I was absolutely terrified of becoming That Guy.
You know exactly who I mean. We've all seen him.
The former athlete who comes out of retirement because he couldn't find anything else that filled the hole. The one who keeps showing up at the old arena, hanging around the edges, telling glory-day stories that everyone's tired of hearing. The one whose identity got frozen in amber at age 27 while the rest of his life kept moving forward without him.
On the Rich Roll podcast, I admitted this fear publicly for the first time. It had haunted me for years during my transition. Kept me up at night. Made me question every decision.
Michael Phelps captured the same terror: "I'm Michael Phelps, a swimmer. But I don't know who I am."
That's the identity crisis every high performer eventually faces. Not if. When. The moment when the thing that defined you for decades is suddenly gone and you're standing in the wreckage wondering what comes next.
Your whole life boils down to this specific moment that happens in a snap—and then it's over forever. You go from anonymity everywhere to suddenly nowhere. From knowing exactly what to do at every moment to having no structure at all.
Just terrifying blue sky stretching in every direction. Total freedom that feels like falling.
This fear of becoming "That Guy" is something I explore in motivational talks with leaders navigating major transitions. Whether it's executives aging out of roles, founders POST-exit, or anyone whose identity was built around something that no longer exists—the pattern is identical. The fear isn't really about clinging to the past. It's about terror of the present.
I've advised founders through their POST-exit identity crises. I've worked with executives who spent thirty years climbing a ladder only to realize they don't know who they are without the title. The achievement level doesn't protect you from this fear. If anything, higher achievement makes it worse.
Here's what took me years to understand: That Guy Syndrome isn't really about clinging to the past. It's about terror of the question: What if the achievements were the whole thing? What if there's nothing else underneath?
In leadership workshops on transition and reinvention, I help people reframe this fear. The goal isn't finding what feels the same as before—that's impossible and keeps you stuck. The goal is discovering what feels true right now.
Instead of asking "What can replace what I lost?" ask: "What am I genuinely curious about that I never had time to explore?"
The answers are completely different. And the second question actually leads somewhere new.
This is why I've chosen to build a portfolio career—speaking, advising, investing—rather than trying to recreate what I had before. Each piece feeds different parts of who I'm becoming, not who I was.
The person you're becoming doesn't need to match the person you were.
That's not regression.
That's evolution. Get after it.
About Apolo Ohno: Apolo Ohno is a sought-after keynote speaker and leadership advisor known for translating elite performance principles into practical leadership behaviors. His work focuses on authentic leadership, executive presence, and the Gold Medal Mindset - helping executives and teams perform with clarity under pressure, communicate with conviction, and lead with credibility when the stakes are high. In his keynotes and workshops, Apolo helps leaders identify the unseen patterns, narratives, and habits that quietly limit performance, then replace them with a repeatable system for focus, resilience, and decisive action.