We all have those moments where we look back at something we walked away from and think, “What if I’d just stuck with it a little longer?”. Maybe for you it was guitar lessons that got shelved after a few months, or that running routine that died somewhere around week three. I’ve been thinking about this a lot lately because false starts are way more normal than we want to admit. But here’s what I’ve figured out about the art of restart: trying something again isn’t really starting over. You’re actually building on stuff you didn’t even know you learned the first time around.
What I learnt is that the first attempt teaches you the rules of the game, but it is the second attempt that teaches you how to win it.
Five Years Ago: All Enthusiasm, No Strategy
Five years ago, I was absolutely thrilled about diving into penetration testing. The whole concept fascinated me – this cat-and-mouse game between attackers and defenders, the mix of technical skill and creative thinking. I dove in with the same intensity I bring to complex cases at work – completely ready to absorb everything at once.
I signed up for online courses, bought the recommended books, set up virtual labs for cracking the OSCP. For a few weeks, maybe even a couple months, I was on fire. Staying up late watching tutorials, experimenting with tools, feeling like I’d found my calling.
Then reality hit. Work got crazy. Family stuff came up. That perfectly planned study schedule? Yeah, it fell apart pretty fast.
I felt like such a failure. Now I realize it wasn’t failure at all – it was research. I was learning what worked, what didn’t, and what I’d completely underestimated. Turns out enthusiasm alone doesn’t cut it. Who knew that building real expertise takes time and patience instead of cramming everything in like it’s finals week?
What My “Failure” Actually Taught Me
Here’s the thing about quitting – we’re so quick to call it failure that we miss all the stuff we actually learned. Those abandoned projects? They teach us more about ourselves than we realize.
That first attempt wasn’t wasted time. It showed me that penetration testing isn’t just about memorizing commands or following step-by-step guides. It’s about thinking differently – looking at systems and seeing not just what they’re supposed to do, but how someone might break them.
I also learned the hard way that getting started is the easy part. Keeping going when the initial excitement wears off? That’s where things get real. I had set these crazy high expectations for myself, then got discouraged when I wasn’t picking things up as fast as some YouTube expert who’d been doing this for years.
Looking back, I was treating learning like a sprint when it’s actually more like training for a marathon. Different approach needed entirely.
The In-Between Years Weren’t Wasted
These past five years, I stayed connected to the cybersecurity world even though I wasn’t actively studying pentesting. I kept reading industry news, following major breaches, watching how threats evolved. It kept the spark alive.
Running “The Cyber Cops” website turned out to be great practice, even though I didn’t realize it at the time. When you have to explain complex security concepts to people who barely know what malware is, you really have to understand the fundamentals yourself. Every article I wrote was basically forcing me to learn things more deeply.
My day job kept evolving too, in ways that actually complement penetration testing perfectly. All those investigation skills – methodical thinking, spotting patterns, staying patient when cases drag on, getting inside someone’s head to understand their motives – turns out that’s exactly what you need for good penetration testing.
The person starting this journey today isn’t the same guy who tried five years ago. I know myself better now. I know what trips me up and what keeps me motivated.
Starting Over? Not Really
Here’s what nobody tells you about second attempts: you’re not really starting from zero. Those courses I never finished? I retained more than I thought. Concepts that seemed impossible back then feel familiar now, like running into someone you kind of remember but can’t quite place.
More importantly, I know what doesn’t work for me now. I need to get my hands dirty right after learning something new, or it just stays theoretical. I learn better when I’m explaining things to other people rather than just absorbing content. I need to see progress regularly, or I lose steam.
That self-knowledge is probably the most valuable thing I got from that first attempt. It’s the difference between stumbling around in the dark and having a roadmap based on actual experience.
Building on What’s Already There
Twenty-plus years of programming, especially Python, means I don’t have to struggle with basic technical concepts anymore. Problem-solving in code feels natural now.
Years of investigating cybercrimes gave me something most pentesters don’t have – I’ve seen the human side of vulnerabilities. I understand why security gaps exist beyond just the technical reasons. It’s usually about competing priorities, tight budgets, legacy systems nobody wants to touch, or just human nature.
This changes how I think about penetration testing. Instead of just finding flaws, I can think about why those flaws exist and what realistic fixes might look like.
I’ve also gotten more patient. When you work cases that take months or years to solve, you learn that good work can’t be rushed. That patience is gold in penetration testing, where thorough work beats speed every time.
And here’s something unique – very few people in this field have seen both sides of cybercrime. I understand how attacks work technically, but I also know how they play out in real organizations with real consequences. That’s a pretty rare perspective.
This Time Is Different
The big difference between attempt one and attempt two isn’t just having more time or being more motivated. It’s my whole approach.
Badge to Buffer isn’t just a catchy name – it’s my way of staying accountable and turning learning into teaching. Everything I figure out, every tool I try, every time I hit a wall, I’m documenting it. Partly to reinforce my own learning, partly to help other people on similar journeys.
Hands-on practice is the core this time. Every concept gets tested immediately and explained in simple terms. No more hoarding theory – it’s all about applying knowledge gained until it sticks.
I’m also being way more realistic about time and energy. Instead of rigid study schedules that collapse the minute work gets busy, I’m building flexible chunks that adapt to real life.
The Psychology of Try Again
There’s something powerful about the word “restart.” It acknowledges that you learned something the first time. You’re not coming back with the same naive optimism – you’re coming back smarter.
This isn’t driven by “maybe I can do it this time” hope. It’s based on knowing I’ve already laid groundwork, even if I didn’t recognize it then. Now it’s about following through systematically, in a way that actually fits my life.
Two Worlds, One Goal
I’m not trying to completely reinvent myself overnight. I’m building penetration testing skills while staying excellent at my IPS job. These aren’t competing goals – they complement each other.
My law enforcement background gives me patience for deep investigations and insight into criminal thinking. Technical skills give me the tools to apply that mindset to digital environments. Together, they create something neither background could achieve alone.
This restart proves something important: it’s never too late to add new dimensions to who you are. False starts don’t have to stay false. Sometimes they’re just the foundation for something better, built with the wisdom you didn’t have the first time around.
The journey from badge to buffer is just getting started, but this time I’m ready – not because I’m smarter or more talented, but because I’m more strategic and honest about what it actually takes.
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