Make Your Side Projects Wildly Successful: Treat Them Like Experiments

I used to let fear of a failed side project keep me from trying new things outside of my normal workload. Or worse, I constantly had ideas for side projects but never actually started any. My day-job was comfortable, so I didn’t want to fail at something new. But, the truth is, I wasn’t pushing myself and I certainly wasn’t growing. My skills stagnated.

Meanwhile, I noticed exampled of other creatives tackling side projects and wildly succeeding at them (and sometimes the “side” projects would take over their day jobs). Tina Roth Eisenberg’s (Swiss Miss) side projects (Tattly, Creative Mornings and Studiomates) helped her put client work on hold indefinitely. Jessica Hische’s side project of drawing drop caps and posting them online led to several jobs/clients (including The New York Times, Penguin Books and Google). Seeing others succeed on the side, I wondered if I had the chops to do the same.

Side projects can be scary. There’s more of us in them so they hit closer to home. This can make them difficult to start or follow through on. But it’s also important to be our own client sometimes, and have side projects that push new skills, flex our creative muscles, and give us testing grounds for new and innovative ideas. I knew I needed to start doing them as well, if I wanted to really see what was possible.

Side projects can be scary. There’s more of us in them.

To get over my own fear of failure with them, I started picturing these ideas as simply being experiments. Experiments don’t “fail”—they simply prove or disprove a hypothesis. For example, despite my day job as a designer I had the hypothesis that I could also write an e-book. I then simply started writing. I didn’t focus on the outcome, how the book would be received or what others would think of it. I figured, “let’s give this a try”.

Framing my side project as an experiment didn’t sound as bad. Experimenting is the only way to prove something, to get that nagging idea out of your head.

Here are few tips I use to frame all of my ideas for side projects as experiments:

  • Focus on the task at hand, not the end result. Focus on the process to allow serendipity and personal exploration to take over. Otherwise you might inadvertently alter things with a subjective idea of how you want it to turn out, rather than what would be best for your long-term learnings.
  • Don’t create your experiment and judge it at the same time. Creation and judgment are very different thought processes and can interfere with each other, and must be done separately. Experiment with exploring every idea completely first (writing it down, drawing it out, actually trying to do it). Only then move into editing, curating, and judging to get to best version of the idea.
  • Break the experiment down into the smallest tasks possible. Then, focus completely on each small task. Only at the end do you tie all those tasks together. This helps you avoid the fear of things being too big or overwhelming to accomplish and lets you slip in your side project around your weekly primary responsibilities.
  • Remember: these are experiments. Not full-time business ideas. First figure out how to run the experiment using the least resources as possible. What is the core or essence of your idea that you can prototype quickly? Get that prototype in front of as many people as possible before pursuing it more. Fail fast.
  • Don’t repeat yourself. The same experiment can’t have a different result unless you change the variables. If you experiment with an idea and it doesn’t work, you need to change things up or move onto a new idea. There’s no point doing the same experiment over and over, hoping for something different to happen. If you want a different outcome, you have to change your experiment up a little—refocus for a new audience, try a different medium, or try experimenting with a new idea completely.

Some of my own experiments have led to great results, like selling thousands of copies of a book I’ve written (writing, for me, started as an experiment in creative expression). Some only proved that there wasn’t a market or opportunity for an idea, and several apps I made didn’t sell a single copy. But I keep experimenting with new ideas, always keeping one simple rule in mind:

Nothing is a mistake. There’s no win and no fail. There’s only make.
— Rule 6, Immaculate Heart College Art Department Rules

By framing the side projects I’ve done as experiments, I’ve had both the confidence to pursue them and the ability to judge them less harshly when they didn’t work.

How about you?

What’s your side project? How has it helped you develop new skills?

