If you were to um If you were to Google my name, well, you wouldn’t find a damn thing. I am 82 years old. I rent a a metal tube, a 1974 Airstream trailer, parked right behind the diner in the middle of New Mexico. My total net worth, if you count the change sitting in my truck’s ashtray, is about $42. I don’t own property.
I don’t have a 401k. I have never been a manager, a director, or a boss of anybody. By every single metric that your society measures a human life, I am a catastrophic, irredeemable failure. And I am, without a shadow of a doubt, the happiest man you will ever meet. See, you look at me and you probably feel a little pity.
You think, “Oh, that poor old man. He must have made some terrible mistakes along the way.” I didn’t make a mistake. I did this on purpose. And I’m going to tell you a secret today that the people running this world, the people signing your paychecks, they are absolutely terrified of you finding out. I’m going to tell you why being a loser is the only way you survive this life.
Let me uh let me take you back to 1961. You probably think I’m just some uneducated bum, right? Just a guy who couldn’t cut it. Well, in 1961, I was 22 years old and I had a full ride scholarship to Yale Law School. Mhm. I was a prodigy, they said. Top of my class. First day of orientation, I walked into this massive, beautiful, gothic building and I looked around at the other boys.
They were wearing these sharp little suits, but I looked at their eyes. They looked like cattle walking into a slaughterhouse. They were terrified. Terrified of not being number one. Terrified of what their fathers would think if they didn’t make partner by 30. They were already hyperventilating and the race hadn’t even started.
I sat in that wooden chair for uh exactly 14 minutes and I realized something. If I stayed in that chair, I would be handing them a blank check for my entire life. So, I stood up. I walked out the heavy wooden doors. I threw my tie in a public trash can and I hitched a ride to California. My parents didn’t speak to me for 10 years.
They told everyone I threw my life away. But I didn’t throw it away. I saved it. I spent the next 60 years flipping burgers, playing the banjo on street corners, and bartending in beach towns. I made exactly enough money to buy dinner and a cheap beer. And when I woke up every morning, my time belonged to me. Let me tell you about my roommate from that first day at Yale.
A boy named Richard. Richard stayed. Richard played the game beautifully. He became a corporate lawyer. Made millions. Bought the mansion in Connecticut. Bought the summer home in the Hamptons. He had the beautiful wife, the private jets. Richard was a winner. Richard died of a massive, stress-induced heart attack at 52 years old.
He dropped dead on the floor of his corner office surrounded by mahogany wood and Italian leather. His beautiful wife had already left him because he worked 80 hours a week. His kids His kids didn’t even cry at the funeral because they barely knew the man. He spent 30 years carrying a 1,000-lb boulder up a mountain just so society would clap for him.
And it killed him. They call me a failure, but I am 82. I am breathing. I watch the sunset every single evening and my heart beats slow and easy. Richard won the game, but what the hell did he win? He traded his actual breathing life for pieces of paper and a title on a door. You see, society plays this massive trick on you.
They convince you that wealth is about accumulation, gathering things. But things are heavy. When you buy a massive house, you don’t own that house. That house owns you. You have to clean it. You have to insure it. You lay awake at 2:00 a.m. worrying about the roof leaking. You have to stay at a job you hate just to pay the mortgage on a house you’re never in because you’re always at work.
It is absolute insanity. I live in a tin can. If I don’t like the view, I hook it up to my truck and I drive to Arizona. When you have absolutely nothing, you have everything. It’s the empty backpack theory. If you’re walking up a massive hill, who is going to enjoy the hike? The guy carrying 100 lb of gold on his back, sweating and groaning, or the guy carrying nothing but a canteen of water, whistling at the birds? I dropped the gold in 1961 and I have been floating ever since.
And now, I look at your generation and it breaks my heart, truly, because you don’t just have the pressure of your parents or your neighbors anymore. You carry a machine in your pocket that compares your life to 8 billion other people every second of the day. You have these these influencers, these kids on the internet, and all they talk about is optimizing.
They are tracking their sleep with computers on their wrists. They are waking up at 4:00 a.m. to take ice baths. They are trying to build a personal brand. A personal brand. You are a human being, for God’s sake, not a box of laundry detergent. You are punishing yourselves. You are trying to turn your organic, beautiful, messy human life into a perfectly efficient machine.
You’re just trying to be a better battery for the matrix. Why? So you can get to the end of your life and say, “Well, I never enjoyed a single Tuesday. But boy, my productivity metrics were off the charts. It’s a sickness. You’re sprinting on a treadmill. And you are terrified of falling off. Let me tell you what actual wealth is.
Because you won’t learn it in business school. Wealth is not dreading Monday morning. Wealth is waking up at 8:00 a.m. Looking at the ceiling. And realizing. That nobody on this entire planet. Requires you to do a damn thing. You don’t want to do. Wealth is the absence of that tight burning knot in your stomach.
I don’t have a 401k. But I have spent the last 60 years. Reading books under oak trees. I have had three-hour conversations. With strangers. In diners at midnight. I have watched the rain fall. Without feeling guilty that I wasn’t hustling. You think failure is the worst thing that can happen to you? You think if you don’t get the promotion.
Or if you drive a cheap car. That you are worthless. Listen to me. Failure. Is just the word society uses. For people they cannot control. When you don’t care about status. Your boss can’t threaten you. When you have absolutely nothing to protect. You become bulletproof. I’m sitting here in a rusted tin can in the desert.
And I am giving you a gift today. I’m giving you permission. To give up. Give up the chase. Stop trying to impress people. Who are just as miserable and terrified as you are. If you want to quit that high-paying job. That makes your chest hurt every Sunday night. Quit. If you want to move to a small town.
And work in a hardware store. And paint watercolors on the weekend. Do it. They will call you a loser. They will whisper about you behind your back. Let them. Let them have the corner office. Let them have the high blood pressure. Let them have the heart attacks at 52. Let them drown in their success. You. You take the freedom.
I’ll see you at the bottom my friends. I promise you. The view down here. Is spectacular.
