My Ego Is Not My Amigo

I first heard that saying, my ego is not my amigo, about five years ago, and thought it was pretty cool. Then I heard it a bunch more times and it sort of lost its coolness. Now, everyone is saying it. But it makes for a good title.

I will speak as an investment professional for a moment—life gets a lot simpler when you figure out that pretty much everyone in the markets is motivated by ego. They’re not actually trying to make money. They’re trying to look good. They want to be liked. They crave affection and admiration. This describes about 95% of people in finance. They would rather lose money privately than be wrong publicly.

There are deep psychological reasons for this. Notice that this phenomenon is even more pronounced among Generation X. Our Boomer/Silent generation parents didn’t pay any attention to us when we were kids. They didn’t go to our Little League games, they didn’t go to our graduations, and in some cases, actively shit on us or campaigned against us. They seemed indifferent to the possibility that we could be greased by a cement truck when out riding our bikes without helmets. Boy, what parenting. Of course, the pendulum has swung completely back the other direction, and the Xers are compounding the errors of the Boomers by raising Zoomers that have a pretty high opinion of themselves.

I see this on Twitter every day. Look at me. Praise me. Tell me how awesome I am. I’m not saying I don’t do it, because I absolutely do. But I’m conscious of it, and I try to keep a lid on it. Your ego is not your amigo, especially in the world of finance.

But finance is depraved. I came of age reading a lot of Ayn Rand, who said that your ego was a good thing. Reasonable people can disagree on this. You don’t want to think you’re a piece of shit, but if you going around thinking you’re God’s gift to _______, you’re going to make a nuisance of yourself. Really, the solution here is to be right-sized. Your opinion of yourself should be correct. Your insides should match your outsides.

Not long ago, my therapist told me that I was full of myself, which sounds confrontational, but in the context, it really wasn’t. I do have a pretty high opinion of my writing ability. I do have a pretty high opinion of my DJing. When it comes to investing, I am pretty humble—there are a lot brighter financial minds than me out there. I am good at what I do, and I stay out of trouble, which is enough. But it made me wonder—is there some aspect of my personality that leads people to believe, like my therapist, that I have a big ego? Is this holding me back in life?

There is that old saying about the guy who was born on third base and thinks he hit a triple. That certainly doesn’t describe me. I was born in the on-deck circle, and I am a self-made man. I think you will see that is one thing that self-made men have in common—they have a pretty high opinion of their abilities. Because they did it themselves, with no help. If I ever become super-famous, maybe someday people will travel to look at my childhood home. They will see that it is…small. I grew up with my divorced mother and my grandmother, who passed away when I was 14. We were not buying ribeye steak, let’s put it that way. A social scientist would have looked at me, at age seven, and declared my case hopeless. And here I am. So yes, I have a pretty high opinion of myself, along with dealing with some terrific health issues along the way.

One thing I always try to be is teachable. I don’t have all the answers, and I am constantly seeking to improve. For the five-and-a-half years that I wrote for Bloomberg Opinion, I was constantly trying to improve as a columnist. I’m writing short stories, and it’s very clear that I don’t know what the fuck I’m doing. Even in my financial newsletter, which I have been doing for 15 years, I am continually trying to get better. You have to be open to feedback. Sometimes feedback is painful, but if you’re hearing the same thing from a number of different people, chances are, they are onto something. The day I stop being teachable is the day that my career comes to an end.

I talked about being right-sized, and how your insides should match your outsides. I strive to have my image of myself match up with other people’s image of me. And my image of myself varies from day to day. Some days I think I’m a hero, other days I think I’m a piece of crap, which is often a function of being bipolar. Neither are true. Really, I’m just a bozo—just like everyone else—trying to figure it out as I go along. One thing finance people like to do (especially on Twitter) is cultivate an air of invincibility—draw attention to the calls that go right, and ignore the ones that don’t. Three of the most powerful words in the English language are I am wrong. If more people said those three words, the world would be a better place. It would certainly deflect a lot of criticism.

The worst thing that can happen to you is that you can become wildly successful. I look at athletes, movie stars, successful people in finance or tech, and they’re superstars, legitimate superstars—they have legions of adoring fans, who are constantly telling them how great they are. It is very difficult to stay grounded under such circumstances. I’ve had a middling amount of success—I’ve made some money, but nothing I’ve ever done has really gone hockey-stick—and I will tell you that it goes to your head. And a large ego can justify not-so-nice treatment of other people. Years ago, I was watching something on TV where Sylvester Stallone’s house help basically had to treat him like a god. If he entered the room, they had to bow their heads, avoid eye contact, and shuffle backwards out of the room. You may think to yourself that there is no way you would act like that if you had that kind of fame. I beg to differ. It can happen to all of us.

I have had a tiny amount of fame. I will be walking down the street somewhere, and someone will say, hey, you’re Jared Dillian! And then they will want to take a selfie. I don’t want to leave you with the impression that this happens all the time, but I will say that it has happened 30-40 times over the years. It happened when I was on vacation in Greece. It happened, of all places, in Carmel, Indiana. It’s happened on planes and subways. I’ve had random people fist-bump me walking down the sidewalk in New York. I won’t say that it’s fun. It’s very, very weird. It’s a good opportunity to stay right-sized, is what it is. And it makes me wonder what life would be like for truly famous people, movie stars and such. You could never leave the house. It would be hell. The interesting thing is that finance is the one profession where you can have the money without the fame—and then people want the fame, too! It isn’t enough to be stupidly rich. Everyone has to love you.

You can’t not have an ego, or else you will be a doormat. If you didn’t have an ego, you wouldn’t dare to take risks, because you would think that you were incompetent to execute on them. But there is a pretty good chance, that you are not as smart, likable, or as important as you think you are. I know that is certainly the case with me.