This article was published in Live Magazine. You can learn more about the magazine and buy the print edition here.
When Jesse Reed and Hamish Smyth were designers at Pentagram, they stumbled upon an old graphic-standards manual for the New York City Transit Authority. They saw an opportunity to combine their design skills and entrepreneurial spirit (as teens, they had both started their own businesses) to create something new: reprinting the standards manual as an aesthetically pleasing coffee-table book. The transit authority was skeptical, but gave the duo its blessing. As it turns out, there was no need for concern—their Kickstarter campaign was funded within a day.
Five years later, Kickstarter is a client of Order, the design firm Reed and Smyth launched in 2017 in tandem with their publishing company, Standards Manual. “Over the course of a few years, [Standards Manual] turned into an accidental publishing business. It was never really supposed to be more than a one-off side project. It was something we did on nights and weekends while at Pentagram,” said Smyth over the phone.
The internet has introduced a new career track exemplified by Reed and Smyth’s trajectory: imagine a game of Snakes and Ladders in which developing a side gig that gets you noticed is equivalent to a coveted ladder that takes you right to the top. If, at one point, to succeed in graphic design was to climb the ladder rung by rung—intern, junior designer, senior designer, manager, partner—now the potential career paths are infinite, and many choose to branch out and make side projects their calling cards. Brand identity, but the identity is for yourself.
A running theme throughout the 2019 DesignThinkers conference in Toronto was this relatively new concept: having fun with your work and shifting freelance projects into full-time gigs. With several speakers who found lasting success through side projects—from Tina Roth Eisenberg’s Swiss Miss popularity to Reed and Smyth’s Kickstarter breakthrough—it appeared as if positive outcomes were the norm.
In reality, having a strong personal brand doesn’t necessarily equal success; most side projects won’t reach the level of popularity enjoyed by the presenters. So do side projects hold value if they don’t lead to owning your own design firm? I think so, but it’s good to approach them with measured expectations. Although jumping to the top of the design-career ladder seems enticing, there are no shortcuts for the lessons learned at larger firms. (Sorry.) No DesignThinkers presenters advocated racing to the top; instead, they encouraged listeners to combine play with entrepreneurship, creating meaningful side gigs that may or may not lead to a career that mixes passion with commerce. It seemed like the speakers were aware that shifting a side gig into full-time work is rare, and to suggest otherwise would be disingenuous.
I realized that all the serious opportunities I’ve been afforded can be traced back to projects I did for fun.Lauren Hom
It’s also possible for a side gig to simply be a passion project—something that exists outside of work that doesn’t need to be monetized. While that goes against the neoliberal hustle, it may also be the answer to a healthy work-life balance and fulfillment without ulterior motives. “You don’t have to quit your job to make personal projects you’re passionate about,” Adam J. Kurtz said in his talk. “If your art needs to sell for you to stay alive then you’re not making art that you love.” While Kurtz was able to turn his side project into a full-time endeavor, he’s quick to point out that he did his time working in agencies and at design firms.
While stories of success are enviable, it’s worth considering benefits that go beyond financial and career gains: side gigs offer the potential to learn new skills, form connections with like-minded people, and, of course, have fun. Many speakers emphasized that last point. “My path to success has always been to follow the fun. It’s a counterintuitive approach to getting serious work with serious clients. But I realized that all the serious opportunities I’ve been afforded can be traced back to projects I did for fun, my passion projects,” Lauren Hom said during her talk. “You can build a serious career out of not-so-serious work.” Eisenberg, who is also the founder of Creative Mornings, expressed similar sentiments about the intersection of play and design: “The things that made me happy were my side projects,” she said. Now, at her co-working space and her other companies, she attempts to cultivate joy for the mental and creative health of her colleagues. Marching bands. Drawers full of confetti. There’s a dress-up corner. You get the idea. “I want to make things I love for people who love them,” she said.
Fun and confetti sound like simple answers, but they don’t predict success. It can feel like there’s a secret equation that predicts which side projects will make it (and which won’t, leaving behind equally talented designers). While some side-hustle success comes down to luck, conversations surrounding side gigs would benefit from increased transparency. I’m confident some of the side projects presented at DesignThinkers were made possible through support that isn’t often publicly discussed. Whether it is flexible employers or a significant other looking after a child, there are often invisible structures that hold up the people we view as successful.
From the stage, however, some tips for successful side gigs surfaced repeatedly.
Meet a demand
If there’s currently an influx of [insert generic design trend], you won’t be meeting a demand by adding to it. Hom’s Will Letter for Lunch began when she noticed that restaurant chalkboards didn’t entice her to come in. So she introduced a bartering system whereby she would hand-letter restaurants’ sandwich boards for lunch—and chalk murals then become one of Lauren’s staples. “I started doing all this chalkboard work basically for fun, and for press. I was paid in cheeseburgers before booking real work for real clients,” she said.
Use your design skills to your benefit
An added perk is that designers are in a unique position to have the tools to market their work. Reed and Smyth’s Kickstarter video looks smart enough to be a television ad. (They casually remarked that it was thrown together.) Roth Eisenberg’s temporary-tattoo project, Tattly, raised suspicion on the first day of business when buyers couldn’t believe it hadn’t been around for longer. It’s simple: use the tools you have to brand not only yourself, but also your projects.
You never know who’s looking
“You never know who’s paying attention,” said Kurtz. He explained that his paper trails led to transformative experiences, including a Penguin Random House editor reaching out to suggest he write a book. This sentiment was echoed by Hom, who shared that she was handing out flyers about her chalk-lettering services (an old-school and endearing marketing tactic) and she happened to give one to the CEO of Skillshare—and that led to her teaching chalk-lettering seminars. Eventually, a literary agent contacted Hom and offered her a book deal. Side projects can start to feel like a snowball rolling downhill; one thing leads to the next, which leads to the next.
Your side gig is a business, so get paid
Having a successful side gig means being an entrepreneur, with lots of learning as you go. All the DesignThinkers speakers wear two hats: they devise fun and creative projects while advocating for themselves as business owners. Kurtz’s work thrives on social media, but he still maintains the importance of holding on to your intellectual property rights. When brands use his cheeky and evocative (and often touching) Post-it Notes art to sell products, Kurtz promptly sends an invoice.
In short, it’s not all fun and games. As one of Kurtz’s notes so aptly says: “Do what you love and you’ll
never work a day in your life work super fucking hard all the time with no separation or any boundaries and also take everything extremely personally.” Despite the conference stories of blending work with fun, there was an undercurrent of business savvy, proving that, at the end of the day, it’s still work and should be treated as such. From employers encouraging designers to indulge their passion projects to Roth Eisenberg’s joy-filled studio spaces, creative side gigs are becoming common. Just be prepared to leave them on the side.