50

I turned 50 a few months ago.

This is the way I look at the world: the 20s are the 20s. The 30s are the 30s. But the 40s are not the 40s. There are the early 40s, and the late 40s. You cannot generalize about the 40s. In your early 40s, you’re full of vim and vigor, going to titty bars and strutting around like a peacock. In your late 40s, you get sleeping injuries. Even your poop changes. You’ve heard the saying: never pass up a bathroom, never trust a fart, never waste a woody. I’ve thrown away more pairs of underwear in my late 40s than I care to write in this essay. Two weeks ago, I shit my pants when I was on the radio. Standing in my office on the phone, squirting chocolate lava into my Under Armour skivvies while talking about how to live a stress-free financial life. If you’re in your 20s, and you’re reading this, you probably are wondering how this can happen. I’ll tell you how it can happen. You literally have no control over your bowel movements. You’ll be sitting in your car, minding your own business, listening to country music and poop will literally come out of your butt, like a disorganized tidal wave with an exceptionally bad attitude. I could write 1,500 words on crapping my pants in my late 40s, I really could.

All kidding aside, the 40s were pretty great. Really great. Wisdom is highly, highly underrated, and you don’t understand how underrated it is until you acquire some. You find yourself in these social situations or work situations, these sticky, intractable problems that used to baffle you when you were young—and you instinctively know how to handle them. You make far fewer mistakes, especially in relationships. Which brings me to Andrew Cuomo. Cuomo, in his 50s, thought he was still in his early 40s. Sniffing blow, watching XVideos, grabbing ass. Actually, I don’t know that he was doing any of these things, but I can guess. As a 55-year-old man, that’s not your role in society anymore. People look to you for wisdom and guidance, not your hammer. The hammer days are gone. Some men manage to extend their sex lives into their 70s, but that is not true for most of us. One of the few interesting things that came out of the Harvard happiness study was that, oddly, conservative men tend to stop having sex in their 40s, while liberal men will continue well into old age. I have no explanation for that.

Back in 2008, I read that 82-year-old casino billionaire Phil Ruffin married the 27-year-old Miss Ukraine. In the comments of the article, someone wrote that she would be licking old balls for the rest of his life. I LOLed at that one, but I doubt she did it even once. I doubt seriously that Ruffin’s honker had any of its old dynamism left. He just wanted a beautiful woman on his arm. And I think about that sometimes. I’m not super interested in treating my body like an amusement park. You know what I am interested in? Going to a black-tie event with a stunningly beautiful woman, and my wife definitely falls into that category. There is something that fundamentally changes in an older man’s psychology about these sorts of things. Status becomes the new sex drive, hence, the focus on expensive cars and toys. I guess that is the thinking.

I never made any 30 Under 30 lists, or 40 Under 40 lists, and it is too late for the 50 Under 50 lists. I am a bit of a late bloomer. I didn’t start my career on Wall Street until age 27, I didn’t start my career as a writer until age 34, and I published my first book at age 37. But Warren Buffett was a late bloomer, too, and a whole bunch of other people. But at age 50, you start to think about how long you are going to live. You contemplate your mortality. With life expectancy for men at about 80, and conditional life expectancy a bit higher, will I make it another 30-plus years? Even if I did, it means for almost certain that I am past halfway done. And that makes me sad. Because I wasted so much time when I was young. And for so long, I had fucked-up priorities. It took me a long time to figure out this thing called life, but I suppose that a lot of people never figure it out.

There is a lot of stuff I still have left to do. Some of it is a secret, but some of it I can talk about. If all goes according to plan, I will publish a fifth, sixth, and seventh book. I’d like to write a book a year for the rest of my life, and it absolutely can be done. I recently met author Ben Mezrich at a conference in Las Vegas. I was familiar with a few of his books, but I had no idea that he had written 25. 25 books! And he’s about my age, maybe 3-4 years older. What the fuck have I been doing my whole life? Elsewhere, I have written about this concept of impact or contribution. In my fifties, I am focused on creating things that will outlive me. Fifty years from now, I want some college student to stumble across one of my books, then another book, and then do a research paper on me, this little-known author from South Carolina, this eccentric character who was fighting against twin orthodoxies in finance and literature with his clowder of cats. I want to be remembered, and not necessarily fondly. I want to be remembered as the guy who made you think and feel. And laugh and cry. I would like to become famous, if famous meant that more people got to read my books, but I certainly don’t want fame for fame’s sake.

