My First Day at OsmSec

I logged into my first day at OsmSec from my tiny desk at home with my hoodie on, coffee in hand expecting the usual remote onboarding routine. You know: some welcome emails, a quick intro call, maybe a few docs to skim through.

Instead, I found myself in what felt like a digital version of Oz but on Slack.

The team channels were alive with activity. People were casually chatting about “CTFs,” “Kerberoasting,” “DLL Sideloading,” “CrowdStrike” and someone even dropped a meme about something called tcpdump(I still don’t get it). I scrolled through, smiling and reacting with emojis, pretending I understood. In reality? I was completely lost.

Then came the moment that really sent me spiraling.

I stumbled across a Slack thread where the team was discussing the company logo. Someone said, “Let’s go with a pixelated flag since we catch flags anyway.”

Catch flags?

What flags? Digital flags? Actual flags?

I sat there, blinking at the screen, thinking:

Did I accidentally join a cyber-themed escape room? Is this a test? Do they know I have no idea what’s going on?

It felt like I have landed in a secret online society of cyber wizards, all speaking an entirely different language. And me? I was just the clueless new kid trying to figure out where the front door was.

Just when the overwhelm started creeping in, a calendar invite popped up: “Google Meet with the founder of OsmSec.”

Oh no.

My stomach dropped. I was sure he’d realized I wasn’t cut out for this.

But the moment the call started, all that panic disappeared. The founder greeted me warmly zero pressure, zero tech-snob energy.

He smiled and said, “Hey, I figured you might be wondering what all this flag talk is about.”

And just like that, he broke it all down like I was a curious student hearing about the internet for the first time.

He explained that CTF stands for Capture The Flag a type of cybersecurity competition where participants solve challenges to uncover hidden pieces of data (the “flags”). These puzzles range from cracking encrypted messages to analyzing logs and spotting vulnerabilities. It’s like escape rooms, but digital and smarter.

At OsmSec, they don’t just train people to solve CTFs. They design and build their own real, hands-on, thoughtfully crafted scenarios that simulate real-world cybersecurity challenges.

And the best part? You don’t need a computer science degree to dive in.

Their approach is designed for the curious not just the credentialed. They break down complex concepts in ways that make sense, even for total beginners. You’re not expected to know everything. You’re expected to ask questions, to experiment, to fail, and to learn. And there’s support the whole way through.

He walked me through the why, the how, and what to do when you’re stuck all in a way that felt more like a conversation than a lecture.

By the end of the call, I still didn’t know how to solve a CTF. But I finally understood what one was.

And more importantly, I didn’t feel like an outsider anymore.

Curiosity had replaced fear.

And that was my day one!