I thought this article was going to be somewhat insightful as to another option for me, as, like many others, I have quite a bit of student loans. Including interest, I owe about $250k (BS and MS). I don't regret going to the school I went to - the experience and what I went through there was life changing for me; however, it does put a severe stranglehold on what I am actually able to do in life right now. I am basically forced to work for others at a decent salary (which I am certainly very fortunate and thankful I'm in the software engineering field) instead of being able to completely set off on my own.
I'll also add that I do understand what you're saying. I have been self employed for 16 years and my wife worked as well so there was somewhat of a cushion. Back in 2008, though, my first son was born 3 months premature and I had this "oh shit" moment where I thought, "ok, wife isn't working, I have a sick baby, we have a mortgage and two car payments, there is no way this is going to end well". I stepped up my hustle big time and five years later we have two kids, very little debt and things are fine. You really just have to take look at the glass as half full. As a software engineer, you're in a sellers market. There are SO many companies out there looking for people like you, you just don't realize it yet.
Either way, best of luck. If you do want to strike out on your own, please don't wait until you're "comfortable" because it will be too late.
I don't follow... how does having student loans put a stranglehold on your ability to set off on your own? Saying you're "forced" to work for others seems a little dramatic. Self employment isn't about working in your PJs as much as it is about being on the hustle every day (http://www.youtube.com/watch?v=5betFZRICVg). There will always be a million and one reasons why working for yourself is harder than having a job, if it's not student loans it will be something else (age, family, etc). You have to look past that.