Earlier quoted context omitted.
Freelance? Start contributing to OS projects and consult? I mean, if you're trying to break in without existing credentials or work product, I would have to think you'd need to create some work product and connections.
I have some creds + experience but I'm looking to get more. I haven't cracked freelancing yet. Places like Odesk seem like a mess and I haven't had good results.
I've actually been on both sides of the table - as a freelancer I never got work through Odesk, I was actually hired through Hacker News once, and when it comes to hiring freelancers, I've recruited through my network (recommendations, etc.) and haven't considered Odesk.
If I were to go freelance again I would make it known in the local entrepreneurship community.