The art of the side project

How to get traction on your hobbies without going mad

Upstatement reserves chunk of time every week for us to work on non-client and self-growth work (we call that time Open Hack). I’ve always found it hard to pick an Open Hack project out of the million things I want to do — and then, once I pick a project, actually finishing it can be a battle.

But then, I went through a breakup. And another. And a few stupid dating scenarios. And I had some sad, angry energy to pour into something — but what?

I’m a big fan of the WNYC show Death, Sex and Money, and around this time they released a breakup episode — accompanied by a listener-created Breakup Survival Kit Google Sheet. That spreadsheet contained hundreds of suggestions for things to do, listen to, think, read, and watch during times of heartache — and I was obsessed with it. I pored over it religiously. It fascinated me that there were always other people looking at it too, since spreadsheets are not the most beautiful or user-friendly way to consume information. I thought, “What if there was a way for people to browse this amazing wisdom more clearly?” Bingo. That was my Open Hack project.

The Breakup Survival guide, on some iPhones!

Here’s the problem: I didn’t really know how to make this thing, which I assumed was probably a website, even though I work at a website company. But I had the idea, the energy, and a bunch of amazing colleagues and friends to poke for questions. A couple months later, I released the project at breakupsurvival.guide

I was proud of it, and it even got a wee bit of press — the Poynter Institute, Pop Culture Expiriment, and even Jetzt, the digital magazine from Germany’s biggest nationwide newspaper. (Wunderbar!)

I learned a ton from making the site, not least of which was how to better organize side projects. And since I’m a digital producer, I couldn’t help but reflect on the process and what made it successful.

Don’t be afraid to quit

Wait, isn’t this article about finishing — not quitting? Yes, but hang with me: The whole reason you have side projects because you have interests outside of your must-do stressful career work. Sometimes you’ll come up with ideas (I should learn Javascript! What if I built a synthesizer? I want to paint 100 portraits of aliens I’ve imagined in my mind!) that seem really cool and exciting, but are daunting or annoying when you actually start them. That’s okay. Just quit. It will give you time for projects that are better.

If you notice yourself procrastinating or feeling overwhelmed by a project, either change the idea or ditch it entirely. Tell your brain you don’t have to do it anymore. If you don’t ever sweep up the cutting room floor, you’ll just feel like a bad person who can’ t finish anything. So what if you already told someone you’re working on it? Tell them you stopped. The end. Move on.

You can delete the idea entirely, or shuffle it away and store it for later if your interest peaks again. Speaking of idea storage…

Keep all your ideas somewhere — but not your to-do list

If you keep a to-do list, which you should, it can be hard to figure out which items are things you actually need to do, and which are potential ideas for projects down the line. But this is a super important distinction, because if you have an infinite to-do list, you’ll probably just feel guilty for getting nothing done. Or, if you don’t have a list at all, your amazing ideas will just be floating in your head until they disappear because you run out of brain RAM.

Create a place for yourself to write down your side project ideas as they come to you — but make it somewhere that feels like a scratchpad. I have a separate list in my Wunderlist app just called “Ideas” where I log anything that pops in my head — from specific stories to pitch to my newspaper friends to a few words around a vague design concept. Any time I have a new idea or some more thoughts around an existing one, I just hop over to the list and write them down. It feels good to get them out of my head and know they’re waiting for me when I return.

You can go back to your Ideas list to decide which project to start next, spin up new ideas, or delete things that don’t feel interesting anymore.

Sneak peak into my Ideas list. Please note that one of my ideas is literally “elephant holding balloon.” I don’t know what it means anymore but I like it there.

Make a tiny thing first

Once you’re actually going to start a project, help yourself by defining what that project actually is. Get more specific about all the things you might want to do. Again, write them down so you can look at them all at once. Then figure out which ones are essential.

Yes, it’s a cool idea to make a 100 alien portraits, but what if you started with 5? Yes, you want to learn javascript, but maybe define for yourself the first step: take one short online course. For me, I had to decide — what’s the least possible work I could do to create the Breakup Survival Guide and have it exist in the world? Agile devoteés will recognize this concept as MVP — minimum viable product.

I had a lot of ideas — I wanted people to be able to see full views of all the suggestions of things to read/watch/do, maybe up-vote or store suggestions, have fancy transitions between going forward and back through ideas, beautiful curated lists of best suggestions, etc. etc. etc.

But when I looked at that list of ideas I realized — I don’t know how to make most of those things. And if I tried to do them all, I might never actually make anything. They were good ideas, just not essential.

I reminded myself that all I was trying to do is help people browse the Death Sex and Money spreadsheet suggestions in a slightly better way. My second goal was to learn some really basic HTML and CSS. Those two smaller goals spun out into a much accomplishable project: One-at-a-time completely randomized suggestions and two text-based pages. All static. That’s it. Nothing else.

By making something simple, I also had to get over the fear that my genius colleagues would think my little website was stupid. But guess what? They didn’t. Because they’re nice and supportive, and know that everybody starts somewhere. And still have all those other ideas written down, but by giving myself a much closer finish line I got the thing done. Someday I may add more features, or maybe not. The freedom to finish something and add more if you _want to_ feels much better than having an endless huge project guilt snowball. Done is better than perfect.

Baby quilts are much cozier than websites

Have a few ideas in the mix

This probably depends from person to person, but I’ve had a lot of luck working on a couple side projects at a time. It allows you to be really productive because you procrastiwork — put off one project by making progress on another (I think Jessica Hische coined that word). During the couple months I was slowly tinkering on the BSG, I also wrote and recorded two pop songs and sewed a baby quilt. If you have lots of interests, try spinning those plates at the same time and just follow your whim in the moment of what is most exciting.

One final note

There’s a weird gross corner of the internet that worships the “hustle” — honoring their glorious years-long passion projects in pristine Dribbbbble shares. That kind of thing can be really daunting when you’re just trying to start sketching an idea you have, so ignore the comparison, the haters, and the social media gurus. Just make stuff you like, when you want to, and quit if it isn’t fun or interesting anymore. Be curious and delightful above all. Happy side-projecting!