Four years ago this month, I hosted my final Promax conference.
At the time, I remember thinking that I was closing one chapter and stepping into another. What I didn’t appreciate was how long it would take for that next chapter to come into focus.
Like most people in transition, I assumed clarity would arrive much sooner than it did. I thought I would spend a few months exploring possibilities, make a few decisions, and settle into whatever came next. Instead, the process unfolded over years. Some opportunities worked exactly as I hoped they would. Others quietly disappeared. Some paths that seemed promising led nowhere. Other opportunities arrived from directions I never would have predicted.
There were periods when I felt energized by where things were heading and periods when I questioned whether I was moving in the right direction at all. Looking back, I realize that I was asking the experience to provide something it was never designed to provide. I wanted certainty. I wanted confirmation that I was heading toward the right destination. I wanted to know that the experiment was working.
What I didn’t understand at the time was that the experiment wasn’t there to provide answers. It was there to reveal things I couldn’t see yet.
Every conversation, project, client, and opportunity taught me something. Some revealed strengths I hadn’t fully appreciated. Others clarified what I was no longer interested in pursuing. Over time, I stopped trying to force clarity and started paying attention to what the experiences themselves were teaching me.
In hindsight, one of the most valuable outcomes of the last four years has very little to do with business. It has to do with understanding myself. I learned the difference between what I thought I ought to do and what I genuinely wanted to do. I learned that some goals were inherited from expectations I had carried for years, while others felt deeply connected to the person I was becoming.
Today, I’m helping grow companies, advising founders, raising capital, and building ventures that I never could have anticipated when I walked off that stage four years ago. What’s interesting is that almost none of those opportunities were visible at the beginning. They emerged because I stayed in motion long enough for the path to reveal itself.
That’s why I’ve started thinking differently about transitions.
Most of us enter a transition believing we’re trying to find the answer. The right job. The right company. The right opportunity. The right chapter. Looking back, I think the real value of a transition is that it gives you the opportunity to discover something deeper. It teaches you what matters, what energizes you, what no longer fits, and ultimately who you are becoming.
Maybe that’s why the last four years make more sense to me now than they did while I was living them. What felt uncertain at the time was actually teaching me something. I just didn’t know it yet.
“Your 50” is a 50-week reflection series about realigning, activating, and expressing what comes next.