I wanted to get other software developers' thoughts on what I was thinking about doing. Just a little bit of background ... I'm 29, have a B.S. in Computer Science, have around 7 years total experience in software development (primarily C++ programming but comfortable with C, Perl, and C# as well). I work in the finance industry in Chicago, USA. I am single and have several months of emergency savings in the bank (which I know is a must for contract work).
Based on what I have read (and it's hard to find topics about this), it seems like I would be a good candidate for contracting work. I have actually done some side contract work in the past for various clients and they were all happy with my work. The problem was that I didn't feel like I could make enough money to maintain the lifestyle I have right now with my permanent job. I was getting work through sites like ODesk.com or Craigslist. I found out that it was hard to compete with people who were willing to do the same work for much less money in other countries, but I still managed to find a few decent gigs and probably could've developed a good client base given time.
Ideally, I would like to do that sort of thing full time except not necessarily though ODesk.com but through contacts I develop over time. I also recognize it's quite risky and for sure I wouldn't be making enough money for the first several months if not longer. I know what it was like to deal with clients who don't pay you on time or ever pay you period. Based on what I have read, working on an IT contract for a 6 month - 2 year period at some company basically feels like you're at a permanent job, but at least you'll have some flexibility and move on to another contract if you don't like the current one. My plan is to initially take on these 6 month - 2 year type of contracts for a while until I develop a good client base and then after that I can become more of an actual "independent" contractor if that makes sense. I understand that I have to develop a good client base first though.
My first question is: Does it make sense to do what I am thinking about doing? Secondly, how do I get there? Should I just search for a contract job on a site like Dice.com and go from there? I found my current permanent job on Dice.com. Am I completely nuts to even think about this? What are your thoughts?