I got my first part time job at 12 working for a neighbour (mentor one) who ran a mail order night vision & surveillance company. I had to build a database (Ability+) on a 286 to record all their sales data. I then entered all of their historical data. I continued working for them through school until at 16 I left home to go to do my A levels in Computing, German and Maths.
Whilst doing this (1996-1998), to support myself I hassled my way (by nagging mentor two) into a p/t job in an internet cafe as a sysadmin (NT4 + Win95+1 Mac) and eventually worked my way up to assistant manager. I dropped out of my A levels. Who wanted learn about serial file access and tapes and Dbase3 when I could be trying out cool new 3DFX cards and learning how to overclock with jumpers and how to sysadmin, right? Wrong - my first mistake.
I then got into some hassle. I was 17, going out with a 28 year old woman who was a pro beach volleyball player and sports centre manager. When the split came a year later I was heartbroken (I was a naive country boy) and I wanted to get away from everything so in early 1999 went to volunteer on a kibbutz in Israel. It was a free holiday, the only cost was the flight, and I stayed there for 9 months and met lots of lovely people, many of whom I am still in touch with.
During that time I did no IT work and was occupied by working in a rubber factory making tyres for forklifts and later refining rubber.
Upon returning home to my parents I couldn't find IT work so went to work in a record shop for a couple of years before moving to the city where I'd done my A levels to work for a telco doing customer technical support.
After that I transferred to a bigger city with the same company doing B2B tech support but then the department was shut down (our boss went away on an unexpected holiday, came back all tanned and announced he'd just been training our Bangalore-based replacements). I transferred to accounts payable and after 6 months of drudgery, left the company. During that time I gained a lot of Mac experience by producing a couple of indy hip hop albums with a friend after getting a grant to buy the kit.
After this I went to do some labouring on my parent's house that they were renovating after having moved to another country. I stayed there for 2 years. After that I returned to my home country and worked in a call centre job doing customer service (it was all I could find) and didn't take it seriously at all. I was then introduced to a FOAF (mentor three) who was doing web design and I went to work for him doing the IT stuff and some web design, project management and sales. This guy is a genius and has sold some very successful businesses including one to Facebook.
However things didn't work out with what we were doing so another friend sorted me out with a job doing telesales for an independent B2B telco and from there I was promoted to marketing manager which meant doing email marketing campaigns, graphic design, producing their brochures and updating their website. It was OK but not really what I wanted to do.
The woman I was with at the time got an opportunity of a position in another part of the country so I left with her and found a job working in academia as an IT technician. It was great, my first real IT job, working with the most skilled IT engineer I know (mentor 4), a true greybeard and some great all rounders. By this time I was 29 and had pissed away the best years of my life but things were starting to change.
After a couple of years in that job, learning all the time, I was headhunted and went to work in the capital at a prestigious private school where I got a massive pay rise (nearly double) and perks.
After a couple of years there I got married, took an extended honeymoon and after that my wife and I went to live with my parents for a while as she got pregnant on the honeymoon so I had to find a job. I got some contracting work, then a permanent job with another company where I was promised field engineer/sysadmin work but ended up doing callcentre stuff. After that I saw my old job in academia was going, applied, found out the role was at a higher level than before, got the job and am now settled and happier than ever.
I feel as though I could have reached this position ten years ago had I stuck at college, but I lacked guidance and my impulsive nature took me round the houses. I've always been 'an IT guy' but not always worked in the field. I urge any young people to take their time making decisions, seek guidance and value your mentors. /ramble