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My first real brush was taking part in GSOC, Google Summer of Code, where I got paid to work on an open source project.
Communication with my project mentor was over IRC and I felt this was a fairly large hurdle for me at the time, learning the lingo and the etiquette.
My project at the time went quite poorly. I attribute this failure mostly to myself. I was unable to wake up at the time my mentor wanted to meet and he became frustrated. My work quality was ok, but not the best.
It turned out I had undiagnosed medical issue (DPSD & ADHD); but it's probably a cop out to attribute all of the failure to just that. I got halfway through the thing meaning I got paid still a pretty sizeable sum for the work I did. But it never got commited, so I feel like I cheated slightly. I feel very bad for my mentor who was trying his best, but I was not very good about communicating back then.
Since then, I've attended FOSDEM, contributed small stuff, and even done stuff on some pretty popular projects. But have never been "in" a community like I was then. IRC still scares me. But I do intend to join when I find something I'm really passionate about.