The Art of the Side Hustle
Girlbosses, unite!!!!!
One of my favorite insults is looking at someone annoying with a withering glare and saying, “You really should get a hobby.” I’ve never had the opportunity to use it but what’s not to love???
The sass!!! The passive aggression!!! Reminding someone that bullying is tacky when you’re punching down!!! (By this I mean if I were to bully, say, Texas Senator Ted Cruz who, strictly speaking electorally, has more power than I do, I would be punching up which would make my jabs funny. If Ted Cruz bullied me, he’d be a tasteless little troll boy.)
But the other reason why telling someone to get a hobby is so fun is because, very simply, hobbies are fun!!! People who have the time to slash reproductive rights or traffic immigrants to Massachusetts are lame and boring. Hobbies are the spice of life—something that equally inspires and grows from your passions and personality. They’re unmarred by your career or your friends or your family…right?
In the post-girlboss era (long live the girlboss) as well as the post-lockdown era1, hobbies are frequently commodified to be deemed worthy of existing in a capitalist environment. It’s either that or they must exist in a way that does not interfere with your ability to participate in capitalism, which is a pressure I personally know well (I’m writing this on the subway between plans on a Sunday).
Without passing too much judgment on these unspoken rules, I wanted to look at a specific dichotomy within this hobby conversation which is: what happens when your hobby is creative and your job is corporate? How does one land there and what feelings arise as a result? In other words, we’re building off of Sandra’s conversation about Gen Z’s participation in capitalism and Bianca’s conversation about commodifying your hobbies.
That’s why this week, I’m talking with my friend Courtney Wong—who is both a brilliant artist and corporate girlie—about her experience balancing her hobby with her job, why she was inspired to do both, and how she views success.
Hiiiii I'm Courtney. I was born and raised in California, went to college in Boston, and now live in NYC! When I'm not burning the midnight oil for my full time job at an advertising agency, you can find me reading, illustrating, cooking a mean shrimp pasta, or watching the same TV show I've already seen 20 times over.
Ah Oui… Árt 🤌
First, can we just start by admiring Courtney’s art for a second?
In the multiverse crossover of my own life, I reached out to Court about commissioning art for my best friend’s birthday. The prints couldn’t have turned out better because, as we can all see, I was dealing with a pro.
I asked Court:
Emily: Can you explain what you do both in your career and with your art?
Courtney: I work full time as a strategist at an advertising agency in New York. As a strategist I help shape the content that goes out into the world, mining and crafting insights in the lead up and analyzing the performance after the creative work is live.
As an artist (which I wouldn't confidently call myself, but we can get into that later), I mainly produce digital illustrations through the help of Procreate and my iPad. Typically, I'm illustrating portraits of people (and the occasional pet ;) ), but I also like to paint just about anything in my free time.
Emily: Is there one you're more passionate about?
Courtney: It's hard to say what I feel most passionate about. My gut instinct wanted me to say "art, of course!" But when I really sit with that thought, I realize I really don't act like art is the route I'm most passionate about. I put most of my energy, time, and mental stamina toward my advertising job rather than my art aspirations.
I would say that I'm passionate about both areas but in vastly different ways. For advertising, I'm passionate about this because I genuinely love the work that I do and value how this job sets me up for (traditional) success, whereas for art, I'm passionate about this because it's a hobby I've carried with me throughout my entire life and I'll always have interest in it.
Emily: When and why did you decide to start pursuing your artistic passions?
Courtney: Technically, I've been creating art since I knew how to hold a crayon. But monetarily speaking, I started in 2020 when the pandemic hit and I, like many others, found myself starved for entertainment. So, I picked up my iPad and began creating digital illustrations just for fun.
Eventually, I started an Instagram account for my art, kept posting my illustrations, and received a commission request that snowballed into a tiny little business that is still running today.
