How do you start?
It depends on the kind of side project—for Daily Drop Cap, I set up some rules for myself that dictated how I wanted the project to go: I decided I was going to draw a letter every day, in the morning when I first got to work, and that I would work through the alphabet 12 times total. I decided I wasn’t going to do them on the weekend, but that I would try to catch up if I got behind for whatever reason (like if I was traveling for a conference).
For some of my web-based projects like Should I Work for Free, it started by wanting to have a place to send people that asked me about my opinion on working for free and low wages (a common interview question). I thought it would be fun to come up with a non-standard answer so I first created the flow chart as a giant jpg, and then reworked it with HTML and CSS when the nerds complained about load time. Generally the projects that I create fill a void for myself or others. People ask me all the time to recommend printers, so I made Inkerlinker so I’d have a place to send them. I’d hear (print) people talk about how daunting the idea of learning HTML and CSS was, so I made Don’t Fear the Internet to teach the skills that I learned. The projects that I have the easiest time working on are ones that I can hammer out in a long weekend of work. Anything that takes more than a few days to a few weeks to complete is a lot harder for me to get started on.
What are the benefits of side projects that don’t pay the bills?
Side projects, for me, are a way for me to exercise creative muscles that are underworked in my professional client work (muscles that I would prefer to not be paid to exercise so they remain fun hobbies and not “work”). I love learning new web skills, but in no way want to become a full-time web designer. I love to write but as soon as I’m paid to do so it becomes a chore.
Side projects also are a way for me to connect with people and to share my knowledge / skills with others. A lot of people have discovered my work because of my side projects, which is an awesome benefit of creating them but not really the reason I started any of them.
How do you get unstuck?
Having different projects to work on. This is generally how I maintain momentum with work—if I have enough on my plate that I can jump between projects when I’m feeling burnt out on one, it’s hard for me to get creatively blocked. I feel the most stuck when I just have one or two projects going on and have to choose from being totally unproductive (not working on them) or dragging through the project that at the moment I’m not completely psyched about.
How do you know if a project was a success?
I feel like if I’m excited about something, there will at least be a handful of other people out there excited about it. Some of my side projects have really taken off and some have only reached a small group of people. Either way, I feel like if I am happy with the result it’s a success.