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!
Any time you have an area in your resume that you perceive to be weak, it makes sense to emphasize your stronger areas - and also show that you are capable of overcoming your weaknesses. Sometimes, this requires a careful refocusing of your resume and your question-answering technique, versus just writing a literal resume showing your work experience or giving simple answers to questions.

While technical skills are important in IT, and it's valuable to show that you have up to the minute experience with specific technologies or tools, employers are also looking for more generic, softer skills. They're also generally looking for people who can follow directions, accomplish tasks, handle exceptions appropriately, and who know how to follow rules or processes versus winging everything.

Since you're concerned about a two year gap indicating that you are out of date technically, it may make sense to emphasize those soft skills in your resume. If you have a paragraph or summary at the top, that's a good place to do so. Also, when you list your past jobs, make sure you show how you did these things, versus just listing bland job duties or acronyms. Some employers may not pick up on this and may pass over you, but that's okay - employers with a narrow focus on specific up to the minute technologies are probably not your ideal employer anyways.

Secondly, make sure you emphasize your ability to learn and adapt to new technologies. If a candidate doesn't have a specific recent skill set, but they can show that they've regularly picked up new skill sets and have been able to effectively use them, that is a strong advantage. Ultimately, employers who are *always* focused on the shiny new thing really need people who can learn - not people who know what's shiny and new right now (because in 6 months they'll be focused on whatever replaces it anyways).

Further, as an option, consider targeting employers who need the skills you currently have, even if you think they are out of date. A big fallacy among people new to IT is the assumption that every employer always wants the newest and only cares about "current" technology. In reality, a large portion of the IT landscape is "old" and "outdated" at any point in time. You may find that there are a lot of employers who are specifically looking for your years-out-of-date skills. My current employer and several before it were all running their core systems on technology that was **decades** old, and it was a huge struggle to fill many positions, because the majority of candidates emphasized "current" technology.

So, don't rule out the potential that you may already have highly desirable skills - at the end of the day, finding a job is a balance of advertising yourself accurately and appropriately, but also making sure you're looking for opportunities that are actually a good fit for you.