I never took any tech class in school, but I always had an interest in those things. My senior year in HS, I built my first computer, and got into building computers. From there, I got into computer case modding while I was still in college. I build a few decent systems, and then all of the sudden computers started to come with a high end paint finish and the cool lights out of the box.
From there I got into Home Theater. I bought an OK TV for my budget, a Home Theater in the Box, and a pair of Wharfedale SP-87s. It was awesome...
After college, I was still interested in A/V, but very budget conscious. I wanted bang for my buck, and there was a DIY speaker building thread at the A/V forum I frequented. So I was convinced to build my own speakers. I had very few tools (my main tool was a Dremel, which I used to do my case modding). I got a router and a flush trim bit, and a jig saw. All of my cuts were rough cut with the jig saw, and then flush trimmed to final dimension.
I built the speakers, and they rocked. But I really enjoyed the building process, and I thought "I have all these tools, why not get into woodworking?". Silly me, I thought I'd get a few more tools, and I'd then be ready to start building dressers and beds and armoires, oh my! Cut to almost a year later, and I'm still building my shop, and not so much woodworking. I saw a Jet 1014 at a local used tool shop. It was $120, and in great shape. I picked it up on a whim. It sat in my shop for a while, and after a bit I got a faceplate and tried a few bowls. I loved turning, and was very very happy to finally have a finished product so quickly.
So, wanting to try more turning projects and have something finished to show for it, I decided to try making pens. I picked up the mandrel, bushings, and a set of HF chisels and just started doing it. No classes, and it was a while before I came across this site, and I've done nothing but improve since then.
So, long story short, the progression is Computers-> Computer Case Modding-> Home Theater-> Speaker Building-> Woodworking-> Turning-> Pen Turning-> Pen Making (more advanced stuff, kitless, etc)(the future!).