I have a friend who, at 30, had decided to fulfill his lifelong dream, and take his wife and travel the country in an Airstream for six months. I had worked with him on the front end to help him avoid common financial pitfalls and was happy to see him go.
Around month three, of what had been a rocky start due to equipment failure, he was settling into his routine and posting gorgeous photos of himself from the road. I called him up one day to check on him. He was pretty down. Things weren’t all going the way he thought they were supposed to go. He wasn’t as organized as he felt he should have been, he had money and that wasn’t a problem but he felt like he should have more ambition to make a lot more money.
I cut him off right there. “Hey, let’s just be clear,” I said, “You’re 30. You run a tech business from an Airstream. You have plenty of money. You’re happily married. You’re living the life you love.”
He agreed, but said, “Yes, but I think my friends and maybe my wife think I should have more ambition to make a LOT more money. But I don’t really care. I love being out here. I’m really happy. What’s wrong with me, why don’t I want more?”
“Because more doesn’t f***ing matter!” I practically yelled into the phone. I began again, “Okay, so let’s say you stop. You buckle down, you go back to your stick built house, and work your ass off for twenty years. You open shops in a dozen states, you get HUGE, you make millions.”
“Okay,” he said, sounding overwhelmed.
I pressed on, “Guess what you’ll be doing at 50? You’ll be selling the business, have plenty of money, buy an Airstream to travel the countryside. You’re 20 years ahead of the game! So what if everybody else wants to work until they’re dead? So what if everyone else values money over freedom. You don’t! And here you are, SEMI-RETIRED AT 30 AND LIVING IN AN AIRSTREAM JUST LIKE YOU ALWAYS WANTED. HOW INSANELY COOL IS THAT!? YOU’RE AWESOME! GOD SAVE YOU FROM YOUR AWESOME SELF!!!”
He started to laugh. “You know, you’re right. I feel much better. I AM semi-retired at 30, aren’t I? I AM happy. I think I’m going to go play outside right now!” And he did. I got an email from him a few days later saying how he’d appreciated the perspective on what he was actually doing right now.