Like pretty much anything else, a ton of it is who you know. People knew me as the guy who was always doing the crazy Linux stuff, and so a little games startup hired me as a sysadmin initially because no one knew anything about how to make the servers run. But sysadmin is basically a part time job if you’re doing it right so I started taking on parts of our programming contracts and learned how to do a good job with it. Then once I had some “I know what I’m doing” evidence to point to and a bunch of people had worked with me it gets a lot easier to tell people you’re worth hiring.

I don’t actually think the “who you know” thing is some bad thing; it’s just people wanting to work with someone who’s proven or who they know knows their stuff. But for me it was a lot more that I was working on hobby projects a lot and tried hard to do a good job once I got hired than that I’m a real people person or anything.