In 1996, I was a walking sack of spermatozoa, a physical specimen who picked up heavy things and ran marathons—and wholly undereducated, from four years of sleeping through college. I had raw intelligence, but nothing in the way of accumulated wisdom. What I lacked in sagacity I made up for with pure, limitless ambition: whatever I tried, I was going to succeed at. If I was going to be a Coast Guard officer, I was going to be an Admiral. If I was going to be a writer, I would make Granta’s list of best young writers. If I was going to be a trader, I would end up in one of those Jack Schwager books.
None of those things happened. But in a couple of instances, I came pretty close.
Things might have turned out even better, if I knew then what I know now.
Here are a few things I’d like to tell my dumb 22-year-old self:
1. Politics matter. One of the things that turned me off about the Coast Guard is that politics was a big determining factor in one’s success, and I didn’t see myself as someone who was in possession of adequate political skills. All it took was one bad tour where you didn’t see eye-to-eye with your commanding officer and you found yourself having a passover party. Of course, the more politically adept officers were able to make it work in any scenario, and they invariably rose to the top. That wasn’t for me. So I decided to work in what I thought was the most meritocratic industry in the world: capital markets. But while I was at Lehman, I was getting paid approximately 1% of what I made for the firm, while some people were getting paid 15%. All a function of politics. When you’re young, you have this naïve belief that all that matters is performance—if you’re the best at your job, you should get paid the most. Nothing could be further from the truth. So in any organization, you have to manage up as well as down. If your boss doesn’t like you, you’re not getting paid. And even if he does like you, if he thinks you won’t leave, and you’ll work for nothing, then you’re not getting paid. I could write a book on this, but some have already been written.
2. Get some sleep. Boy, was I stupid about this. I used to think that the less time I spent sleeping, the more time I had to work. This is true, but you work a lot more efficiently if you’ve gotten a good night sleep. I started getting a full night’s sleep around age 32, and it changed my life. That is not an understatement—it changed my life. I couldn’t write a book when I was sleeping two hours a night. I could barely think. It took me a while to finally stop the tough-guy act and go to bed at 10pm. To this day, I get eight, sometimes nine hours of sleep. Last night, I actually got eleven. The next day, I’m Superman. My performance in school would have been a lot better if I wasn’t constantly pulling all-nighters on stuff, and managing my time a bit better.
3. Sex is not that important. It’s just not. It’s one of the least important things you can do. Stop thinking about it all the time. You’ll have more space in your head to think about more important stuff.
4. Generosity matters. Not in the sense that you should donate 10% of what you make, because when you’re young, that’s hard, and you need to be accumulating wealth and letting it compound. But don’t be a lousy tipper. And if you can’t donate money, donate time. A mentor of mine was trying to get me to volunteer in animal shelters about 12 years ago. I demurred. 12 years later, I am doing it. Why did I say no? Well, I thought that my time was valuable, and that I was so important, etc. Not the case. Give the gift of time, if you can’t give the gift of money. Visit with sick people, old people, and animals. I can tell you that charitable organizations would be very surprised—and happy—to see a 22-year-old show up and help out.
5. Pursue your dreams, sort of. When I was 22, my dream was to become a writer. A family member told me that was a terrible idea, because I would be poor. Most young people, when they get that advice, plow ahead anyway, and end up poor, and poverty is no fun, no fun at all. I went to business school instead, made some money, and now I am pursuing my dreams. I think I did it in the right order. Now, if your dream is to be a musician or a poet or something like that, and it’s really what you love, then who am I to say no? Just know what you’re getting into—a lifetime of deprivation. Money matters. Creature comforts matter. The economics of the artistic world are terrible, so you might as well be a working stiff and do music or art or writing in your spare time. If I had obtained my MFA right out of college and gotten a job at a university somewhere, I’d be content, but under constant financial pressure. Pursue your dreams, but make some darn money, and don’t blame someone else for your choices.
6. Do it without the rope. Remember that scene from The Dark Knight Rises, where Bruce Wayne is trying to climb his way out of the underground prison, and the old blind man tells him to do it as the child did—without the rope? When I left the Coast Guard for Wall Street, there was no Plan B. If I didn’t get a job, I was totally stuck. No rope. When I left Lehman Brothers for the newsletter, there was no Plan B. If it failed, I was completely stuck. This is part of a larger discussion about taking risk and risk appetite in general, and also betting on yourself. Betting on yourself is like trading on inside information—you have an edge, because you are in control of the outcome. I hear that Zoomers are not big risk-takers. That is too bad, because we need young risk-takers. We need people to bet it all on themselves, and win. And the nice thing about taking risks when you are young is that there are very few consequences if you fail. When you get older, there are huge consequences if you fail. No spouse, no kids, no house—take the risk. There is no playing it safe in your twenties.
