisfies him. [09:56.0]

That’s what the steward’s posture is the way out of, not just a moral upgrade, but a way out of a life that, on its current terms, won’t become any more fulfilling, no matter how much further along the dictator gets. So, how does someone actually become a steward instead of a dictator? It comes down to two thresholds, neither of which the dictator ever crosses, but both of which the steward does.

Okay, the first threshold is mission. The dictator has never worked out what his work is actually for beyond merely more of it. He’s done the work for so long that the doing of it has replaced the question of what it was for in the first place. If you ask him, he’ll give you the language of the field he’s in. He’ll tell you about the company or the deals, or the next thing, but he won’t tell you what any of it is really pointed at, because that question stopped being interesting to him some time, I don’t know, in his late-20s, and he hasn’t bothered to revisit it since. [10:54.1]

For the steward, the one stewarding the money, that question has been answered, and the answer isn’t the same as a mission statement on some website. Instead, it’s a clear sense, like on a Tuesday afternoon, of what his next 10 or more years are legitimately pointed at, a contribution, a body of work, a problem that he’s solving for people who aren’t him, a legacy he’s willing to put his life behind, and once he has that answer, his money has somewhere to go besides his own consumption. It moves in a direction instead of just sitting there, guarding itself.

The money is no longer the point of the work. Now the work has a point of its own, and the money is what lets the work happen. For the dictator, the money is the scoreboard, and if you take the scoreboard away, there’s nothing the work is really for.

The second threshold is commitment to specific people he cares about. The listener I described earlier, the one who has pictured the wife and the children and the Christmas table years from now, but hasn’t actually committed to anyone yet, he has nowhere for his money to go beyond himself, which is exactly why the money is owning him. [12:02.4]

The steward sends what passes through him onward toward people and purposes outside himself, because a single self can’t hold a life’s worth of accumulated capital. It’s unhealthy. It’s like food that just gets stuck in your gut and then rots.

The two thresholds resolve together. The work gains a purpose outside the self, and the love gains people specific enough to be committed to, and both leave the money somewhere to go, besides back into the same person’s consumption. [12:34.3]

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.”

Neither of these can be solved in isolation. They either come into place together or not at all. So, what does paying attention to any of this actually get you? What’s the return on doing this type of inner work? Okay, I’m going to point out five returns, and each of them is substantial. [13:38.0]

The first is clarity in your work. The person who knows what his work is for makes different decisions every day about that work. He stops making moves out of mere momentum and starts making them out of conviction, saying no to the things that look like opportunities but are actually distractions, and yes to the things that on paper might look smaller but that pay out in the direction that he set for his life. The compounding return on that over 20 or more years is enormous, both for himself and for the projects. [14:10.3]

The second is recovery, deep real recovery. The first thing he checks in the morning is no longer the number and a market correction is news rather than an attack on his worth, and he sleeps deeply, a kind of nervous system rest that’s been unavailable to him for years and it finally comes back. The shoulders come down. The jaw lets go. The mornings have a different quality.

The third is that the people he cares about come even closer. He has something to offer beyond a polished résumé or a portfolio, because a person with a life pointed at something bigger has a different proposition from a person with just a portfolio. The trust problem we described earlier, the question of whether anyone is with him for reasons that have nothing to do with the money, that begins to dissolve, because there’s now a “him” to be with that the money isn’t the center of. [15:07.8]

The fourth is that his wealth gains a valuable direction. The money that he’s stewarding compounds in two registers—financially, because it’s being managed seriously, and morally, because it’s now doing something valuable while he’s holding it. The same dollar that sat in the dictator’s account, doing nothing but reproducing itself, is in the steward’s hands, also working on the contribution and the people he’s committed to. The steward gets the financial return, plus a return the dictator never sees.

