Over the next few weeks, we're spotlighting women who juggle a full-time career or day job and an after-hours passion project. Some have even hustled their way into running their businesses full-time. Doing what you love takes some serious work—but it's seriously worth it.
The Backstory
I went to school for theatre, and I’ve always enjoyed writing personal essays and non-fiction, so storytelling was a perfect fusion of the two passions. I was interning at the
Upright Citizens Brigade Theatre here in New York and had the opportunity to take a class with
Margot Leitman, who really opened my eyes to storytelling as a performance art. After a few years of going to
Moth StorySLAMs and other open mics, my friend
Sharon and I decided to create our own show,
Gems, to share our own stories while supporting other storytellers.
I found myself telling a lot of stories about a traumatic time right after I moved to New York, when I got hit by an SUV while walking down a city sidewalk. I was broken enough that I had to move back in with my parents in New Hampshire while I healed and went through physical therapy. Through storytelling, I started sharing the serious moments from that time, but also a lot of surprisingly funny ones, and I loved it when audiences identified with those experiences. I realized I’d written enough material around this to write a book, so now I’m working on a memoir about that experience.
How She Stays Motivated While Hustling (+ Juggling)
I'm completely ruled by my Google Calendar! I take time every Sunday evening to look at the week ahead and fill in my after-work hours with shows, open mics, or writing time. Once it’s in the calendar, my brain sees it as a real commitment that I can’t go back on. (Similarly, I put my work hours in my weekly calendar, which I’ve learned is totally weird, but it helps to see that visual time commitment!) Knowing that each of those blocks of time gets me closer to my goal of being a better performer and writer is motivating in itself.
Having a day job keeps me social and in touch with reality [as well]. I think if I did this full-time, I would get in my head too much. Also, being a technical writer at
Squarespace has made me a better editor of my own work and has helped me approach bigger projects with a structured plan.
I do sometimes feel burned out, and the most helpful practice for me lately has been to leave one weekend day totally open and, when I can, one weeknight. When I have my Sunday night calendar time, I sometimes fill in a night with a big “NOTHING” label as a reminder to take that night to chill and step away from projects. Taking a night off here and there helps me re-approach my work with fresh eyes later.
Her Must-Have Tools
I’m fortunate that I’ve chosen a hustle that doesn’t require a lot of tools—I could get by with only a pen, paper, and a microphone if I really needed to. However, the aforementioned Google Calendar is crucial to my day (especially the notifications) and I use Facebook, Twitter, and
my own website (hosted on
Squarespace!) to promote shows.
On the writing end of things, I recently discovered
Scrivener, which has been an awesome tool as I try to bring all the pieces of my book together. I also love
Evernote for keeping track of multiple projects at once.
On the Importance of Online Presence
It’s so important to have an online presence—even more so when my medium isn’t always a visual one. I have a love/hate relationship with Facebook and Twitter, but I find they’re still necessary for marketing and inviting people to shows.
I love having a
blog on
Squarespace, as that’s become the main space for my writing that doesn’t quite fit into other outlets. It’s also easy to keep
a running calendar of upcoming shows and
links to social media and
writing on other platforms.
Her Advice to Other Hustlers
What’s some advice you’d give someone looking to start a side hustle? What’s something you wish you’d known when you started yours? Any mistakes you made that taught you something major about running a hustle?
Be sure you’re doing something because you truly enjoy it, and not because you feel like you should. I spent a lot of time chasing other types of comedy teams and writing gigs because I felt like those would get me the most exposure, but they didn’t feel authentic. I didn’t start seeing success until I chased my real talents.
Also, having a co-host has really helped share the workload when it comes to producing a show. If you can find a partner who’s equally passionate and driven, pair up and hustle together.
What’s your best financial or business advice for someone who wants to run a side business?
At this point, I’m not making any money writing or performing, so I’ve sometimes had to spend some of my own money to produce shows. Depending on your hustle, that might be a necessary sacrifice. But again, be sure you’re not sacrificing too much—you gotta eat! See where you can make some compromises. For example, my co-host and I picked a venue for our show that’s an hour commute from where we live, but they let us use the space for free because we bring in an audience that buys drinks and food.
Where do you look for inspiration? Any other hustlers out there that you admire?
I enjoy going to other storytelling shows, since listening to other people’s stories almost always makes me think of something similar that I can write about or share on stage. Whether it’s a big show like The Moth or a small open mic, going to shows is the best way to stay connected to the scene. On the writing side, I like reading memoirs to see how other writers structure personal stories.
I’m a big fan of
Sara Benincasa, who literally
wrote the book on keeping your day job. She’s taught high school, been a stand-up, and written both fiction and non-fiction and never let any one job define her.
Where to Find Her
Images via Molly's website and Instagram.