Question: I've worked for a company in the media industry as an IT support while I was in CIT college and due to some circumstances I dropped out of college but kept on working there for 5 years. I've gained a good amount of experience in desktop and network troubleshooting, server management, and some vendor-specific devices in the media industry. The company ceased operations 2 years ago and since then I've been working non-IT related jobs.

**My question** is what is the best move for me now to get back in the field and land a good job? With nothing but 5 years experience and a 2 year gap? 

I'm working on getting Cisco CCNA Routing & Switching before the end of February although I don't know if I can really be ready for it in time. Also I'm planning to tackle Comptia A+ certificate next and maybe Network+ in case I miss CCNA R&S deadline.

My end goal is to get a job in the IT field again and find some way to finish my degree even if I have to start over.

Answer: 
I think first you should make up your mind about the technology you want to work with; but as per your 5 years experience and your zeal to pursue CCNA R&S, I will assume you want to work in "Infra" field in an IT company. 

* Start scanning job portals and read about the latest expectations of the companies, what do they expect out of their next Infra hire.
* Try to give some interviews, and most importantly, expect not to be selected but you will definitely gain some crucial areas where you lack now and then you will have leads on what to improve. (A certification does not necessarily mean a good hire but practical experience does!)
* Then prepare a list of what you need to brush up more, practice all concepts with hands-on experience.
* Try giving more interviews, eventually your confidence will become high and I am sure you will land up with an IT job soon.
* Your gap won't matter to a company if you can prove you can work according to their expectations and have relevant experience.
* Once you land up with a good job, then you can try to find a college that offers that degree from correspondence, meaning you just need to clear all exams and not necessarily attend all classes. You will have to manage your time on weekends.

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* Now if you want to change your IT field to a Development or Testing job then that requires expert knowledge of a coding language OR some Automation Testing experience can help you land up a QA job.

All the best!
As Paul K mentioned in a comment, location will matter a lot.

Easy steps could be to dust-up your (or create a) Linked-In profile and if that's not already done, look-up your former colleagues and classmates. Then in the options, mark yourself as available (and add the areas where you are looking for, and open to move to).

Usually when I do that, offers start flooding and it's more a matter of finding out which are spam and which are legitimate. That's how I've landed all my jobs since graduation. But I'm a software engineer though, not a network specialist or a sysadmin (even though that's what my initial degree was in), and the market for engineers in France is in extreme deficit.

Now, I use Linked-In, because I think it's the best tool for my situation (engineering consultancy in France) but there are plenty of other sites. If you look over to Stack Overflow, there's a job offers site and I hear it's good for positions in the US/UK for example. So my advice boils down to this: show up online.

And good luck for your CISCO cert.