Twelve Years, Five Job Titles (Part 1): Before Any of It Had a Job Title

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If you scroll my LinkedIn from the bottom up, it doesn't read like a plan. Document indexer. Ebook converter. Hotel IT guy. Program analyst. Systems engineer. And now, CISO. Twelve years, five job titles, six companies. If you're waiting for the part where I tell you I always knew where I was going, I didn't. Not even close.

This is part one of two, and part one doesn't even get to a paycheque. It's just how a curious kid ended up wanting to do this in the first place. Part two picks up with the first job and everything after, including a hotel year I've written about before in "Life in a Hotel", which is worth a read on its own if you want to know how a hotel management system once turned a lunch buffet into a Rs. 2300 hamburger.

Before any of that had a job title

Let's be real: none of the job titles are actually where this started. That started with a promise to buy a computer.

I was always the curious kid who wanted to know how things worked, and my father knew it. There'd been a promise: if I passed the Grade 5 scholarship exam, I'd get a PC. That year the exam itself got delayed from August to December, island-wide, because of flooding (as I remember it, anyway). My father bought the PC anyway, on the promise, before I'd sat a single paper. I did end up doing well and got into a good school off the back of it. But he'd already paid up before I'd earned it. All this because of that and he never scolded me when I broke something out of curiosity, whenever he was repairing something I remember he explained me what exactly each part does.

To get back to the topic the PC itself was a Pentium 1, 64MB of RAM, a 1GB hard disk. I couldn't even run IGI on it, and it took me a while to work out why: the onboard graphics quietly took 1MB off the top, and IGI wanted a minimum of 64. One megabyte short, and I had no idea what "onboard video memory" even meant yet. I got there eventually, mostly by breaking things and rebuilding them, which turned out to be good practice for the rest of my life. Along the way I picked up microcontroller and hardware programming, wrote small applications in C and VB, tried Windows XP once and retreated back to Win98SE within days as it was slow as hell. Got online through dial-up over a serial cable plugged into a CDMA phone, because that's just what internet was in that era.

Then, grade 8, I found a CD in the shop across from school (the same shop we bought games and movies from). Cardboard sleeve with a picture of humans in a circle holding hands. A name on it I'd never heard and that meant nothing to me: Ubuntu. I took it home anyway, out of pure curiosity. That CD is more or less the reason I ended up doing anything with computers for a living. I started ordering every Ubuntu release on CD straight from Canonical, picked up a few openSUSE discs too, and lost count of how many times I wiped that hard disk trying to get dual-boot working, because I genuinely didn't understand partitioning yet.

I lost my mother at the end of grade 9. My father worked till evening most days, so a lot of the hours in between were just me and that machine, which is probably a big part of why I got so much practice wiping and rebuilding it. That Pentium 1 lasted me until O/L, when I finally got a Pentium 4. It had earned its retirement.

By the time O/Ls came around I made it official and took ICT as a subject. Did the same again for A/Ls. Not that I needed convincing by then (I was already working as the family IT guy to prove that), but it was nice for once having the syllabus and the hobby point in the same direction.

If I'm honest about why I'm even writing this series at all, it comes down to two things. First, my father trusting a kid with a PC before that kid had actually earned it. Second, a random CD in a paper sleeve that cracked open a whole different side of computing I didn't know existed. Everything after that (the job titles, the certifications, all of it in part two) was really just following that thread.

None of this had a job title yet. That's part two: five job titles, twelve years, a night shift starting at 8 PM, and eventually, CISO. (Link to Part 2 goes here once it's published.)