TryHackMe: Rekindling my Passion

Reflections

What is TryHackMe?

TryHackMe is a CTF-style “browser-based cyber security training platform” (/about). It’s been running since 2018 and has over 6.5 million users at the time of writing. From someone who experienced, and still holds dear, the old style of “hacking challenge sites”, this is truly a welcome evolution.

Where did my passion go?

Looking back on my career, it’s clear what happened: I needed a job. I initially got interested in development as a means to an end - understanding how to build software so I could break it. Along the way, I got pretty good at it and eventually came to enjoy it on it’s own. I graduated high school and wasn’t too thrilled with the idea of college so I started looking for entry level jobs in the industry.

I got my first job at an MSP that also developed their own monitoring software. In the grand scheme of things, this was a small company, but it still served up a healthy amount of culture shock with me being fresh out of school and never having held a real job.

Not only was this my first time being introduced to “business”, but it also came with ample opportunity to explore new tech. Up until this point I hadn’t used any sort of version control so SVN and then Git came into play. I used virtual machines for the first time, learned about SNMP, and message queues. I built and debugged production level software in languages I never planned to really dive into, and I learned about concepts like the OSI model and OSPF.

Once that job was over, it was natural for me to pursue something familiar. I ended up at another MSP. This one, however, also develops, hosts, and manages sites for other businesses. While the new tech was limited, it’s helped me to refine my skills and gain a few new ones. It’s exposed me to cloud services like AWS and Azure. It’s also helped me gain some adaptability - having to jump from project to project.

All that said - there’s always been something missing. It’s always felt like a job (I know, it is). Certain problems that I run into give me that rush when I solve them, but they’re few and far between. One thing that is sure to give me the rush, though, is when it involves security. Even our “security trainings” have become something I look forward to. Sure, they’re mostly just “don’t get phished”, but the stories bring me joy.

What pulled me back in?

Every year TryHackMe does an “Advent of Cyber” - a series of 24 tasks, one released each day of December until Christmas. I had done a few of the challenges last year, but was always frustrated by the time limit on the attack box. This year, I decided I’m going to buy a subscripton and that was, I think, my best decision of 2025. I did the advent of cyber while working through their Jr Penetration Tester learning path. Every day I couldn’t (and still can’t) get enough. I’ve completed that path and am working on the Web Application Pentesting one now.

Doing these modules feels like a return to form of sorts, but with the added benefit of my decade of professional development experience.

What’s next?

I have a year subscription so I’m going to be doing as many of the learning paths as I can. Once I’m satisfied, I’ll be pursuing a certification - likely the PT1 certification at first, if only because I’m familiar with their environment now. Afterward, I’m going to pursue something more recognized like the OSCP or CPTS.

Thanks TryHackMe

Thank you to TryHackMe for reminding me of my goals and giving me the kick I needed to start pushing forward on them!