How I switched careers and got my first IT job and the CompTIA trifecta in 3 months

As of my last post, where I passed the Sec+ exam, I’ve started working as an IT tech at a network of motorcycle dealerships wearing many hats under the direct supervision of the manager who was running the show by himself before he hired me. It’s an amazing job so far in terms of the variety of things we handle day to day which include account administration, networking, troubleshooting software & hardware, ticketing & remote support, managing and optimizing servers, disaster planning and response, phone systems, etc.

This post will be an overview of how I got here and a broader roadmap for anyone who may be on the fence about switching careers or may want to go for the trifecta but isn’t sure how to proceed. This post is gonna be long, but I think it’s important to share what I went through and pass on what I learned to help anyone who may need this.

I was feeling stuck and frustrated in my previous 8-year long teaching career with not much to show for my years of hard work and not much opportunity for growth. A friend in infosec recommended that I check out IT and showed me the roadmaps to get into different fields. He’s a pentester now and I really fell in love with the uniqueness of that field. The opportunities to self-learn and continuously learn, the creativity and problem solving, the adrenaline of discovering something that’s hidden, and not gonna lie, the pay and perks seem pretty sweet, too.

Of course, everyone wants the badass high-paying job but we were both aware that if I wanted to do that one day, there would be a long and difficult road ahead of it. And I knew I needed to prove to him that I was serious if I wanted to benefit from his mentorship. If you’ve ever taught or mentored, you know it takes a lot of time, energy, and patience, so I didn’t want to take it for granted.

He recommended I check out Sec+ as a starting point and see how I feel about it. He skipped A+ and Net+ because he worked with electronics and computer systems in his previous job and as a hobby before, so he was able to get his Sec+ and use his background to jump into a security analyst job right away. I knew this would probably not work for me given my complete lack of professional experience with IT or computers, but I began to study for Sec+. I bought Professor Messer’s 601 notes, watched his videos, and proceeded to take notes.

I’m very glad I didn’t pay for or schedule the test at this point because once the materials started to mention networks, port numbers, and servers, I panicked, realizing I was in over my head. Imposter syndrome hit me hard. I knew A+ and Network+ are considered precursors to Sec+ and contain more foundational knowledge but the thought of having to study for, pay for, and pass 3 OTHER exams, just so I could get to the point where I was then (studying for Sec+) was almost discouraging enough to make me quit. I crunched numbers in my head, thought about it, and even tried to make excuses for myself: “It’s not like computers are my real passion, like art and writing are, anyways, maybe I can live off of commissions,” “I’ll have to get a lower-paying entry job if I do IT anyways, and it’s probably gonna be depressing.” I lived in this limbo for a week or two, not yet taking the plunge to study for A+, but paralyzed in my current studies.

Eventually, I decided to take the plunge and go for it. The summer was coming up anyway (no work!) and I reasoned that if I really buckled down and grinded like it was a full-time job I could theoretically get the trifecta and a new IT job before summer’s end. This would be a challenge, and knowing myself, I knew I wouldn’t be able to resist a good challenge. You gotta know yourself enough to figure out how to push yourself when the motivation just isn’t there.

One thing I did that helped a lot was to try to soak myself in IT and cybersecurity media to see if it really was something I would find interesting or not. My friend made me a list of youtube channels to follow and podcasts to listen to. I began to listen to Darknet Diaries and the Social Engineering Podcast and watched a lot of Network Chuck and I absolutely fell in love with these stories and concepts. I found myself absorbing this stuff in my free time and that’s when I knew that IT, and cybersecurity specifically, was a budding interest that I could definitely grow to love once I dipped my toes more. I especially became fascinated with social engineering and pen-testing and I knew this was the goal I wanted to shoot for!

I studied hard for the A+, made lots of mistakes, and developed a pretty solid roadmap by the end of A+ and was thrilled when I passed with a 799. That was all I needed to push me through the other 3 exams. You can read my roadmaps and see what resources I used in this section of my site: Roadmap to the CompTIA trifecta. I won’t go into detail here about my exams since I already did that in the posts on the linked page, but basically, Professor Messer and Jason Dion are the MVPs.

I was able to refine my study plan and cut down the time studied for each exam. I had started sending out applications after passing A+, but once I passed Net+, I really began to focus seriously on sending out job applications for entry-level IT jobs after reading posts on Reddit and listening to this episode of Network Chuck. Most entry-level jobs were helpdesk or field technician jobs which in some cases, didn’t pay very well. Now, I wasn’t earning a whole lot as a teacher, but it was enough to pay the bills and save some cash, it was comfortable. The idea of cutting my salary by a good chunk to start from zero in a new career is not super appealing and was a bit nerve-wracking. But I didn’t even have a job offer yet! This was one of the most stressful parts of my efforts since I was in the middle of studying for Net+, which I scheduled to take 3 weeks after passing my A+ core 2 and it took a lot of time and energy to balance studying for this and looking for a gig.

This was the other part of this process that almost made me feel like quitting. Not only was I busting my ass off hustling to break into IT, but I had a resume with nothing (except an A+ cert) to show potential employers that I was qualified for an IT job. The idea was to find a remote helpdesk that would allow me to have a good work-life balance and make money doing art commissions as I got some IT experience.

