My dad was self-employed as a barber who owned his own barber shop. Just a one-man place (although he did have 2 chairs). He never did retire. He was still cutting hair, because he enjoyed it, until about 3 months before he died at age 79. One night, he fell in the living room, and went downhill quickly from there. Spent the last 3 months of his life in the hospital and finally a nursing home, in and out (mostly out) of reality, until he died of pneumonia. I don't think retirement ever entered his thoughts. He was old school.
MY mom was a legal secretary, who worked for just one law firm from the late 50's until she finally retired, for the last time, after age 72, I believe. That would have been in about 2003. She's 81 now. At the firm, she outlived the attorney who originally hired her, then she worked for his son, who she also outlived! Once she finally decided to retire, they kept calling her, begging her to return for short periods because they could never find another secretary who knew all she knew and had all of the "old school" skills. Even after her "final" retirement, she continued to do specialized work that one attorney would drop off for her at home, which of course she got paid for. I think it made her feel good that they seemingly couldn't get along without her. Apparently, today's secretaries are prima donnas who aren't always willing to get in the trenches & do the hard stuff. My mom was a super secretary! And now, at '81, she's still very healthy, drives, shops....does whatever she wants. However, she's not thrilled with my plan to retire at age 55. She believes that WAY too young, and that I'll be bored out of my skull.