May 2019: The month I decided to try to create an experience to allow people to apply improv comedy principles to their work & life.

I used the classic startup mindset: jump before you’re ready, and find the ground as you’re falling.

I sent a message to a couple of group chats, inviting everyone to an improv comedy workshop specifically for entrepreneurs. I sent the text on Thursday, and I scheduled the workshop for Saturday. I had two days.

As people started to RSVP, I realized, “Wait, what am I actually gonna do in this workshop?” I was honestly winging it. I had no concrete plan for the workshop. But I did have two days.

Our first workshop lasted for two hours, and looking back, it was pretty rough. We did traditional improv exercises, and when I asked participants to relate the exercises to their communication skills, they struggled. I hadn’t adapted the exercises from pure improv exercises into work-style, communication-focused exercises.

Despite its flaws, that first workshop was very important. Among the attendees was the CEO of a local company who would become our first paying client.

Of course, founding stories don’t always pan out perfectly, but consistently putting yourself out into the world does increase the chances for opportunities to come your way. I’ve found that I hold less regret for trying and failing, learning from the process, than never taking that first step at all.

You don’t need all the pieces in place to take that leap. Just take the leap.

So, what’s your first step?