Side project slog

Over the past decade, I’ve always had stuff that I’m working on outside of my “day job”. As time went on, I started to accept more and more of these side gigs as a quick way to build some portfolio pieces and help out friends who need design work done. And that’s all it was for a long time. Just fast little fun projects for the sake of doing them. But sometime around three or four years ago, they started to feel like a chore to work on, and I would dread even booting up my computer to work on them. What happened?

A big distinction to make is that in early 2010-11, I was in the beginning stages of being a “designer”. I would frantically look up any design challenges hosted online and would rush to try and make something cool from the creative brief. As my skills started to improve, my peers began to take notice. They would reach out whenever they needed a poster for an event, or a logo, or a drink label. And it was fun to work on these. Even through my first job as an engineer (which I hated), working on design projects on the side got me through the boring grunt work of comparing technical specs during the workday.

But when I actually became a full-time designer, things started to change. I was now doing what I used to do for fun as part of my day job. This is literally everyone’s dream. I got to design, create mockups, and I got paid for it. It took a while for my brain to process that it was actually happening. Once this switch happened though, I didn’t feel the need to crank away after work pushing pixels and taking on side work to get better as a designer. I was already sort of getting that at work, so I didn’t want to burn myself out by staring at screens after work as well.

Once this motivation to actually pursue side projects wore out, so did my desire to work on them. I found it more and more difficult to continue working on things I had committed to a year or two ago. I used to easily be able to fill up entire Saturdays sitting at a coffee shop and working continuously for six to eight hours on two or three totally different projects. Now, I could barely get through an hour of getting myself worked up to even begin to think about working on it. Part of this is burnout, and a part of it is just natural due to how much it feels like work now.

I used side projects as a hit of design dopamine and a way to get the creative juices flowing when design wasn’t my full-time job. Now that it was, it was actually quite draining to be creative on-demand 40+ hours a week. I started to cherish every moment I wasn’t being asked to come up with ideas or designs to solve some problems, so you can imagine how much of a toll it takes when you also start doing the same thing outside of work. I needed a break from it all, and I wish I had recognized this sooner.

I’ve currently got around three side projects that I’m working on outside of my day job. They’ve all been going on for over two years in some form or fashion. One of them is UI/UX design for an upcoming video game, another one is an illustration for a book cover, and the last one is a series of small projects for non-profits and other charitable organizations that’s been in progress for a while. I accepted all these for various reasons: to test if working on game UI design is something I’d like to pursue full time, to keep my illustration skills sharp (as I don’t get to do it much at work), and to experiment with aspects of design that I enjoy but don’t get to flex much in my fay job — like motion design and kinetic typography.

All these projects start the same way, there’s a burst of enthusiasm and excitement to get rolling on something new, which lasts a couple of months. But after that initial exciting phase has worn off, it turns into a real slog. My relationship to the project changes from being motivated by the work to being disgruntled in dealing with all the detailed feedback and changes requested by the client. At some level, I get it. It’s their baby. It’s their project. To me, it’s just one of a hundred things in my portfolio of stuff I’ve worked on. To them, it’s one of maybe two or three big things they’ve accomplished in life, and possibly even their crowning achievement.

So I gladly go along with all the micromanaged changes and feedback that the clients have. I painstakingly make all the little tweaks and edits they want, and this is what just completely kills the passion in it for me. Even though I rationally know why they’re asking me to make this tiny change that no-one is ever going to notice, I can’t help but constantly think “You hired me for my creative expertise, why aren’t you happy with it the way I have it?”, which then leads to a dangerous spiral of imposter syndrome and doubting my own skillset.

Thankfully, starting my full-time design job at a design agency and dealing with tons of irritating clients has given me enough thick skin to not take anything personally. The clients are just critiquing the work and they have an idea in their head of what they want it to look and feel like, which they’re expressing in the best way they can. For a lot of them, it’s their first time working with a freelance contract designer, so they may also need a lot of handholding and education as to how to effectively work with me.

Despite this, it’s this constant dance of small changes and refined feedback that completely saps the excitement I originally had to work on it. And no matter how much time I have available to work on it, mustering up the motivation to do it is a different story entirely. I had three entire months off between jobs earlier this year, and the pandemic had just started forcing us all to be in lockdown. Perfect time to get side project work done, right? Wrong. I barely worked on anything in that time. I could not work up the energy to boot up Figma and start reviewing feedback. I could not find the mental headspace to sit with a sketchbook and plan out my design. And it led to a of internal frustration and self-loathing, especially when I actually started the new job and felt like I had “wasted” three months doing nothing.

Needless to say, I’ll be taking a little break from side projects for a while once the ones I’m currently working on are wrapped up. I’ve relentlessly pursued them for many years without realizing how my relationship to them has changed when analyzed through the lens of my day job and mental energy I put into thinking about design and creative work as a whole. And it’s starting to suck the joy out of design a bit for me. I think I’ll still work on personal projects from time-to-time, because when you’re the client yourself, you can just decide that it’s good enough and move on. Or, you know, abandon it in the WIP state forever and never come back to it.

I guess that’s one reason side projects work well for folks who struggle to finish something — having clients gives you accountability to actually see it through all the way, and also results in some nice publicity if it takes off. But for the rest of us who are just doing it for different reasons, it just starts to feel like a never-ending slog where the relief of completing it far outweighs any benefit in skillset you achieved, any fame you got, or any income you made, throughout the course of the project.

I do have a couple of lessons for anyone about to start taking on side projects that I’ve learned through all this though. The first one is to never work for free. I did this a lot when I started, and honestly, I’m not sure if I would’ve even built up a good enough portfolio of work for others to hire me if I didn’t have this body of work to rely on. But if you’ve already got this, don’t just take on a side gig for free, even if they’re friends or family (especially if they’re friends or family). You have no idea what it’s like to work with them and it can cause an uncomfortable rift in your relationship if the project goes sideways.

The second lesson is to always charge by the hour. As a general rule of thumb, do not charge a flat fee or exchange your services for something else. I cannot tell you how many times clients have asked for a laundry list of changes and edits, and I simply respond with my estimate of how many hours it would take to make those changes and how much it would cost them, to which they almost always say “You know what, let’s cut that list down”, and you can then work with them to figure out what the top three or five most important changes are. You wouldn’t be able to swing this with a flat fee and get stuck working for endless hours on infinite revisions.

There are clients that will only pay flat fees though, and if you absolutely do need to take those on, I’d suggest agreeing on a set number of revisions or edits upfront (maybe 3 or 4). Clearly communicate that you’re talking about V2 or V3 in each call, and explicitly state that there’s only time for one more revision or round. It gets them to see the priorities of the project from a different perspective and will adjust their feedback accordingly.

The side projects I’ve worked on have been invaluable to me for many reasons, but I don’t see it as a sustainable lifestyle now that my day job provides me with deep understanding of design as a whole. I initially started doing them to get the creative juices flowing, but now I need a break from those juices constantly flowing during the work week. Gotta take a break from it for the juices to eventually taste better. Hopefully, my small personal projects are enough to satiate my desire for more varied and interesting design work in the meantime. For now, it’s time to wrap up my existing side projects over the next few months and then figure out what’s next from there.