July 14, 2021

Would IT experience from 5+ years ago help me land a job?

Hey guys, for a little background, back in my teen years I was obsessed with tech. I had taught myself a wide range of skills such as programming and security, and in between school and friends I made a little side money doing freelance web development and game programming, participated in CTF challenges, did bug bounty hunting (before it was really a “thing”, and was doing it without expressed permission and luckily never got into any trouble as everyone was grateful and was even offered a job as a pen tester by one company).

After high school, I joined the military in an IT position and actually gained some real world experience, starting in a basic help desk position before moving onto Windows and Linux server administration and dealing with things like virtual machines, active directory, installing security updates, monitoring logs, gaining certs such as Sec+ and CCNA, basically the whole shebang, before eventually moving into a managerial role.

However, after 5 years in the military I started to realize my whole life was tech and I knew nothing else. So since then, for the last 5 years, I’ve been out of the tech scene doing things like fighting wildfires for a living, traveling the world, learning unrelated skills, gaining new experiences, etc.

My passion for tech never really died and I’ve kept sort of up to date on things and now I really want to get back into it as a career after having accomplished unrelated life goals.

My plan is to use my GI Bill to go to school for computer science and really start actively catching up on things. However, if possible I’d like to get right into the cyber security scene without going back to a basic help desk role. Would my out-dated work experience still help in my job search or do I need to start back at square-one and work my way back up?

Any thoughts would be greatly appreciated, thanks!

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