Owen Williams ponders how feasible such an endeavor really is:
The online blogging space is so saturated with content that it's very hard to get started. Almost impossible in fact. If you didn't start out in the industry a few years ago, and don't already have a major name for yourself, it's like screaming in a room full of people. If you don't have the platform or the momentum behind you, it's an uphill battle to get yourself heard. Money has to be made to pay bills and it's hard not to get it without selling out.
Where do you start? How do you get yourself heard? How do you make your content different? In a world of blogs, how do you separate yourself from the crowd? How do you convince readers to bet on you? Why would people pay for your content?
I'm currently in the process of reassessing my career with the school district, and thinking a change would be in order. As successful as I've been over the past decade at what I do, the reality is it doesn't allow me to fully utilize my talents. I'd love to fall into something that makes use of my skills, while also being not as physically (and emotionally) strenuous.
All this said, it'd be awesome to be able to write for this site full-time. The thing is, it's just not economically feasible; my site's not big enough in terms of readership so as to support it. As Williams notes, that Gruber does Daring Fireball for a living is certainly the exception, not the norm. He's very fortunate, and that's great for him and his family. As for me, I definitely know I want to focus on my writing more as I'm extremely passionate about it. For now, though, it's more realistic that it be limited to being simply a "hobby", which is okay by me.