How one question from my mentor made me rethink what I was really chasing.
I told my mentor I felt stuck and had felt that way for a few years. He asked why. I told him my long-term aim was to become CEO. He asked why that.
I didn’t have an answer. Not because I hadn’t thought about it, but because I had been circling that question on my own for a while without landing anywhere. He didn’t try to land it for me either. He just kept asking: what would that role actually let me do, why did it need to be that title, what was underneath the wanting. By the end, I understood something I hadn’t been able to say out loud before: I had been reaching for the position and hoping the meaningful work would show up once I got there.
I’m not walking away thinking titles or executive roles don’t matter – they can matter a lot. What’s changed is the order. A startup makes sense if I find a problem nobody else is solving and that’s genuinely the structure it needs, not so I can call myself a founder. Moving to another place or another function makes sense if what I can do lines up with what they need more than it does where I am now. And if either comes with a bigger title, fine — I don’t have to turn it down.
I just don’t want to go looking for the title first anymore and back into the work. I want to find the problem, understand the impact I could actually have, and let the role be whatever shape that requires.
So the question isn’t “what position should I reach” anymore. It’s closer to: where my strengths meet a problem worth solving, at the largest scale I can take on. That still leaves a lot open: staying put, moving somewhere else, taking a bigger role, eventually building something of my own. What I’m watching for now is whether I’m choosing because of the problem, or because some part of me still wants to prove something.
The title can still come. It just isn’t the reason to start.