That's a very interesting take on it. I don't think I plan to do freelancing simply as a "stop-gap." We'll see how my mindset changes as time goes on, but I do

That's a very interesting take on it. I don't think I plan to do freelancing simply as a "stop-gap." We'll see how my mindset changes as time goes on, but I do hope to actually build a business out of it -- make a good living myself for a while, then hire teams, work on bigger projects, etc. Like I say in my blog post, I will be just creating another job, but it will hopefully be a job on my own terms, essentially. There are the issues you mention -- easy to pick up more work, etc -- but I can do it at my own pace and on my own time. Building software products are, to me, like investing -- building a separate source of income. I'd love to have many different sources of income, one of them being freelancing. I assume once my "investments" can sustain me -- and, as time goes on, I end up with more responsibilities (like a family) I may cut back on the freelancing thing. But for now it sounds great. My point for the OP was that I do think he can sustain himself indefinitely on things like freelancing or part-time jobs that allow him more time to focus on his projects. You do have a point though -- it might not be a bad idea for someone in his position to pick up an unrelated job like bartending.