I was a lecturer in computing when I got a job teaching chess full-time.
I was a dolphin trainer for five years, quit, and became a successful software engineer in the late 70s.
I spent 7 years in Alaska running a small chain of Photo Huts, then transitioned to fabricating camper shells while all the while working as a photographer. Then I returned to SoCal, where I’ve been a high school Social Studies, English and Science teacher and Debate coach for the last 36 years. Reasonably eclectic.
That’s who I was going to mention. Not only got his PHD, but was Chancellor of Liverpool John Moores University for five years.
A friend of mine from college was an inspector for the FDA, then a dental assistant, and is now a reflexologist. I haven’t seen her in ages, but she’s coming to Boston in a couple weeks.
I’m currently job hunting. I’ve been a software developer, then a tester; I’m trying to decide if I want to try something new; maybe work with robotic hardware, or a flight dispatcher.
I’ve been paid as a curling instructor, but it 's barely a side hustle.
I knew a man who worked in a ship-building yard when he was young, then got a job as a biology professor, then worked as a high school teacher for a little while before going back to work as a university professor.
For famous people, there’s Kris Kristofferson who started as a writer and Rhodes scholar, then moved on to be a composer, a helicopter pilot in the Army, a helicopter pilot for an oil services company, a singer and an actor.
She wanted to be a music teacher, and received a BS in music education from Northern Arizona University in 1978. She taught for a while, then decided to go back to school. She received an MS in electrical engineering from the University of Arizona in 1988, with a minor in mathematics. She went on to work for Microchip, Texas Instruments, and Maxim. She authored a book on analog electronics and has a monthly column in Electronic Design News (EDN).
One which I just remembered: John Mahoney. He had been an English teacher, and editor for a medical journal, before taking acting classes while in his 30s, and becoming a full-time professional actor in his late 30s or early 40s.
Speaking of someone who doesn’t know short stories 
Seriously I enjoyed every well-written word. Your evocative description of Dr. Bok was wonderful.
But the juxtaposition of that story and your Mom’s comment was just too good to go unremarked.
I met my best friend around 4th grade. At that young age, all he ever wanted to do was be a pilot. Wanted to fly 747s. Worked his entire life to get there. Had to do it the hard way, because of his vision. No Air Force shortcut. Went to ERAU, lots of hours as an instructer, lots of dangerous cargo flying in bad weather, yada yada.
He made it to the second tier, I guess. Was a co-pilot in L-1011s, and DC-10s.
Had a heart attack, lost his pilot’s license and ended up mowing his neighbor’s yards for cash before drinking himself to death.
More of a hobby than a career, but my grandfather ran a truck farm after he retired from a government job. (Supposedly he wrote those official descriptions of jobs which government agencies use).
According to his bio on Wiki Shaq worked as a rapper and a wrestler after he retired from basketball. Although I feel these were just PR stunts.
As a former teacher, I have to say a teacher becoming something completely unrelated or vice-versa is the least unusual kind of career change. Teaching is the initial or fall back career for a huge chunk of the college educated population.
It’s fairly common for immigrants to the United States (and probably other countries as well) to go from professional jobs in their home countries to blue collar work in this country. One of my wife’s friends was a nurse back in Africa but started working construction after coming here.
It’s a description she usually applies to herself, me, and several other members of our family. I come by it honestly! Thank you for the compliment. ^-^
My father was a PhD research chemist for years, back when companies did “blue sky” research. I’d been to his corporate research lab in the Chicago suburbs when I was young, very very mad scientist vibe, weird equipment everywhere. He had multiple patents related to plastics and oil exploration. Then he grew tired of that, went back to school, and became a Patent/IP lawyer for Amoco, with an office way high up what was once called the Amoco building (now Aon) in Chicago. It was cool taking the train downtown to meet him for lunch in the Loop when I was a teenager.
Ouch! Medical condition is a cruel Joker lurking in everyone’s deck.
When my first airline was absorbed by another, almost all our employees were laid off for nearly a decade before we were so graciously allowed to come crawling back on our knees to our new corporate overlords.
Many folks went into very different lines of work. Some (such as myself) later came back to flying while others never did. And yes, some number of them drank themselves to death, shot themselves, or made other drastic hard-to-correct life errors.
One guy started a lawn care business. When almost a decade later his turn to come back came up he said “Hah, take a pay cut to work for you a$$holes? Not F***ing likely.” AFAIK he doesn’t have a drinking problem, but I know he does have a lot of lawn care trucks and keeps a lot of crews busy. Revenge is schweet. And smells like newly-mown grass.
I should maybe note that I’ve worked for the postal service, in private security, as a home health aide, and as a cremation operator for a mortuary - this all before I started working in libraries at the age of 28 or so. I’m a full-time librarian now, and I’m finishing my Master’s in library science this May! I think mortuaries → libraries is a pretty good candidate for an unusual career move.
I spent 21+ years in the Navy (mostly on submarines), then worked at Sears for 15.
Friend was a music producer in LA, now runs a successful enterprise IT shop.
Either way you’re shelving stuff in little cubbies. Stuff that doesn’t talk back but has / had a lot to say.