In addition to writing newsletters, I also enjoy reading them. In a recent issue from Ryan Levesque, he wrote about his 14 year old son heading off to boarding school:

“And when he expressed desire to apply to one of the top high schools in the country, one filled with other kids like him from all over the world, we opened our hearts to that possibility

And still, when he was accepted, the news was bittersweet. Because I thought we had so much more time. I thought I’d have my (now 14 year old) boy with me at home, for at least another four years.”

It was the line “I thought we had so much more time” that made me stop. Partly because I have a son around that age. But also because I say a version of that line to myself all the time.

As context, Ryan didn’t put anything off. He wanted his son to fly further than he had, and when the chance came, he took it. What caught him wasn’t regret, it was the unexpected compression of time. He had four more years in his head, and an acceptance letter told him the calendar wasn’t under his control.

That’s the part that keeps running through my head. When I tell myself I have more time, I’m not being optimistic, I’m really just avoiding a decision. And the part I tend to forget is that the decision still gets made eventually, just by circumstance, on a schedule I didn’t pick.

We do this with our businesses a lot. We plan to get the business to a place where we’re not needed in it every day, and the timeline is “eventually.” Eventually we’ll build the team. Eventually we’ll get out of the weeds. Eventually the business will support the life we started it for.

But we already have deadlines. We just haven’t looked at them as deadlines.

Your daughter is a sophomore. The lease has four years left. Your partner wants out at 60 and he’s 54. Your knees at 55 are not your knees at 45. None of those things are waiting for you to be ready. They arrive whether you chose anything or not.

I talk with owners about freedom a lot, and the easiest mistake is treating it like a finish line. Hit the number, sell the thing, and freedom starts. It doesn’t work that way.

Freedom is knowing what you need and knowing you’re doing the things that get you there. It’s a place you live, not a door you walk through.

“I have more time” doesn’t buy you anything. The time gets spent either way. If you aren’t choosing what it goes toward, other things will, and they aren’t shy about it. The client who pays the most and asks the most. The part of the business you’re better at than anyone else but should have handed off two years ago. The problem that turns out to be urgent every single week. None of them are villains. They just fill whatever space you leave open, and living inside their choices is its own kind of unfree.

That’s the part of Ryan’s story I keep coming back to. The letter took his four years. It didn’t touch what he wanted. He’d already decided he wanted his son to fly further than he had, so when the calendar changed on him it hurt, but it didn’t cost him anything.

The deadlines will land when they land and you don’t get a vote on that. What you do get a say in is whether the time before them went toward something you chose. Arriving isn’t the loss. Arriving having never chosen is.

~ Nolan

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