One would call me a generalist system admin. Everyday bouncing back and forth from fire to fire. Knowledge is a mile wide and an inch deep, I’m fed up.

I have a bachelors degree in IT, 3 years help desk, 2.5 years system admin, active security+

I need to move towards an “official” security related role. In my heart, that’s what I want.

My resume paints the picture of a generalist system admin. I’m proud of my wide skill set…. but… is it hurting me when I’m applying to list things that are somewhat irrelevant?

Does anyone have any similar transitions? Should I work on my resume? Work on hack the box? Learn python? Strengthen Linux skills? Study for cissp? None of the above? All of the above? Throw my life savings into crypto?

I’m so confused and burnt out being a generalist system admin.

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  • Rud2K

    November 21, 2021

    Have you even committed a felony? If not since it have sec+ look into DOD contracting

  • Teddy141345

    November 21, 2021

    I am hoping to give you some guidance here but we will see how that goes. I was the same way as you started off working a number of different positions that gave me quite a wealth of knowledge but no specific focus early in my career. I did phone support, system administration, network administration, database administration, DevOps. I think you get the idea. After about 7 years of doing all these different things I was able to transition into a Cyber Security role. Then after 6 months in cyber security I became the manager and a year later I became the director of engineering. I had Security Engineers, Software Developers, DevOps, and Project Management all reporting to me. While it may seem like your career is all over the place now it can turn into bigger things down the road.

    I was never one to get certifications so I still do not have any but for some it does advance their career quite nicely. If I were in your position with today’s job market I would start looking at entry level security roles. If you want a ton of experience quickly I would recommend looking at an MSSP, that would help jumpstart things.

  • tim-brottsling

    November 21, 2021

    I went from non-infosec system engineering (5 years) to infosec, through a master’s in infosec. If it was pure luck or not I’ll probably never know.


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