Playing the Game.

When I started my first business I had no idea what I was doing. Wracked with insecurities and imposter syndrome, I jumped feet first into the newly buzzing local startup conversation. I attended startup events which led me to startup communities and put me in the presence of people with answers — predominantly, white men in positions of power.

What began as a desire to meet and learn from the startup community quickly became a chase for validation.

This wasn’t the first time I tried to prove I could hang with the boys. 

Morristown, Indiana. Spring of ’92. Second grade. Recess was in session and Corey, the class-crowned basketball champ, challenged me to a game of one on one. While some kids headed for the swings, many more gathered around the cracked, black concrete to watch. Knee socks pulled high and ponytail even higher, I stood tall in my usual tomboy attire. Pressure bubbling up inside, I stepped out on the court. We checked the ball at the top of the key and the game began. I played it hard. 

With my sweet victory came bragging rights, a new title, and the stress of upholding it.

Startup culture is disturbingly similar to my second-grade playground. Although I wasn’t afraid to step onto the court, it was exhausting having to prove myself again and again. A few years into my startup journey, it was clear that raising capital was the name of the game. But with limited places to secure funding, the gatekeepers—mostly older white men—held all the power. Whoever could prove they were most worthy won the cash.

So I played the game and played it hard. I participated in countless pitch competitions and demo days, talked at length with Shark Tank producers, and was featured in TechCrunch articles and on Good Morning America, touting the latest raise or greatest feature. 

But after a decade of being a female founder in a male-dominated startup world, I realized that, unlike basketball, entrepreneurship doesn’t have a buzzer. There is no winning in business. No finish line. Proving myself in a game that can’t be won only results in a few minutes of satisfaction before the fulfillment fades. 

So I shifted my mentality from proving myself to believing in myself—not overnight, but little by little, each day. Titles and bragging rights have lost their appeal. When people in power challenge me to play the same old game, I still feel the reflex to respond like my second-grade self. They say I’ve lost my drive to compete in business, but I don’t see it that way. I’ve simply decided to do business differently. I’m building a profitable business rooted in my values, and I’m freer for it. Trading the chase for lasting wins.