“I didn’t choose the game, the game chose me.” Maybe as applicable to starting a business as it is to rap? Freestyling in rap, doing a improv scene, and getting a business off the ground all require a comfort with the ambiguity of going on a journey where the destination and path are unknown.
I don’t come from a family of entrepreneurs. My parents had solid, traditional jobs that they kept for decades. My father worked as a software programmer at a corporation and my mother taught nursing at the local community college. I never went to any camps, programs or workshops about building a business. Yet, entrepreneurship found me and chose me, even after my repeated denials.
During my downtime while working abroad, I would sketch out travel business ideas for organized group travel to far off places. I wrote it off as idle daydreaming because who was I to think of starting a business? I didn’t have the credentials, I didn’t work in the travel industry, and lastly, people who started businesses were different than me. They were brilliant, savvy with finances, and very established. I was a 22 year old college grad with a major in psychology. That was definitely not me.
But then, two years later that was me. I secured my first two contract gigs for two different nonprofits. I provided one with translation services and conducted market research for the other. I had no idea what it meant to structure and negotiate a contract. I accepted the first without doing any research but had started to dig deeper into dos and don’t by the time the second contract rolled around. In that process, I discovered a world of people who were much like me in terms of the personal and educational backgrounds starting to work for themselves in small ways, or outright start businesses. I thought improv was limited to comedy, and was fascinated that it could apply to the world of work as well.
Entrepreneurship is a lot like improv. The first rule of both disciplines involves listening. With improv, you need to deeply understand the other characters so you can construct a world for both the other actors and the audience. With entrepreneurship, you need to listen to your customers to understand their needs, values, motivations and challenges so you can build a solution that works. And both are most successful when the storytelling is strongest: two characters explore a situation or a founder works to solve a problem.
Both work best when you say “Yes and” to the feedback you get rather than trying to shut it down or otherwise deny or reject the reaction. I didn’t become an entrepreneur overnight. I worked on a few different contracts over several years both in between full-time work as well as alongside full-time work. I needed the feedback from those opportunities to build an area of expertise.
Entrepreneurship and improv teach you how to not fear failure. This last lesson was the scariest one of all for me. As a recovering perfectionist, I spent most of my career overly planning for every contingency under the sun. When you’re an entrepreneur you simply don’t have the bandwidth to do this. Overpreparation can kill a business because you can launch too late. I had to work to be ok with being good enough and learn how to reframe failure as learning opportunities.
I adore intellectual agility and flexibility that entrepreneurship requires. Running a business is an experience like no other. You build the plane while you are flying it. But much like improv, the jokes don’t always land the way that you expect. Sometimes this is a positive surprise when you uncover new opportunities. Other times, you learn that a door has closed. I’ve learned how to be ok with both scenarios.
After nearly four years of being an entrepreneur, I’m now returning to full-time work. I can bring these improv skills to a new stage and new audience. Many think the power of comedy improv lies in people being funny. Really it’s about the actors working together to build an interesting story and universe that enables humor to emerge. My capacity for storytelling as an entrepreneur has grown which will serve me well in a role with a larger platform. I’ll also be able to test out new approaches now that the risk of failure is lower. Unlike improv, you can be an entrepreneur without having a team. You have more creative and interesting sketches when you have other team members to bounce ideas off of and work to level up skills. Ultimately, it’s the creative collaboration that powers the magic of improv as well as entrepreneurship.
I’m writing an unedited personal essay everyday of November for #NaNonFicWriMo, the non-fiction spin on #NaNoWriMo. You can find daily prompts on my Instagram. Want to join in? The only rules are at least 750 words about the daily prompt and tag #NaNonFicWriMo to share.