Reminiscing about 25 years in IT

2024-12-07 16:54:00

I like to hang out on Discord. As we know, I like it a little bit too much.

This month, I was asked two questions which got me reminiscing about my career. About when I decided to quit IT, about when I almost lost my CISSP. And about how I've been doing things the past ten years. 

First off, someone asked me:

"What was the worst job you had?"

The worst job I've had in IT was not a problem with the job, it was a problem with me.

The time I was at my lowest, was after my first five to seven years, around 2006. I was in contracting (as in I was employed by an agency who rented me out to customers), in a job where I was tape jockey and only did minor systems administration. I wasn't motivated to learn or expand, because my employer had a very strict development path where they demanded I first do a few certs that I really didn't want. 

So I gave up. I hated that job, slacked off a lot, spent a lot of my time exploring the building instead of working. 

And while I did that, I did night classes and one day a week at college to become a maths teacher. This I loved! Mostly because I was challenging myself and because I was working on getting out of IT. 

In 2008 I finished my first year with full marks. I even finished a class from second year as well! And I had an internship lined up, so I could go into fulltime teaching. Then we learned we were having a kid and I had to go back to IT, because of money. 

A good friend of mine helped me out. I started working with/for him, and really started challenging myself again... Lots of learning, lots of studying, doing difficult jobs again.

So... My worst job? It was when I gave up.

Today, after I told a little bit about my freelancing, someone else asked me:

"I know you've got a LOT of certs, would you say that made the biggest difference getting you to the position you're in now or was there another factor?"

I have 25 years of experience in IT, but somewhere around 2007 I decided to actually get out of IT. That didn't go as planned, but in 2008 I did get a nice "reset" of my career. I took what experience I had to get a solid job in contracting (not yet freelance) and from there on out started applying myself. 

In 2009 I slowly started getting a few certifications, most importantly CISSP. That's what got me "qualified" for a few other security positions. After that though, I stupidly started slacking again. I even blogged about it then.

I managed to retain my CISSP, but I was still not really applying myself in "continuous improvement". I did some trainings here and there, listenend to podcasts, read books. In 2013 I'd had enough of that, kicked my own ass with the help of a good friend and made a plan. 

Only 11 years ago did I start my "continuous improvement" journey. Every year, I make a list of goals to achieve by the end of the year. A list which grows and fills and shifts throughout the year, with things I feel I need to learn or research... 

In 2013 I made sure to keep my CISSP and get my RHCSA. After that, it's been cycles of three years to renew CISSP, renew RHCE (the followup to RHCSA) and also renew other certifications. Plus do other trainings and certifications, which feed into the renewal cycles, but are also actually helpful. 

As Auti says: it's the journey. I make a plan for every year, I do 2-3 courses and/or certifications every year. I make sure to keep learning new things. 

On the one hand I do this, because I'm honestly afraid of becoming too "old and outdated" for the IT market. But I also do it because my customers value this attitude: I keep improving my value on the market, but staying in touch with tech and skills that are relevant and recent. 

Plus I diversify: pentesting, Linux sysadmin, auditing, teaching/didactics, cloud. There are risks in generalizing as I do, but specialism isn't my thing.


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