Magic number for leaving w-2 job

[Arta Montero]

For those of you that have left W-2 job wondering at what point you felt comfortable doing that, was there a certain magic number you had to have, did you have a plan in place before leaving, did you ever look back, what did you end up doing, and how did you manage getting health insurance. I am in engineering/project management and like my job, but sometimes wonder when can I be independent regardless.