Ambition

Sometime in 2003, when I was in the throes of mental illness and addiction, I came across a book on Amazon called How To Disappear Completely and Never be Found. I didn’t buy it, but I spent a lot of time staring at that page and reading the reviews. The idea of disappearing completely and never being found appealed to me at that moment in history. I thought I would hitch a ride to Rawlins, Wyoming, wash dishes for $7/hour and live in a $400/month apartment and live out my days in solitude. That was my greatest ambition at that point in my life. It was a fantasy that I indulged from time to time, packing up my shit, going completely off the grid, and never being seen again.

Needless to say, I’m glad I didn’t do that. Let me start by saying that life is hard. Property taxes. Jury duty summonses. HOA fees. Fucking income taxes. Speeding tickets. Broken relationships. Death. Constant annoyances. Wouldn’t it be nice to just pick up and move into the woods like the Unabomber? You could spend your time writing a 2,000-page philosophical manifesto, or you could just watch your shows. In 2003, life weighed on me like a thousand encyclopedias, and that’s without taking into account the shitshow that was Lehman Brothers. I was about done with it.

Well, I got my shit together and decided to participate in life for a change. I paid those property taxes. I paid those HOA fees. I bought and sold houses, which is one of life’s great pains in the ass. I moved 700 miles south. I started my life over. I’ve spent the last 15 years dealing with these hassles, big and small, and I’ve grown as a person, and I’ve grown my bank account as well. There isn’t too much I don’t like about my life these days, apart from the constant annoyances. They are still there, but I have the maturity to deal with them.

I’ve touched on this in bits and pieces in other essays, in particular one called “The Best Days Are Ahead,” but I am getting close to 52 years old, and there is still a ton of shit I want to do. Books I want to write, clubs I want to play, funds I want to manage. I have ambition. I don’t think as big as some people, but I do think pretty big. Playing in Vegas—the audacity of it. I’d love to be managing $300 million someday. I play the lottery—because I expect to win. Not because I hope to win, but because I fully expect to win. I think there was a point in my life where I wanted fame and attention, but not anymore. I do want one material thing: a condo in the Setai building in Miami Beach, but apart from that, I just want to do cool stuff. And I’ve always wondered if that ambition has an expiration date, if I am going to get to 65 or 70 and say, welp, you know what, I’m going to stop working and just chill out and chase a white ball around. I am the opposite of happy-go-lucky. I am driven as hell. And I think I am going to get to age 65 or 70, and still want to DJ in Vegas. I mean, it’s only 13 years away.

I’ve known some people who were not too ambitious. And I’ve known some people who were too ambitious. I’ve had some friends with sole prop businesses who, if they did a few simple things, could have doubled or tripled their income. They were unwilling to do it for whatever reason; mostly inertia. And I have had some friends who were convinced they were going to be centimillionaires, and took too much risk and went down in flames. There is something to be said for being appropriately ambitious. Get rich slow, etc. The thing with social media is that we are surrounded by successful people, and we get to see it, up close and personal, every day. There is always someone who is richer/smarter/better-looking. In my world, the financial media world, you have raccoons who chase the new new thing, attracting followers and subscribers (and money), the media adores them, the camera loves them, but as Jay Powell says, it is transitory. You can probably tell from these essays that I don’t give a fuck—about anything. Someone else is making more money? Good for them—I’m on my path, and they’re on their path. I mean, why else would someone write over 200 essays on life, creativity and meaning—for free—with no discernible benefit apart from the occasional pushing of the like button? Writing this newsletter doesn’t get me business, it doesn’t get me subscribers, and it hardly gets me any engagement on my SoundCloud page. I do it because I love it, which is the only reason to do anything—otherwise you’re not being true to yourself. You might say to me, Dillian, if you put as much effort into marketing The Daily Dirtnap as you do screwing around on Substack and SoundCloud, you’d probably have 10,000 subscribers by now. But then I would be a striver. There would be videos of me floating around on Twitter in front of a step-and-repeat with earbuds in offering my opinion about something I know nothing about—for what? For fame, for money, for admiration. The way I look at it, is that fame or money is a byproduct of doing something really well and doing it for a long time and then getting extraordinarily lucky. Maybe I get to be like Stan Druckenmiller one day, or maybe I don’t. It’s not up to me. And the difference between me and everyone else is that I know it’s not up to me, and everyone else doesn’t. If God wanted my fat ass up in that tree, he would have miracled my ass up there.