In a piece for The Interlude Magazine last year, Anita Ramaswamy wrote about how “nearly four in 10 people in the U.S. pursue some sort of side hustle, and during the pandemic, nearly every platform geared toward content creators saw downloads skyrocket, from Substack to Cameo to Twitch to Patreon.” Ramaswamy goes on to interview several individuals who have different reasons for turning their hobbies into hustles.
What stands out the most (and what Ramaswamy goes on to explicitly address) is the very evident gender gap:
a majority of women rely on their side hustle to cover their regular living expenses compared to a minority of men. The pandemic has also taken a disproportionate economic toll on women, to the point that some economists have dubbed its effects the “shecession.” With female unemployment hitting double digits this year for the first time since 1948, more women feel pressure to monetize their hobbies and passions to make ends meet.
As Courtney explained, she didn’t set out to create art with the intention to sell it but realized it could grow into supplemental income. I asked:
Emily: When did you decide to start monetizing your work and how has that impacted how you view its importance in your life, if at all?
Courtney: Honestly, I only started monetizing my art once I had received requests on Instagram to commission work from me. It was never something I consciously planned for with my digital illustrations.
I think what I’ve found from trying to build my Instagram account and commissions is that because art is such a safe place for me to express my creativity, it’s easy for external pressures (like money, Instagram followers, likes, etc.) to make the act of creating art less fun and turn rotten. The expectation to post X amount on Instagram, to earn X amount of dollars a month, to have X amount of followers, causes my art to feel like a chore rather than a choice.
Recently, I’ve been trying to avoid falling victim to this by letting my inner desire to illustrate or paint organically tell me when to create something, rather than forcing myself to illustrate because I haven’t posted in a certain amount of days, for example.
This is the part of our conversation that is almost too meta for me as I’m writing about it here on my own side hustle. While Substack is designed so that writers can charge for their work (or art), I still don’t think of this very newsletter as something anyone would deem worth paying for.
But why? I take E4P as seriously as I take my job in terms of accountability, quality, and the energy I invest. I’ve been told this is informative and entertaining to read (and yes—it has 1000% gone to my head). I’m one Cat video away from going viral enough to generate ample traffic to this site. Still, no matter what, there’s always a needling little voice telling me that because this isn’t my career, because I’m not an established (or even very professional) writer, because this is kind of just a glorified hobby, I shouldn’t ask other people to value it as much as I do.
And that, girls, gays, and theys, is my imposter syndrome talking.
Nooo Don’t Have Imposter Syndrome You’re So Sexy Aha
According to bestie Wikipedia, imposter syndrome is “a psychological occurrence in which an individual doubts their skills, talents, or accomplishments and has a persistent internalized fear of being exposed as a fraud. Despite external evidence of their competence, those experiencing this phenomenon do not believe they deserve their success or luck.” The original 1978 study the term is derived from looked at high-achieving women and “posited that ‘despite outstanding academic and professional accomplishments, women who experience the imposter phenomenon persist in believing that they are really not bright and have fooled anyone who thinks otherwise’” (X).
I’m going to go on a little tangent here because the article referenced above is from the Harvard Business Review and is titled “Stop Telling Women They Have Imposter Syndrome.” The core argument of the piece is looking at how the legacy of systemic racism and misogyny (among other biases) in the overall workforce has gaslit women—namely women of color—into believing that they are unqualified the second they enter any physical or metaphorical room because “imposter syndrome directs our view toward fixing women at work instead of fixing the places where women work.”
But what about when there is no workplace, just yourself and whatever you’re creating?
I asked Court:
Emily: What is your relationship like with imposter syndrome?
Courtney: I've always struggled with imposter syndrome, long before I even knew it had a name. I've always believed that I don't deserve what I have, and in the art arena where you can define success in a million different ways (especially when it's not your primary source of income), imposter syndrome often feels debilitating.
For one, I have imposter syndrome about even calling myself an artist, even though Google's definition is: "a person who produces paintings or drawings as a profession or hobby," "a person who practices any of the various creative arts, such as a sculptor, novelist, poet, or filmmaker," "a person skilled at a particular task or occupation." By every definition of the word, I am an artist. But my imposter syndrome would never let me introduce myself to anyone as an "artist."
