A Brief Study of Creativity, As Seen Through Side Projects

Chances are, you’ve had a side project.

Maybe you don’t have one right now, or maybe you do.

Maybe you don’t call it that. Maybe it’s a hobby or just that creative thing you do for fun…on the side. But it’s this thing you do because it brings you some joy, sanity, freedom, control or all of the above. It gives you a time and space, when everything else may be out of your control, to do something just for you.

We don’t usually think about how side projects have often been culturally, creatively and even economically significant and led to many things like creative breakthroughs, career transitions, billions of dollars in business, and more.

But it makes a lot of sense.

Side projects, regardless of what they’re referred to as, are the backbone of creativity. After all, the very definition of creativity involves engaging a different way of thinking, a deviation, a freshness, a newness.

And it’s hard to get that from something that is simply a continuation of what already exists and what has only previously been defined as important and worthwhile.

New ideas are often born from side projects, except perhaps for the rare and privileged few who can afford to tinker around with random ideas full-time.

Even so, people who are full time creatives, even very famous people, whether they work for themselves or for others, have side projects too. Because regardless of how much money or clout someone has, there’s usually something new and off the path that they’re interested in exploring. And even if it’s not a financial risk, it can still feel very risky in a different kind of way to put your reputation on the line and try something outside of what you’re “supposed” to be doing.

Here are some side projects you may or may not have heard of across all kinds of creative fields, from the side projects of creative people to side projects within companies, from people of the past to modern creatives, from ultra-famous celebrities with side projects to side projects of people like you and me.

• Harper Lee, famed author of To Kill a Mockingbird, dropped out of law school and worked as an airline ticketing agent while writing on the side.

• Agatha Christie was a pharmacist’s assistant when she started writing detective novels.

• World renowned film director Ang Lee was a househusband in his thirties before he made his first film. I’m pretty sure he didn’t just outright abandon his kids to make his first movie.

• Developer Eric Barone graduated from college studying computer science and couldn’t find a good job. He ended up working as an usher at a local theatre company and spent the rest of his time working on developing a game that he hoped would become a project he could showcase to prospective employers. After 4 years, he released his game, Stardew Valley, which as of 2020, has sold over 10 million copies worldwide.

• Author Cheryl Strayed was a, wait for it—waitress, youth advocate, political organizer, temporary office employee, and emergency medical technician—throughout her 20s and 30s, while travelling and writing, according to Wikipedia. Contrary to popular opinion of what exactly constitutes a “real” writer or creative, Cheryl binge-writes. She doesn’t write all the time, every day. She works, travels, writes in between. Once, to a woman who said that she could only write once a month because that was the only day that she didn’t have the kids, Cheryl once said, 1 day a month is 12 days a year and said,

  “You can do a lot of beauty in 12 days.”

• Basecamp a project management software, was the side project of a web development company called 37Signals. Later on, the company refocused and even changed its name to Basecamp

• Unsplash was the side project of Crew, with ambitions that it might make a great traffic generator for their main product, a marketplace to hire design talent. It launched as a Tumblr blog in May 2013 and today, is the go-to for not sucky stock photography. Meanwhile, Crew sold to Dribbble in 2018 and no longer exists.

• Facebook was originally a hot-or-not app built on the side of Mark Zuckerberg’s college education stint at Harvard.

• Superstar Robyn Fenty, better known as Rihanna, may best be recognized for her music. She has 14 number-one singles is one of the world’s bestselling music artists of all time. But the bulk of her fortune actually comes from what used to be her side ventures: beauty and fashion lines now worth over $17 billion. Guess she can give up her day job now.

• Jessica Hische, designer and author, has a degree in Graphic and Interactive Design but actually built a career in lettering and illustration from the side projects she did including Daily Drop Cap, in which she spent anywhere between 20 minutes to 2 hours illustrating a drop cap every day.

• Tina Roth-Eisenberg aka swissmiss couldn’t stop thinking about her daughter’s temporary tattoos, which she felt were displeasing to her Swiss taste, and ended up creating Tattly on the side while working with clients and running her blog. Tina is a serial side projecteer. She also created on the side while working with clients and running her blog. Tina is a serial side projecteer. She also created Creative Mornings and Teux-Deux.

• Jenny Gyllander was a venture capitalist working for a firm when she started taking photos of products she was testing against foam core, and put them up on Instagram. She now runs Thingtesting full-time.

