I was walking back home after a long late-evening walk when I realised: ā€œProduct Managementā€ by itself was no longer fulfilling enough for me.

I had my logic, my reasons. I had my clarity on what fulfillment even means for me. And rationale to why do I need it in the first place. But in that moment, I just felt free and scared at the same time.

Free to look for meaning elsewhere instead of guilt-tripping myself about not working hard enough on finding meaning in what I was doing. Or not being ambitious enough or grateful enough.

But the question that stared back at me was: If not this, then what?

Who picked your path for you?
Who picked your path for you?


I think most people don’t have goals of their own. They have chores.

Back in the earlier days, our goal was simple: to survive, to stay alive. It still is for some unfortunate few. But largely, society solved survival for most of us. It keep us alive. But being alive is still not the same as truly living, is it? That still needs a purpose, a goal.

And so the society offered us a structured template. The next promotion became the goal. Getting married, buying that house, raising your kid, saving for retirement. That’s the standard path with clear milestones. And you know the direction towards the next one.

Only, that direction seems so … same. Dull even.

Did I dream about these milestones growing up? May be some did. Or may be we picked what was on the menu. And some of us may not have have had even that luxury of choice either. Personally, it does not seem like this path leads to a goal that was ever my own to begin with.

There’s a character in this book I just read - A Psalm for the Wild-Built - who says it better than I can.

ā€œI woke up hollow… I packed up everything, and I learned a brand-new thing from scratch, and gods, I worked hard for it… I’m good at what I do. I make people happy. I make people feel better. And yet I still wake up tired, like… like something’s missing… I threw myself into my work, I went to all the places that used to inspire me, I listened to music and looked at art, I exercised and had sex and got plenty of sleep and ate my vegetables, and still. Still. Something is missing.ā€

Mind you - the template isn’t bad. Far from it. It has worked for billions of people. But it’s harder for those who want something off-catalogue. No next rung on the corporate ladder, may be no kids either. Owning that house in the suburbs doesn’t matter that much.

~~~~ ~~~~ ~~~~ ~~~~ ~~~~ ~~~~

Sure, being in a position to reject the standard path - whether thanks to the choices you made or luck or often both - is an absolute privilege. But the thing is is - you still need purpose. Only now you have the much harder job of building it yourself.

Like not buying a flat in an apartment because you want something more ā€œyouā€. And then realizing you have to find that plot of land, get the designs done. Revise it 17 times. Actually build the thing. It’s exhausting! You might even be sleeping in a half-built structure for a while. And after everything, what you built might still not feel quite right.


That’s the thing nobody tells you about opting out:

The freedom doesn’t come with instructions. You’re just tired in a different way.


I have my own half-built structures. I’m writing, building software, building communities, making friends. But mostly, I’m still exploring. Partly because choosing feels final. Like my future self gets stuck with what the current me decided for it.

I have this rule: keep 2 hours a day free for creative play. Sounds nice - until there are days in a row when I stare at those hours wondering what counts as ā€œcreative playā€ and whether I’m wasting them.

I’ve spent some time over last year to launch a company with a few friends - called it NextFive. Not because I needed the money. Because I need a purpose? Something to point to? Still not sure. And that uncertainty makes it harder.

The ListenerCircles worked out though. Started as an experiment to see if I like the company of other people. Now I host them too. But that took two years of just showing up without knowing if it mattered.


I don’t know if this is better than the standard path. The people on the standard path know where they’re going. I envy that sometimes. But at least when I’m tired now, it’s from building something mine. Even if I’m not sure what that something is yet.