In mid-life I had to write a CV using Word and found it bloody annoying (I had caps lock on, then accidentally hit the insert key and so on) - but thought I understood what was going on in the background at least.
Then I replicated the front page of a newspaper in PageMaker, and thought this was cool.
Then I did a short Photoshop course at the local dark room (I was into BW photography at the time) and have never touched a Mac since.
Then I did an Autocad course, then got a job testing the GUI of a large GIS project, then took some time off and taught myself web-programming - html, css, vbscript (yes, I know, I picked the wrong book off the shelf then) vml and video.
Then I installed PHP and because I got stuck I asked a question on IRC and got two kind and helpful answers from 2 people in 2 countries within an hour or so - and was totally and utterly hooked.