How my lifestyle business enabled my gender transition and, why I wouldn’t trade it for building a unicorn

How my lifestyle business enabled my gender transition and, why I wouldn’t trade it for building a unicorn
Photo by Kristin Wilson / Unsplash

There is a popular narrative in the startup world that encourages the go big or go home mentality. It prioritizes eye-catching financial success at all costs and dismisses anything else as a lifestyle business. It stems from the mindset that the size of the financial outcome is the only thing that should matter to startup founders. To be honest, that is probably true for a lot of young entrepreneurs (especially men), and the venture capital industry that needs those big wins to justify their business model.

My business SupportBee launched on this day seven years ago. By all measures of the startup world, it can be classified as a ‘lifestyle business’. We are a small team of five humans (and one cat) working remotely from four different countries in four different timezones. We never raised any investment (except for a small grant from Startup Chile), and while we have been profitable for the last six years, we haven’t grown as much as some of our peers who have raised money. I used to secretly resent this but that changed about three years ago when I realized that I am transgender.

I then made the conscious choice to pull back on my professional ambitions and create space for my gender transition. It was a difficult decision to make but one that I am incredibly proud of. My business is not as big as it could have been with venture funding but I am happier than I would have ever been on that path. While in some ways I was forced to make that decision by circumstance it helped me see the incredible power of creating a profitable business with a small team. Because of the size of my business, I could mentally check out of it for a little while and focus on my transition fulltime. I doubt that I would have had that luxury in a venture-backed startup.

Although I make it sound like this decision came naturally to me, unfortunately, it didn’t. Up until that point I had already spent almost a decade in the startup world. Long enough that my sense of self-worth was entangled in the success of my business. Slowing down to focus on my gender transition felt like a cop-out. When I looked around there was a complete lack of a support network. I could hardly find any other transgender entrepreneurs to talk to. However, there was plenty of inspiration to be had in music. And I was very grateful for it. Nevertheless, as my transition grounded me down completely for a few years, I kept hating myself for not giving enough mind space to my business. This was always aggravated by the fact that my friends in the startup world didn’t understand what I was doing and would always want to talk to me about startups and would rarely ever ask me about my transition.

As I enter what I consider to be the last leg of my transition, I can look back and better appreciate the choice I had to make. Gender transition is a long, and painful process. At times it can feel like a bottomless pit. Much more so than I was willing to give it credit for. In hindsight, I wish I had allowed myself more space, and laid lesser guilt upon myself for doing what was necessary for my happiness. I now believe that as an ecosystem we should encourage more people to pick their goals based on their life’s situation and stop celebrating the one single milestone of becoming a unicorn, or die trying. We should rather celebrate the fact that a small profitable business enables you to pursue your goals as a person, and arguably that is more important than trying to make a dent in the world as an unhappy person.