I’ve never really liked being in charge. And I’ve never loved having someone in charge of me.
Some people thrive in leadership roles. I mostly felt trapped in them — like I was always supposed to have the answers, always expected to absorb everyone else’s uncertainty.
It’s one of the reasons I work solo these days.
But here’s the kicker:
I love collaboration. I love jamming on big ideas, building something real with other humans, delivering an amazing product. The difference?
Collaboration feels like a circle. Leadership often feels like a ladder.
In a collaboration, we show up as equals. In leadership, there’s hierarchy, decision rights, power dynamics — even when it’s subtle. And I didn’t love being the one making calls about what people could or couldn’t do.
When Anna and I started Stoked in 2011, we had no real plan to scale. But the work grew fast, and soon we had to build a team ~ 8 people, mostly in Nashville, a few remote. And suddenly I was a “boss.”
I didn’t want to recreate the toxicity I’d experienced in past jobs. I wanted the opposite:
A flat org. Freedom. Psychological safety. A place where everyone could experiment.
I thought if we were kind, open, and creative enough, our team would naturally rise to the occasion. That they’d feel ownership and be bold.
But here's the hard truth:
They didn’t want freedom. They wanted structure.
They didn’t want a collaborator. They wanted a leader.
And I didn’t want to be one.
They wanted scaffolding. I wanted them to build their own.
They wanted clarity. I wanted emergence.
They wanted management. I wanted autonomy.
Tears were shed. People quit. People were let go.
And honestly, maybe we’re all better for it.
What I learned:
- You can’t lead well by simply doing the opposite of your shitty boss. Reaction is not a strategy.
- Leadership is its own role. It takes time, emotional bandwidth, and a skillset separate from your craft.
- Employees want leadership, not vibes. If you want co-owners, say so. If you want employees, show up like a leader.
- Clear communication beats good intentions. Just because you’re nice doesn’t mean you’re being helpful.
- And me? I work best with collaborators, not employees. Equal footing or bust.
So if you’re an entrepreneur thinking about growing your team, just know:
Leadership isn’t something you can tack onto your current role.
It replaces your current role.
And if you’re imagining the kind of leader you’ll be, don’t start by asking,
“What would my old boss have done?”
Start by asking,
“What does this team actually need — and am I willing to give it?”