We knew where we came from
In my previous blog, “Time Races Ahead Before You Blink,” I shared the journey I’ve had alongside my brother navigating certifications, late-night streams, constant battles to move forward, balancing school, and leveling up mentally, physically, and emotionally.
This blog continues that story and dives deeper into the challenges and victories that have shaped my path in cybersecurity;
My name is Olaoluwa Olakojo, a 20-year-old born and raised in Lagos, the over-rated southwest region of Nigeria. I’ve been passionate about offensive security for six years, with five years of professional experience.
My journey began with platforms like TryHackMe, Hack The Box, Facebook, Stack Overflow, YouTube, and good old Google, these were my primary sources of learning back in the day. Growing up in a military school where most devices were banned, and with limited internet access at home, I had to be resourceful. I remember stealing my mum’s hotspot because, well, where else would a 14-year-old in my country get the funds to buy a data subscription?
Back then, I had a huge knowledge gap and honestly didn’t know what I was doing. But I studied hard, following cybersecurity experts like NetworkChuck, John Hammond, David Bombal, Stok Fredrick, NahamSec, and other top infosec influencers. Eventually, I landed an internship with an Indian company, which felt surreal, a place where I could finally grow, especially in hacking web applications.
Later, I secured a hybrid role with a company in my region where I gained hands-on internal pentesting experience, even though I was still very much learning. From there, I took on various freelance gigs and built my skills steadily.
My breakthrough came with the Certified Red Team Professional (CRTP) course I found on YouTube. It made me realize how much I struggled with Active Directory but also gave me a huge boost in key topics like enumeration, trust mapping, domain privilege escalation, Kerberos attacks, SQL Server trusts, and defenses and their bypasses.
After clearing CRTP, I jumped straight into the Certified Penetration Testing Specialist (CPTS). It was tough!, so tough that I fell seriously ill during the course. My family wanted me to quit because they had never seen me that bad, but I pushed through and passed, which gave me the confidence to finally tackle the OSCP.
I played over 100 CTF boxes preparing for the OSCP exam and, after nearly 15 hours of intense testing, I made it out alive with 80 points which is probably a different topic entirely.
This is pretty much where I come from. I’ve invested time and energy, sacrificed fun, pushed harder than ever, and bled for every step forward to see myself here today. But believe me when I say; this is only the beginning of my growth.
Now, let’s dive into why I decided to write this blog in the first place.
You always don’t have to push beyond what you can’t handle
Fast forward to about seven months ago, I got a firsthand experience of why some people endure pain even maltreatment without complaint. Sometimes, it’s not because they want to suffer, but because they have no real options, no one they can confide in, and no one they look up to who offers advice that makes them feel safe.
I was referred to one of the most toxic jobs I’ve ever encountered (no direct call-out here), but honestly, that organization was wild, from the management down to a few staff members.
I loved the role because it was in consulting. It gave me invaluable experience running penetration tests for banks, fintechs, pension funds, and major players in Nigeria’s finance sector. It felt like a dream come true, and career-wise, I was truly growing and making things happen for myself.
But here’s the catch; my personal life was draining. I had no time for myself, no time for family, no time for my partner. The exhaustion seeped in deeply, and I began to feel the heavy weight of depression.
Every time I tried to voice my concerns, the response was the same: either “we’ll deduct your salary” or “you have to be at work before this time and after that.” They never really understood.
I loved that job, but they didn’t see that I was stuck. When was the last time I did personal research, played CTF boxes with my team, or worked on a passion project? It felt like I was supposed to learn from thin air.
In my opinion, without self-improvement labs, research, learning. how can you expect to apply knowledge effectively at work when you’re not even growing your skills? This made me feel unsafe.
Honestly, this was just the tip of the iceberg when it came to what I was facing. I won’t expose too much, out of respect, but I do sincerely wish them the best of luck in whatever they pursue next. Because if I ever started speaking out fully, I honestly believe that organization might not survive the fallout.
Moving in circles
I’ve come to a strong conclusion, not just an agreement that the best way to land a role is through building genuine relationships. Let people know about your struggles, your journey, and most importantly, your willingness to give your all to whatever is entrusted to you. Don’t put yourself above or below the bar; just show up consistently and let your true value shine. Demonstrate that you’re not only technically skilled but also respectful, open-minded, and genuinely interested in building meaningful connections.
On April 6th, 2025, I passed the OSCP and OSCP+ exams and honestly, that felt like a major milestone. What’s wild is that I barely prepared for these exams beforehand. The previous organization was draining me completely, and I’m thankful I got out as fast as I did. Imagine working somewhere that knows you have a huge certification like that coming up, self-sponsored by you, yet they don’t give you a single paid day off to prepare. Instead, they only offered me one free day the week of the exam, despite expecting me in the office four days a week. I was commuting long hours daily, and weekends were almost non-existent due to other responsibilities.
I’m grateful I prepared ahead on my own; making cheat sheets, notes, and a quick-response plan to ensure I didn’t “run out of time before running out of options.” By God’s grace, I excelled.
Things would move right; when you least expect
My very close twin, Rami, passed his exams, and honestly, it was one of the best days of my life. We’ve never struggled so hard alongside someone else and for once, we both won together. This could very well have been our second big victory. On that day, I was overwhelmed with joy, I cried like never before, genuinely happy because everyone in our circle, not just Rami, had this achievement locked down through sheer, relentless hard work.
I even had to download Discord on my phone just to send a voice note and really express the happiness bubbling inside me. In that moment, it truly felt like the sky was the limit.
I’ve known Oxygen for over a year now, one of the realest and most trusted people in my network. We’ve collaborated on securing real-world startups, and he’s not just a top-tier AppSec professional, but also a true big bro who’s taught me valuable lessons beyond security lessons about life itself. Hats off to this cracked legend when it comes to web app pentesting.
It had been a while since we last worked on something, but Oxygen was one of the few people close enough to understand what I was going through in that toxic role. Bro is truly blood from another mother. I respect him deeply, and God bless the day our paths crossed.
When I needed it the most, Oxygen referred me to one of the top fintech companies in Nigeria, and guess what? I got the offer. This time, the contract was plain, honest, and straightforward. I cried when I saw that offer because for once, it felt like the universe was finally aligning for this young boy. Even though I had a few gigs to keep me standing after losing the previous job, this opportunity hit different. I was finally stepping into a role that valued not just what I bring to the table but me as a person.
Truly, I sit and imagine; what if God never sent “Oxygen” to me? How would I have survived that phase? I was exhausted, mentally drained, and already had therapy in mind because it was starting to feel like too much. If he hadn’t shown up when he did, things might have taken a much darker turn. It would’ve been tough, really tough to realign again, especially after all I’d lost. But God did send him. And for that, I’ll always be grateful. People like him don’t just help you with jobs; they remind you that you’re not alone in the storm.
🌅 Outro: From Pain to Purpose
If there’s one thing this journey has taught me, it’s that growth rarely comes from comfort. The setbacks, sleepless nights, losses, and emotional toll weren’t just battles, they were shaping tools. Through the chaos, I found clarity. Through the pain, I found purpose.
To anyone out there grinding in silence, feeling unseen, doubting themselves; your time is coming. Just keep preparing, keep pushing, and surround yourself with people who see your value, even when you don’t.
This blog isn’t just a story, it’s a mirror of what it means to fight through the noise and still find your voice.
To everyone who stood by me, my brother Rami, my Family, my big bro Oxygen, my mentors, my team, and those silently rooting for me this win is ours.
I’m not at the top yet, but I’m no longer at the bottom.
And this, right here, is just the beginning.
