Dear Ryan,
I turned 52 this spring. My firm manages just under $4 billion. I have 47 employees, a fully inbound marketing motion with a waiting list of prospects, and a compensation structure that most of my buddies in high school would consider embarrassing in the best possible way. By every measure I was taught to care about, I won.
So why am I writing this?
My oldest daughter started college last fall. Move-in day was a Saturday on the East Coast. I was at a client event on the West Coast. I told myself I’d make it up to her. I told myself a lot of honest lies over the years, about a lot of things. She was gracious about it, as always, and that somehow made it worse.
I’m not in crisis – midlife or otherwise. I’m not looking for permission to quit or a therapist’s couch to shrink my head on. What I’m looking for is someone who will have the honest conversation that nobody in my life will actually have with me. Everyone around me either tells me I’m an inspiration or quietly resents what I’ve built. Neither is useful.
Here’s what I keep coming back to: I know what I built. I’m just not sure anymore that I know why I built it. I know doing so has racked up a “large bill” in my life, and I’m starting to wonder if “worth it” is even the right question – or just the one that’s easiest to ask.
— Built It, Not Sure What For
Dear Built It, Not Sure What For,
Let’s skip the part where I tell you that you should be proud of what you’ve built. A slap on the back isn’t why you wrote.
You ended your letter with something I want to stay with: maybe “worth it” is the wrong question. You’re right. It is. And I think you already know why.
“Worth it” is a transaction. It implies a ledger where the sacrifices sit on one side and the outcomes on the other, and somewhere a number tells you whether the math worked. But that’s not how any of this actually works. Your daughter’s move-in day doesn’t net against your AUM. The version of yourself you were at 34, before the firm became the whole story, is long gone and I bet what you remember isn’t exactly how it was. The ledger metaphor is seductive because it suggests there’s a calculation that could settle this. There isn’t.
Your daughter’s move-in day doesn’t net against your AUM.
Here’s the question I’d actually ask: not whether it was worth it, but whether you made it consciously.
Because there are two kinds of leaders who end up where you are at 52. The first kind made a series of deliberate choices (eyes open, tradeoffs understood and values intact) and arrived here having chosen this life. The second kind got very good at moving fast and calling it intention because things went their way. Both end up with $4 billion firms but only one of them looks at a career mostly lived without flinching.
I don’t know which one you are. But I suspect the reason nobody in your life will have this conversation with you is that you haven’t decided yet which answer you can live with.
Your daughter was gracious. She always is. Sit with why that made it worse.
That’s where your answer is.
— Ryan
Ryan George is the Chief of Staff of Docupace.