• As detailed in the memoir Shoe Dog, Nike founder Phil Knight sold imported Japanese running shoes for years as a side project, first as a student then as an accountant.

• Gwyneth Paltrow was an affluent, successful and famous Oscar winning actress when she started sending out a newsletter of things she liked, and named it Goop after a brand expert told her all successful internet companies have double o’s in their names. She started it in her (probably very nice and expensive) kitchen, and now runs a $250 million company. Acting has taken a backseat and is probably now the side project to her empire.

• By the way, in case you think famous people are immune to failure, here are some side projects that didn’t make it: Blake Lively and her lifestyle shopping destination, Preserve, Lindsay Lohan’s nightclub and a whole string of celebrity restaurants, for that matter, Kanye West’s pre-Yeezy fashion venture that never made it off the ground. More money does not automatically mean success. It sometimes actually means bigger failure.

• Liz Wells, senior product designer at SuperHi, also runs DeskLunch, a newsletter served at lunchtime featuring the voices and stories of marginalized genders.

• My grandmas had side projects: nainai loved to paint, and she continued to do so every week until she passed away at the age of 92. Did she ever aspire to become a professional painter? I don’t know, but she was happy doing it anyway. My other grandma, laolao, had stacks of magazines that she collaged out of, making her version of Pinterest.

• To help them always move the needle towards making new things rather than just improving current roadmapped features, many companies in tech have built-in side project days. Google’s 20% and Shopify’s Hack Days are two examples of probably many, and maybe many more to come.

• Slack, the team communication platform and tool, was a side project of a gaming company built by Stewart Butterfield, originally made as an internal tool for his employees.

• Salesforce was originally founded while Marc Benioff was on a 6-month sabbatical from Oracle. In fact, Oracle founder Larry Ellison was an early investor in Salesforce!

• Kim Kardashian’s day job for over 13 years was filming her reality television show, Keeping Up With the Kardashians. She parlayed that into a lucrative career as an influencer with many side projects over the years, from a fragrance line to bodywear to The Justice Project, a documentary on prison reform.

• And then of course, there’s the infamous Tommy Wiseau, subject matter of the film The Disaster Artist, and portrayed by James Franco. The man is a mystery. Instead of spending years honing film-making skills like most other people, he took some money and made a film, skipping a bunch of steps and ended up creating a terrible, probably F grade movie that also happened to become a cult classic.

  Everyone can tell he made a nonsensical movie but did he fulfill a deep passion of his and get to tell his story? (Even if no one quite understood what the story was actually about.) Yeah, I guess he did. I don’t know if this counts as a side project, given that it took a while, day and night, to make the movie. But maybe a side project isn’t always done on the side of a full-time job. Sometimes it’s done as a brief stint on the side of…whatever rich, strange, mysterious men like Tommy do.

These are just the stories of side projects and people who’ve turned them into something more. Many of them have blurred lines between what we can say is a side hustle and what is a side project.

Many of them were done on the side of full-time jobs, but some were done on the side of a career entirely.

Many of them ended up making money, some of them even making more money than their original intended purpose. Some of them were built out of necessity, some out of the more abstract and nebulous concept of fulfillment.

Some are designed with an intent and end up becoming magnets for jobs, clients, fans.

I think of some of the people on this list and how I discovered them: through their side projects. I discovered Jessica Hische when I started freelancing many years ago and came across her 2011 side project, “Should I Work For Free?” And now here I am, almost a decade later, and I still remember this.

Whatever your side project life looks like, whether you became famous for it one day or not, however often you do it, just know that side projects are everywhere around you, they can take on any shape or form, and come with all kinds of surprises.

They may find themselves strangely but magnificently weaving their way into your work, as they did for Agatha Christie, whose day job as a pharmacist’s assistant provided her with a working knowledge of poison and drugs, influencing her work as a mystery writer.

Side projects may not end up where you thought they would go (or not go). They may end up becoming more, or they could end up exactly as they are meant to be: an experiment, a journey, a trial, a fun time.

And finally, as fascinating it is to start to notice all the side projects that exist around us, we don’t really talk about all the hidden side projects that serve simply to keep us happy, for us to feel that we can die empty rather than full of stories and work we wish we hadn’t kept inside.