The fifth is that he gets the rest of his life back. Instead of spending those years just managing his relationship to the money haunting him, he spends them inside the abundant life the money was supposed to fund, which is what he thought he was building all along. [15:55.1]

Plenty of wealthy people talk the steward game, but then act as dictators, a giving pledge that’s mostly reputational laundering, a family office that treats the family as mere subjects, a charity the donor manages as his personal kingdom and tax shelter. What the person says about his money isn’t the real test. The test is whether what he’s doing with the money is actually for someone other than himself or whether the whole arrangement is still organized around him, the dictator’s giving is still a dictator’s giving when his name is on the building, when the timing serves his reputation, when the cause is the one that makes him feel like the person he wants to be seen as.

The steward, though, is doing something different. The recipient is the whole point, not the donor. There’s a socio-political version of this that’s worth pointing out, because most listeners will have made some version of this argument, maybe at a dinner, like “The state spends my taxes badly. I’d spend them better. Therefore, I owe the state nothing, and the people who depend on it, I owe them even less.” [16:56.2]

Notice what the argument has done. It’s converted a question about civic obligation into one about mere personal preference, and it’s made the wealthy person the judge of what the society he lives in deserves from him. Even his charity becomes an act of personal sovereignty rather than an answer to anything deeper.

The award-winning philosopher Michael Sandel makes this point in his book, What Money Can’t Buy. When we decide a thing will be allocated by money rather than by some other principle, we’re deciding what kind of good it is, not just how it gets distributed.

For example, a scholarship funded by a billionaire’s whim is a different kind of good from a public education funded by shared obligation, even if the dollar amount is the same. The child receiving the scholarship is no longer a citizen with a claim on the commons. Instead, he becomes a supplicant, wishing or hoping that a wealthy stranger feels moved this year. The dictator doesn’t see what he’s done. He thinks he’s being generous, when, in fact, he has demoted that child from citizen to beggar, and demoted himself from member of a society to its private patron. [18:02.2]

Now, who actually pays more for this arrangement? The instinct is to say the child pays more. He’s lost to something. He’s no longer standing on his rights, but on someone else’s mood, and that’s a serious loss to him. But the deeper damage falls on the dictator himself.

The dictator has placed himself outside the society he lives in. He’s no longer a member of it, but a private patron of it. The people around him come to him as petitioners and leave as recipients if they’re lucky, and nowhere in that arrangement is there a person who meets him as a peer.

The child loses a scholarship that he might have had on different terms, but the dictator loses the possibility of a life in which other people are with him as equals, as equally valuable potential connections. He signed himself up instead for the patron’s loneliness, and the people in his life have material reasons to keep their arrangement going, so he can’t even easily test it. [18:59.8]

This is what the dictator’s posture costs the dictator more than it costs the child in that Sandel example, more than it costs the society he’s placed himself outside of. He has paid for the life that he built with the very thing that the money was supposed to deliver, and then he wonders why he feels so disconnected and lonely.

There are people who have done this right, though, and they’ve done it visibly enough that I can refer to them, and we can study how stewardship might work at scale. Here are two examples: Warren Buffett and Charlie Munger.

The annual Berkshire Hathaway letter is at a certain level a steward’s accounting. In those famous letters, Warren Buffett tells the shareholders what he did with their capital, why he did it, where he went wrong, and what they should expect next.

Charlie Munger’s line that he wanted to leave his children enough to do anything, but not enough to do nothing, that is a stewardship move. Mere generosity of spirit wouldn’t think that carefully about the effects on the next generation. The refusal to churn the holdings is the same posture. Capital isn’t something to be worked for its own sake. [20:09.0]

Then there’s the Giving Pledge, which Warren Buffett spearheaded back in 2010. Warren Buffett has, by his most recent account, given away more than $60 billion of what he built, substantially more than his entire net worth was when he made the pledge in 2006. The pledge has 256 signatories, based on my internet research, and the follow-through across all of them has been pretty bad, even uneven, but that move itself is a stewardship move.

A person with $10,000 can be a steward or a dictator with that $10,000, and a person with $10 billion can be a steward or dictator with the $10 billion. The number doesn’t decide the posture.

