Most of life is spent training for a destination we never actually examine

I keep a small drawing on my desk. A line that rises — possessions, association, the slow accumulation of what we call a life — climbs toward a peak labelled “material is important,” then bends downward toward a single point marked dead. Somewhere on that downward slope sits a moment I’ve labelled “learn to disassociate” — the point where we finally learn what actually mattered, usually too late to do much with the knowledge.

I didn’t draw this to be morbid. I drew it because it’s the most honest account I have of how most professional lives actually run.

We spend the majority of our working years becoming capable. Capable of earning, capable of climbing, capable of acquiring the things that signal we’ve arrived somewhere. And then, at some point — often later than we’d like — we realise material wealth was never the destination. It was fuel. Something to burn to get somewhere else. The trouble is most of us never defined where “somewhere else” was.

It gets worse. That wealth, that position, that accumulated identity — none of it is permanent. It can go in an instant, without notice. A redundancy. A diagnosis. A death. And it’s usually only through losing something — a well-paid job, a loved one, our health — that we’re forced to learn the lesson we could have learned on purpose, on our own terms, years earlier.

Here’s where I think leadership development gets the training backwards. We train people to become capable money-makers. We rarely train them to think clearly about the kind of life they actually want to live — the kind of person they’re being shaped into by the choices they’re making daily. What they’ll come to enjoy. What they’ll come to resent. The relationships they’ll end up cherishing, and the ones they’ll end up enduring.

If you want a framework that actually holds up, it’s this: start with the end in mind, then work backwards. Define what “good” looks like before you start measuring your progress toward it. Without that definition, you have no clarity of success — you’re just accumulating activity and calling it direction.

And this is the part that separates the people who drift from the people who don’t: they revisit the question. Regularly. Are we heading toward the direction we planned, or have we quietly drifted off it? Are we progressing — or are we just busy? Activity disguises itself as progress more easily than almost anything else I’ve watched executives and organisations fall for.

Success can’t be defined the same way for everyone. Money can’t be the only benchmark — not because money doesn’t matter, but because a single benchmark applied universally is how organisations and individuals end up optimising for the wrong curve entirely.

So here’s the question I’d actually sit with: if you drew your own curve right now — the one you’re living, not the one you planned — where would today’s mark fall? On the way up toward “material is important”? Past the peak, already learning to disassociate? And whichever answer is true — did you choose that position, or did you simply arrive at it by not stopping to ask?