The Ethical Hacker’s Dilemma — Day 34

Where I’m At Right Now

I think AI is about to pull up a seat next to me at work.
Should I give it a cup of coffee or my resignation?

I say this jokingly, but let’s be real — AI is creeping into cybersecurity faster than we’re figuring out how to use it. It’s weird knowing that, in the near future, I’ll have colleagues that don’t need sleep, don’t complain about meetings, and definitely don’t drink coffee.

But if AI is just another system to be hacked — another entity entering the battlefield — then I need to learn how to work with it, break it, and ultimately outthink it.

This has been on my mind a lot lately because, once again, my focus is shifting. I came into cybersecurity aiming for DevSecOps, automation, and engineering. But the deeper I go, the more I feel drawn toward ethical hacking and penetration testing.

Why? Because penetration testing makes my mind move the way it was designed to move. It’s about creativity, problem-solving, and seeing through the cracks of the system. And the best part? Automation is still a major piece of it.

I still love security engineering, cloud security, and AI-driven automation, but the way I approach them is evolving. Instead of just locking things down, I want to understand how everything breaks. Because when you understand that, you can rebuild it better — or burn it down and start over.

Cyber News Breakdown: What’s Actually Happening?

Here’s what caught my eye today:

Penetration Testing Mindsets

Types of Penetration Testing (Article)
Black Box = The outsider, guessing everything.
Gray Box = The infiltrator, working with partial knowledge.
White Box = The insider, seeing everything.

I see these not just as testing methods but as life strategies. Sometimes you have to brute-force the door. Sometimes you social engineer your way in. And sometimes… you were always inside the system; you just didn’t realize it.

AI & Automated Security Attacks

AI is changing email security and phishing tactics. (Article)
AI is being used to simulate attacks and predict vulnerabilities.
Phishing emails are now AI-generated — which means we’re fighting against machines that learn faster than humans can detect them.

This is cyberpunk in real-time. We’re watching AI evolve from a tool into an adversary.

The Offensive Side of Cybersecurity

“The best defense is a good offense” applies to hacking, too. (Article)
Defenders react.
Attackers predict.
To defend a system, you have to think like someone who wants to destroy it.

And isn’t that the world we live in? Sometimes you don’t win by playing by the rules. You win by knowing where the rules bend, break, and rewrite themselves.

The Hacktivist Perspective: The Bigger Picture

I’ve always felt like an anomaly in this space.

Some people walk through open doors. Some people get a key. Some of us learn to pick locks, not because we want to — but because we were never given access in the first place.

Some people play by the rules. Some people write the rules. And some of us spend our whole lives figuring out where the rules can be bent, bypassed, or rewritten entirely.

There are those that look at security as defense — putting up walls, locking things down, making sure nothing breaks.
I look at security as a dynamic battlefield — one where understanding the offense is just as important as the defense.

And let’s be real…
Some start with a map and a manual — they know where they’re going before they take the first step.
Others get a vague set of directions — it takes trial and error, but they eventually figure out the path.
And then there are the ones who get no map, no manual, and no instructions — just a locked door.

If you’ve never had to reverse-engineer your way into a system that wasn’t built for you,
you might not understand why hacking isn’t just about security — it’s about survival.

So maybe that’s why I feel drawn toward ethical hacking.
Because penetration testers don’t just follow the rules — they expose them

Execution Plan: What’s Next?

Deepen penetration testing skills (Hack The Box, CTFs).
Test AI-powered automation tools for offensive security.
Refine my approach to ethical hacking & documentation.
Start conceptualizing what AI-powered hacktivism looks like.

Final Thought:
I still don’t know exactly where I fit in the cybersecurity space.
But I do know this is where my mind wants to be.
I do know I want to keep hacking — everything.

So I’ll keep moving forward. Keep learning. Keep breaking things apart to see how they work.

Because that’s what hacking is.
And maybe… that’s what I am, too.

Now turn the key. Execute.