I would feel like I'm setting myself up to disappoint them, because I'm not at the level they would presume someone who calls themselves an "artist" would be. Even as I say this out loud I know how ridiculous it sounds, but it's harder to claim that title as my own as opposed to my advertising job where I was quite literally given the title of "strategist."
Maybe, then, the HBR piece was only having one part of the conversation. Maybe there was something to be said about the internalized biases we all carry as well as explicit institutional discrimination.
Courtney’s answer made me think: if she can’t call herself an artist when she’s someone I sought out and commissioned art from, at what point would she ever call herself an artist? Turning the tables a little too introspectively, I wondered: at what milestone or achievement would I ever call myself a writer?
But babes, the tables didn’t stop turning there!!!!!!
I started thinking about why Courtney and I were both clearly searching for a level of credibility to assure us that we were successful at our passions, and I realized how twisted that was!!! They’re our hobbies—they’re not tests to be graded, or prized pigs to be judged.
Then I remembered I asked Courtney about that very same notion (which made me feel a little icky and very Olivia Rodrigo):
Emily: Since your art is a form of self-employment, how do you mark your growth and success the way a manager in a more traditional role would?
Courtney: My art was never something I thought I would need to measure success in. Since I started this from the pure pursuit of something I’m interested in and love doing, it’s been a bit of a struggle to also give it a measurement of success. For so long, how I measured my success in art was my ability to evolve, and that is largely still how I measure success for myself today — growth, improvement, progress.
Now that I’ve been able to make some money from my art, I could easily say making X amount of dollars or receiving X amount of orders is how I measure success. But I’ve found that applying that type of traditional measurement of success to my work taints my relationship with art, making it less pleasurable and sacred to why I love doing it in the first place.
Emily: How does your definition of success in your corporate job differ from how you define success with your art?
Courtney: In my corporate job, I measure success very traditionally. It is easier for me to equate my success with my salary, title, praise from managers, etc. than with art where I decide what success means to me. Sometimes measuring success in my art feels like a moving target, whereas my corporate job has a clear roadmap of achievements laid out in front of me.
Well, if success is not an easily distinguishable metric, then what is?
And it hit me… the answer has been right in front of me the whole time. The archetypal story structure is not called the Hero’s Great Success—it’s called the Hero’s Journey. The end result (money, fame, other things Drake raps about) is only worthwhile because you put in the work to get there… you know… you started from the bottom, and now you’re here.
The best metric to measure a passion by is not external success but internal commitment and effort, so I asked Courtney about some of the trickier moments she has had to work through:
Emily: Do you ever find it hard to balance growing in your career with growing your personal brand and business?
Courtney: My corporate job feels comfortable. It’s a place where I am making a good salary and have established expectations set. Day to day I spend 75% of my energy and time in my advertising career. By the time I log off for the day or make it to the weekend, I’m spent. That other 25% is going toward resting, cooking, errands, and other things I need to fuel myself to get through the days.
So, yes I’ve found it has been hard to balance my corporate career growth with my art and personal brand’s growth. Art, unfortunately, hasn’t become even close to a priority yet in my life because I’ve been cushioned by my corporate job to stay afloat.
Emily: What has been the biggest stressor or stressors when it comes to putting your art and yourself out there to reach an audience?
Courtney: I talk a big game about how success can look like so many things beyond traditional measures, but at the same time I have a big fear of failure.
Putting myself out there with my art and really trying to grow that business is A) scary because I’m not fully confident in who I am as an artist yet B) feels embarrassing to publicly try and then not have it go anywhere.
I try to remind myself of that quote (by Winston Churchill): “Perfection is the enemy of progress.” If I keep waiting until I feel like I’m 100% ready to really invest in myself as an artist, I’ll never do it. I’ll never feel 100% ready.
