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From Bug Bounty Blahs to Breakthroughs: Navigating the “Never Enough” Trap in Cyber

6 min readJun 13, 2025

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Medium Story

If you’re anything like me, a cybersecurity enthusiast, a pro in the field, or just plugged into any tech career, you’ve definitely seen them. Your LinkedIn feed, Medium articles, YouTube videos… they’re all jam-packed with stories of rockstar careers, overnight successes, or that one person who seems to know absolutely everything about, well, everything.

So, why does this even matter? Because, let’s be honest, we all end up playing the comparison game. And it’s usually not a fun one. You scroll, you see, and then BAM! You’re left with this gnawing feeling that you’re just not good enough, that you’re not cutting it in anything specific. There’s this constant, heavy pressure to be studying 24/7, just to keep from being left in the dust.

But what if I told you that feeling is completely normal, and it’s a trap many of us fall into? Let’s talk about it.

The Comparison Trap: A Universal Story

You’ve seen the Medium posts: “How I found my first $1000 in bug bounty!” or “Easy XSS finds that netted me $5,000 in bounties.” Maybe even a “Walkthrough for an impossibly hard CTF that you spent weeks on and found absolutely nothing.”

Know what all these posts have in common? They lead you down the same destructive comparison rabbit hole, and it’s nearly impossible to climb out. You start thinking, “Why is finding ‘X’ vulnerability so easy for everyone else, but for me, it feels impossible?”

Let me tell you why, with a simple analogy:

Imagine you follow about 500 people on Instagram. Every single week, at least one of them seems to be on vacation. Meanwhile, you work all year just to squeeze in one trip. Now, in this scenario, does that mean those 500 people have better lives than you?

Have you ever stopped to think that because you follow so many people, the chances of at least one of them traveling each week are incredibly high? Maybe they’re in the exact same boat as you, only traveling once a year. Your life isn’t worse.

Bringing this analogy back to the cyber world: yes, there are hackers finding vulnerabilities, flagging CTF challenges, and cashing in on bounties every single day. But that doesn’t mean it’s the same person, or the same level of success, every single day. Each time you compare yourself, you’ll feel worse. Eventually, you’ll hit a wall, get completely stuck, and guess what? That happened to me. And I’m willing to bet it’s happening to a lot of people right now.

My Story

So, let me tell you how this all played out for me. I started diving into cybersecurity, CTFs, bug bounties, all that good stuff a little while ago. Before that, I was actually a backend developer. Like any enthusiastic student, I just devoured content. I signed up for countless VDPs, participated in so many CTFs, and worked through so many labs that I honestly felt like the most productive person on the planet. But, inevitably, that fire starts to cool over time.

For the past two years, I’ve been working as an AppSec Engineer. And throughout these two years through my job, online forums, and even right here on Medium, I kept seeing so many brilliant people. So many folks finding millions of vulnerabilities, crushing labs, while, in contrast, it would take me two months to even report one vulnerability in a VDP, or weeks to solve a medium level lab on Hack The Box. That’s if I didn’t get completely stuck and end up looking for walkthroughs (which, full disclosure, I’ve done some o them myself, and plan to do more of in the future).

But how did this constant comparison impact me? Well, after seeing everyone else seemingly so successful, I gradually started to get discouraged. Every day, I felt less and less motivated to keep trying because, hey, there was always someone better, right? This feeling just kept growing and growing until I finally had to look inwards, realize something was seriously wrong, and actually CHANGE.

Shiffiting Your Focus

First things first: I’m not telling you to never read another Medium post or to get mad at the accomplishments of your colleagues. You can learn a ton by reading reports, and you absolutely should make it a habit. The problem arises when you start believing you’re not capable of doing the same. And here’s a little secret for you: You are!

So, how do you climb out of this seemingly bottomless pit?

Step One:

Fall in Love with the Process, Not the Result.

This might sound cliché, and I’m sure you’ve heard it before, especially from other hackers. But it’s the absolute truth. Why do you need to find a vulnerability to be happy? Have you ever stopped to think that if your happiness always depends on a specific outcome, you’re probably going to be sad for the rest of your life? Why do you constantly feel like you need to “be there” to succeed? Your life is happening now, and so is your journey of learning and exploration. Focus on that first, fall in love with that. The rest is simply a consequence.

Step Two:

Read Reports as a Form of Study, Not as a “Wow, this vulnerability paid X, I’m going to learn it to test and earn the same.”

I’ve been there, and it’s almost impossible for that to happen. Every application is unique and behaves differently. Learn from the reports; don’t just blindly copy everything from them. That will only lead to frustration. Instead, focus on understanding the methodology, the thought process, and the underlying principles demonstrated in successful reports.

Step Three:

Start Small!

This third and final step helped me immensely when I was really discouraged. In the beginning, I had the disposition to study for hours on end, but it was a blind passion. If you, like me, have lost a bit of that drive to study or try, come back, but start small! Begin by studying just 20 minutes a day, nothing more. Or spend 20 minutes getting started on a bug bounty or a CTF. Do not exceed that established time limit at the beginning this is crucial. Make a commitment to yourself to study for only 20 minutes every day, and gradually increase it. But never go over your set time. If 20 minutes feels like too much, try less. The important thing is to just start and get back into the habit.

I know I’ve approached this topic without diving super deep into every single nuance, but please understand this: if you’ve ever felt this way, you are absolutely not alone. Thousands of people are going through the exact same thing.

If you found this helpful and would like to see more posts about overcoming these challenges, please feel free to comment and let’s chat about it. This has been one of the most important subjects I’ve tackled, mainly because it affected me personally so much.

But for now…

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Leviiatan
Leviiatan

Written by Leviiatan

Bug hunter and CyberSecurity Specialist

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