How To Have A Side Hustle With A 9-To-5

Illustrated by Ivy Liu.
After graduating in 2012, I moved to New York City to pursue comedy. For two months, I lived on a couch. I had no job, no apartment, no plan. But, with nothing to lose, I took risks. More than once I approached a musician in Washington Square Park and asked if I could sing a song or two with them. That’s actually how I got my first gig: singing with a horn band at a jazz bar in Williamsburg.
Despite being almost completely broke, I felt fearless. Eventually it translated professionally, and I talked my way into a stable job in advertising. Sadly (and perhaps predictably), I soon became invested in a career that didn’t fulfill me.
I eventually moved to a different company in the same industry. I developed significant friendships there, I found important mentors and role models, and I worked really hard, which felt good. I rediscovered my creative energy and developed a one-woman show that I got to perform at various off-Broadway cabaret theaters around the city. My colleagues filled the theater every time, and I still feel so lucky for that support. With this newfound momentum, I started feeling that itch again. I was seriously considering pursuing comedy full time — and then, bam, I got a shiny new job offer.
I thought this new job would satisfy me creatively, but it ended up being a monumental disappointment. Every day for nine months, I felt professionally and emotionally defeated. It did, however, push me to a point where I couldn’t ignore the discomfort of feeling unstimulated.
Before the crummy job — and the letdown that came with it — I had no routine for pursuing my extracurricular passions. I did creative things when I had time and without an overarching strategy. I’d seen relative success with these projects, but I definitely wasn’t working toward a bigger picture. At the new job, where I felt like I had little control over my happiness and time, I was more determined than ever to work on something personally inspiring and meaningful. I developed a regimented routine to stay on track, and I considered my passion projects to be one unified job, outside of a less-fulfilling day job.
Now, I have a full-time job that I really love at a new company. While I feel more professionally fulfilled than ever, I’ve continued to pursue my passions outside of work. I’m able to do this because I exercised the right muscles during that nine-month period prior. In 2016, I appeared on live TV, wrote a sketch that went viral, and committed to a bi-monthly run of my one-woman show at a theater in the West Village.
Ahead, I share my tips for pursuing your passion projects — whatever they might be — while working a full-time job.