But I would suspect that many readers of this newsletter are lacking in the ambition department a bit, and that is why we are here today. You are a sales trader at XYZ bank. What is your ambition? To run the bank? To be CEO? Probably not. You are getting paid pretty well, relative to your intelligence and work ethic, and you put on the fleece vest and go to work every day and you get some stale food from Pret a Manger, you take the bus or train home and pet the dog. Repeat ad infinitum. You see, I was on that train, and I had to get off that train. One of the reasons I left Lehman (among many) is that it was pretty clear that there was no path upward for me. I was a great trader (legendary, some might say), but they were never going to let a delta one guy run the derivatives desk. I would have spent the next ten years trading ETFs. I would have been compensated well, but I thought there was more I could contribute to this world than knife-fighting over pennies on executions. Is that ambition? I think it is. The idea that anybody is capable of bigger and better things. Funny thing about the banking world—it is a lot like the Coast Guard. If you look at my classmates who made it the farthest in that organization, the vast majority of them came from near the bottom of the class, academically. In other words, the smart ones did the five and dive and got out. Banking is a lot like that, too. The smart monkeys go on to hedge funds or private equity. Not to say that there aren’t smart people in banking (or the Coast Guard), but there is a lot of adverse selection. In both organizations, you have to put up with an inordinate amount of bullshit, and the people who are willing to stay and put up with the bullshit typically have no other options.

If you have a small business, then why not turn it into a big business? Well, I can think of a lot of reasons not to turn a small business into a big business. Bullshit, being one of them. The bigger you get, the more complexity there is, and at some point you start running into regulations and attention from the government. Say you are worth $10 million, and if you grow the business, you will be worth $100 million—if you put up with the bullshit. Notice that I said I’d like to be running $300 million, and not a billion. Bullshit! There is something to be said for running a small, artisanal business that pukes out a small amount of money and everyone is reasonably rich and happy. We don’t all have to be Bezos. Or Musk. The thing is, when you get to the scale of Bezos or Musk, you have armies of people who will handle the bullshit for you, and I think it actually gets easier. The same is true in academia as well. You decide you want to work in administration, so you get a job as associate dean, and after a few years of this, you decide there is too much bullshit and you want to go back to regular faculty. Bullshit has a price, and you can measure it with precision.

This is all a long way of saying that you should optimize for money and happiness—not just money. What is the thing that you could do that would get you the most money and happiness? If it’s money that you want, there is plenty of it out there, you just have to go out and get it. But if you don’t love what you are doing, you will be spiritually bankrupt. If it’s happiness you are after, there are plenty of things you could do that make you happy. For me, it’s writing. I’ve made about $300,000 from writing six books—over 14 years. I could sit around and write books all the time, but I would be living at the subsistence level. No, the key is to balance money and happiness. This is going to be different for different people. For some people, all the money they need is to ensure that their basic needs are met. I need a little bit more than that, to buy that condo in Miami. Some people meet their material needs but neglect their spiritual needs—they do that sales trader job for 25 years and get riffed, and look back and wonder what the hell they were doing for all those years in the prime of their life. A woman I worked with at Lehman now owns a pilates studio. Mind you, it is a very high-end pilates studio in a very fancy neighborhood, so she is probably not hurting, but she is doing what makes her happy. There are many such cases. I used to go to Coast Guard Academy reunions and fuck with people. I’d be talking to some classmate, and he’d tell me that he was commanding officer of some air station somewhere. And I’d ask him: “Are you happy?” Did not compute—he didn’t know how to answer the question. And then I’d continue: “Hey, if you’re happy, I’m happy.” Totally flummoxed. If someone asks me if I am happy, I’m telling them that I am jacking off all over the place. Happier than a puppy with two peters.

Ambition is a funny thing. The one thing we know about ambition is that if you smoke enough pot, you will lose it. I have never smoked pot in my entire life. What, I’m going to take this drug that makes me fat, stupid, and lazy? Cocaine may make you an asshole, but it’s going to rev up your ambition. When they’re training German Shepherds to be police dogs, they look for the dogs that have drive. Literally, the ambitious ones. Dogs have drive, and people have drive. Nothing frustrates me more in the world than wasted potential, and all of us have wasted potential, present company included. We could all be doing so much more, and we constantly underestimate our own abilities.

Also, if you don’t stop and smell the roses once in a while, you’re a stiff, and nobody likes a stiff.