I didn’t get any bites yet, and only some rejections, but the rest was silence. I really retooled my resume and tried to write a more targeted cover letter. In my desperation, I also began to randomly apply for instructional design jobs since they paid more out the gate and related to my teaching experience. The idea was to maybe find an instructional design job at a tech company so that I could then slide my way into a tech job with more experience.

I realized that I was neglecting my Net+ studies because I was dreading the Net+ exam and was finding any reason to procrastinate. I even tried to push forward the date, but all the dates for a month were packed so I knew I needed to focus. I studied hard and passed the test. Now here’s something I didn’t know that was a GAME CHANGER. Once you get your A+ and your Net+ certs, you automatically earn something called a CIOS – CompTIA IT Operations Specialist certification. CompTIA awards stackable certifications when you get a certain combination of certs that certify you for deeper mastery given the combination of certifications you have earned and can open up more interest in employers. You can see all the stackable certs here.

Well, that CIOS badge was looking really nice next to my Net+ and A+ badges and that’s the moment I really started to take my achievements seriously and began to believe I was qualified for a job in IT. I erased my title on Linkedin from something like “Teacher and graphic designer specializing in tech” to “IT Operations Specialist, Educator, Graphic Designer.” After all, CompTIA itself told me I was an IT operations specialist, I had the cert, so why not advertise it? I felt a little weird putting something like that on my professional bio given my utter lack of professional experience in IT but my mentor thought it was a great idea to do it since it would make me look more serious about IT and qualified if I led with this.

I began to really take the time to focus on how I presented my tech skills on my resume and it paid off. I also started to follow up on my job applications and if I could find some contact info for HR or the IT hiring manager, I made a point to send them an email with my resume and cover letter and express my interest in the role more personally. I got a call back for an IT Help Desk Technician at a company that owns several motorcycle dealerships the following day after applying for it and scheduled an interview for the day after.

I had no idea what to expect from an IT interview. I anticipated some technical questions, but I was also upfront on my cover letter that I have no professional IT work experience. Because of this, I made a point to highlight the important skills I’ve cultivated as a teacher and focused on the customer service, problem-solving, organization, documentation, resourcefulness, and creative thinking skills required in teaching. It was pretty chill and low-key. I made sure to ask questions, and if I didn’t know something: I was transparent. I would say what I did know, or how I would approach it, but also what I would do to figure it out if I didn’t know it. For example, he asked if I’ve ever worked with a help-desk ticketing platform. I told him I worked with simulations (the PBQs did have simulations!) and not the real thing, but I mentioned comparable software or platforms I’ve worked with for documentation, logging info in databases, and communication. I tried to be confident but not cocky, relaxed, and curious. I made sure to have questions prepared, and we even got to chat a bit at the end about hobbies.

I really wanted this job! As I mentioned in the intro. This job was not so much a help desk gig, but it would be helping him install, maintain, document, optimize, secure, and troubleshoot all the tech, accounts, and networking of these dealerships. Help desk ticketing was a part of the job, but given the small-ish size of the company, he said there would be between 0-20 tickets a day, so much of the job would require creative approaches to optimize the company’s tech. I knew this would be a perfect first job for me: I would be working directly with the IT manager, I would get hands-on experience in virtually all aspects of managing IT for a company, and I would be able to implement my own initiatives to optimize the department.

Fast forward to the end of the week and I got the job offer! Pay is definitely less than what I’m making now, but it was on the higher end of what I expected for an entry-level job.

Now that I had locked down an IT job, and had a start date (a week after I was scheduled to take the Sec+) I focused on passing Sec+, and I did! I wrote a post detailing my roadmap and experience preparing for the 601 here: plumapapel.com/passing-comptia-security/.

I now have the trifecta and have been working for a few weeks as an IT tech, and I’m starting to hit a good stride. It’s pretty surreal how fast it’s gone by and I’m glad I didn’t quit those times I got cold feet or felt like an impostor. It felt weird having a job locked down and having A+ and Net+ under my belt only to find myself where I was at the start of it all: studying for Sec+, but the backtracking I did made all the difference for me.

Take all of this with a HUGE grain of salt. If you are struggling or taking longer to get through your studies, don’t feel discouraged or feel like you’re doing anything wrong, are less qualified, or less passionate about it. I had no other commitments this summer so I was able to study for up to 10 hours some days. I am aware that this is not a realistic benchmark for most and I pushed myself in a way that may not be okay for others with more on their plate. I am also a teacher, and as such have a LOT of experience with learning, creating study materials, and administering and taking tests so I know how to play that multiple-choice game. I’ve always been a great test taker and have always enjoyed the experience and I know that for many, exams bring a lot of anxiety so I am not going to pretend like it was easy, I just had a lot of advantages going into this. All this to say: if you can do it and find this helpful, great, but if not, take what information you can and is applicable and tailor it to your own experience.

All in all, I just wanted to write this post to thank everyone who helped me out along the way and encouraged me to take a risk and give back some of what I learned from others here and the resources I used. Please don’t hesitate to reach out with any questions or comments.