An exciting, intriguing experiment brewing behind the scenes just might evolve into your life’s work.
13 min read
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What do abstract expressionist art and virtual reality have in common? They were both pioneered as side projects.
Jackson Pollock was a school janitor by day and spent after-hours working on his illustrious drip paintings. With a full-time job at USC, Oculus founder Palmer Luckey spent evenings in his garage building the future of virtual reality.
And they’re in good company. Google, Twitter, Buffer, Todoist, Space X, Apple, Product Hunt, Trello: these are just a few of the hugely successful businesses who started their lives as an experiment — molded and polished in off-the-clock minutes — while "real work" carried on in the backdrop.
With solid internet access, a little time and a lot of devotion, a seed of curiosity can flourish into something groundbreaking. Side projects inspire. Side projects energize. Side projects change lives. What’s stopping you?
Take it from me.
I’ve always been a tinkerer. Before founding JotForm in 2006, I entertained a merry procession of side projects. Some related to my core competencies; others, I dived into just because they tickled my fancy. I built prototypes. I learnt carpentry. I wrote code. I started blogs.
My real job wasn’t the place to explore tangents, dabble and experiment. So, I used my little projects as guinea pigs, to test hypotheses or apply learning from the latest book I’d devoured.
Some side projects fizzled out. Others made me a bit of money and eventually provided me with the safety net I needed to quit my job. But all of them taught me something invaluable: about marketing, sales, product development and myself.
Today, my circumstances are a little different. But I’m still tinkering; only now, I’m doing it with the JotForm team by my side. We’re a bootstrapped company. And without VCs breathing down our neck, we have the freedom to take as many playful, calculated — or uncalculated — risks as we please.
So we do. Risk and pressure-free, side projects mark the most fertile territory for innovation and creativity there is. I think everyone should start one.
Side projects make you smarter, happier and more creative.
The most common misconception about side projects? That starting one will distract you from your real job. Or tire you out. Or just complicate things. But in fact, the opposite is true. Fiddling around in new territories will actually make you better at the stuff you already know.
I love chatting to staff about their side projects and hobbies. For one thing, it shows they have enough free time and security to take pleasure in things beyond their job. But usually, their personal interests end up informing their work at JotForm.
Dawn Sharifan, Slack’s director of People Operations, agrees, “At the core of it, people that have hobbies or side projects say that they are on a path for continued improvement, intellectual curiosity and well roundedness.”
Another side project advocate is Google, which famously allows their employees to spend 20 percent of their time exploring them. It’s thanks to this system that Gmail, Google News and AdSense came about. Spotify hosts week-long hackathons to encourage staff to explore their passions. Even Y Combinator asks its applicants for a side project idea when they apply.
And there’s research to back this up. When psychology professor Dr. Kevin Eschleman tested the effect of having a side project on over 400 people, those who had one were deemed more helpful, collaborative and creative.
That’s because side projects counteract the pressures of regular work, in the same way we might go for a drink with friends to blow off some steam after a long day. But instead of drinking a large glass of Merlot, we’re honing our skill-set, sparking our curiosity, testing our intellectual capacity. This is fulfilling. This is restorative. This enhances well-being.
Running a business or simply having a real job is inherently stressful. You need to earn your keep. People must be paid. There’s pressure to perform and be successful. Your side project, though? It’s not putting food on the table. It’s not paying the bills. So, if it crashes, no one gets burnt.
And that very freedom is the elixir that has taken so many side projects from the garage to the boardroom. Begin to lay the groundwork for one of your own.
Find the time.
Kidding! Unless you’re cruising around on an adult gap year or a self-inflicted sabbatical, long stretches of time where you can knuckle down and figure things will never be found. And that’s fine. You don’t need them.
Side projects blossom in windows after work, before breakfast, during lunch break, on the subway. Everyone has those magic-making minutes, even the busiest, hardest-working CEOs on the planet.
Squirreled away in the grander scheme of your day, they don’t make much difference. But over weeks, months and years, they start to pack a real punch. You’ll probably have to deduct these minutes from something else. So cut back on Netflix binges. Have a shower instead of a leisurely bath. Push back your morning run.
Because, as Paul Jarvis says, “It takes sacrifice to make something great. In order to shift your mindset and experiment with ideas, you have to choose a new path. You have to change your paradigm from consumption to creation.”
So free up those spare moments and protect them like you’d protect a lunch with your oldest friend. Make a date in your Google diary. Switch your phone to airplane mode. Put a Do Not Disturb sign on your door. You might lose grip on the latest Suits plotline, but you’ll gain something much better.
But remember, this isn’t about enforcing a regimented schedule. Manageable deadlines are helpful to keep things chugging along, but don’t beat yourself up if you miss them.
Nothing kills inspiration off as swiftly as trying to find, fast. Now’s not the time to inflict time pressure on yourself. You’re doing something because it fascinates you, not to get it shipped for express delivery. Lose the timer.
Plus, if you and your side project are having fun together, it will flow along naturally – like a playdate, not a tutoring session. Hang out and see what happens.
Be into it.
You need to justify the time spent with your side project. So it has to be fun. If it’s not, you will find excuses not to show up — and there are always excuses. You’ll resent the time you do spend. It will feel like a chore.
Without that fizz of excitement, you may as well be clocking extra hours at the office. Because, for the time-being at least, enjoyment is going to be your only form of reimbursement. I love Denim Huit Co’s description of a side project: a low-risk, low-pressure labour of love.
