The Checkboxes Were Never the Point: Finding Meaning After You've Done Everything Right

How many of you feel like you're checking all the boxes for what you're supposed to do, and still feel like you're waiting for the happiness and meaning?

Maybe you're sitting in a house you worked hard for, with people you love, and somewhere in the back of your mind there's a low hum asking: is this it? Not because anything is wrong, necessarily. But because something just feels…missing.

Here's my theory: we were never actually taught how to find meaning. We were taught a script instead. Go to school. Go to college. Get a good job, make good money. Get married, have kids, get the house, get the nicer car. Do all of that, and happiness is supposed to show up as a kind of reward at the end.

We've come a long way as a society in a lot of ways. Life looks a lot different today than it did 50 years ago. (If you're my age, you grew up without smart phones, or even computers) But on this particular point, we haven't moved much at all. The script is still running for most of our lives, mostly unquestioned, because it's the only one most of us got.

The problem is, I've met dozens of people who ran the whole script: degree, career, married, kids, house…And are struggling with accepting this as “it.” Maybe they're not broken or depressed. Not ungrateful, even. Just a sense of “unfulfilled”, and they feel like they can't voice it because by every external measure they've lived "right." If they complain about it, others will squash them down: “Oh boo hoo, with your house and your family and kids, your life is so hard!” And yet sometimes, something just feels missing, or meaningless.

That's the tell. Meaning was never in the boxes. It's not a reward you unlock by checking enough of them. And that's exactly why it's so hard to teach — what's meaningful to me might do nothing for you, and vice versa. There's no universal answer here, which means there's no universal script either. The one we've been handed was never built for meaning. As a matter of fact, I'm not really sure what that script was written to achieve.

So if the script won't get you there, what will?

Start smaller than you'd expect. Start by learning what you actually like, as opposed to what you've been told to like. Carry a small notebook for a year — genuinely, try this — and jot down what you enjoyed today and what you dreaded. Not big questions, just small honest notes. Do it for long enough and you'll learn more about yourself than a decade of assuming you already knew.

Then start paying attention to what you're good at, and where that could actually be useful to someone else. Meaning, in my experience, is rarely a solo project. It shows up in community, in being needed, in contributing something real to people around you. It's less "find yourself" and more "find your fit."

This is more or less the whole starting point of the coaching work I've been developing. Helping people figure out what they actually value, separate from what they've been told to value, and then helping them build a life around that instead of around the next box. More on that soon.

For now, here's the question underneath it all: the life you're living right now — did you choose it, piece by piece, or did it happen to you because it was the script everyone handed you by society, your parents, or school? There's no wrong answer. But there's a real difference between the two, and only one of them will feel like yours.