Would you ever resign from your job before you have another one lined up? What about to move to a dream location, such as NYC or San Francisco?
What circumstances would need to be in place to have you even consider? As a single person only responsible for yourself? What about a sole breadwinner of a family?
If I did something like this I would need to dip into my home equity and/or 401k savings.
Health insurance would either be through COBRA or ObamaCare.
I am currently miserable where I am (the boss, not the work).