0:00 I met a man some years ago now and a meeting crossed my mind just a week back when I was going through some of my old notes. He was in his late 60s when we met and he had by any reasonable measure a great deal of money. Now I won't tell you how much money partly because I don't really know and partly because the number is not the point anyways. The point is that he had enough that he never needed to work another day in his life and enough that most people if they met him would have assumed a certain kind of life around him. A big house, a bigger car, a calendar full of the things that wealthy people are supposed to fill their calendars with. And none of that turned out to be true. He lived in a modest apartment he'd been in for something like 30 years in a part of the city that had slowly become
0:45 unfashionable around him without him really noticing or maybe without him caring at all. He made his own tea. He answered his own phone. And when I walked in to meet him, he was reading a novel. This surprised me a little because I'd expected something else, some business book or animal report, but instead it was just a novel. We sat for about 2 hours that afternoon and the strange thing was that he ended up asking me more questions than I asked him. When I left and was walking down the stairs, I remember thinking that I just met someone whose life was put together in a way I could not quite name but wanted to understand. And I've been trying to understand it ever since. That was just one conversation, but there have been many others over the years.
1:31 Over the last 20 years or so, between the people I've I've had on my podcast and the biographies I've read and the handful of people I've watched up close from some distance, I've started to notice a pattern. It's not really about how wealthy people make money, which is a crowded subject that everyone and their uncle has written or talked about. What I started noticing is something really different. It's about how they live once they have the wealth, what they do with the freedom, and maybe more importantly, what they refuse to do with it. Who they become and who they quietly decide not to become. Now, most of what gets said about wealthy people, I think, is wrong or at least misleading because it's either written by people who haven't really spent time around them or
2:18 it's the wealthy themselves performing a version of their lives for an audience. What I want to describe today isn't the performance part. It's a thing I watched mostly in private over a long long stretch of time. The first thing I noticed and which surprised me because I expected the opposite is that the wealthy people at least a lot of them I came to admire they stay remarkably close to ordinary life. I'd assumed that money would carry people away from the small textures of daily living and for a lot of people it does. But the ones whose lives I ended up respecting a lot almost without exception, they kept doing small things for themselves long after they could have paid someone else to do it. They went to the market. They knew what vegetables cost. They drove
3:04 themselves places. In fact, there was this one founder I met years ago and I asked him once why he still drove his own car when he could obviously afford a driver 10 times over. And he said something I've never really forgotten which which was that a man who forgets how to drive forgets other things too. And I think he wasn't really talking about driving. He was talking about the very small competencies. These little things, daily things that seem like nothing that they anchor a person. If you lose enough of them, you start to drift even inside your own life. You see the same thing in the biographies. If you read enough of them, the wealthy people whose lives held together into old age were almost always people who kept doing ordinary things themselves.
3:50 And the ones who outsourced everything, who forgot how normal life even worked. I think they usually ended up as strangers to their own days, surrounded by staff and lonely in a way that was not obvious from outside. If you want to test this for yourself, it's actually quite simple. Just think about the small tasks you've started handing off over the years to other people. Some of them you handed off to save time and that's fine. That's a reasonable trade. But some some of them if you've been really honest with yourself, you handed off because at some point you decided the task was beneath you. Now those are the ones worth taking back. Not all of them, just a few. Enough to stay in touch with what a regular day actually feels like.
