80s: Dad bought me a Big-Trak and later a Commodore as a child, Mom an Intellivision, and I took to them all quickly. But, I used a computer rarely for almost a decade after that because it was
so early.
90s: Had given up temporarily at community college because I didn't know what I wanted to do, i.e. was aimless and had no guidance. After getting laid off (with severance pkg) at a good hospital job I had by chance, I decompressed for a week or two and contemplated what to do with my life. Any medical industry advancement required a four-year degree, a no-go in the short-term.
At random chance, a catalog for the local "adult school" came in the mail with lots of "computer classes." I thought well, this stuff isn't going away, it just keeps growing every year, and imagined whatever office-drone job I ended up at would need "computer skills." Things had changed a lot, Commodores/TRS-80s were obsolete and everything was PCs and to some extent Mac. (I knew nothing about big-iron, War Games was my only exposure. :-) What the hell, let's take a class, shrug, couldn't hurt. Thankfully, it was study at your own pace, which I always loved. No dummies to hold you back, amirite?
A few days later a lightbulb popped up over my head... it was 9:30 pm and the school said it was time to shut down for the night. I'd been there since eating lunch and completely forgotten about dinner. It was perhaps the third night of the first week, pushing ~40 hours already. "Wait, what am I doing here?" Playing with computers all day and night. "Woah, I must love this stuff." Not too surprising from this angle, as I loved tinkering with gadgets and playing video games as a youngster.
In a year or so, I'd gotten a PC computer-repair certificate, a Mac desktop-publishing certificate, got Netware certified, hooked on multi-player Doom, all of which had taught me about "LANs" which were becoming the rage. Built computers from spare parts. I saw a magazine article and asked the teachers about Unix. One said he'd used it and it was "more elegant" than DOS. Intrigued, I downloaded a trial, maybe from a BBS (can't remember), I think it was a version of Minix, and kicked the tires for a few days. (Also, met a friend still in high school, as mentioned below.)
Mid 90's: Having exhausted the adult school, it was now time to get a job. I walked into my first or second interview at the Rockwell Science Center (think Space Shuttle) and talked about what I'd learned. Can you start Monday? God, I miss that. Now had a fun IT job with incredible resources at my disposal: PCs, Macs, Suns, SGIs, Crays, Networked printers, even a VAX held on tight by an old curmudgeon scientist.
It was a great time to be there—we were on the internet at work 24/7 via T1 with no firewalls. I was crushing my job and still running Quake servers on the side. Was a sought-after expert at loading DOS TSRs into high memory to get lab equipment working. Had a front-row seat to the rise of Mosaic, Netscape, Winamp, and Napster. First learned Linux from installing Slackware from tens of floppies, until a guy said, "Oh, I've wanted to try Red Hat."
Later, I became the resident Windows 95 expert as well, because my friend from school was providing me with the betas he'd signed up for. Once, we were having our weekly IT meeting with my boss (and boss's boss) and he was pleased we were getting an early drop on W95 as it was a big change coming.
"So, who is your friend? Is he some VIP at a big-company getting access?"
"No," I said. "He's a high-school student!" BWAH HAHA HA....
Not long after that I realized I liked programming too, and that it made good money. Went back to community college, this time with a purpose and got an AS degree in CS. Wish I'd continued because stopping there became an impediment later. But, I was making big-bucks at 25 and loving it, more school to learn theory didn't seem like a good deal. Also didn't anticipate degree inflation and hordes of "fakers." :-(
After XP I'd decided I'd had enough of Windows and moved to Linux and FLOSS full-time, though a few jobs have forced me to use it briefly. Lots more to tell, but that's good for now. ;-)