I started using Apple II computers in my local public library when I was 8 y/o. I was just drawn to them-- I can't say why. I can't remember not knowing Applesoft BASIC!
When I was 10 my father bought a white-box PC from a local guy and started using a DOS accounting package for his small businesses. I started playing with GWBASIC on the machine and was hooked. I decided that I was going to "sell computers" when I was older, after seeing the "exciting" lifesytle that this local guy had, what w/ having multiple computers in his house (some with color monitors, even!).
I did a lot of DOS programming. I got some Unix (Xenix, System V) experience after becoming interested when I read a manual at the local library. I started using Linux fairly heavily in the early 90's and was very, very excited to have my own Unix-like machine at home. (I remember installing from floppies... ick!) Somewhere along the way I acquired some various Commodore (C-64, C-128D, Amiga 1000) and Atari (800XL) machines, but I was never really into these platforms like I was w/ the Apple II and PC.
Out of high school I did some "odd computer jobs" for a couple of local businesses but wasn't able to garner any real business. I strung some thin-net on a job with a friend and did some "Windows for Workgroups" installs. I started doing "LAN parties" with friends. I remember being amazed at getting IP connectivity between a couple of Linux boxes on my basement floor over a piece of thin-net cable. After having used a lot of serial "Laplink"-style cables I was shocked at how fast Ethernet was.
I started at a local community college and ended up in an internship doing sysadmin work for a nearby K-12 school. (I never did tell them that the first time I saw Windows NT 3.1 was first day I was on their site and touched their "server"... heh heh...) I stayed there for a couple of years before getting hired by the local "mom and pop" shop.
I ended up staying at "mom and pop" for 7 years (perhaps a bit too long) doing stuff like building PCs and server computers, installing small office networks, and doing contract jobs for larger firms installing routers, switches, etc. I became the company's in-house sysadmin somewhere along the line, and eventually ended up managing some other technicians and doing project planning / quoting.
I left "mom and pop" to start my own business just over 5 years ago. Two partners and I are "outsourced IT providers" for a small (but very interesting and engaging) Customer base, and I act as a "hired gun" subcontractor for some small local IT firms doing work for them when they're in over their heads technically or have too much work to do. I grew up in a family that owned small businesses, so I always knew that I wanted to own my own business. It took me awhile to get there, but I'm happy with how things are working. I get to be exposed to a variety of environments, people, and business sectors. My occupational fate isn't tied to the success or failure of any one company, and I have a lot of freedom to plan my time (though, at the same time, a lot of opportunity to spend all-nighter after all-nighter doing work for different Customers).