I've Made A Terrible Mistake

In 2004, I went to a bachelor party in Southeastern Connecticut. You read that correctly. A bachelor party in Connecticut. My thinking was that there’s all kinds of things to do in Southeastern Connecticut: minor league baseball, the casinos, hopelessness, and despair. Perfect place for a bachelor party. And in my stomping grounds, so I knew my way around the swamp.

Things didn’t go according to plan. We had great seats at the minor league ballgame, and I was this close to catching a foul ball, but it clanked off my hand. We went to the Mohegan Sun and threw some dice and actually came up winners, which we freerolled into some steaks. But I ate too much and got indigestion, and for whatever reason, I decided to ride back to the hotel in the trunk of the car, asphyxiating myself with my ass. I continued the olfactory assault back in the hotel, forcing my roommate to drive back to Boston in the middle of the night.

After the Night of the Steak Butt Bombs, I decided to go for a run the next morning. The hotel wasn’t in the best location for running—I had to trot along busy roads. Naturally, halfway into it, I have to take a dump, so I duck behind an abandoned building, pull down my running shorts, and drop a deuce on the pavement. As an avid runner, I’m an experienced outdoor pooper, so all I need is a leaf. I grab a sturdy one off the ground, give my butt a thorough wipe, and I was on my way.

A few days pass, and I’m back at my desk at Lehman Brothers, pissing into the wind trying to trade index arbitrage, fighting against the robots. I detect a tingling in my nether regions, which turned into a full-blown itch. I’m dragging my butt back and forth on the seat like a dog, trying to relieve the discomfort. I leave the office, and I’m walking through Times Square, scratching my ass the whole way.

I get home and my wife is there. “Can I ask you a really big favor?”  So I’m bent over the bed with my pants down in a state of total humiliation, and she looks and says, “You know, if I didn’t know any better, I’d say you have poison ivy.”

Poison ivy. In my anus. I took that leaf and stuck it in my anus.

As it turns out, if you want to wipe your ass with a leaf, it is best to get one out of a tree. My plant identification skills are not so hot.

I have done a monumental amount of dumb shit in my life. The poison ivy incident, without a doubt, is not even close to the stupidest thing I have ever done—only the funniest. But sometimes I wonder about how some people get these really big decisions wrong—picking the wrong job (or leaving the right job), picking the wrong spouse (or divorcing the right spouse), or a momentary lapse in judgment that results in an encounter with law enforcement. All of these poor decisions can result in a lifetime of misery. And I’m not talking about economic decisions—people think the Instagram guys want to jump off a bridge for selling to Facebook too early. My guess is that they are doing just fine. Bad money decisions you can recover from. Bad life decisions, not so much.

After graduating high school, I went to the Coast Guard Academy. I don’t talk about this a lot, because public service, the military, and especially the Coast Guard are held in very high regard, and people generally don’t like it if you rag on it. But I found that experience to be profoundly negative. It was a bit like the Tall Poppy Syndrome you find in Scandinavian countries—you can’t be too good, too exceptional, or people will try to bring you down. It’s not that the culture of the military tries to drag down all successful people—just the people who think they are successful. Many cadets at the Academy deliberately performed worse—wrinkled shirts, dirty brass, unshined shoes—because they knew the disapprobation they would face for standing out. And so the performance evaluation system was turned upside down—it actually rewarded the worst performers, not the best. Think about the type of person that thrives in such an environment. Wall Street was better, but there I learned that there is no such thing as a true meritocracy. It simply does not exist.

My experience in the Coast Guard was so traumatic that it resulted in a profound change in my psychology. As a teenager, I was fearless (especially with the opposite sex), optimistic, and happy. After four years at the Academy, I was fearful, anxious, depressed, and so fucking cynical. As you can tell from this newsletter, I have used my cynicism to great advantage. But if I could go back in time to senior year to high school and go to, say, Wharton, I’d be a lot happier. Hell, I might even be a billionaire.

The decision to attend the Coast Guard Academy was partially driven by economics—there was no money to go to an expensive school without a fair amount of debt. It was also partially driven by family legacy—my father and grandfather both went to the Academy and had long careers as aviators. But ultimately, it was a horrible decision, and it set me back 5 years. I started my career at age 27 instead of age 22. But who knows what they want to do with their life in high school?  I didn’t, but some kids do, and they go through life with the certainty that they know what they are doing is right. It took me years to get my head out of my ass.

I’ve heard from many people, even from within my own family, that they were shocked that I went into the military. They said it wasn’t a good fit with my personality. I was a musician, an artist, a creative type—not a tough guy with a high-and-tight haircut. But like a lot of kids who go into the military, I had to prove that I was tough. I proved it, I graduated from that fucking place, and now I don’t have to prove it anymore. I don’t measure my self-worth by the size of my pecs. And having served in the military is social currency—people sometimes thank me for my service. Which is funny, because I served during the longest stretch of peacetime in recent history. But I earned it. I’ve learned over the years that the service academies in the early 1990s were perhaps tougher than at any point in history.

One of the things I talk about in my personal finance curriculum is that it’s not the million small financial decisions that you make on a daily basis that determine if you’re rich—it’s a handful of big decisions: what house you buy, what car you buy, and how many student loans you take out. We have a tendency to think that small things and small habits determine our destiny (think James Clear), but it actually isn’t true. You will arrive at 4-5 big decision points at various times in your life, and if you get them wrong, the results will be catastrophic. Where you are today is the sum total of every decision you have ever made in your life, good and bad.

And you can get these decisions wrong, and still survive. It’s not the messes we make, it’s how we clean them up.

Go fuck yourself,

Jared

Music Recommendation: My music!  I recorded a mix a while back and posted it a couple of days ago. It’s called Drop Dead Gorgeous, and that’s exactly what it is. Bright, beautiful, downtempo house music. Go for a long drive and turn it up.

P.S. We’re Gonna Get Those Bastards will always be free. Feel free to forward to as many people as you like.