My first attempt was that Star Trek emulator thingy, too. The boss has a few years on me, though. I learned C on the job (those were the days... wizard hats all around!) and spent a couple of years building a cost-estimating system for a conveyor manufacturer. The hardest part was having to resort to assembly language to make this newfangled gadget called a "mouse" work properly.
My favorite anecdote is the time my IBM PC crashed, and they came and REPLACED it, because of course it must have been broken. I sure do miss knowing exactly how everything worked, and I still have a little frisson of WTF every time the answer is to just reboot the damned thing. Might as well just wave a dead chicken over it.