I graduated Construction Engineering Technology, worked manual labour and moved into an estimating/quantity surveying role at a small construction firm. I was still site foreman at the time, and did just as much physical labour after graduating as I did before.
I decided physical labour was not the life for me. Got hired on at a small oil and gas engineering firm which engineers specialty products for large diameter pipeline construction. What was I doing? Reception. Answering phones. Doing dishes. Booking flights. All the administrative things which were (I thought) far and below me, the educated man.
Fast forward 6 months, I've had two promotions, two raises, and am having my IIBA membership and classes paid for. I still do some reception duties, but rarely.
I think there's a lesson to be had here. I was pretty upset moving into a role at the bottom of the pole, after being fairly "high up" in my old role (well, lots of responsibility even if the pay didn't quite reflect that). But, now I'm making more money than I was, with as much schooling as I (reasonably) want paid for. I showed up with a good attitude every day, and no matter how remedial I felt the work was, I put in 100% effort. It paid off. It's continuing to pay off.
tldr - Started as a receptionist, now am much more
I think that it qualifies as both unthinkable and impressive (albeit mostly in terms of collateral damage).
TL DR: Air Force enlisted to CEO.
Edit; Now that I think about it, I also worked for another company who's CEO had started of enlisted in the military (army national guard iirc). So two enlisted to CEO stories.
Talk about a radical switch.
Soldier in the navy, served enough to fully retired. While being on retirement he learned HTML, CSS, PHP (around 2000s) and he is contractor to this day.
Manager in warehouse. He was working there for 5+ years starting as the lowest paid employee (some other physical jobs before that), decided to start coding. He learned front end dev in 2 years on online courses and landed his first dev job just before he turned 30.
While my pay wage was something of a joke, although at some sites it was more than others, but 4 years later and a penny raise (boss probably did it as a joke), I realized, I was stuck in a dead end job with no opportunity to grow.
I went back to college, having no idea where I would end up. I continued working security jobs in order to help me pay my way through college. I was interested psychology (which I have my degree in) and eventually wanted to do something with career counseling -- helping college students find their place or helping people who decided to have a career change later in life.
During my latter years in college, I got out of security and worked for student life, which only paid some minimum wage, but I got to do a series of jobs such as orientation leader, secretarial work, and even campus card (I took photos of everyone), and even worked at a liquor store in downtown Chicago for a year.
Anyways, after college, I moved to Israel for a year, where I taught English to elementary and middle school students, and although it was nice, I wasn't very interested in working with kids. This nonprofit organization needed a website so I volunteered to do it for them and loved it. It gave me some insight into web design.
I moved back home and I was desperate for a job with no money and student loans to pay off... so I did the only thing I knew to do: I applied across the boards on Craigslist. I figured I had a college degree now, who wouldn't hire me? Only one company responded, a software company that licensed out their autobody shop software, a program created in Visual Basic 6.0. I had experience in it personally, having taught myself when I was like 11 or 12, but not any experience professionally, but they took a chance on me, and I worked there for a year and a half. I was hired to make the UI more friendly and fix bugs.
After that, tired of a tyrant boss, I moved on to full-time web designer for a Solar Panel company, working in Flash and did the animations for them that displayed on a kiosk for companies in their lobbies. At the same time, I also got hired as a web designer for the media (Solar Panel company on location from 8 AM - 5 PM, media company remotely from 6 PM - 2 AM). I was also freelancing on the side as a web designer. So for almost 2 years, this was my life.
I was eventually laid off from the day job and currently still have a job working for the media, but I am no longer working remotely. They gave me a choice: move across the country or get laid off. So being one of the only employees who chose to move, out of about 20, I negotiated a nice salary rise and they even paid for my move across the country.
If you asked me just a decade ago what I would've been doing today, I probably would have never guessed I'd be working as a web designer / web developer.