7. Hungry like the wolf. I have had about twelve interns over the years, all very bright, very capable people, but none of them were as hungry as I was. When I was getting started in my career, I read every single book on finance, over two hundred of them. I subscribed to Barron’s and The Wall Street Journal, and read them religiously. I learned absolutely everything there was to know about finance. Other people were not so hungry—they went home at night and watched their shows. I was going to outwork you, and I was going to outsmart you. I’ve never met anyone like me, who have that level of passion and intensity. I bring that level of intensity to writing, too, going to get my MFA and publishing four books and submitting to hundreds of journals. And here is the thing about being hungry—it can’t be taught. It absolutely cannot be taught. So if you are 22 and reading this, and think you might be slacking off, it is because you probably are. There will be time to relax—later.
8. Don’t drink or do drugs. I never made any career-ending mistakes while drunk, but I had some close calls, and I was drunk a lot. There was a lot of drinking on Wall Street. Half the trading floor would show up hung over on any given morning. Which is crazy—we were like highly-paid professional athletes, supposedly performing at our peak, and we’d be out at strip clubs until four in the morning and roll in with a bacon, egg, and cheese, barely able to function. I regret every drink I took. Plus, it messes with your sleep. 90% of people who get fired for cause do so because it is as a result of some alcohol-related incident. Sounds like Zoomers drink a lot less than Xers, so you are well on your way. But stay off the weed, too—it’s an ambition-killer, which is worse.
9. Think big. Let’s say your goal is to become CEO. Well, there are a lot of steps in between where you are now and becoming CEO, so it is going to take a lot of time, and it is going to take a lot of patience. But have a goal. Maybe the goal is to make seven figures. Maybe the goal is to become head of the desk. Maybe the goal is to retire at 50. What’s always shocked me is the number of goal-less people who kind of plug along, punch the clock, earn a paycheck, and don’t think too hard about the next steps. I still have goals, and I’m still reaching them. My goal is to publish a short story collection in November, but that’s secondary to my real goal: to revolutionize literary fiction. I’m a one-man wrecking crew. You’d much rather think too big than think too small. There are no consequences to thinking too big, but the consequences to thinking too small are severe. Don’t just think big—think huge. Your ambition is your most precious commodity.
10. Communication skills are the most important thing. If you are the best public speaker in the world, you know what you get to be? President. If you are the best writer in the world, you know what you get to be? Maureen Dowd. Kevin Williamson. Jonathan Franzen. The people who rise to the top of any organization or industry are always the best communicators. I got a Commendation Medal in my second tour in the Coast Guard because of my writing skills—no joke. I was a legendary trader on Wall Street because of my writing skills—also no joke. If you’re good at a thing, like manipulating spreadsheets, you will be a worker. If you’re good at a thing, and you’re also good at communicating, you will be a leader. All the job interviews in investment banking test the wrong things, unless your goal is to simply hire indentured servants. But if you want to hire someone who will eventually lead your investment banking division, you can’t just look at their spreadsheets. And now, because of AI, nobody will learn how to write ever again. It’s terrible.
This is only a partial list—I could go on. College graduates have the foresight of a ferret, and the attention span of a goldfish. You should sit down and write out a plan for the next 20 years—all your goals, and how you are going to achieve them. Print it out and save it. Read it again in 20 years, and have a good laugh. God laughs at our plans. But God has a much bigger imagination than you do, and He has a bigger imagination for you, too.
Wow – every single one of these hits home. I've more or less learned these lessons at various times throughout my life (I'm 60) and wish I had taken them to heart earlier.
I'd add "stay positive." Stuff happens and by pushing through the challenges of crap in life, people develop character and depth. Everyone is negative at points in their lives, but those should be points, not persistent. I've never seen a negative person achieve their potential.
I recall in college telling people that I was interested in a LOT of things, but I was getting a degree in civil engineering because I was confident that I could always find a good job that would let me support a family, and would generally leave me time to follow my interests and hobbies. Looking back 50 years later, it worked out pretty well.
I never had the drive that you speak of, and I suggest that it is not something that I could have developed. I considered options that required that kind of drive a few times, and in every case I realized that it simply was not part of my character, and trying to force it would make me miserable.
Having said that, I have accomplished a lot of things in my life, and I am happy with where I am now. I am still, even in retirement, working and progressing, curious and adventurous (within limits), and looking forward to doing more interesting things.