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The original was posted on /r/sysadmin by /u/Deceptivejunk on 2026-03-29 03:27:41+00:00.

Hi everyone, kind of stuck and figured I’d ask a bunch of people with more experience.

Little background on me, I broke into IT about 5 years ago working for a small nonprofit. I have a bachelor’s degree, but it isn’t related to IT in anyway. I did go back to school for about 2 years and took some cybersecurity classes, but did not graduate; my employer at the time paid for my education but obviously ceased once I quit. I also have no certifications.

At the nonprofit, it was just a two person show, me and my boss. My boss eventually quit and I was promoted to IT Manager. I was in charge of the entire on-prem infrastructure (and Microsoft365) and hired a helpdesk employee to assist. I did this for a couple of years before seizing an opportunity to work fully remote as a security engineer for another company, where’s I’ve been for the last 6 months.

I’m not really sure where I should go from here. I make about $75k/year and live in a LCOL area so I don’t struggle at all. However, I want to progress my career and make significantly more money. I’m just not sure what I should look into or lean towards; most of my knowledge has been learned on the job so there are definitely gaps in fundamentals and I feel like I know a little about a lot. I’m also mid-30s so I feel like I’m way behind and struggling with imposter syndrome. I guess I just need some insight on picking a direction to go towards and what other skills I may need. Any help or words of wisdom would be greatly appreciated.

P.S. my current job doesn’t offer any kind of education reimbursement or leadership programs.