Hi Dwayne,
I've been a professional developer since 94, and have been freelancing since 96-97. It's been my only source of income since then, except for two brief jobs from 1998-2000, and in 2003. In 98, I hadn’t really thought about it, and just defaulted back to a job. In 2003, I was gun shy after the post 9/11 work environment.
Basically, in 96, I quit my job on good terms to transition to another technology, which I liked but had rusty skills. After my brief ‘sabbatical’, I ran into my old boss, who offered me a small project ... then another .. then another ... eventually, other people started giving me work, and most kept using me. I currently still have 2 clients who I’ve gotten work from every year for over a decade.
Obviously, you need to be innovative, design good UI’s, understand your customers needs, develop a system from concept to deployment, maintain your own code, and write quality software. But I’d say the reason I’m doing this now comes down to making myself available to do extra projects when any sane person would say no, and accepting almost any programming project.
Also, just so you know what you’re getting yourself into; having a boss breathing down your neck is easy. You pass the prioritization decisions back to them and work 15 hour days till you’re done. But being freelance means you’ll have multiple bosses, which will occasionally all be demanding, and they’ll all be expecting 60+ hour work weeks, and won’t know or care about your other 5-6 projects. This can be stressful, and make you wonder why the hell you’re doing this to yourself!
If you have a good friend or two who share your vision, you might also want to talk about a partnership. Not having others who care about your success and will help you out when you’re stuck on a tech support issue that you have ZERO idea how to resolve definitely sucks!
Personally, I’ve come to the conclusion, that I probably won’t have another job again, but independent consulting isn’t exactly a cake walk either.
Good luck.
PS-Don't ever lower your estimate because it looks too high and you're afraid you'll lose the project. In my experience, you're better of losing the project, than getting it under these circumstances.