Turning 40: What 21-Year-Old Me Got Wrong

I turned 40 this year, and despite telling myself it's just a number like any other birthday, I couldn't help but reflect on it more than usual. There's something about reaching the crest of a particular hill that makes you want to look back at the climb, and ahead at what's coming down the other side.

If you'd asked a freshly-graduated 21-year-old version of me what life at 40 would look like, the answer would have been pretty different from reality.

He'd have guessed I'd be a C-level executive by now, running a large team at a big, established company, the traditional definition of "made it" that gets handed to you early in a career.

Instead, I run a one-person business. I've been through four acquisitions across roughly twenty years in operations and RevOps roles, learned an enormous amount at each one, and eventually decided to build something of my own rather than keep climbing someone else's ladder.

What's interesting isn't that the path diverged from the plan. Almost everyone's does. It's which assumptions turned out to be wrong. The 21-year-old version of success was almost entirely about title and scale: bigger team, bigger title, bigger company. The 40-year-old version looks more like: do I have control over my time, am I doing work that actually engages me, and am I building something that's mine.

Neither version is "right." But it's worth noticing how much the definition of success quietly shifts over twenty years, usually without you consciously deciding to change it. It just... does, based on what you actually experience along the way.

If you're closer to 21 than 40 reading this: the plan you have right now is fine. Just don't be surprised when it changes, and don't mistake "this isn't what I planned" for "this isn't working."

Originally posted on Linkedin. Join the conversation here.

Hi5, LD 🌶️