Sounds like he had the will and desire to fulfill your unfulfilled dream. I bet your jealous. 
Are you going to do the whole back packing/ Eurail / hostel thing?
I can only think of two plans, really. My first was to get a job sailing yachts from the South coast of England to the Mediterranean for rich people. I never finished my day skipper courses, focussing instead on racing dinghies.
My second was to join Footlights at Cambridge University, as a way to become an actor or writer. I gave that up once I realised how much time acting takes up when you’re at university, and my tiddlywinks and roleplaying responsibilities took precedent.
I did have a dream of being cherry-picked for MI5 on the day of my graduation by a serious-looking man in a brown overcoat, but somehow I knew that it wouldn’t happen 
My main plan, though, was to get a job that didn’t take over my life and which gave enough time and spare cash to keep having fun. Mission accomplished, as far as I’m concerned.
On first read, I thought that, after being disillusioned by the missionary outfit you worked for, you now work in a whorehouse.
It actually kind of makes sense.
My cousin is working his way through your list. It helps to start with money, I think.
My high school hopes focused more on getting any girl to like me. Eventually one did and everything else after has been a pleasant surprise. Except for never having built a giant robot. Or even a medium sized one.
This did happen to a couple of friends when I graduated Bristol Uni.
They both got Firsts in Physics, and were invited to interview with MI5/6. I think one of the physics profs must have had contacts with the security services and fed through suitable names.
They both went through the initial rounds but quickly decided it wasn’t for them, and they went off to join the City.
Although maybe that’s just what they wanted me to think… come to think of it they both travel a lot “on business” and have generically mundane finance roles, which would be a perfect cover. 