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.
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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.
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Illustrated by Ivy Liu.
The first thing I did was to create a document to more accurately track all of my out-of-office initiatives.

I didn’t immediately see the tracker’s full potential; it initially just felt nice to see that I’d done stuff. About two months into the process, I met with my friend and mentor, who helped me reframe how I think about the document. He suggested that beyond simply keeping track of my work, I should try to “level up” each month, filling in more squares on the calendar,

Because the document is so visually simple to digest, it’s been equally simple to get a quick sense of how productive I am, where I'm slacking, and how I can push myself. It's been the most effective tool I've used to date. It’s also something I can look back at with pride, as I continue to push myself creatively outside of work.

Copy the template and try it for two months. Or, if you hate this idea, print out the calendar and burn it Viking-funeral style.
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Illustrated by Ivy Liu.
I’m results-oriented; I want to see pay-off for my work immediately. I’ve learned over time that being impatient about my work goes hand-in-hand with reactive thinking. I see something I want and I respond, rather than actively teeing myself up for future success on my own terms.

Playing the long game is smarter. Reframing how you understand goals and achievements across a longer timeline allows you to be strategic; you can approach things in a more organized manner. In the words of postmodern prophet Fergie, “A little [foresight] never killed nobody.”
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Illustrated by Ivy Liu.
I hate the phrase “elevator pitch” (almost as much as I hate the word “guestimate”). There’s real value, though, in learning how to articulate a concise statement about what you want and like to do.

For me, this was tough. It took many conversations and creative experiments to distill my passion into a sentence. For a long time, I assumed this was because I’m an extremely complex and layered person, and I simply can’t be put into a box. That’s wrong though. I can be put into a box. Furthermore, it’s good to be put into a box. Figuratively.

By refining your interests, you can communicate them more efficiently. It’s important to have a succinct explanation ready to go so you can get your point across clearly and intelligibly (and confidently and efficiently and eloquently) whenever you happen to meet someone who should know about your passions. You never know when you’re going to meet that person!

Tactically, I’ve seen concrete success using this technique: A few months before being offered my current job, I landed on a concise career statement: “I want to work in a branded content video studio.” Now, I do just that.
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Illustrated by Ivy Liu.
Good advice is really good. When I graduated from Haverford, I reached out to an alum I’d read about who is a successful television writer in L.A. Rather than a “follow-your-dream-believe-in-yourself” response, he wrote back with very specific advice that continues to inform my creative process. (My favorite line, pulled directly from his first email to me in 2012: “Don't send stuff to people who can help you before it's ready. Really ready. You only have one chance to make a first impression, so make sure you make a good one.”)

I’ve continued to collect the philosophies and opinions of people I admire. When I come across individuals in NYC and beyond who resonate with me (often by reading about them or their projects), I reach out and ask if they’d be up for grabbing a coffee or a drink.

I’m careful about my initial emails: Asking for advice is markedly different from asking for a favor, and it’s crucial to express the former. I’m straightforward about why I want to meet with them, and I’ve done my research so that I can be specific about what I admire, and what I want to learn.

There’s endless value in seeking out people you look up to and talking to them about how they’ve achieved success. And coffee is just the beginning — as you build a network of advice-givers, you’ll find motivation from knowing that they are invested in your success.
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Illustrated by Ivy Liu.
As a theater performer, most of my work lives only on stage. I’d put time and money into my shows, and then after my one-night performances, the work would disappear forever. I hadn’t given much thought to capturing my live work and — more importantly — creating work engineered specifically to live online.

After I started thinking about how to make work that I could send around to people, my creative world expanded significantly. I now have a library of original work (from videos to illustrations to writing) that I can share instantly and with anyone.

Focusing on creating shareable work has extended beyond reactive emails. As part of my “leveling up” approach, I’ve told myself I need to create three pieces of shareable content a month, that I can send around in a newsletter to a small distribution list. Keeping my friends up-to-date about my efforts helps me continue to produce new work. And if Aunt Judy ever finds herself in conversation with an Industry Person™, she’ll know exactly what I’ve been up to and can share stories of my achievements.
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Illustrated by Ivy Liu.
Spreadsheets are as exciting to me as W2 forms (which are not exciting to me). But being an organized freak maximizes efficiency. For me, this primarily manifests in categorizing my contacts. I have a number of different distributions lists (show invitations, newsletters, press outreach) that I continuously update as I meet people.

With these lists ready to go, it’s easy for me to send personal notes to the right people about relevant projects. For instance, for all of my shows, I like to send individual invitations to my “Show Invite” crew. In addition, leaning on my regularly updated contact list, I use Google’s “Canned Response” plugin to speed up the process.

The value of Tracy-Flick-level organization extends beyond my rolodex. (Do rolodexes even exist anymore? Oh yeah, they do.) Breaking down creative projects may feel like you’re sucking the romance out of them, but when you itemize everything you need to do in a tactical way, you have a better understanding of the required time and task management.

Get an overpriced notebook, steal a pen from your local bank, and do the To-Do-List Shuffle.
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Illustrated by Ivy Liu.
Reach out to people who are doing what you’re doing, and create with them. Some of my most valuable friendships and collaborations have come from reaching out to people I’ve casually crossed paths with and asking if they’d be up for “doing something together.”

Most of the people with whom I’ve created work (from video sketches to five-person musicals) began collaborating with me as distant acquaintances (this includes my hair stylist). Only good things come from talking about ideas with people you respect artistically.

And hey, on that note — any questions, thoughts, ideas you want to talk through? Send me an email!
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If 2017 is the year you've vowed to whip your bank account into shape, rapper, comedienne, and bargaining badass Awkwafina is here to help with her series, "Ballin' On A Budget." Catch all of her hilarious hacks for stretching your NYC paycheck as far as possible on Comcast Watchable, and always remember: just because you’re broke doesn’t mean you can’t still be a baller. Watch the episode below for her tips on perfecting your side hustle game.
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