My Complicated Relationship With Side Projects

I’ve always felt a certain frustration when it comes to side projects. An idea strikes, I process it in my mind, create a few files on my computer, get excited, dive deeper, and then I read a post on Hacker News or on some random guy's blog and think: man, I’d love to work on a project like that... So, I start questioning my own idea, I realize it doesn't really have all the features I’m looking for (more on this below), I get discouraged, and the cycle starts all over again.

The result of all this is, as mentioned, intense frustration. I am well aware that I could work on a project simply for the joy of doing it, without any specific goal. But that’s an approach I just can’t seem to adopt. There is something wrong with me.

Side projects are fun, and they should be fun. Don't get me wrong. But I overthink it and turn something that should be easy into a burden. Choosing a new project is a conflict for me.

I don’t know if this emotional struggle I have with side projects is something other people experience. Because sometimes I feel like that’s not the case. It doesn’t just happen with programming. I have the same attitude towards music. I don’t want to bore you with my musical tribulations, but I have similar issues there, too. And I don’t seem to see this in my musician friends. So, maybe it really is just me.

But let’s get back to programming. For me, a side project must satisfy specific requirements:

• It must have high educational value
• It must be complex
• It must be monetizable
• I have to feel it

I like learning new things, so this requirement is very important. But it’s easy to satisfy because there are so many areas I’d like to explore and don't know well. However, combining the first point with the second is harder, especially if I want to be at least somewhat realistic. There's no point in fooling myself by choosing to work on a project that would take 10 years, financial resources beyond my reach, and so on.

Making the choice even harder is the expectation of at least some monetization. I don’t have a millionaire's bank account, so I can’t afford to overlook this aspect. I have a full-time job, family and kids, so my most precious asset is time. At least as a best-case scenario, a project must be monetizable in some way to allow me to earn money and, consequently, buy back time by reducing my dependence on a full-time job.

I have to feel it. And this is crucial, especially in moments when enthusiasm is at its lowest and energy is lacking. I believe it’s very difficult to abandon a project that you truly “feel”, which is why this might turn out to be my main requirement for a side project. Mind you, I myself have worked on a couple of projects for extended periods (6–15 months) without having any particular attachment to what I was doing. So it's possible. But I probably had more energy and less burnout from web development back then.

To be clear, though: I am not talking about the problem of abandoning projects halfway through due to laziness or lack of perseverance (a problem musicians know well, as proven by folders filled with hundreds of half-finished tracks). I’m talking about the difficulty of choosing, the struggle of finding something worth spending a couple of years on that won’t leave you feeling too unsatisfied (after all, working on one project means not being able to work on other equally interesting ones). For those with certain standards and aspirations, this choice represents a mountain to climb. Or maybe it’s just me having a completely wrong approach to these things. I probably can't accept the fact that there will always be a more interesting project developed by someone else. And that I'll never be able to know everything.

I have other passions in life besides programming that I cultivate daily. Combine that with family and work commitments and you'll realize my available time is very limited. That's why I put so much thought into choosing a side project, since I can't have more than one at a time.

As I write this, I’m about two months into a new project. I don’t want to go into too much detail, but I think I’ve found something interesting to work on for the next few years. It’s intellectually satisfying, just far enough from web development, and it forces me to read papers: a dream! And yet, I’ve already found myself doubting it a couple of times. On one hand, because although it is monetizable, I don't think it’s the kind of thing that will make me rich. On the other, because lately I’ve been getting interested in some areas of programming that are really tempting me. And this makes me want to dive into them, to study new concepts and expand my skill set. You see? I am completely vulnerable to this problem!