Perhaps you don’t need to be 100% of an artist to call yourself one—you just need to make art or code or play video games and enjoy it enough to say, “Well, I’m going to keep doing this. So I guess that makes me… a person that does this.”
Otherwise, I think, we all become Mark Zuckerbergs: he took his passion for being a misogynistic twerp and morphed it until he had created a capitalistic Frankenstein. If we measure success the way he does (money, fame, other things Drake raps about), we lose what we loved in the process.
Good Vibes Only!!!!
We’ve talked a lot about the problems that come with pursuing a hobby: imposter syndrome, moving targets, capitalism. But what about the amazing things that come from taking the passion and love from something inside of you and allowing it to exist out in the world? How beautiful is that?
To turn the tables á la Kevin and Nick Jonas again, I asked Courtney:
Emily: Where do you find your best inspiration comes from?
Courtney: My best inspiration definitely comes from Pinterest and TikTok. Pinterest has such a plethora of niches and genres, so there really is a never ending platter of inspiration to choose from. Sometimes I'll search for something specific like "cocktail wall decor art," and sometimes I'll let my curated algorithm naturally inspire me.
I find art content seems to hit my TikTok FYP less frequently than I would like (probably because food, fashion, and pop culture gossip dominate my feed), but the art videos I usually see are ones about painting, so I'll use TikTok to inspire me when I'm working in the paint medium specifically.
Emily: How have your parents inspired you to pursue more creative endeavors?
Courtney: My parents have always been my biggest inspirations and supporters. Without them I probably wouldn’t have stayed interested in art for as long as I have.
All my life people have said that I seem like the perfect mix of them. While they’re both pretty much retired at this point, growing up they both modeled how you can be successful in life while enjoying what you do. They both have a creative spirit, and I think I’ve picked up a lot of talent and ambition from them. For a majority of my life my mom has worked a corporate job while my dad has pursued a variety of creative avenues (ie working at ad agencies in the creative dept, woodworking, selling on Etsy, etc).
I was able to see so many different definitions of success, allowing me to feel free to pursue what I actually have heart for no matter what that looks like.
Emily: What is your favorite thing that you have created and why?
Courtney: I have a painting hung in my bedroom that I have a special place in my heart for. I painted this piece last summer, and it was inspired by a lot of mixed media paintings I was seeing on TikTok at the time.
(Side note: I have just realized I have never formally named my paintings...I don't know if that's something you do if you don't have any plans to sell them...)
This painting from last summer has a poker theme with actual playing cards mod podged all over it. The act of creating this piece was really fun and new for me, as it involved a lot of techniques and ideas I hadn't explored before. The reason my mind thinks of this piece of art and not any of my digital work is because this painting was never truly meant for anyone else but me.
I created it cause I wanted to... and I had fun doing it.
Emily: What would you say to someone looking to start pursuing their passions? What do you wish you knew before you started creating your art?
Courtney: Honestly, I’m glad I didn’t know much when I was getting started. I learn so much by doing, and I’ve always enjoyed the process of finding my style, rhythm, and voice with art over time. So, no. There’s actually nothing I wish I knew before, because everything I’ve learned has been an important lesson to have lived through myself.
As Nike says, “Just do it.” There will never be a better time to start than now. If you keep waiting for the perfect time, it’ll never happen. Also, you fully do not have to monetize your hobby if you do not want to. You are allowed to preserve that interest and still introduce yourself as an artist, a writer, a dancer, a designer, an anything.
Because you are.
Thank you a billion to Court for being so talented in addition to being brilliant and insightful!!!!
While we’re on the subject (if you’ve made it this far): the majority of people who have come on E4P and spoken about the things they love often apologize to me or ask me if I’m sure I wanted to talk to them. They feel the same weight of imposter syndrome that Court described today and have convinced themselves they have not hit the arbitrary imaginary level of credibility to talk to lil ol’ me.
If you’re going to remember one thing Courtney said today, I hope it’s that you don’t have to be 100% of anything in order to participate in—or even just talk about—anything.
Not post-Covid!!!