Some of you are aging yourselves! 
Elmwood, I’m glad you mentioned the Apple Lisa. I was planning on mentioning that, and saw your post.
I’ll get to that in a bit.
The Apple ][+. Every summer beginning in 1982, my father used to bring one home from the school where he taught. I taught myself BASIC and would program my little fingers off - nothing spectacular, but that (and piano lessons - manual dexterity) taught me to type. (I’m now at 100 wpm.) The kids at school would make fun of me and call me a geek, but ::ahem:: look where we’ve come. I now work in the computer industry, though not as a programmer.
Dialing into a BBS for the first time. I felt so restricted with my Apple at home. A neighbor down the street was an Apple dealer and had all of the latest and greatest. The first time he dialed me into a BBS and I was in contact with other users “out there” - now this was what it was all about! 
The same Apple dealer introduced me to the Lisa. I remember playing around with it in his living room, not quite getting it, after years of doing nothing but typing on a green-and-black screen. But it was my first taste of a GUI, even though the GUI had been developed at least 10 years earlier at Xerox (a company, that, interestingly, I went on to work for as a graphic designer).
A year later, my Dad stopped bringing home an Apple ][ and starting bringing home a Mac 128K. I’d do horrible drawings in MacPaint and print them out on the ImageWriter, but at least I could write stories in MacWrite. The pain was switching between system (boot) disks and storage disks, since there was no hard drive on at least this Mac.
Dial-up and email. It was only in 1992 that I discovered these when one of my professors gave some written instructions into dialing into the university’s then-crappy email client, and using the InfoMcGill bulletin board for what not. I found my second apartment through InfoMcGill.
IRC. I discovered that about a year later. I was hooked. I showed one friend, who showed another, and so on. It was nothing like using mIRC today - it was all commands (I still prefer to use commands rather than buttons - matter of habit) and monochrome. It then opened me up to a whole new world of meeting other guys, and indirectly led to the breakup of my second relationship.
Windows 95. Not to defend Micro$not, but to have an actual drag-and-drop GUI on a PC changed things a lot for me. (I hated Win 3.1.) Soon thereafter, I got my first post-university job as a graphic designer (see above) and learned all of the major apps inside-out.
The Web. Porn on demand. 'Nuff said. :eek:
MIDI music sequencing. With nothing but an external peripheral, software, some cables, and a keyboard, I was finally able to realize the fully-orchestrated music I would hear in my head but could never express beyond just me and a piano.
I won’t get into cell phones, pagers, and the lot, because I quite frankly don’t care for them.
I now work in the field of digital video editing, which has revolutionized the way filmmakers and editors let us see things, from CGI designers, to your average wedding videographer. The apps I work with now make MacPaint look like an Etch-n-Sketch. 
I love the fact that my nieces & nephew accept computers as a way of life, and send me e-cards on my birthday. 
So I guess the geek they all made fun of made good after all. 