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Becoming Robin: My Path from Sysadmin to Cybersecurity

Superheroes

At first, the idea of playing a “Robin” in the world of cybersecurity might sound a bit unconventional—after all, who wouldn’t want to be Batman, the caped crusader? But as I’ve discovered, sometimes the sidekick’s role is just as important (and sometimes a bit less dangerous). This is the story of how my journey through IT and security began, how community played a critical role, and how stepping into unexpected roles led to growth, new opportunities, and a few laughs along the way.

About a year and a half ago, I took a Threat Hunting class taught by the brilliant Chris Brenton. This class introduced me to Antisyphon and their innovative Pay What You Can model. At that time, I was new to IT, with only a year and a half of help-desk experience under my belt. Though I was self-taught and eager to learn more, my knowledge of information security was minimal—mostly limited to some Linux command line skills and a fair amount of Googling.

After following Antisyphon for a while, I had the chance to take John Strand’s SOC Core Skills class. While much of the material and stories he shared went over my head at the time, I was captivated by his teaching style and the enthusiasm he brought to the class. Despite my limited experience, his passion made a lasting impression on me.

I’ll admit, the OSI Model comments had me scratching my head. I was lost, but I was determined to push through. As I set up the labs, I ran into a few hiccups, but the community stepped in with such generosity and patience. The way everyone rallied around to help and share their insights turned what could have been a frustrating experience into a truly uplifting one.

Seeing how the community rallied around me, I was pumped to dive in myself. I chatted with friends about joining in, and soon enough, I was volunteering for the next class. Armed with my newfound setup skills, I jumped in to help. While I was still a bit like a deer in headlights, I was at least a more informed deer. The experience was fantastic, and I became more involved in the community. I signed up for the Getting Started in Security class, where I bombarded everyone with questions—some of which were probably pretty basic. But the warmth and patience of the community made every “oops” moment a learning opportunity.

By this point, I was all in on the weekly webcasts from Antisyphon and BHIS, and I’d become a familiar face in the Discord servers. I ended up meeting some really fantastic folks—so fantastic, in fact, that I’d call a few of them friends. When the next Pay What You Can class rolled around, I was ready to dive in and tackle some of the virtualization issues. After four days of helping out, I earned my “Nerdherder” (Robin) badge. And no, it’s definitely not a cult—though with the amount of enthusiasm and support flying around, it might feel like you’ve joined a very friendly secret society!

Moderating classes had become second nature by then, and I had already assisted with several, including MITRE ATT&CK Framework. That class opened my eyes to the ATT&CK matrix framework, but I still had a lot to learn—especially about Active Directory. When I went through the Defending The Enterprise class, it was like flipping a switch. The way the course broke down AD security was unlike anything I had experienced before. Suddenly, AD wasn’t just a piece of Windows infrastructure—it was a battleground, and I was hooked. This course didn’t just teach me; it gave me a direction. From that point on, I knew AD security was the path I wanted to follow. It felt like I had been given the keys to Batman’s cave, with all the gadgets and tools at my fingertips to explore and experiment with.

As I dove deeper into AD security, my role in moderating and volunteering continued to grow. It wasn’t just about being part of the classes anymore; it was about immersing myself in a community that was both supportive and inspiring. My involvement with the Antisyphon and BHIS Discord communities introduced me to incredible people who shared their knowledge and experience generously. This environment helped me conquer my self-doubt and chronic imposter syndrome.

The community’s encouragement was instrumental when it came time to take on new challenges. I was given the opportunity to give my first-ever talk, an experience that I wouldn’t have had without the support and push from my mentor and friends. My mentor (who I’ve met as part of involvement in the community) was the primary force behind this opportunity, and the confidence and skills I gained from being part of this vibrant community were crucial in my growth. It’s not just about having resources and tools; it’s about having a network that genuinely cares and helps you succeed.

Whenever we try to learn new things or accomplish goals, we’re often looking for shortcuts or hacks. While there may not be an easy route, having a supportive community to talk to and seek advice from can make all the difference. That, my friend, is the real cheat code. I’m still working on my transition into the infosec career, but it’s been quite a journey, mainly due to the community here. So, if you’re on a similar journey, come join us and see how the right community can transform your path.