I spent my first seven years out of college working as a high school theater director at a high school in Brooklyn. Growing up a theater kid, teaching was never on my radar as a possible career path; I wanted to be a performer. The truth is—and I know it’s dangerous to compare—I never enjoyed performing the way my peers did. I did it because I was good at it and because it’s where I made the majority of my friends. That said, when I discovered directing/teaching, it was the most passionate about anything I’d felt in my entire life. Seeing my students taking their final bow was the stuff dreams were made of. By the time I started what would be my last year at the school, I was still directing but I had been promoted to Arts Department Chair and eventually Assistant Principal. I was 28 years old and, for the most part, I was content. But things changed mid-way through the year when a sudden health issue caused me to lose sight in my right eye. It was devastating. I had to undergo two surgeries that saved my eye, but not my vision. People always tell you life is short, but they never tell you that even if life is long, your senses and body can change at any time and in life-altering ways. Ironically, losing my vision gave me greater insight into what I wanted my life to look and feel like. It made me realize that mere contentment was not what I wanted for myself and that, while working as an educator was fulfilling, it was all-encompassing. The system that currently exists does not set up educators or students up for success. All of my relationships outside of the school building were hanging on by a thread and that included my relationship with myself. This led to the first huge leap of my adult life: resigning from my first and only real job. But the end of one phase of my life gave light to the next, a stage defined by me saying YES. Yes to life. Yes to risk. Yes to me.
I spent the next year or two working as a freelance teaching artist and finding odd arts and education-related jobs. I was barely making ends meet compared to what I was making when I left the school, but I was happy to have the freedom to figure out who I was and what I wanted my life to be. Here are a couple of things I said yes to:
I bought a one-way ticket to Paris to spend a month writing a musical with my best friend.
Raised $50,000 crowdfunding to get the musical produced after it had been accepted into the New York Musical Theater Festival.
Looking at my experience in the world and saying “I am an expert” and began branding myself as consultant.
Joined a theater organization/community where I’ve met life-long friends and my future husband.
Going back to Paris to get married in the Spring of 2018
Today, I work primarily as a Diversity, Equity and Inclusion consultant. When I finally gave myself the room I needed to breathe and figure things out, I realized that all of my life experience, passions, challenges, and triumphs were rooted in my relationship with my racial identity—my being a black man in the world. This understanding and the internal and external work I do to strengthen it has been leveraged into a career in which I get to do what I’m passionate about and get to do it on my terms. That means that not only do I get to work as much or as little as I want, but my time is literally worth more. It’s worth whatever I say it’s worth. I no longer go on interviews; instead, new professional opportunities are the result of conversations in which I and potential clients discuss what we have to offer each other. At 34, I work half the time I worked when I was 28 and make far more.
None of this happened over night and working for yourself doesn’t necessarily mean you are working less, it just means you’re working on your own terms. My advice is to build alliances with larger organizations whose business model relies on the use of private contractors. Let them find the work for you. Plant as many seeds as possible. Whether its via email, social media, conversations with friends – people have to know what you do in order to send people your way. Almost all of my work comes to me because people have said, “I actually know someone who might be great at that.” Sometimes it’s scary. Most of us are programmed to view security and a 9-5 job as synonymous. And fear is real, but it shouldn’t keep you from moving toward where you think your joy and passion are.
The best thing about having a flexible schedule is that I get to carve out real time to think about what’s next. I’ll say this: the next time I’d be willing to go back to an office is when I OWN the office. And I have my eyes set on taking the things I’m passionate about and good at, and creating something big that requires me to find other passionate and talented people to join me on this journey. To be continued…