Trying to Break Into IT After 10 Years of Already Trying

I've been trying to get into IT for a pretty damn long time. And when I say “trying to get into IT,” I mean I genuinely never got the opportunity to establish myself in the field in the first place.

I graduated from ITT Technical Institute in 2014 with an Associate of Applied Science in Networking Systems Administration. I had the education, I had the interest, and I was trying to do what I thought I was supposed to do: graduate, find an entry-level IT position, get some experience, and start building a career. That didn't happen.

I currently have 2-3 windows desktops, and probably 7-10 laptops of varying ages running around my house that all still function and I keep them as long as they do. Never been able to afford a brand new one yet, never had the opportunity to build one or take one apart yet, either.

I applied for IT jobs, tried to get interviews, and tried like hell to get someone to give me that first opportunity. I ended up with exactly one interview for an IT position. I never actually got the opportunity to work in the field. So I went where I could actually get hired.

Over the years, that meant customer service, call centers, retail, caregiving, Direct Support Professional work, and other jobs that weren't really related to the career I'd originally gone to school for. That wasn't necessarily what I wanted my career to look like, but I still had to work, pay bills, and keep moving forward, and here's where things get a little weird. I'm trying again.

Except now my IT degree is about ten years old, technology has changed considerably since I was in school, and the “entry-level” IT jobs I'm looking at now seem to want more experience, more specialized knowledge, and sometimes even more education than the entry-level jobs I was trying to get when I graduated. It's gotten pretty to be a fucking frustrating position to be in.

I understand that my ten-year-old networking degree isn't going to make me an expert in every technology an employer might use today. I'm not expecting anyone to look at my résumé and assume I have ten years of enterprise IT experience when I don't. That would be ridiculous.

But I also haven't spent the last decade sitting around doing nothing. I've been working since 16 (technically had a paper route income at 12-13)

Twenty Years of Work Experience Isn't the Same as Twenty Years of IT Experience

This is probably the most frustrating part of the current job hunt.

I've been working for more than twenty years, but almost none of those years count as traditional IT experience. If a job posting says it wants someone with three years of enterprise IT experience, I can't honestly tell them I have three years of enterprise IT experience. I don't. That doesn't mean those twenty-plus years didn't teach me anything, though.

I've worked in customer service and call centers, where I've had to learn different software and systems, troubleshoot both non-IT and IT problems while people were waiting for answers, communicate clearly with frustrated customers, document information, and figure out how to solve problems without necessarily having someone standing over me.

I've worked retail and other customer-facing jobs. I've worked in caregiving and Direct Support Professional positions where attention to detail, documentation, following procedures, recognizing when something isn't right, adapting to unexpected situations, and staying calm under pressure were all pretty important parts of the job.

Those aren't necessarily “IT skills,” but they're still professional skills. After twenty years or so of working, I've learned a lot about how I actually function in a workplace, what I'm good at, what I enjoy, what drains me, and what kind of environment I want to work in.

I don't think that's nothing.

What I'm Doing to Update My IT Skills

At the same time, I'm not going to pretend my 2014 networking degree is automatically enough to make me current in 2026. Technology has changed a lot in the last decade.

There are platforms, tools, security practices, cloud technologies, enterprise systems, and general IT concepts being used today that either weren't part of my original education or weren't nearly as prominent as they are now. That's one of the reasons I'm back in school.

I'm currently pursuing my bachelor's degree in Information Systems with a concentration in cybersecurity. I'm getting the opportunity to refresh some of the technical foundation I already had while learning newer concepts and technologies along the way.

I'm also building projects, working on technical documentation, refreshing networking and cybersecurity concepts, and generally trying to make sure that what I know isn't just based on what I learned ten years ago.

I'm not trying to hide the age of my degree. I'm trying to make it less relevant. If an employer sees that my original IT education is ten years old, I want the rest of my résumé and portfolio to show that I haven't stopped learning.