More insights on: Career Development

Paul Jarvis

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Paul is a Gentleman of Adventure. He's also a web designer and author. If he's not in nature on some Thoreau-esque tangent (but with wifi), you can find him on twitter at @pjrvs.
load comments (125)
  • David Sadler-Smith

    Thanks Paul. I particularly like your point about repeating yourself… I often repeat an “experiment” without realising it and I don’t recognise it as a repeat until I’ve wasted a load of time. I need to develop some kind of experiment memory bank… I think it would also help me to fail faster… and maybe succeed more :)

    • Paul Jarvis

      David, I think we all do that. Once we’ve started down a path, even if it’s not working or something we’ve done before, we’re already down the road a little… so it’s hard to go back to the start and try a new one. I’m the same sometimes.

  • Olivier Lépinoy

    Very good post ! Thank you.
    I work full-time and also have several side-projects.
    When do you think a side project can become your day job ?

    • Paul Jarvis

      When it makes enough to support you :)

      • Olivier Lépinoy


  • rebecca

    This comes at a perfect time when I am thinking about entering an art show with a specific theme. I’ve only done this once before and it pushed me to actually get some work done. (I’m an artist with a full time side job). I’ve been putting it off, but as I read this article I started having some ideas for pieces and now I have sticky notes everywhere!

    • Paul Jarvis

      Best of luck with the art show!

  • Patrick Ryan

    Excellent advice! I’m working with a coworker on a side project currently. When we have free time we add small things to keep the motivation up and feel a sense of accomplishment. Our project can be found here Its a work in progress but I think its amazing how much work we’ve gotten done, both of us working full time! Thanks again for the post!!

    • Paul Jarvis

      When you prioritize correctly, there’s always a way to find time.

  • patrice

    I struggle with this a lot lately… wanting to get into a number of interests on the side (I’d love to sketch more, learn more about web design, etc.) and that’s where I get stuck. What’s your advice for choosing which side project to move forward with, so your doing and not just left wishing?

    • Paul Jarvis

      Simple—stop thinking about them, and start one :) If you aren’t into it, move onto the next.

  • Yohanes Steven

    I actually did one side projects, and it resulted in a huge failure (tried to create a blog, targeting 3 blogpost per week, but eventually got so few visitors). But I’m happy I did it because I learned a lot, and I’m ready to do my next side project by the lesson I got.

    I have to say this article’s advice is excellent and I wished I’ve read this before starting my failed side-project.

    • Paul Jarvis

      Thanks! It’s good to learn from things and use that knowledge for the next thing.

  • Teresa Guzmán Martínez

    I have the desire to administrate some social nets (community manager) but I didn’t how to begin, I mean, I wanted to have a real client to begin. But after reading this article, I’ll start a personal experiment and, let’s see what happens then. Thank God I read this article. Nice day!

  • Georg Kettler

    Dear Paul,

    having just finished a side project myself your article was a great read! Although I have to admit I probably just did the opposite in every aspect.

    Together with a friend I made an app for iPhone designed to connect people in near field for collaborations, etc. Although it is a pretty simple idea, it took us two years to finish.

    Having a pretty clear vision of the finished product right from the start, we constantly revised it on the fly, polishing and redoing it (repeating the experiment, I guess). And while doing that, I skipped a lot of client work. So, occasionally our little side project became an actual full-time job, even before it was finished.

    The app is called “I am…” (shameless self-promotion *on*), further infos can be found here: I’d really appreciate your feedback! Thanks in advance and thanks again for the insightful article.

    Kind regards Georg

  • josh

    So pumped about your advice. And at what time!! I just made my first sale in my first “experiment”. Seeing it this way, is so more liberating and adds fuel to the process. Genius man. Thanks for sharing.

  • Katie

    I love this article… especially being a scientist! What a simple way to change from fear of failure to excitement of discovery. Change perception to realize you are learning lessons either way.

  • Aileen

    I’ve been stuck for a little bit on my personal projects and this is exactly what I needed to shift my thinking. Thanks so much for this article Paul!

  • Juan Wmedia

    That’s the inspiration and motivation I needed. Thanks for sharing.

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