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You want to know what grinds my gears? When people say they have no regrets.
What? Who has no regrets? I have a ton of regrets. I regret things that I said, I regret things that I didn’t say, I regret things that I did, I regret things that I didn’t do, and I regret causing psychic pain to people totally by accident. My life has been a series of one fuck-up after another, leaving a bunch of damaged and broken relationships in my wake. I don’t understand when people say that they have no regrets. Are they psychos or something? Have they lived flawless, unblemished lives? Do they not care about the people they’ve steamrolled along the way?
Exhibit A out of 5,000 exhibits in my life: I broke up with a girl in high school. That wasn’t the issue. It was how I did it. Later, I ran into her at the 10-year reunion, and she wouldn’t talk to me. I liked her, personally, I and I would like her to talk to me, so this causes me pain. Actions that I took when I was fifteen years old cause me pain. There was another guy, in college, that I ratted out for getting some cuddle time underneath the altar in the dorm chapel. I could see him from my window. I mean, it was absurdly bad behavior, but crucially, it was none of my business. Anyway, I ran into that guy at the 25-year reunion, and he wouldn’t talk to me, either. There are probably a hundred people that I’ve crossed paths with in my life that won’t talk to me. And I think most people would consider me to be fairly well-liked.
Having said that, the goal isn’t for everyone to like you, because that’s an impossible task. You can’t please everyone—and that is broadly true. People unsubscribe from this newsletter all the time. I’m not everyone’s particular brand of vodka, and that’s fine. And the more successful you get, the more haters you will have—this is just human nature.
I think the purpose of regrets is so you don’t make the same dumb mistake twice. It’s okay to make a dumb mistake—two of the same genus and species is stupid. I’ve made a host of personal and professional mistakes. They cause me pain and discomfort, and the purpose of the pain and discomfort is to make you learn, and then you don’t make the same mistake again. I’m sure you’ve heard the phrase “The definition of insanity is doing the same thing over and over again and expecting a different result.” The types of people who make these types of mistakes fall into a specific category: addicts. Get drunk and fuck your boss’s wife. I have no idea how that happened! Get drunk and crash your car. I have no idea how that happened! Get drunk and make out with your best friend’s boyfriend in the closet. I have no idea how that happened! The one thing that defines addicts is the failure to learn from their mistakes—until one day, when they figure it out. Or they never do. And addiction is the very definition of insanity.
When I was at Bloomberg, I wrote an op-ed about a commodity ETF, and I did some sloppy research, and the head of the ETF issuer wrote in all pissed off, and I had to issue a correction. In the grand scheme of human wickedness, this was not a big deal, but it was embarrassing, and I vowed to never do it again. And I didn’t. Back in the early 2010s, I used to get political in The Daily Dirtnap, and I pissed off a bunch of people, and lost some subscribers. Good subscribers. That caused me to re-evaluate my priorities, and I never did it again. Life is a continuous process of trial and error, getting feedback along the way. Some people think that if you’re making everyone mad, then you must be doing something right. I don’t share that belief. I guess it is true in some cases—Macron is raising the retirement age in France, and people are burning down the country. He is doing what is right, and unpopular. Maybe history will view him more kindly in 20 years, or maybe not. In Macron’s case, he doesn’t have much in the way of blue-collar sensibilities. Only Nixon could go to China, etc.
There is a corny saying: The past is history, the future’s a mystery, so that’s why we live in the present—it’s a gift. I have regrets, but I don’t dwell on them. And you get enough distance between you and the things you fucked up, and maybe you can get to the point where you can laugh about them after a while. And after that, you can get to the point where you can use your story to help someone else going through the same thing. We don’t dwell on the past, we learn from it. There is nothing in the past but pain. Don’t go back there. Which is maybe what people mean when they say they have no regrets—that they are living in the present. But I doubt it. I think those people are dickheads.
I will tell you a thing that I do. I live in fear of future regret, so I try not to do things that will cause me regret in the future. One aspect of this is that I treat every phone call, every meeting, every interaction as if that is the last time I will see or hear that person alive. Dumb example: I called my wife this morning and told her that my flight was canceled. I told her I loved her. She told me she loved me. But I don’t treat our goodbyes as routine or commonplace. I think to myself that if this ended up being the last time I ever talked to her, that I would remember those words forever. I don’t just do this with my wife—I do this with everyone. Every phone call might be the last call. You talk to one of your buddies on the phone, you don’t hear from him for a few years, and then you found out that he’s dead. Then you rewind and think about that last interaction—was it positive? If it is not, you will have regret. I wrote a short story about a couple that got into a fight, and then then husband got into his car and was killed in an accident. Imagine the guilt! You never want to be in that position.
And yet I continue to make mistakes, both acts of omission and commission. The key is that they really are mistakes, just dumb screw-ups—I really don’t have a malicious bone in my body. And the crazy thing is that at the age of 49, I keep making mistakes—you think I would have stopped by now. I just keep coming up with new and creative ways to fuck up. It’s super frustrating. And even at the age of 49, I don’t know how to handle all situations. Experience counts for a lot, but it’s not everything, and I can tell you that I am not in possession of the best people skills in the world, and I am very jealous of people who do. There are situations which absolutely baffle me, and that’s why I’m a writer, and not an admiral or a CEO.
Regrets are my superpower. I have them, but instead of pretending I don’t have them, I use them for good. If you’re going through some shit right now, there is a 100% chance that someone you know has gone through the exact same thing. And his or her willingness to talk about his or her experience will make a difference in your life. The most valuable thing that we each have is our story—the things we did well, the things we did poorly. All of human experience is one human being talking to another human being. If we’re not talking, we’re sunk.