I Do Finally Have Some Recent IT Experience

I also recently got a small amount of actual professional IT experience as a Support Technician for Open Dental Software. It was less than three months, so I'm not going to pretend it suddenly gave me a decade of professional IT exposure. It definitely didn't.

But it did give me something I didn't have before: recent professional experience working directly with technology in an actual IT support environment.

It also reminded me that I genuinely enjoy this kind of work. I like troubleshooting. I like figuring out why something isn't working. I like learning unfamiliar systems. I like taking a problem that initially looks like a pile of unrelated information and trying to find the pattern that explains what's actually happening. That is a big part of why I'm continuing to pursue this, and I just need to find employers willing to give me the time my brain needs to process and retain and grow with the company and as a professional.

The Problem With “Entry-Level” These Days

One of the things I've found particularly frustrating during this job search is how wildly different the definition of “entry-level” seems to be from one company to another.

Some entry-level positions genuinely seem like they're designed for someone who is new to the field and willing to learn. Others want a bachelor's degree, two or three years of experience, multiple certifications, knowledge of several enterprise platforms, and enough specialized technical knowledge to make you wonder what exactly they consider entry-level.

At some point, you have to ask where people are supposed to get that experience. I'm not expecting to walk into my first full-time IT job knowing everything. I expect to need training. I expect to learn whatever systems and tools a company actually uses. I expect there to be things I haven't encountered before. That's normal.

In fact, that's kind of the point of getting into a new environment. What I'm looking for is an employer that's willing to say, “You have a foundation. You have some relevant skills. You clearly know how to learn. We'll teach you the parts that are specific to us.”

That seems like a pretty reasonable expectation for an entry-level position.

I'm Entry-Level in IT, Not in the Workforce

This is probably the simplest way I can explain my current situation.

I'm entry-level in IT. I'm not entry-level as a worker. I've been working for more than twenty years. I've dealt with customers, coworkers, supervisors, stressful situations, changing expectations, difficult people, new software, documentation, procedures, deadlines, and all the other things that come with having a job.

I've also learned what I don't want. That's actually pretty valuable, in my humble opinion. I'm not looking for just any job anymore. I'm not looking for a J.O.B. I've worked enough different jobs to know that I wanted my next career move 10+ years ago, and I'm still hoping to get into it, rather than simply being another paycheck until the next thing comes along and I then have to start over at the bottom again.

What Kind of IT Work Am I Looking For?

Right now, I'm most interested in backend and infrastructure-focused work, systems, networking, technical support, cybersecurity, and eventually areas like incident response and log analysis.

I'm particularly interested in work that involves troubleshooting, pattern recognition, documentation, and figuring out what's happening behind the scenes. I'm also trying to move away from jobs that are primarily sales or heavily phone-based customer service. That doesn't mean I can't communicate with people. I've spent enough of my career doing that to prove otherwise.

I just don't want customer interaction to be the primary purpose of my job anymore. I'd much rather be the person figuring out why the system isn't working than the person explaining to someone for the hundredth time why they need to restart their router.

Although, let's be honest, sometimes the answer really is “have you tried turning it off and back on again?”

So, What's Next?

For now, I'm going to keep doing what I've been doing. I'm going back to school. I'm continuing to build projects. I'm refreshing my technical skills. I'm learning more about cybersecurity and infrastructure. I'm building out my technical documentation portfolio. I'm applying for jobs and trying to find someone willing to give me that first real opportunity.

I'm also trying to be realistic about the fact that I may not land exactly where I think I will. Maybe I end up working in cybersecurity. Maybe infrastructure or systems becomes my thing. Maybe I discover some completely different area of IT that I haven't even considered yet. That's okay.

The important thing is that I'm finally moving toward the field I originally went to school for instead of continuing to wonder what might have happened if I'd ever gotten that first opportunity.

I'm not trying to become the person I was supposed to be in 2014. I'm trying to figure out what I can do with everything I've learned since then. And yeah, I'm still trying to get someone to give me that first real shot at getting into IT full-time. Hopefully, this time, somebody opens the fucking door.

Once I get that opportunity, we'll see what I can do with it.