4:37 Another thing I started noticing which took me a bit longer to see because it looks like nothing from outside is that a lot of wealthy people protect long stretches of uncheduled time. A wealthy person's calendar if they are in the kind of the kind of people I'm describing has these strange gaps in it. Whole afternoons with nothing in them. Some sometimes whole days and and when you ask them what they they're doing they say reading or walking or nothing. and they actually mean it. They're actually doing nothing or close to it and they've somehow made peace with that in a way most of us haven't. Then there's the other kind and I have met plenty of them too over the years. The busy wealthy. Their calendars are packed. Their phones
5:23 are always buzzing. They're flying somewhere tomorrow and somewhere else day after. And and they'll tell you how busy they are with the kind of pride the way a poor man might complain about his wages. But if you sit with them long enough, you start to see that the busyiness is a way of not noticing something. What they would actually do with an empty afternoon if they had one, whether they'd even know how to be alone with themselves for a few hours. They filled the calendar because a full calendar was easier than an empty one. But the ones I came to admire had done the harder thing. They had earned the right to an empty Tuesday and then they'd actually taken it and then they'd done it again the next week and the next until an
6:09 empty afternoon stopped feeling like a failure of some kind and started feeling like what it actually was, which was the whole point of having gotten wealthy in the first place. Here's a small test for this one. If you really want to perform it, look at your calendar for the next week. If every single day has something on it, you might be wealthier than you realize and still not using the wealth in the way that really matters. Something else that shows up everywhere once you start looking for it is that a lot of wealthy people keep their old friends. Now this comes up in biography after biography in interview after interview. A lot of such people whose lives held together into old age were almost always people whose closest friendships predated their success. The three or four people they'd
6:56 called if something went badly wrong were people they' known for 30 or 40 or 50 years. Not new friends made in the rooms their wealth gave them access to, but old friends from much before. The ones who replace their old friends with richer friends, I've watched this happen more than once. They aged badly. I don't want to be unkind about it, but the pattern is consistent enough that I have come to trust it. There's something about being in rooms where everyone is as rich as you are that makes a person smaller rather than bigger. Your sense of reality kind of flattens. The friends who knew you before any of your success happened, they are the ones who can still tell you the truth because the relationship with you doesn't depend on who you've become. The friends you
7:44 acquired afterward, they've invested in a version of you almost without meaning to be. and they can't tell you what they see as easily because they have something at stake in what they see. Try this one just as noticing exercise. The three or four people you would actually call it 2 in the morning if something went really wrong, the real ones, not the ones you post about. When did you meet them? If all three or four or four of them are from the last five years, something might be drifting. And it's probably worth asking why. [snorts] The wealthy people I come to admire almost never fully retire either, which is the next thing I want to talk about. They keep doing something whether it's writing or teaching or building small
8:30 things or advising a few people or just tending to something that matters to them. But the work has lost its edge of desperation. that tightness you hear in the voice of someone who still needs the outcome. They're not doing it because the result matters to their survival. They're doing it because the doing itself is interesting. I've interviewed investors in their 50s and 60s and 70s who still read annual report in the evening the way some people read novels and and they don't have to but they want to. If you want to find the work that's actually yours, the question worth thinking about is is what you would still be doing in some form if nobody paid you for it, not what you would do on a vacation. That's a different question. What you would do with your
9:17 life week after week, year after year, if the money just stopped mattering. Most people when they sit with that question honestly find the most of what they currently do would fall away and something smaller and more specific would would actually remain. That smaller specific thing is usually the work that will carry a person into old age without breaking them. Then there's a matter of giving which I've come across in the strangest places. biographies of people who seemed in public to be hard and transactional and completely unscentimental and who turned out after they died to have been paying for things for decades that almost nobody knew about. It may have been a brother-in-laws or niec's education, a friend's surgery, a small library in a village they come from, something like
10:02 that. The giving was specific and granular and completely unrecorded. There was no donor pages and in many cases even the recipients didn't know who it had come from. The pattern repeats often enough that I have come to believe loud giving and real giving are more often than not different activities. Loud giving serves the giver. It builds the brand. It signals the values. It appears in animal reports. Real giving is the kind of thing which I'm describing. It wants the opposite. It's just wants to disappear. The givers have noticed somewhere along the way that the moment the giving becomes visible, something about it is spoiled. And I don't fully know why that is, but the act and the recognition seem to need to be kept apart from the act to stay