There is probably a 99% chance that I will pass away before my wife. She has great genes; I have terrible genes. There is a small, but decent chance I won’t see 60; hence, the life insurance. My wife will probably live to 100. I joke with her that I’m her husband for the first 40 years, and then she will find a husband for the next 40 years, but she assures me she has no interest in remarrying. But I really, really hope I don’t die suddenly, like of a heart attack or in a car accident. I want to die of cancer, in a hospital, holding her hand, and I want her eyes to be the last thing I see on this earth. Now, let me tell you—these are not the sorts of things you think when you’re 25. Everyone knows that 25-year-olds are immortal. But I feel pangs of death. I went to Miami recently, getting up at 2:15 in the morning to catch a 6am flight out of Charleston, and I got breakfast with my friend Mike at IHOP, and I looked at him and told him that I was dying. I mean, sure, I was exhausted from getting up so early, but I felt like absolute shit, and I feel like absolute shit most of the time. I’m falling apart, and it happened fast. In the last five years I’ve gone from being a healthy, active adult male to a gray-haired senior citizen. Now, I realize that a lot of this is a state of mind—if you think you are old, then you will act old, and you will be old, and nobody wants that. But gee whiz, when I was in Miami a few months ago, I had the opportunity to go out clubbing at Do Not Sit on the Furniture, and…I passed. I knew I wouldn’t get back to the hotel until four in the morning, and I would be a zombie the next day. I am no longer Superman. And I really, really value my sleep. It was a sad day, actually. I love hearing some whomp whomp whomp every once in a while. And there’s nothing like being the gray-haired guy at a club. It’s like wearing a cloak of invisibility, but occasionally people try to buy drugs from you.

From a medical standpoint, the 50s are the danger zone. I have an uncle who is a well-known orthopedic surgeon, and an all-around genius, and he said that if you make it through your fifties, you have a good chance of living to your seventies. The 50s are when all the problems start to crop up: heart disease, high blood pressure, cholesterol, cancer, and if you can survive that, the 60s should be a breeze. I’ve made a commitment to focus on my health in my 50s. I just moved into a new house that has a gym in it, with weights, a treadmill, and an elliptical, and a TV so I can watch the market. My brother, a fitness expert, tells me that all I have to do is move for 30 minutes a day to stay healthy. I was a daily racquetball player up until the pandemic, and I was in outstanding shape, but since then, I haven’t set foot into a gym, and I turned into 240 pounds of chewed bubblegum. So it is time to reverse that process. I’m not one of these people who is obsessed with longevity—you could put all this time and effort into your body and then get greased by a Ford F-350 on the highway—a lot of it comes down to luck. But if by putting in a little bit of effort I can extend my lifespan by about 5-10 years, I will do it. And if I turn into the hardbody silverfox turning heads at the Setai, even better.

Here's an interesting thing to think about: in 12 years, I can start collecting Social Security. Yes, that’s right, if I wanted to, I could retire in 12 years. That is absolutely bonkers. And about 50% of people do start collecting Social Security at age 62. There is so much I have left to do. I wouldn’t know what to do with myself if I retired. You know my feelings on retirement: I am not a big fan of unstructured free time. There’s no way in hell I’m going to retire in 12 years. Something amazing: I am going to start collecting my government-rescued Lehman Brothers pension in 2026. You had to work at the firm for seven years to vest, and I worked there for seven years and three months. It’s not a huge amount of money, but it will cover the landscaping, the pool, the housekeeping, and the homeowners insurance with a little left over. I figure I earned it.

At the beginning of each decade is a feeling of promise. My 20s were about ambition. My 30s were about renewal. My 40s were about purpose. If the 50s are going to be about wisdom, we are not off to a good start. I shit my pants on my birthday.