I was five years old the first time I took apart something that didn’t belong to me.
A clock radio. My parents were asleep. I had a screwdriver I had no business using and a question that just wouldn’t leave me alone: what’s actually happening inside this thing?
I got it open. Stared at the board, the coils, all these components I had no names for. I didn’t understand any of it. But I needed to see it. That felt more important than whether I could put it back together. Which, for the record, I could not.
Nobody taught me that instinct. It was just there.
1988, Ten Years Old, The Commodore 16
My first real encounter with a computer was a Commodore 16 with a German manual I could not read.
That was fine. I wasn’t interested in the manual.
Loading games from cassette tape. Waiting through the static and the blinking cursor. Watching the screen for minutes hoping the read wouldn’t fail halfway through. It failed a lot. So I started looking at why. I learned that games loaded differently depending on how the tape head was aligned. I learned that some programs had protection schemes built in, designed to fail on purpose if you tried to copy them. I learned that other people had already figured out how to get around those schemes, and that this knowledge circulated on photocopied sheets and in Italian computer magazines that cost more than I could reliably afford.
I read every page of those magazines twice. Including the parts in German.
I have no idea how much of the German I actually understood. Probably none of it. But I read it anyway.
Mid-90s, Cracks, Trainers, and Learning DOS Without Meaning To
By the time I was in my mid-teens the PC had arrived and with it a completely different set of problems to solve.
Games I couldn’t afford. Copy protection I couldn’t beat the legitimate way. So I found the other way. No-CD cracks. Trainers that let you modify values in memory while the game was running. Patched executables that skipped the license check entirely. None of this came with instructions. You found a file, you ran it, it either worked or it didn’t. If it didn’t you went looking for a different one.
I spent a lot of time in DOS directories trying to understand what each file actually was. Why some executables behaved differently than others. What a hex editor was showing me when I opened a binary I wasn’t supposed to touch.
I did not think of any of this as learning. I thought of it as getting games to work.
That’s probably the most honest summary of how I’ve learned most things in my life.
Late 90s, The Internet Arrives
The late nineties are something I genuinely don’t think I can explain to anyone who wasn’t there.
Suddenly there was a network. FTP sites with directories full of things you weren’t supposed to have. IRC channels where people shared ISOs of software that cost hundreds of euros at retail. Warez. Scene releases. NFO files written by groups with names like they were hacker handles, because they were.
I set up my own FTP server at home. A machine I kept running overnight, hidden from my parents’ electricity bill line of sight. I learned port forwarding before I knew what a port was. I learned that keeping a server running required understanding what was trying to connect to it, and what I wanted to allow.
The first time I read my own access logs I realized I was already doing something that felt like security. Just from the wrong direction, looking outward instead of in.
Early 2000s, The Xbox, Solder and Smoke
The original Xbox came out in 2001 and I wanted to run homebrew on it.
The only way to do that was a modchip. A small board you soldered directly onto the motherboard, wired to specific points that disabled the boot signature check and let you load unsigned code. The instructions existed online in broken English and forum posts from people who had already burned their boards trying.
I burned my board.
Then I bought another one, read more carefully, and got it right the second time. The moment that Xbox booted into a custom dashboard running Linux in a secondary partition was one of the more satisfying things I’d done up to that point in my life. Hardware doing something it was specifically designed not to do. Using a soldering iron, patience, and the willingness to destroy something expensive if I got it wrong.
I got it right on the second try. That’s still my record for hardware modding. Not a record I’m proud of exactly, but it’s the one I’ve got.
The Long Way Around
Life moved. I went into design, then into software quality assurance. Testing systems, finding edge cases, writing down what broke and why. Then into management, architecture, strategy. Years of building things correctly, making them reliable, aligning them with things like business objectives.
Real work. Work that required understanding systems deeply.
But I kept thinking about the other side of the table. I would spend months hardening a process, reducing risk, training teams to recognize threats. And I’d find myself wondering: what does this look like to someone who doesn’t care about any of that? Someone who just wants in?
I didn’t have an answer and it bothered me more than it probably should have.
The Question I Kept Not Asking Out Loud
It wasn’t a single moment. More like a slow accumulation.
What if I was on the other side?
Not the architect. Not the manager. The one who finds the crack, pulls the thread, sees how far it goes.
Offensive security is honest in a way that defense isn’t, at least in my experience. You can build the perfect governance framework and still get owned. You can pass every audit and still have some box sitting open on your network that nobody thought to check. Defense lets you believe you’re done. Offense tells you whether that’s actually true.
I wanted to know if it was true.
What This Actually Looks Like Now
I study alone. That’s genuinely the hardest part of this. Not the technical difficulty, but the silence. No one to turn to when something doesn’t click at 11pm. No colleague to think out loud with. Just the box, the terminal, and the problem.
PicoCTF challenges. The HackTheBox CPTS path. More CISSP reading than I’d like to admit. Failing at things that should probably be obvious by now. Occasionally getting something to work and feeling like that kid who finally got the Xbox to boot.
The path isn’t straight and it isn’t fast. I’ve made peace with that. The five-year-old with the screwdriver wasn’t trying to be efficient. He just had to know what was inside.
Why “obstinatus”
Latin. Persistent. Stubborn. Relentless.
The box doesn’t open on the first try. Or the second. You stay until it does and you write down every failed attempt, because the failed attempts are usually the more useful half.
This blog is that notebook. Not polished, not complete. Updated as I break things.
If you’re on a similar path, welcome. Let’s figure it out.