Automotive engineer. hasn’t changed, I’ve been doing this my whole career.
Me too. I seem to recall you once saying that arguing in court is the most fun you can have standing up. 
I feel the same about research, preparing, and arguing.
Holy cow, Richard, you flew a Pitts? I will never worry if you are at the controls of any flight I am on.
I didn’t say I flew it well…
Believe me, we patients don’t like it either. I’ve mentioned some recent heart problems here, and one thing I can say about my new cardiologist is – he looks just like the top of an HP laptop. Because that’s all I’ve ever seen of him. He sits at a desk behind a laptop and, thus far, has never actually touched me. It’s questionable whether I would recognize him in public, and I’m sure he wouldn’t know me.
Getting back to the OP’s question:
2000: Programmer, large engineering firm, simulation software
2019: Programmer, DARPA research lab, autonomous vehicle controls.
and the biggest change
July 2019: Retiree, boat, fishing
Side note - my GP doctor has gone electronic, and I’ve not noticed any decline in care. He does all the normal things, asking why I’ve come in, checking the affected bit, and only goes to the computer when it’s time to check prescription history. He’s got my prescription history, the Cub’s, and Mrs Piper’s all available easily, can print out the prescription, so no handwriting issues, and can send the prescription directly to my pharmacy of choice. I understand that the prescription history is available to all doctors and pharmacists, to prevent double-shopping for prescriptions and so on. He just enters the new prescription on the spot, and done.
Of course, it probably helps that the prescription database was set up by the provincial health system to improve patient care, rather than to make a buck. 
This. Of all the doctors I see, my favorite it my nephrologist. He’s an osteopath and is interested in every aspect of my life and my health. But I keep forgetting what he looks like, since he’s glued to his laptop on our visits. He has to enter every datum 2 or 3 times.
2000: Just started my first post-college job as a reporter for my local newspaper.
Now: Own my own organic lawn care business.
In between: Worked in organized labor as an organizer and educator.
I’m currently happier than I’ve ever been in my professional life. I work outside all summer, set my own hours, and take the months of November-March off (being in Michigan, that means I can sit back and watch all the commuters struggle through the snow and ice and sip my coffee in my pajamas :)). With our business, we’ll never be rich, but we’re comfortable, and the one thing I’ve learned in the past 20 years is that free time and doing something you enjoy is more valuable than more money.
Well, if we can go back to Y1999 I was on a Y2K project because a core piece of our mainframe system used 12/99 as the available date for “put it out of service”. We found the quickest and most cost effective solution was to change it to 12/70 since our company started in 1971 and besides we would be changing systems in a few years. They are still using the same system… so now it may be something my grand kids or great grand kids will have to deal with.
As far as me, I’m still in the same industry but with a different company doing mostly the same job but now in an office instead of a cube and much happier.
2000 was a crazy year. I started it unemployed, having spent the last year and a half back at my parents’, “helping” to care for Dad (read: primary careworker) and working short-term contracts, mostly as a lab tech. He died in February; on July 3rd I started working at a local factory. Two new positions had been created as lab tech, 4th shift: our initial contracts were 6 months and if we worked out ok we’d be made permanent. At the end of November we were told we weren’t being renewed; on December 27th the factory manager walked into the lab as I was working and told me I was, in fact, being renewed: confused because the reports that “the new lab girl” contradicted themselves, she’d investigated and found out that the bad stuff was all about “the short one”, the good stuff all about “the tall one”.
A year later I was already working in the project that implemented SAP in that factory, which eventually led to my current job as a self-employed SAP consultant
In 2000 I had a position called “Construction Coordinator”. Since then, I held the jobs of Director of Construction, Chief Operating Officer, RV Salesman, Facilities Manager and Quality Control Manager. Retired in 2008. The last was my best occupational description.
County Deputy Sheriff in 2K.
Full retirement in 2K7 after 25 years service.
Now a police officer for a municipality.
I celebrated Y2K in Abu Dhabi, United Arab Emirates, as a US Army civilian employee working as a liaison between the UAE Air Force and the US Army on a helicopter program. Returned to the USA in 2003, retired from the US Government in 2015 after 34 years, and am happily performing one of the seven deadly sins (sloth) daily without dying yet.
2000: Customer service for a car rental firm, mostly handled international issues since I’ve always had a great knowledge of geography. Early days of the internet, so I still had an atlas library to consult at times.
2019: Back office work for a brokerage firm. I’m job searching as my current job and work environment is beyond toxic.
2000: Teacher/Director of Forensics for a public high school. 13 years experience.
2019: Teacher/Director of Forensics for the same high school, but with more of an attitude. 
I’ve gotten used to teaching the kids of kids. I refuse to still be around for Generation 3.
I didn’t start full-time work until 2011, after graduation from college. Started work at a university and am still here after eight years; never left.
Forensics? 
The Accounting kind, the “ok, who did this” kind or the “wounds come from a blunt instrument wielded by a left-handed red-headed male” kind?
I also wondered about that job title. It suggests an … interesting … high school curriculum.
IIRC, Forensics = debate. I’m sure many of Silenus’ students are master debaters. It’s quite popular with that age group.
Same job, new desk, better computer.
Better parking spot.
Y2K I was the accounting department for a small credit union.
Today I’m in the accounting department at a large insurance company.