Approaching a Pentest like an Endurance Challenge
I wrote this more for myself than anyone else — something I needed to remind myself of. But if it resonates with even one of you, that’s a win.
If there’s one thing I’ve learned from both cybersecurity and sports, it’s that endurance wins. Sure, hacking into a network might not leave me breathless like a high-altitude hike or a Hyrox workout, but the mental stamina? The strategy? The constant battle between pushing harder and knowing when to hold back? That part, yeah, that’s the same.
We are all programmed to chase easy dopamine; we constantly need a win. But in cybersecurity, as well as in sports, there are no easy wins. You need to learn to find the highs in the process. And that by itself is one hell of a struggle.
So I try to make it fun. I approach every engagement like an endurance challenge. It’s never just about breaking in — it’s about outlasting, outthinking, and outmaneuvering. And just like in sports, the best moments happen right when you think you’re about to hit a wall.
The Sprint vs. The Marathon of Hacking
Some attacks are a full-speed sprint — quick, aggressive, and over before you break a sweat. Think of the classic smash-and-grab exploits, phishing attempts, or misconfigurations just begging to be exploited. Easy wins, like the cybersecurity equivalent of a fast 5K.
Then, there are the ultra-marathons. The deep recon. The slow-burn privilege escalations. The days of persistence, trying every angle, waiting for the perfect moment to strike. That’s where the real test begins.
Patience is a weapon in both worlds. In a race, you don’t go full speed from the start unless you want to burn out before the finish line. In pentesting, the same rule applies — you can’t force a breakthrough; you have to read the terrain, test the defenses, and find the path that gets you in without raising alarms.
Training for the Unknown
No matter how much you prepare, both pentesting and endurance sports throw unexpected challenges at you. The weather shifts. Your gear fails. The target network has better defenses than you expected. That’s when you adapt, pivot, and grind through.
I’ve had pentests where everything looked airtight — until one overlooked misconfiguration cracked the whole thing open. Just like in sports, sometimes the difference between winning and failing isn’t raw skill; it’s the ability to push through when others stop looking.
The Endorphin Rush of Breaking In
There’s nothing quite like the moment when everything clicks. That runner’s high? The sheer euphoria of finally landing a move you’ve trained months for? That’s what it feels like when you crack a tough network, elevate privileges, or pivot into a system that looked impossible to breach.
It’s addictive, but it’s also humbling. Every pentest teaches me something new, just like every race or challenge forces me to push past limits I thought I had. The moment you think you’ve “made it” is the moment you stop improving.
All Gas, No Brakes
Whether I’m testing security controls or pushing through another workout, one thing stays the same — I don’t do things halfway. I don’t just play the game; I break it down, master it, and push it to the limit.
Because at the end of the day, pentesting isn’t just about hacking. It’s about strategy, resilience, and playing the long game. And if there’s one thing I know how to do, it’s endure.
Let’s keep in touch
I’d always be willing to discuss more, exchange ideas and continue the hash talk. If you liked this, follow and subscribe to see more of it!
- Reach me at: evaincybersec@gmail.com
