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Big Ideas

Make Your Side Projects Wildly Successful: Treat Them Like Experiments

Set your fear of failure aside and get that nagging idea out of your head, once and for all. The benefits can help take your creative career to new heights.

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?

Comments (127)
  • Traktor Tips

    I like this quote — ” Experiments don’t “fail”—they simply prove or disprove a hypothesis”.

    • Paul Jarvis

      Thanks Al!

  • Tim Lind

    Nice one. So true: “Creation and judgment are very different thought processes and can interfere with each other, and must be done separately”

    • Paul Jarvis

      Thanks! It’s tough to do, but it’s so important not to imped brainstorming with self-criticism.

    • Melanie Biehle

      This one is so tough. I often edit as I write. I even edited this comment. Make it stop. Please. Just make it stop. 🙂

  • theirmind


  • Sven Read

    I actually have two sideprojects in the mean time. First, Words: & second, Readability: Currently starting out on the second one. Words is already matured quite a bit.

    • Paul Jarvis

      Hey Sven, those both look like amazing side projects (and I’ve come across them before).

      • Sven Read

        Awesome. And thanks. Would love to hear what you think about the book as soon as it is ready.

  • hello_design

    Other things that are helpful is not to have Jessica Hische or Tina Roth Eisenberg expectations. Also not instantly sharing and expecting your project to take off. Also do it for yourself and not for the wrong reasons.

    • Paul Jarvis

      If you continue reading the article, you’ll see that I say the same thing. It’s better to not have expectations or think into the future for projects—hence the whole framework of experimentation 🙂

  • Srinivas Rao

    I couldn’t help but click on headline, and then of course I saw it was written by you :). I love the idea of experiments. I incubate stuff constantly. The nice thing is you do these quick tests, and get feedback without spending a fortune.

    • Paul Jarvis

      Sweet! You’re definitely an amazing example of this. I’m stoked how much you’re experimenting with drawing now too, I love when they show up in my IG feed.

  • Melanie Biehle

    Great post (as usual), Paul! My side project used to be my blog. I started it in 2009 with one goal: start writing creatively again. I was completely burned out from living in L.A. working in movie marketing and I had stopped working on all of my own creative projects. Three years after starting my blog I was able to leave my full-time day job as a pediatric research manager (I know…BIG career shift from Hollywood) to start my own business and further pursue my own creative dreams. My whole life changed from a side project.

    • Paul Jarvis

      Thanks Melanie. It’s amazing how we can renew our passion for things when we take the helm of exploring with them. Congrats!

  • Tara Roskell

    Hi Paul, Great article. I love side projects – just hoping one will eventually turn into something full time. It’s only through side projects that I think you can work out what you really like doing. I have done a lot of different things blogging, trying to invent things (I blog on inventing too), creating characters, creating a design course. My latest is learning to code (which is going pretty slowly). Great reading what everyone else is doing.

    • Paul Jarvis

      Thank you! Side projects put you in charge, and it certainly seems like you’re in charge of exploring with yours (which is awesome).

  • Jeffrey James

    For me, side projects are projects that I like to work on more than my day job. I’m hopeful that one of my side projects will eventually do well enough to allow me to lose the day job and turn the side project into a full-time project.

    I like the idea of thinking of them as experiments, too. Though I think for a lot of people, the difficulty isn’t fear of failure as much as it is shifting gears from consuming to creating.

    • Daniel Sanchez

      You just read my mind. We are on the exact same page…. I am actually working on taking that next step of quitting my day job and persuing my passion for Digital Art

      • Paul Jarvis

        Best of luck!

    • Paul Jarvis

      That’s a valid point—if there’s more focus on creating than consuming, it’s easier to find time and let yourself exist in a mindset where you’re just doing things you like to see what happens.

  • Chatman Richmond Jr.

    A lot of my side projects (released and unreleased) have been a result of trying to scratch my own itch. If I end up making something that helps me, I might consider if it can help others in some way. Then I just kind of put it out there and keep going.

    I bet that’s the way a lot of side projects develop. Little experiments, as you said, that explode into huge ventures. Even the successful ones that eclipsed the day job were probably the result of a thought that went something like: “You know what would be fantastic to have?” and the project results from making it for themselves.

    I doubt they’re formed from a mindset of making money or becoming a day job replacement from the outset; it just sort of happens that way. There are a lot of people actively pursuing the “next big thing”, but that tends to come more from happy accidents and experimentation than a deliberate attempt to replicate another’s success.

    We should always keep this in mind.

    • Paul Jarvis

      That’s the rub—too many people get caught up in future thinking about where it could go or making it a huge success. It’s better just to get to work and start creating…

      • Mike Kennedy

        This and “analysis paralysis” get me every time. Eventually you just have to say “frig it” and get it out the door.

        That’s what I’ve done with, an funny user-submitted Edmonton content site, and my other sites.

