An honest look at my
by Hilary Robles
February 16, 2026

Tech had been on my radar for a while, but for the longest time I could not figure out which direction to go. At first software engineering had me intrigued, then the idea of penetration testing felt like the coolest thing in the world. Over time, as I learned more and got a clearer picture of the field, I found myself gravitating toward Identity and Access Management. But before any of that clarity came, I just knew I wanted in. So I made a move.
I was coming from a completely different field when I decided to bet on myself and sit for the Security+. I will save that full story for another post because it deserves its own, but what that chapter taught me more than anything was how to actually learn. Not just how to pass a test, but how to make information stick.
Self studying takes a tremendous amount of grit. I have always been strong academically, rarely settling for anything under an A, always in honors classes. But self studying is a different animal entirely. There is no teacher, no deadline, no one checking on you. So I studied how to study. After discovering spaced repetition I immediately understood why teachers assigned readings before covering material in class and why homework was given daily. It all clicked. After finishing anything new I would close my notes and repeat back to myself exactly what I had just learned. I became very intentional about it. I did not want to just pass a test. I wanted the material to actually stick.
None of that prepared me for what came next though. Passing the Security+ did not open the doors I expected it to. Throughout that year I had already begun applying, so the job market was humbling me in real time. The rejections were constant, sometimes not even a response at all, just silence. It got to me. There is only so many times you can put yourself out there before you start questioning whether you are on the right path.
Eventually I regrouped. I had already built out an Active Directory home lab shortly after passing my Security+ to make sure I was not just studying theory but actually getting hands on with the tools. I also put together a Raspberry Pi travel router with a VPN for a trip I had coming up to Peru, which sounds like a fun side project but honestly it was just another excuse to keep building and stay sharp.
Those projects kept me sane during the rejection period. I then finished a Udemy course on IT support technician skills, tweaked my resume, and started applying again at 2 AM. I told myself that this time rejection was not going to knock me off my pivot.
That following morning at 11 AM I got a message on Indeed from a company asking to meet. We scheduled the interview for Friday, which gave me three days to prepare. I made a list of common entry level IT questions and studied them thoroughly. I recorded myself doing mock interviews, asking and answering questions out loud, watching myself back. It felt ridiculous. It worked.
Friday morning I was buzzing. Not just nervous but genuinely grateful. Someone was giving me a chance. Even if I did not get the job, I had made it to an interview and that meant something. The hiring manager and I hit it off immediately. The conversation went from my home lab to gaming without missing a beat. By the end of the call he told me he liked how I articulated myself and that I would be hearing back. I was elated. A new fire burned in me, not just because I had proven myself to them, but because I had proven something to my toughest critic. Myself.
My first week on the job was electrifying and I mean that literally, not as a hyperbole. Seeing the tools I had studied in my home lab being used in a real environment was incredible. Active Directory, Exchange Admin Center, Microsoft 365, Jira. I had touched all of these before. Then they brought in Barracuda, Cisco Endpoint Antivirus, Cisco Umbrella, and Cisco Unified CM Administration. I had always heard how intimidating Cisco products were, how brutal the CCNA is. But sitting in front of those tools that first week I realized they were not as frightening as I had built them up to be. Unknown territory can feel like standing at the edge of a cliff. The difference is whether you lean in or step back.
My first real task was setting up a new hire, which turned out to be the perfect introduction because it touched almost every tool at once. Creating mailboxes in Exchange Admin Center, assigning licenses in Microsoft 365, configuring permissions in Active Directory, setting up phones in Cisco Unified CM Administration. I was not overwhelmed. I was hungry for more. My team was incredibly supportive and wanted to ease me in slowly given it was my first professional role in tech. I appreciated that. But I wanted to get into tickets.
Which brings me to my first mistake.
I am a big note taker. Always have been, to the point where I used to sell my notes in college. Notes are my safety net. Being able to refer back to them at any step keeps me grounded and reduces my anxiety. So naturally my first mistake came from not referring to my notes. Ironic, I know.
An end user requested email forwarding. Simple enough. Instead of forwarding their emails to their supervisor I added their entire mailbox to their supervisor's account. Not the same thing at all. The supervisor came back saying they had not received any emails and I was immediately embarrassed. How did I fumble something so straightforward? But that embarrassment was useful. I learned why it matters. Adding a mailbox that way can cause it to crash entirely, which thankfully did not happen here, but understanding the why behind the mistake made it stick in a way that just reading about it never would have. I went back to my notes after that. I have not skipped them since.
Mistakes like that are actually what keep me going. There is something about getting something wrong in a real environment, with real consequences, that makes you want to understand things on a deeper level. It is a different kind of motivation than studying for a cert. It is personal. I am now setting my sights on the SC-300 and want to get serious about PowerShell scripting. The more I learn the more I realize how much there is still ahead of me, and honestly that does not intimidate me the way it used to. If anything it feels like exactly where I am supposed to be.