10:49 clean. This one has a practical handle, though it's a strange one. The next time you give something, try to give in a way where the recipient doesn't know it came from you. Now, it's harder than it sounds and it teaches you something about why you were giving in the first place, which is information most of us honestly would rather not have. Now, the habit that surprised me most and the one one I still find hardest to explain is that these people have chosen a small life even though they could have had a large one. The wealthiest people I've envied over the years of watching and observing have almost always lived smaller lives than their money would have have allowed. Bun whom? not five. A handful of restaurants they kept going
11:34 back to, not an endless rotation of new ones. Two or three places in the world they returned to year after year rather than a different city every month or every year. They had every option available to them and they deliberately narrowed the options down to a few that actually mattered. Now, this runs against everything the world tells you wealth is for. Wealth in the common story is supposed to give you unlimited options and more is supposed to be better. But the people I am describing seem to have noticed something the common story misses which is that past a certain point options stop being liberating and start becoming a kind of homelessness. If you can be in 10 cities you're not really in any of them. If you eat at a different restaurant every night you'll
12:20 never build the kind of relationship with the place that makes it yours. optionality which everyone chases has has a ceiling and past that ceiling it starts to eat the life it was supposed to enable. The habit if you can call it that is a willingness to stop collecting options once you have enough to commit to a few places like a few restaurants or a few homes a few people and let the rest of the possibilities go. The next time you're tempted to add something, maybe a second home or a third membership or a new city, try asking yourself whether you've actually used the ones you already have. Most of the time, if you're being honest, you haven't. The last thing, and the deepest one, which I have saved for last, because all the others sort of rest on it, is that these people have made peace
13:07 with being misunderstood. They know because they can't help knowing that the outside world looks at them and imagines a life that has almost nothing to do with the one they're actually living. The world assumes the big house and the big calendar and the loud giving and the endless options. And they've chosen in a thousand small ways a life that contradicts all of that. Which means they spend their days living inside a gap. The gap between the life people assume they have and the life they actually live. Most of us couldn't hold that gap for long. We'd start closing it one way or the other. Either we would start living the louder life to match the assumption, which is what most wealthy people end up doing, or we would start explaining ourselves constantly to
13:52 everyone, justifying the modesty, defending the choices, making sure people understood why we lived the way we did. And that I think is exhausting. And it also slowly turns the life itself into a performance of itself. The ones I have come across to admire have done neither. They just accepted that most people will misread their lives and they've decided quietly that the misreading isn't their problem to solve. They don't post. They don't explain. They don't correct the impression. They've figured out that explaining your life to people who have already decided what it it should look like is a waste of the life itself. And so they've let go of the explaining which has freed up a lot of energy for the actual living. Now, this one doesn't really have a practical handle to be honest. It's more of a question that you can sit with if
14:39 you want to. Whose approval are you still performing for? And what would your life actually look like concretely next week if you just stop performing for them? That's what I've seen. None of it came from any one book or any one conversation. As I said, it's a slow deposit of years of watching people who had more than enough and noticing which of them looked at ease in their lives and which of them didn't. The ones who looked at ease had almost without exception built a life that didn't need their wealth to make sense. The wealth was part of the life sure but the life would have made sense even without it. The others had built wealth that needed a life to justify it and hadn't yet found one and some of them never did. I don't know which kind of person I am I'll turn out to be finally and I don't
15:25 think any of us really knows that until we are well into it. But I know which kind of I'd like to become. And I know more and more as I get older that the becoming is made out of small choices rather than large ones. It may be an empty afternoon that gets defended. It may be an old friend that gets kept, a small task that doesn't get outsourced, maybe a home that doesn't get collected, a gift that doesn't get announced, or a calendar that doesn't get filled. The man I met in his flat that afternoon died a few years after I met him. I heard about it from someone we both knew who mentioned it almost in passing. The way the death of a quiet person often gets mentioned. There was no obituary in the big papers. There was no long
16:11 tributes, just a small notice and then nothing. But I remember history and the way he answered his own phone and the novel he was reading when I walked in. And I think sometimes that the life he built which nobody from outside would have called remarkable was actually the one I've seen that was most worth copying. If there's one thing to take away from any of this, maybe it's that the lives most worth copying are rarely the ones that look from the outside like they're worth copying. They are much quieter than that. If any of this resonates with you, here's one small thing you could try this week. Take a Saturday morning, not a full day, just a morning. And don't put anything on it. No plan, no errand, no task, no call, no
16:58 meeting, just an open few hours. And notice what you do with them, what you reach for first. Whether the emptiness feels like a gift or like a problem you need to solve. That hour, it turns out, is where most of the answers actually are. It's also where most of us, if we are really honest, have never spent very much time. I'll see you in the next one. Thank you so much for your time.
