In my case I started as IC. I accidentally choose Drupal for a blog for me and my friends. I found Drupal architecture fascinating and started playing more. At

In my case I started as IC. I accidentally choose Drupal for a blog for me and my friends. I found Drupal architecture fascinating and started playing more. At the same time I registered at oDesk.com doing some small stuff for people - fixing perl auction software, writing Delphi tool to parse some pdf file to excel spreadsheet, etc. I started from $8/hr there (I am from Belarus - it's more or less enough). At some point I found a job posting where client wanted to build simple social site - forum, posts, Q&A. I applied and recommended Drupal as a base. I was still novice, but I "felt" it was good enough long-term wise. By this moment I was charging $15/hr - this is after 3 months after starting at oDesk.com After another 3 month I was top one for Drupal on oDesk.com and was charging $35/hr for Drupal projects. I felt pretty self-confident in this area. Also, I figured out there much more to learn - I continued. After another 6 months I stopped to apply for new contracts since existing clients kept me quite busy. By this time I was charging $50/hr. For someone from Belarus (where average monthly salary is $250) getting from $8/hr to $50/hr is pretty good. So. You already have expertise (which I was lacking back in the time). You now need to find place to look for Java contracts (I am not sure oDesk is good place for this. May be eLance?). If this skill is not work good for IC area, learn new skill. Seems like ruby/php/python/nodejs is popular with remote contracts. Stick to it. Eventually you will build clients base and you will not need to market your self that hard. You will be able to choose projects and work as much as you want.