How did you start off your career?

ConradJ

I left high school and went into college (AS-levels for those in the UK) and did computer science, business studies, psychology, general studies and electronics for one year. I never wanted to go into further education after high school, but was pressured into it. Three days into the second year I walked out of the classroom and went and enrolled in the local community college to do a welding course.
Whilst doing these I worked the local supermarket pushing trolleys (carts).
I applied at a local steelworks as an apprentice welder. At the end of my interview the director offered me a job working in the drawing office instead. I accepted and worked in there for a year, learning draughting and general DO work.
Then I got headhunted by the head of estimating and worked in there for two years.
While in there I proved my knowledge and ability with computers, having just been interested as a hobby and took on the role of in-house IT guy. The company gave me a nice budget and I organised a new server rollout and top-to-tail re-wiring of the entire office building.
I then moved to Canada and worked on a farm then in a warehouse, both jobs as labourer. The outsourced IT guy for the company my mother works for mentioned to her that he was looking to hire someone. He came in on a Saturday to do some after-hours work, so I volunteered to help out. We got along, he gave me the job.
Unfortunately the work was paid on a call-only basis i.e. I got paid per job. This didn't work out too well, sometimes I would get 20 hours a week, sometimes only three, so I continued to work in the warehouse from 3am - 12pm, then IT work in the afternoons.
So, I saw a job for another local IT company and applied, he had already hired someone to fill the position but offered me the same as I was doing for the other guy, so I started there on Tuesdays and Thursdays and the first place the rest of the week.
I then enrolled in school to get my education in IT, and was offered a place at the second place permanent part-time. I finished school three weeks ago and now work full time. We specialise in small to medium business outsourced on-site and remote support.

Aldur

I kind of "lucked" into IT. The college I attended has good relations with JTAC. So after a few classes and a bit of self study I was able to jump on the SSL-VPN team at JTAC. After 4 months of being on that team I moved over to the IPG(router) team. After being there for a little less then a year I picked up my JNCIE-M. About a month after that I moved on as a Resident Engineer with Juniper. In about 6 months I picked up my JNCIE-ER. Then about a year later I landed this sweet 100% work from home job developing courseware for Juniper's Edu department.

It's been a wild ride so far and I'm pretty happy with how things have worked out.