Who says founders shouldn’t have side hustles?
Peter Thiel was running a hedge fund while also serving as the CEO of PayPal. Jack Dorsey has long led both Twitter and Square. Elon Musk has Tesla, SpaceX, the Boring Company, Neuralink, and who knows what else.
Not all founders can (or should) take side projects to the extreme levels that these guys have.
But all founders can (and should) self-diversify through side projects that inform their personal growth and/or contribute to the success of their companies.
By this point, we all know how personally toxic entrepreneurship can be. Founders both report mental health issues at a higher-than-average rate and more commonly have histories of mental health struggles. I know from experience how entrepreneurial tunnel vision can damage the other dimensions of your life.
Self-diversification means finding ways to engage and develop the other parts of yourself and your life. It’s necessary both for your personal health and the health of your company.
How my side hustle makes me a more thoughtful, present leader
For me, it’s writing.
I’ve always enjoyed reading and discussing ideas with people whose minds I admire. Last year, I finally formalized the practice: I began to turn what would have been private discussions/thoughts into public written content. It has numerous benefits:
- Systems thinking. I’m naturally a systems thinker, meaning I tend to think in terms of uniting disparate concepts. (The opposite is a linear thinker—I recently wrote about the interplay between these types.) My strength—and responsibility—as a founder is seeing the big picture and identifying opportunities that might not be obvious to other people. An outlet for systems thinking is necessary for this.
- Blind spots. The concept of personal/professional blind spots is one I’m constantly thinking about. Blind spots are the weaknesses we don’t know we have, and that we can only learn about through experience. Being an entrepreneur has repeatedly shown me my blind spots. Writing gives me a chance to reflect on them and articulate ways to grow.
- Network. This is maybe the most important piece. Distilling my ideas and publishing them gives me a thoughtful way to engage with my network. Networking has innumerable benefits—from having people to call in tough moments to simply surrounding yourself with people who can help you grow.
- Peace of mind. A big part of entrepreneurial anxiety comes from the idea that if your business fails, you personally fail. Your livelihood is endangered and you have to start from square one. Writing helps quell this anxiety. It’s not the main reason I do it, but I’m aware that the bigger my platform gets, the greater the potential for me to turn this into a second career. This peace of mind helps me approach my company in a more measured way.
Here’s how you can identify your side hustle:
- What do you engage deeply with in your leisure time? In other words, what activity do you love to do because of its intrinsic rewards? Maybe it’s martial arts, maybe it’s playing music, maybe it’s woodworking. There are no limits or definitions as to what your side project should be.
- In which of these activities is there a natural connection to your main gig? The connection doesn’t have to be as direct as, “Writing might help me find new customers or employees for my startup.” It could be more indirect. For example, woodworking might give you a tangible alternative to the cognitive work you do as CEO, and this could ground you and help reduce your anxiety.
- How can you use it to show up for your community? We tend to think about all projects—main gigs and side hustles—as income-generating or bust. That is, if it doesn’t produce revenue, it’s not worth it. But especially with side hustles, one of the main benefits is simply showing up for your community. Showing your people that you exist, and that you want to share the fruits of your private thinking/growth. Even if you can’t immediately trace this benefit to something more tangible, it’s inherently valuable.
Ultimately, self-diversification is a way for founders to round themselves out. Founders are a naturally myopic species; we need to be proactive about getting out of our own professional/personal bubbles.
