Once you're behind bars for decades any money you had stashed simply evaporates supporting your family, and any action you had going dries up as well. Old associates die, and most everyone who might have watched out for you is gone or in trouble themselves.
It becomes a much different world 99.99% of the time. Thats a fact. These are the hidden headaches guys live with aside from the obvious lost years spent in stir. It ain't easy thats for sure.