A few years ago, a mentor gave me a rather unusual exercise: “Never have I ever…”

The idea was simple. Every once in a while, complete that sentence honestly, but not as a game. Think about something you have never done, experienced or explored, and ask yourself why. More importantly, ask yourself whether you still want to do it.

At the time, I did not think much of it. But over the past few years, this question has helped me reflect on where I want to go next.

Being firmly in the 45+ group, I see a similar shift happening around me. Almost everyone who was my batchmate, old colleague or friend is now in the same stage of life. And our conversations have changed. They are rarely about salaries, designations or the next promotion. They are much more about family, parents, children, health, relationships and, increasingly, about what might still be missing in life.

That is where this simple question becomes interesting. “Never have I ever travelled alone.” “Never have I ever built something purely because I wanted to.” “Never have I ever taken a long break without feeling guilty.” “Never have I ever learned something just because I was curious.”

The point is not to create a bucket list. The value is in noticing which answers make you pause. Some things we have never done do not matter at all. Others stay in our minds because they point towards something we care about but have continually postponed.
Earlier in our careers, the questions are often about achievement. What can I accomplish? How far can I go? What should I build? At some point, the question starts to change.

What is actually worth doing now?

For me, “Never have I ever…” has become a simple way of exploring that question. It has helped me identify the things I do not want to keep postponing and, more importantly, understand what matters to me in this next phase of life.

Maybe finding your North Star is not about discovering one big purpose. Maybe it is simply about paying attention to the things you keep telling yourself, “I have never done that.”