The Benefits of Side Projects

TLDR: Side projects and design exercises are an antidote to a fixed mentality. They take your brain on a road trip, stop to see the world’s largest ball of earwax, and are really in a hurry to get nowhere, but eventually do.

Even meaningful design work you love occasionally becomes… just work. Product design in an app that’s alive and loved can feel like remodeling a home while wearing a straightjacket. Instead of a green field full of possibility, creativity entangles with user needs, resourcing, business goals, fear, and too much caffeine. There’s a danger of preemptively squelching ideas before having a chance to fully explore or externalize them. This isn’t a state of mind you want to remain in for great lengths else you lose tenacity and develop a censored imagination. As a designer, it’s important to continually find ways stimulate creative thinking.

Recently, Stéphane Martin organized an exercise for the product design team that went something like this: “Imagine that there were no boundaries, no stakeholders, no problem definitions, and no code limitations; what would you design for X?” (But in a French accent of course.) We called it our 5% Fun exercise.

Each designer stole a few hours throughout the week to work on the project. We met back up in our secret personhood at the end of the week to discuss our ‘concept cars’. Many of us had solved the same problems even though they were never clearly defined, and the approaches were unique.

Work became play, and there were a lot of good ideas generated in a relatively short amount of time. We now had an even deeper understanding of what the problems were. The discussion focused on what was innovative or interesting and was quite invigorating.

In fact, the team was so excited that the conversation quickly began shifting toward “What if we actually made a version of this happen?” As we crossed the threshold from our world of fluffy clouds and rainbows back into reality, something interesting happened — stress and disagreements began to form around the team.

Partially because this didn’t match our product development structure and there were too many owners and none of them were from any of the other essential disciplines, but a bigger part of it was because our regular limitations and self-imposed boundaries resurfaced. There are few, rare times when an iterative development process merits a green grass approach, and really these types of designs are loaded — what is seen can never be unseen. Even a good idea can be a disruption if resourcing, roadmaps, and strategy don’t align. Sometimes “We ain’t got no time for that right now.” is an appropriate reaction.

So are these potentially fruitless pursuits worth it?

Heck yeah, they are.

Children use play to explore ideas about why and how things happen in the world around them. It’s a safe place without the weight of consequence where ideas are pliable. This is what the team was doing with the 5% Fun exercise.

I can’t think of a side project where I didn’t learn a new skill or a new approach to solving a problem that wasn’t eventually applicable to another situation. As a matter of fact, I’ve got a hard drive full of unfinished projects that have contributed something new and good to a later project that actually shipped even though the play never saw the light of day. These are mental seeds full of potential.

A key strength of a good designer is her/his ability to take ideas from multiple inputs and realize them as something new and relevant. Creative problem solving builds intuition, rejuvenates a growth mindset, and generates a strength to continually consider the improbable possibilities.

Beagles need to run, dancers gotta dance, and designers have to live in a state of perpetual discovery. Plus imagine the alternative — getting into your car, driving directly to your destination, and never noticing the world around you.




Stories and lessons learned while building Stack Overflow.

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Kurtis Beavers

Kurtis Beavers

Design Manager at Microsoft working on Developer Learning Tools / Formerly Creative Director at Stack Overflow

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