What is the greatest paradox of becoming wealthy?

A few years ago I was invited to a gathering at the house of a very rich man in one of the upscale desert cities southeast of Los Angeles. For the sole purpose of parties and weekend retreats, he had built an Italianate villa on a large piece of land opening up onto the desert wilderness. The house was partially circumscribed by a crescent shaped infinity pool that fell off into nothingness before the great rolling hills of the Sonoran landscape. The walls retracted so that the entire dwelling seemed intimately joined with this outdoor paradise. Its interior was appointed in the most opulent manner, with imported marble floors, expensive original paintings from contemporary artists, and, most impressively for me, a massive wine cellar full of hundreds of rare wines and scotches.

I was there only by the thinnest thread of associations: I knew somebody who knew somebody who knew somebody. I was not then living in Los Angeles but was merely in town for a job interview, which, in spite of some high hopes, had left me disappointed once again. Unemployed for more than a year, I was now facing the grim reality of my own financially precarious situation.

At some point in the evening I found myself at a small table with the Gatsby-like character who was hosting this gathering. He was a man in his 50’s, very physically fit, with the kind of upper body musculature that, at that age, can only come from daily workouts and perhaps some pharmaceutical help. Although he had long lived in Southern California, and now had the easy, understated quality that passes for good manners there, he also retained the directness and lack of pretense characteristic of the Midwest of his childhood.

I complimented him on his choices in architecture, which he discussed with considerable knowledge and pride. He became more philosophical, however, as I expressed my envy for his position in life. I told him that I had always lived for my passions. I studied philosophy in college and graduate school and had ever since pursued just those experiences I thought would lead me to a better understanding of the world and of myself. I said, perhaps not with absolute sincerity, that I now wished I instead had given more thought to making a living. Who, I asked, would not want to be able to build such a beautiful home for himself?

Be careful what you wish for, he said, glancing upward at the desert sky. I could immediately see that he had put great thought into what he was about to tell me. He seemed to have a lot on his mind, and he had found a sympathetic ear in me, someone, moreover, whom he likely would never see again. Over the next hour I played the role of drinker’s confessor, listening to him express some of his most personal misgivings about his own life.

While this all came out over the course of a long and meandering conversation, what follows is my best effort to compress what he said into a single monologue. It is constructed out of many actual phrases and sometimes complete lines he spoke to me that evening. I think it gives a very accurate impression of the man and his point of view.

When you don't have money, you think money is going to solve your problems —and to some extent it does. But at a certain point it brings its own problems with it. Having money is like having a child. You have to care for it, you have to tend to it, you have to watch it every minute! You do this not only to make sure it grows, but also to make sure it doesn’t shrink. Money is alive and volatile! That means I am constantly thinking about my money. It’s what I think about first thing in the morning. It’s what I think about before I go to bed... Now, that makes it sound like a burden, and sometimes it is a burden. But the brutal truth is that nothing in my life gives me greater satisfaction than making money. If you’ve never experienced it, it might be hard for you to understand. Take this house for example. I made all the money for this in one year, just one small stock investment that I hit exactly right. I turned one hundred thousand dollars into 3 million dollars. Every day I would just wake up laughing as that stock kept going up. In one single day my shares went up over 50 grand! Amazing feeling! But that’s what’s crazy. I mean, I enjoy all this stuff well enough. All my junk amuses me a little bit, keeps me from getting bored. But as far as my possessions go, honestly — and I’ve really thought about this — I get more pleasure from my dogs than anything else. That’s the truth, the absolute truth. Materially, I don’t need much to be happy. I already have everything I want. What I am working for, if I am entirely honest, is just the thrill of making more money. It’s like playing a game, a game in which the prize is power, the power that is represented by that money. Power for what? It doesn't matter! The prize is the power itself. It’s all about the feeling of power. There is a sensation I get when I make money… If you haven’t experienced it, I can only compare it to sex, or gambling, or cocaine. It’s exactly like that — maybe even better. So my investments and my business ventures are like various casino games, except in my games the odds usually favor me…. And what I live for on a daily basis is just the thrill of playing those games. It’s the damn’d truth! If I quit trying to make money, I wouldn’t even know why to get out of bed in the morning…. I first started to realize how fucked I was when I found myself thinking about other people’s professions in terms of the bottom line. I mean, I have a pal from childhood who is a doctor, and I found myself thinking what an irrational job choice this was for him. He cares about money too, and I just thought, what a waste… how inefficient a use of his time and talent, since there are so many better ways to make money. Crazy, huh? I don’t know what the hell it’s like to be a doctor, but I would guess there’s a whole level of meaning there that people get off on. That doesn’t make any sense to me. It’s like all I really understand is money…. What I realized as I entered my fifties a few years ago is that business has become my identity — and I am not sure I like who I am. But I have no choice, no more than a lifelong drug addict does. I see businessmen bullshit themselves about why they are really doing it — you know, that they are trying to improve society, or it’s all for their family, or whatever other bull crap. That could just be PR, but it also can be self-deception. Don’t fool yourself, I think. I know you! You’re just feeding the monkey! …. So, that’s my story, KP. I am not entirely proud of my life, but I accept it. I try to be as comfortable as I can, to have as much fun as I can, but I’m not in denial about anything. I know I’m basically just a junky living for the next hit.

As F. Scott Fitzgerald famously said, “Let me tell you about the very rich. They are different from you and me.” As the words of this man reveal, some of these differences work in their favor, some not. No matter what goal one pursues in life, there will be unintended consequences. These consequences are part of the total package. You can’t take the good without the bad. For this reason, it’s wise, in any deal, to understand the totality of what you are signing on for. There are many paradoxes to being wealthy, just as there are with other positive things in life (being beautiful, being young, being highly talented, to name a few). But one of the greatest paradoxes of all has to be that the possession of wealth can insidiously undermine the freedom of the wealthy person to fully enjoy the fruits of their wealth. What at first seems to be the clearest path to power and the enjoyment of life actually undermines one’s ability to truly take possession of these things.

As I see it, the moral of this story is not that wealth is bad. That’s an open question for me. The main thing I worry about, in that regard, is what it means to be wealthy in a world in which so many people have so little. But that’s a different issue.

The real moral of this tale concerns an even deeper truth of human nature. We humans are always torn in two by these kinds of paradoxes. There I was, a man who had spent his whole life “seeking wisdom,” and, as a consequence, was now close to being unable to take care of himself financially. What good is wisdom if you don’t have the power to take action in the world? And yet there he was, a rich man of great power, with no clue at all as to what worthwhile thing he might do with that power.

There’s nothing absolute about any of this. There surely exists a both/and that subsumes the either/or on which these paradoxes are built. But I do believe that, in any individual case, the path to finding this balance is far narrower and more fraught with pitfalls than most of us know