Never. No one in my family has ever retired and they've certainly had the financial ability to do it. When my grandfather was in his 60's he sold his snack company for enough money to live VERY well for the rest of his life. He bought a 2K acre functioning cattle ranch and got up, put a suit on (with a bolo now instead of a tie - and he wore a cowboy hat - he was SO into the fact he was a "cowboy" now, lol) and went to his office on the farm every day. He even kept his office down by the Atlanta airport until he died in his upper 80's.
My other grandfather sold specialized marketing and had customers he had had for decades. He was filling an order when he died that my mother and grandmother had to finish up to get it to his customer.
My Dad is in his 70's and started 2 companies last year.
Now, I have to admit, the wimmin folk in my southern families haven't worked much. I will probably be the only one who keeps finding things to do forever since I was also one of the first females in my family to have a "real" job - which was pretty much a neccesity after getting divorced and having a baby to raise.
My mother is retiring in 6 months. She's only been working for about 25 years, but she found a way to do it so she could get her "to the grave" retirement/assisted living/nursing home completely paid for, lol. We're sneaky too.........