This comment sharing more of my life than I'm strictly comfortable with and coming off as patronizingly preachy is my highest point earner. Go figure.
I'd recommend you determine your acceptable level of financial exposure to disaster and get competent legal and financial advice to protect yourself and fully understand the potential ramifications of your self employment and/or startup decisions.
As I was reading ops post, I personally latched on to the writer having what sounded like a family that actively cared what happened to him. That's not something that everyone has. Going to bed hungry and not knowing where your next meal might come from will alter your level of comfort with employment risk.