New to TE, trying to shift gears after 12 years so far in IT

Hi All, new to the group here. I've been in IT for roughly 12 years now. Started off like everyone as a desktop analyst and have most recently for the last 8 years been Manager/Director of IT for a decent size ($10m) non-profit with a few people working under me. The job I miss the most I think is working for a private DoD contractor in the InfoSec line of work. I was very entry level doing it 9 years ago, but I should have pursued it, and didn't.

At this point now, my career is stale due to the non-profit. Totally sucks. Haven't got a raise/promotion in 6+ years (no where to go) and due to the nature of the business we're not even getting cost of living increases. I need a change. I managed to convince my office to allocate some funding for me for some training so with that my intention is to back and get my A+, Network+, Security+, Cloud+, and Project+ certifications within in the next 4-5 months and I already enrolled to start a Master's program in the fall. I already have ITIL v3 Foundation, but haven't quite decided how far to pursue that yet.

I know the first thing people will say is don't bother with A+, but I figure since my career has been so stale, the more letters with +'s I can put next to my name, the quicker opportunities may come available for me to move on. I really think I'm going to push back towards the InfoSec field and realize I'm probably going to have to take 5 steps backwards in my career to do it, but I think it could be rewarding.

Do you all think I'm a little too ambitious going for 5 certifications in 5 months and then starting a Master's program? Will someone hire a mid-senior level manager like me without the Master's degree or should I just plan on staying here for a few more years? Not sure I have it left in me!

Looking forward to seeing what people think. Thanks!

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scaredoftests wrote: »

What are you interested in? If you are working, would your company pay for it? If so,go on from there.

My job prior to the one I'm in now I worked as a DoD contractor on a help desk but I was the sole liason between us and the security services department doing virus/malware forensics and remediation stuff. it was very much entry level (given my position at the time) but I loved that work. I still love that work so I'd love to shift gears towards security work. All my recent experience is Management/Client services which I also love but I'm getting somewhat tied of dealing with customers (coworkers).

My company won't pay a dime of it, I'm on my own at the moment. We didn't even get a cost of living increase this year and I've been there 8 years. Budget is very tight with the 7 month old sitting next to me as I type this right now.