I can relate so much to this post.
I’ve built an immense amount of side projects over the years and I can’t say I’m entirely satisfied with the result. Full disclosure: I work at Google as a Software Engineer since 2006 until the present, I don’t feel entirely unsuccessful, I just, humm, say, expected my side projects to be more successful than they are (I don’t share the desire to make money with them though).
A lot can be said about the benefits of side projects, but I think you are already aware of them (e.g. you learned new things, had fun, etc).
I spent the last few years re-thinking my approach too, and, while I don’t yet feel like I have a good plan, I think I’m leaning towards a couple of interesting directions:
- the bazaar and the cathedral
- foundations versus ceilings
The former is a very interesting concept: sometimes, building successful projects has more to do to with coming up with something small and unique and enabling a constellation of users to evolve it in non prescriptive ways. Along the same lines, the second direction, from timbl, explains that using slightly different terms.
I hope these resources help, and, if you ever find yourself interested in hanging out and chatting about your/my side projects, I’d love to grab beer sometime (I’m in Saratoga, CA next to Boulder Creek, CA).