Powerful Student's Stories #5 - Why Sharing My Failures Makes Me a Better Coach (and a Better Human)

I’ve always believed that I can have a great conversation with anyone. Seriously—anyone. You could tell me, “This person is the dumbest person alive,” and I’d still think, Nah, I bet we could have a conversation that would be worth a podcast. And I truly mean that.

But why?

Because connection isn’t about intellect, it’s about openness. And one of the most powerful ways to create that openness is vulnerability.

When I share my own failures—when I admit the times I messed up, doubted myself, or completely fell on my face—it does something interesting. It makes me human. And in that moment, the other person feels like they have permission to be human too.

I see this in coaching and learning all the time. People come in, guarded, afraid to say the “wrong” thing, afraid to look stupid. But the second I open up about a time I struggled, something shifts. They relax. They share more. And suddenly, we’re not in a rigid teacher-student dynamic anymore—we’re just two people learning from each other.

I also have this rule for myself: If I can’t get someone to talk about the coolest stuff they’ve experienced, then I’m failing.

Because that’s where the real gold is. Everyone has something amazing in them—an insight, a story, a weird experience that shaped them. And if I don’t get to that, it’s not because they don’t have it—it’s because I didn’t make the space for it.

Maybe it helps that I’ve never had a straight CV. My own path has been all over the place, which makes me naturally curious about all kinds of people. That curiosity? It makes vulnerability easier. And when you mix the two—curiosity + vulnerability—you get conversations that actually matter.

So yeah. Show your failures. Take the risk. Be human first. It makes all the difference.