Man I feel this in my bones. My uncle did almost the same thing, sold his insurance business after 20 some years and started doing woodworking out of his garage. Took him a long time to stop feeling like he messed up. The scary part is you really don't know if you're the type who can jump until you're already falling, and by then it's too late to climb back up. Good on your brother in law for sticking it out those first two years, that's the part that breaks most people. Hope he's still smoking those ribs and doing alright.