I fought against the need to quit my job for over a year while I was working on startups on the side. It took an idea that I was wildly passionate about and a well-timed layoff to make me realize that being "all in" wasn't just a poker metaphor the already-successful used to look down on plebes like me.

That said, I'm stupidly well-placed to be working on my own idea, unpaid - I'm using the self-employment assistance program through my state's unemployment department to get UI checks without having to job hunt (I do, however, have to submit business plans and the like). I also have enough in the bank to cushion me when the government cheese runs out.