Now, the two traditions that thought hardest about this question, and this was 2,000 years ago, were the Daoist and the Confucian. The first move in both of these is to stop thinking of wealth as something that belongs to you and start thinking of it as something passing through you. [21:03.3]

Think of the people who stood in this line before you, the ones whose work or whose family, or whose accident of history, put resources into your hands, and think of the ones who will stand in this line after you. The money was here before you, and it will be here after you, and the work is to carry it honorably through the stretch that’s yours.

Zhuang Zhou puts it simply—the person who clutches loses what he clutches, but the person who holds open keeps it longer than he expected. The Daoist isn’t telling you to give up your wealth. He’s telling you that holding it the way the dictator holds it is the surest way to be held by it, and owned by it, controlled by it in return.

The confusion reading goes to the patriarch. The person who treats the family fortune as personal property corrupts the family, while the steward, who treats it as held in trust, strengthens the line. The fortune isn’t the patriarch’s. He’s merely a custodian of it for the people who came before him and the ones who come after. [22:05.5]

Now, you may not be a patriarch yet. You may become one, though, I don’t know, in 15 years, or maybe you won’t, but the way you hold your money now will harden into the way you hold it by the time anyone arrives to inherit anything from you. The choice is being made daily, not at some future moment when your children appear.

What comes back to you when you make that choice daily is what you came here for in the first place, and that was never the money itself. It was a life with a sense of purpose that your hours are pointed at, a kind of fulfillment that doesn’t thin out the closer you get to it, a meaning that doesn’t require you to keep buying it back each quarter, a legacy worth leaving, a connection with people that has nothing to do with what you can give them or do for them, and the possibility of being loved by someone whose love does not require you to keep producing. [22:56.8]

That’s what the steward’s posture opens the door to, and what the dictator’s posture, however carefully maintained, forever closes and locks up that door. The dictator can never get beyond that door. The posture itself is what produces the enslavement, no matter how hard he tries. He could buy another house or retire to another country, or hire another team to manage his portfolio, and he would carry the enslavement into all of it.

The arrangement isn’t a function of his circumstances. It’s a function of the question he’s asking in every decision his money is involved in about who and what the money is for. As long as the answer to that question stays “me,” then nothing in his life can deliver what he’s actually looking for.

We started with whether you own your money or your money owns you. The grip doesn’t weaken with scale, because the control comes from how you view the money, not from how much you have. The dictator’s posture, asking only what he wants with what’s his, is what produces the grip, that control over him. The steward’s posture, asking who and what the money is for beyond himself, is the way out. [24:06.9]

The steward crosses two thresholds the dictator never crosses. He works out what his work is actually for and he commits to specific people he cares about, and once both have happened, the money has somewhere valuable to go besides his own consumption.

Now picture the dictator at 65. He’s still clutching. He has more than he ever did, but the grip over him is tighter than it was when he started. He’s in the house he built, large and it’s all his, and empty in a way the square footage couldn’t account for. There’s no one beside him at the dinner table, because no one was ever entrusted with anything authentic or vulnerable, and no one has ever gotten to see the part of him that the money didn’t build. The work is behind him, and he can’t tell you with any clarity what any of it was really for. He’s won by every measure he set for himself 30 years ago, but he doesn’t know what he has actually won. [25:00.8]

Now picture the steward at 65. The wealth has been carried honorably through the stretch that was his. The work has clarified into a contribution that he can point to without flinching, and the people he committed to are around the table with him—the partner he chose, the children that he wasn’t sure he’d have, the few friends who have known him long enough to see him on the days the work is going badly.

He isn’t afraid of anything or anyone in the room, not the people, not the years still ahead of him, not the question of whether any of it really mattered. He already knows the answer. The money was never yours. That was always the secret. The exit, the bonus, the inheritance, the company, the years of work, none of it was really yours in the way the dictator means it. It came through you on its way to somewhere that you value.What you do with the thing that was actually never yours, except in trust, is the only question that matters, and the only answer that gives you back the years you have left, the work you really came here to do, the authentic deep connection with the people that you care most about, and the people that you will care most about that maybe you haven’t even met yet. [26:13.9]