From First Blood to Humbled: A Week in HTB

A couple of weeks ago, I got my first blood on Hack The Box. The box was Browsed, and seeing my name at the top of that list - knowing I solved it before anyone else in the world - is a high that’s hard to describe. All those late nights, all that practice, all those boxes where I struggled for hours suddenly felt validated. For a moment, you feel like you’ve cracked some code, like maybe you’re actually getting good at this.

This week brought me back to earth. Hard.

I was excited for this release. Genuinely hyped. I cleared my schedule, had my notes ready, VM spun up, coffee brewing. This was going to be another good week. Maybe not first blood again, but I felt confident. Momentum was on my side.

Eight hours later, I’m staring at a Medium box without a user flag. First Blood was long gone - both user and root - and I did not even feel competitive.

I had a simple shell but I felt I saw the path forward but time after time nothing worked. Just enumeration results I’ve read fifteen times, rabbit holes I’ve crawled through twice, and that creeping frustration that comes when you know you’re missing something obvious. The kind of obvious that’ll make you feel stupid when you finally see it - or worse, when you read someone else’s writeup after the box retires.

It’s humbling in a way that’s hard to explain to people outside this field. Last week I was on top of the world. This week I’m questioning whether I actually understand anything at all.

But here’s the thing I keep coming back to: this field is vast. Incomprehensibly broad. Web exploitation, binary analysis, Active Directory attacks, cryptography, cloud misconfigurations, hardware hacking, mobile security, malware analysis - each one of these is deep enough to spend an entire career mastering. And they’re all interconnected in ways that mean you can be excellent at one thing and completely lost the moment a box requires something adjacent.

Getting first blood on Browsed didn’t mean I’d conquered HTB. It meant I happened to have the right skills for that particular puzzle on that particular day. The techniques clicked. The enumeration led somewhere. The exploitation path was one I’d walked before.

The next week’s box was asking for something different. Something I clearly don’t have yet. And that’s not a failure, it’s a signpost. It’s pointing directly at a gap in my knowledge, saying “here, this is where you need to grow.”

That’s what I love about this field, even when it’s frustrating. The learning never stops. You can’t coast. The moment you think you’ve figured it out, something comes along to remind you how much you don’t know. And there’s something weirdly beautiful about that. Every box that humbles me is a teacher. Every skill issue is a curriculum.

So I’ll keep pushing. Keep failing. Keep enumerating. Maybe I’ll get user tonight. Maybe I won’t. But either way, I’ll know more tomorrow than I do today.

The scoreboard resets every week, but the knowledge compounds forever.