I'm seriously thinking of also walking the path pioneered by Fan27. At the moment I'm employed with a good salary but in a domain completely unrelated to my interests, experience and drive. Perhaps it's possible to live a life of grindwork when you've got zero drive to it, but if I can help avoidig it, I'll give my best shot to escape from it.
Question's how much of personal finances would you consider reasonable to risk into a self-employed venture and how long would that be reasonable to take?
The question on how long is important: a woman won't give birth to a baby earlier than 9 months, if I could do the things I wanna do in 2-3 months, I wouldn't need to quit my job to work full time on that. I'd say 9 months - 2 years, problem's I've only got money for the lower estimate, so 9 months.
On how much to risk: ideally less than 25% of savings, in my case it would be 50%. So sort of 4x more risky than my own conservative view. Yours might differ
Final thoughts: why the heck would I (people in general) need to quit their job in order to make real progress on something meaningful, outside the soul-sucking corporate job? In my experience, the job only provides enough to live through, and in exchange asks for what is effectively all my available time and energy to work on crap that will never get me out of the hole, just provide enough so I don't succumb either. Of course it doesn't help at all having a wife and kid, as a bachelor at least I had full weekends to grind on my own stuff and 2x12 hours undisturbed makes wonders. Now when the job is not sucking my time, the family is.
“A man is a success if he gets up in the morning and gets to bed at night, and in between he does what he wants to do.” ( Bob Dylan ). I'm probably at the lowest point in my life from this definition of "success" and feel that if I don't do something about it I'm gonna get stuck here forever.