        Sometimes I fantasize, or plan, about the future – where the project will be, etc., while failing to even start or work on it – which is kinda the most important part! lol

    • Mike Kennedy

      I think all my projects and ideas are the result from trying to scratch my own itch. Lets just say I’m really itchy!

  • Florence Tsai

    Wonderful article! Couldn’t come at a better time especially since I’m planning on starting some side projects. It’ll be fun to have control over all aspects of a project and being able to go as crazy (or not) as I want to. 🙂

    Thinking them as experiments make it feel much less daunting (and more fun) than I had originally framed them as in my mind. And the point about not judging the experiment is fantastic…thanks very much for the article!

    • Paul Jarvis

      Brilliant—glad to be of value.

  • Al

    I have too many side projects to list 🙂 I am lucky to have a day job which is reasonably relaxed and flexible!

    My latest idea/ experiment:

    • Paul Jarvis

      You’re in the best scenario then, a day job that allows for experimentation.

    • JC Roxas

      Im happy that I read your comment. Made me realized something 😀

  • Heath Brockwell

    Thanks for the article. What a fantastic way to start off the weekend. I have been kicking around an idea, but thought it was lame. But now the idea is an ‘experiment’ and it will be pretty incredible and I’m excited!

    • Paul Jarvis

      Awesome! Now go find a lab coat (lab coat not required) and get going.

  • Y0UNiverse

    Thank you so much. Seriously. Every creative (industry or not) can benefit from reading this at least once a week. This is a gift.

    • Paul Jarvis

      You’re welcome!

  • Brandon Hilkert

    I try to keep a list of new programming techniques I found around the interwebs. When an idea comes up, i grab one of those and say “I’m going to write it doing ____”. This way I get to try out this new techniques on real world applications. Hello World doesn’t cut it.

    • Paul Jarvis

      Nice, that’s a great plan of attack.

  • Ross Simmonds

    Great post Paul. For me, the power of a side project or side hustle is something that can’t be overstated. Between my blog, a disproved hypothesis and a handful of awesome experiments – I learned more than I ever thought possible. At the end of the day, reading about other peoples stories and successes is great but nothing can replicate the power of actual doing.

    • Paul Jarvis

      Thanks Ross. Exactly, you don’t know what’s possible until you actually try.

  • Pedyson De Leon

    Inspiring… before I read this I was experimenting on a project I recently finished… and everything I did fits on what you said… but I did repeat my experiment, on the other hand I change a couple of the variables, having different results… and now with this article is clearer now how I will approach my new experiment (very nice term for a Passion Project)..

    Thank you

    • Paul Jarvis

      Thanks Pedyson! Glad to have provided some value.

  • markadamdouglass

    This is a deeply insightful piece of writing. I love the 5 tips. Inadvertently, we were using a few of them today as we work through a little side project of our own. It is nice for these ideas to be reinforced from someone who has been successful with their little side projects.

    Great writing Paul.

    • Paul Jarvis

      Thanks Mark!

  • Torrie

    I’m a student and I just started my first true side project called Made In Orlando. I love “Side projects can be scary. There is more of us in them.” I keep trying to act how I kind of think a real business woman would, but that takes away the fun and makes it less meaningful to me. I need to reread this every day!

    • Paul Jarvis

      Thanks Torrie! It’s WAY more fun to act like you instead of a “business” person. People are afraid to be themselves, which is interesting because when people are true to who they are it’s magnetic.

  • Parrus

    This is a really inspiring post… thanks so much for sharing. I’ve had so many ideas for side projects but get frustrated that I haven’t been giving myself time to develop them. You point to treat them as little experiments rather than a colossal business project hit home… I agree with the comment below, I need to read this post everyday!

  • Tk Kelly

    This was a good read. I found myself in a similar situation and this was a good boost. Thnx for the write up!!!

  • Dhiraj bajaj

    Very Nice Article. Initially when i started learning Ruby on rails, I had similar notions as you have written. I made around 3-4 side projects then, deployed them and got some traction while I was doing another job.

    As a result, Now I have excelled at creating more usable apps.

    • Paul Jarvis

      That’s a great way to learn—by doing!

  • JC Roxas

    I was on the same boat earlier but after reading this article, it definitely gave me a big boost as to the things that I can do, the things that I should be thinking and looking at the things that matter. Thank you thank you. This post really means a lot to me.

    • Paul Jarvis

      You’re welcome JC! Now get to work 🙂

  • Jonny Philp

    Really great article Paul, and just shows what you can do if you change the perception a little! I’m trying to figure out if I can revive this old coffee brand at the moment and when you class it as an experiment it’s not quite so intimidating! 🙂

    • Paul Jarvis

      Nice! And that looks like an amazing hand-grinder, something I’ve been in the market for too.

  • Jim Spelman

    I’m always experimenting and this gives me new thoughts on how to make them successful…thanks!

    • Paul Jarvis

      You’re welcome!

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