There's been a trend lately that I like. For some time, experienced independent Mac software developers have been blogging about how they got to where they are, what risks and tribulations were involved in getting to where they are, and what mistakes they made on the way to being an indy dev.
Gus Mueller from Flying Meat, makers of the fabulous Acorn Image Editor and VoodooPad, recently blogged about How to become an independent programmer in just 1068 days. I'm a user of Acorn, and these guys are really great. Bug reports are responded to with real responses and, if needed, a prompt fix. Yet, even with how hard they worked, theirs was not an overnight success story, as you probably guessed from the title.
Daniel Jalkut from Red Sweater Software then wrote an entry about The Road Less Traveled on his blog. I don't know Daniel, but have been reading his blog for quite some time, and it is almost always worth the read. I find his perspective especially interesting because he left a job that many of us (me included) would love to have - a job working as a developer for Apple.
Lucius Kwok, author of Sound Studio gave his story in Why I write software. I met Lucius very briefly at WWDC and again, briefly, at Macworld, and Lucius comes across in person like a very nice, very genuine sort of person, which is exactly how he comes across in his blog. Lucius is very forthcoming in his blog posting about how he got to where he is, even going so far as to tell you how much he made in different years.
If you're an iPhone (or Mac) dev who is considering going full-time as an independent, it is well worth your time to read these three posts. They will give you a nice grounding in reality. There are a lot of gold-rush type stories that make it seem like you can do anything and make a fortune on the App Store, which simply isn't true. The App Store has changed things, and it's definitely a boon to indy developers, but it's no panacea. Being self-employed is incredible, but it can be challenging, and unless you hit the fart-app lottery, you shouldn't expect to get wealthy writing iPhone just one iPhone App.
I'm a little different from these three guys in that the bulk of my income comes from doing contract iPhone development work and writing books and articles as opposed to creating and selling my own products. But if I were to lay out my story of how I got to where I am in a similar way, I think you'd see many of the same themes as you see in those three blog postings above.