There are millions of people who are self employed in an industry where they could be maimed or killed if they screw up who manage to make it to retirement.
I think the better question is how you get a system in which people are only responsible for any one facet to get the same performance out of people that a painter can get out of himself when he's setting up his own ladder that he personally has to climb on.
I don't think the GPs point is about personal safety of workers, but rather critical safety systems that rely on one person with no backups. Like an ATC tower for a busy airport staffed by a single person on an overnight shift.
A painter who does a bad job setting up a ladder is going to have a bad time, a lone ATC operator having a heart attack potentially puts multiple large aircraft full of people in danger...
Any system that requires perfect performance from any one human will fail.