I’m working with a CEO who keeps saying yes to opportunities that drain him. He knew his last company wasn’t the right fit months before he left, and after it went public, he took significant time off and swore he wouldn’t do it again.
A year later, he was pulled back in by an even bigger, more prestigious opportunity. He came to me wanting to understand how he could see the pattern so clearly, move all the way through a transition, and still end up in the same place.
Almost everyone I work with in transition wants to get to the other side as quickly as possible. One of the most common questions I’m asked is, “How long will this take?” I always answer, “It depends.”
Sometimes life doesn’t leave much room to be patient or slow down. We have a mortgage, bills to pay, and people counting on us.
More often, the uncertainty is unbearable. The structures that once held you have fallen away, you're not who you used to be, and you don't know what's next. That's when the old patterns come online to get you the hell out of there.
You reach back for the life you just left, or jump ahead into the next role before anything has really changed, because you know its shape and rhythm. There’s comfort in the familiar, but hitting rewind and fast forward lead to the same place: right back where you started.
During my own transition, I hit rewind twice. Right as I was becoming a coach, I was recruited to Primary as a venture partner. Despite my hesitation, I said yes because it was familiar and I didn't know how to stay in the uncertainty. When I finally left venture to focus on coaching, I raised a $5 million angel fund as a side hustle. I kept one foot in the old world, just in case.
In the thick of my own transition, my mentor Jerry Colonna told me the story of the boy and the cocoon from Zorba the Greek. Years later, I shared that same story with the CEO.
One morning, a boy notices a cocoon clinging to a branch. He stops. After a moment, he sees it moving. What timing. A butterfly is slowly working its way out. He crouches down and watches this miracle.
It’s slow. Impossibly slow. But he can’t look away. A tiny opening appears. He can see the butterfly strain, then rest. Then strain again.
The boy stays with it as the sun climbs across the sky. Eventually, he can’t bear watching it struggle any longer. He leans in and warms the cocoon with his breath.
It works. The cocoon begins to soften. Eventually it breaks open, and the butterfly emerges.
The boy’s delight lasts only a moment once he realizes the wings are not fully formed. They’re folded against its body, damp and fragile, and the butterfly trembles as it tries to open them.
He leans in again and warms it with his breath, hoping this time will be enough. It isn't. The wings never open, and the butterfly never flies.
It dies in his palm.
The boy carried that small butterfly on his conscience for the rest of his life. He learned that some things must unfold at their own pace.
I’ve come back to that story again and again in my life and coaching practice because it reminds me that change has its own pace. If we want something new to emerge, we have to stay in the cocoon long enough for it to happen.