The Night I Ran Out of Hiding Places

My boss had invited me to a dinner during a summit. A room full of founders, investors, nonprofit leaders, people building ambitious things in the world.

And then there was… me 😭. Or at least that’s how it felt in my head.

The room was already loud in that warm, overlapping way dinners get when everyone has settled in before you. People leaning toward each other mid-story. Glasses clinking. Someone halfway through laughing before the punchline even landed. Every chair had already been pulled tightly toward the table, like the room had unconsciously sealed itself shut.

And I remember doing that very specific kind of social math in my head.

One seat there. No, taken.

Maybe that corner? Nope.

Okay. Cool. Awesome.

There wasn’t a place for me.

Which, objectively, was SUCH a small thing. Tiny, honestly. But it landed with way more emotional weight than it should have because I think it tapped directly into a feeling I’ve quietly carried for a long time:

other people belong in rooms like this. Not me.

So before anyone could notice or do the awkward “we can squeeze!” thing, I quietly slipped back out of the room.

The hallway outside was darker and quieter. There was this thick curtain hanging between the hallway and the dining room, half pulled across the entrance, and I remember standing there pretending to check my phone while listening to the muffled sound of conversation happening on the other side of it.

Which feels almost AGGRESSIVELY symbolic now that I’m writing it out.

But at the time it didn’t feel symbolic. It just felt… familiar. That feeling of hovering right outside something. Close enough to see it. Close enough to hear it. But somehow still assuming the people on the other side belong there more naturally than you do.

And honestly, I think I spent a surprising amount of my life doing versions of that.

Not physically leaving rooms necessarily. More internally. Standing slightly off to the side. Trying not to insert myself too much into conversations. Trying not to take up unnecessary space. Framing myself primarily as helpful. Useful. Supportive.

Which are all things I genuinely value. I actually LOVE being the person helping other people build meaningful things. I love strategy and storytelling and connecting ideas and helping visionary people bring work into the world.

But somewhere during that summit week, I started wondering whether I had also quietly built an identity around standing ADJACENT to power instead of fully testing my own.

Then, my boss Sheila walked out into the hallway, spotted me immediately, and went:

“Wait, why are you out here?”

And I explained there weren’t enough chairs. Which, in hindsight, is maybe one of the funniest possible reasons to accidentally trigger an existential crisis.

But she immediately went back into the room, found another chair, and told me to come back.

And the strange thing is this:to get back to the table, I had to walk through the curtain.

Just physically. A few steps forward. Fabric brushing against my shoulder. That’s it. But I remember pausing for half a second because suddenly it felt like the curtain represented WAY more than a curtain should reasonably represent.

It felt like a threshold.Like one of those tiny invisible moments where you quietly decide whether discomfort means:

“You should leave.”

or

“You should enter anyway.”

So I walked back in.

And I ended up next to Jason, who started telling me about a moment earlier in his life when a friend asked him to join a startup after his cofounder dropped out. Saying yes meant walking away from a much safer path. Stable job. Predictable future. The kind of life that sounds responsible when you explain it to relatives at dinner.

He told me he packed up his car and started driving toward this completely uncertain future, and at one point, he had to pull over because he started crying from the weight of the decision.

And before turning around, he asked himself a question:

Why not me?

Then he kept driving, and that company eventually became a unicorn.

And weirdly, that question seemed to follow me through the rest of the summit.

Why not me?

Because over and over again, I found myself around people gently challenging the invisible limits I had placed around myself.

At one point during the summit, I was walking back to the hotel with someone who asked what I did. And I gave the answer I usually give. Something about supporting my boss. Helping with strategy and storytelling and operations. Being useful. Helping bring ideas to life.

Then somehow the conversation drifted into the kinds of things I actually love thinking about. Creative ecosystems. Why some stories resonate for decades while others disappear instantly. The invisible infrastructure behind meaningful work. The way visionary people often need someone helping protect the story while they’re busy building the thing itself.

And I remember talking faster and faster the way people do when they accidentally wander into something they genuinely care about.

At some point she stopped me and went:

“So… you’re a future founder.”

I immediately laughed. Like ACTUALLY laughed. “No no no no,” I said, before launching into what was basically a rapid-fire presentation on all the reasons I would never do that. I like supporting people. I’m better behind the scenes. I don’t think of myself that way. Etc etc etc.

And after listening to me talk myself out of my own potential for several minutes, she just looked at me and asked:

“Why not you?”

And honestly? I didn’t have a clean answer. Because I think somewhere along the way, I became very comfortable orbiting the thing instead of fully walking toward it.

If you stay adjacent to the room, you never fully risk rejection from the room.

You can always say: “I was helping,” or “I was supporting,” or “I was nearby.”

But eventually I started realizing:proximity and participation are not the same thing.

I also realized I kept talking about leadership as if it belonged to people much older than me. And maybe that’s part of what surprised me most about the week. Realizing how many people building meaningful things are not operating from certainty nearly as much as I assumed they were.

Then I heard a founder at the summit describe one of the ways she decides whether someone is actually serious about wanting her mentorship. She gives them a mountain bike and tells them to get it to the top of a hill by the end of the day. She doesn’t even care how they get it there. Carry it. Drag it. Push it inch by inch if you have to. The point is whether they keep going.

And I think that completely rearranged something in my brain because for so long I imagined leadership or creativity or building meaningful things as something people arrived at once they became fearless enough or impressive enough or credentialed enough.

But maybe that’s not it at all. Maybe the people who build meaningful lives are just the people willing to keep dragging the bike uphill. … Not gracefully either, just stubbornly.

And honestly, when I think back on the summit, the moment that stays with me most still isn’t some huge speech or breakthrough conversation. It’s standing outside that dining room, convincing myself the lack of a chair meant I should quietly disappear before inconveniencing anyone. Then being called back in. Then, walking through the curtain anyway. 

And maybe growing into yourself isn’t always some dramatic transformation where suddenly you become fearless and certain and fully self-actualized overnight.

Maybe sometimes it’s much smaller than that. It could be realizing the room might not be as closed as you thought. And maybe the people we admire most aren’t always the people who felt the most confident walking in. They’re just the people who kept walking through the curtain anyway.