And on that note, you need to love it if you’re going to labour at it for free. So make it something you’re into. Something that really makes you tick. Start a sentence with I’ve always wondered… and take it from there.
Is the answer related to your core career? Cool, you’re building a portfolio of skills that will undoubtedly help you in the future. Is there absolutely no connection whatsoever? Awesome! You’re about to become multi-talented. Or, perhaps you’re like me, and your side project idea stems from a problem that’s been bugging you.
In my first job as a Junior Developer, I had to design custom web forms every day. It was boring. It was slow. So slow, in fact, that it got me thinking – could I automate this process? I imagined a simple drag-and-drop form builder that people who didn’t know coding could use.
And the rest is history. As Y Combinator founder Paul Graham once wrote, “The best way to come up with startup ideas is to ask yourself the question: what do you wish someone would make for you?” Have a problem? Solve it. Feel something’s missing? Build it. Have an itch? Scratch it.
Make it simple — then simplify that.
If your regular job is a steam train trundling in the same direction every day, your side project should feel like a paper airplane. It should be a minimum viable product stripped down of all its baggage, and then some. Or, as Mikael Cho of side project-Hail Mary Crew succinctly summarizes, “Solve a problem in a much simpler way than anyone else.”
Zapier CTO Bryan Helmig echoes this sentiment: "Keep it lightweight and fun — don’t bog it down with process. Try to focus on a small nugget of value that isn’t critical but might be parallel to your core line of business.” Leave the finer details, red tape, and business strategy out of the picture, at least to start with. Now’s not the time to obsess about scaling or growth.
One of my favorite side project stories is that of Sophia Amoruso, founder of Nasty Gal. She collected vintage clothes as a personal hobby, selling them on eBay from her tiny San Francisco apartment. Soon, she realized people were willing to pay big bucks for her pieces, and the company took on a life of its own; today, it brings in hundreds of millions of dollars.
But the million-dollar company is a happy consequence of her side hustle — not its starting point. And I bet she would have continued to sell from her pokey bedroom if the glossy LA offices never materialized.
Embrace the chaos.
You and your side project are hanging out on the regular. It’s fun. But it feels a bit… chaotic? Confused? Amateur? Wrong? Hey. Relax. That imperfection is perfect for a side project. It’s supposed to be messy. And with a side project, there’s no such thing as right or wrong.
Why? Because it’s an experiment: nothing more, nothing less. A side project should feel like a grown-up playground. Tinker, mess around, amble down avenues that lead to dead ends, just for the sake of it. Embrace the chaos.
That’s the thing about experiments: they can’t fail. You’re just testing a hypothesis. There’s no pressure to succeed, no consequences to consider, no failure to fear. And right in that triangular sweet spot, the magic happens.
As Sheryl Sandberg famously asked, "What would you do if you weren’t afraid?" You'd absorb information differently. You'd take braver risks. You'd make deeper connections.
Lose the goal posts.
If you’re anything like me, a big part of your life is already mapped out in red pen. There are goals to be scored, KPIs to be ticked and expectations to be met.
You might feel a little hesitant about investing time, energy and money into something without a clear strategy or end-point. It’s unnerving to loosen your grip on the steering wheel. So why not get the red pen and start scribbling out a future?
It’s exciting to dream about the places your side project could whisk you off too. But when you start setting goals and analyzing results, that excitement will start to. Deflate a little. Obsessing over success can quickly spiral into paralysis, and disappointment when things don’t go to plan. That’s no fun.
The thing is, side projects aren’t meant to go to plan, so making one is a waste of everyone’s time. Take your eyes off the road altogether. Embrace the chance to go somewhere without any pressure to get somewhere. Enjoy the journey.
Share your work.
Don’t keep your seed buried in the ground forever. Light, fresh air and some other human’s eyeballs will do it a world of good.
I used to have a blog where I wrote about my side projects and asked for feedback. That same blog helped me sell my side projects, and ultimately funded JotForm. Whatever stage you’re at, cranking open up a two-way conversation will take you forward.
For Noah Kagan, the idea of AppSumo came from talking to users at his other startup, KickFlip, a payment company for social games. “I started AppSumo since every game company kept mentioning they needed less monetization tools and more customers. We wanted to solve that for the apps market.” he said.
Explaining your idea to others will help you spot gaps in it, to then fill them. Roll it back and forth. Ask for feedback. Keep iterating, clarifying and refining.
As soon as you share your idea, whether it’s on Medium, YouTube, a Podcast or just a conversation, you’ve made it real. You’ve given it to the world. And that’s how you build an audience. That’s how you build a following. That’s how you build a startup.
Chew on it.
If you devote time to something that truly tickles your curiosity, there’s no such thing as a bad result. It won’t detract from other parts of your life; it will feed into them. As Gumroad founder Sahil Lavingia put it, “Don’t be afraid to bite off what you don’t know you can chew. You’ll learn to chew it.”
At best, your side project will blossom into a grown-up start-up. At worst, it will teach you an invaluable lesson and prepare you for your next experiment.
Remember, success doesn’t just equate to wealth and professional achievement. There’s a quieter kind that comes from learning new skills, pursuing what you love and feeling personally fulfilled.
So flex your creative muscles. Explore a tangent. Build something. And share it with the world when it’s ready.
But whatever you do, don’t sweat it. It’s only a side project.