You want a bigger life and you’re trying to get there without changing anything about who you are.
Doesn’t work. Never has.
Every man wants the upgraded version of his circumstances. The bigger business, the better marriage, the body that doesn’t hurt when he gets out of bed. And almost nobody wants the part where the guy currently running the operation has to be retired.
But that’s the trade. That’s always been the trade.
He Was Built For Different Problems
Here’s what nobody explains about the version of you that’s driving right now. He’s competent. He’s not a failure, and that’s exactly why this is hard. He got you out of whatever you came from. He handled the twenty-five year old problems, the thirty year old problems, the ones where you had nothing and had to be scrappy and paranoid and willing to take a shot at anything that moved. He was good at those. He should be. He was built for them. The trouble is he keeps solving those problems. He goes looking for them. When you hand him a forty-year-old situation that requires patience or delegation or an honest conversation, he reaches for the twenty-five-year-old tool, because that’s the tool that worked and he’s got a lot of evidence it works. So you end up running a bigger operation with a smaller man’s instincts, and you cannot figure out why the same effort keeps producing the same size result. Familiar and stuck feel almost identical from the inside.The Part Men Won’t Do
You have to let go of who you believe you are. Not adjust. Not optimize. Let go. And most men won’t, because that identity is comfortable and it’s known and other people have agreed to believe it. You’ve got a story about yourself that your friends will confirm. The guy who came up hard. The guy who doesn’t need anybody. The guy who works harder than everyone in the room. Those stories were true once. Some of them were even useful. But a story you’re defending is a story you’re stuck inside, and you’ll notice you spend a certain amount of energy every week proving it’s still accurate. That energy is the tax. You’re paying it to stay the same. I’ve had to do this more than once. The guy who built the first business was not the guy who could run it at scale, and the guy who came out of my divorce was not the guy who went into it. Both times it felt like loss for a while before it felt like anything else. That’s normal. Everybody rushes past that part when they tell the story, but there’s a stretch in the middle where you’ve set down the old version and the new one hasn’t shown up yet, and it’s genuinely uncomfortable. Go through it anyway. It’s a season, not a destination.3 Tactical Ways To Retire The Old Version
- Name the story you’re defending. Write down the three things you say about yourself most often. The self-descriptions that come out automatically when someone asks. Then check each one against the last twelve months and ask whether it’s still true or whether you’re just maintaining it. At least one is a costume you’ve been wearing past its usefulness.
- Find the tool you keep reaching for. Everybody has a default move. Some men work harder. Some go quiet. Some blow it up and start over. Identify yours, then find one situation this month where you deliberately use a different one. It’ll feel wrong. Wrong is the correct feeling. It just means you’ve never done it.
- Ask what you’d have to stop being. For the next five years to look nothing like the last five, who would you have to stop being? Answer that honestly, in writing, and you’ll have named the actual obstacle. It’s rarely the market. It’s rarely the money. It’s usually a version of yourself you’re still protecting.
Final Thought
You can’t become the next version of yourself while defending the current one. Pick one. The old guy doesn’t get a gold watch and a send-off. He just gets set down, quietly, on a Tuesday, when you decide to handle something differently than you’ve handled it for the last fifteen years. Here’s the challenge. Sit down this week and write one page titled “who I have to stop being.” Not what you need to do. Who you need to stop being. Most men have never separated those two and it changes everything when you do. Write it, then send it to me. I want to see what you’re carrying. – Sean Whalen
