The product will be competing with my current employer's (no non-compete, no stolen trade secrets, most legal questions already answered), so for legal reasons I have to quit my day job before launching. I am in a good enough financial situation that, even in the worst case scenario, I can go for a year before having to bail on my startup and start looking for a new job.
So HN, tell me your story of quitting your day job or otherwise convince me that leaving my well paying, comfortable job isn't horribly reckless. How do you know when the time is right to launch your product? Should I have so much faith in my product that I would be alright with marching into my boss's office tomorrow and telling him I quit?