This is the big thing for me. I know full well that failure is not only possible but highly likely, and that the price is my financial safety net being expended

This is the big thing for me. I know full well that failure is not only possible but highly likely, and that the price is my financial safety net being expended. The ego hit isn't the problem, it's the resulting inability to pay bills. Thankfully I like my day job quite a lot so my strategy has been to try to drive down cost of living where reasonable and accumulate more padding than is actually necessary, so when I finally commit to doing my own thing I'll be able to fund multiple attempts, preferably with some downtime between each to prevent burnout. Success is still anything but guaranteed but I figure that my chances are better that way than if I were stressed and in a hurry trying to make things work before my bank account ran dry.