Conquering the CISSP
- KdotWill
- Mar 27
- 2 min read
Structured daily grind
Each domain a stepping stone,
Mastered, nine to five.
Back in 2018, I started studying for the CISSP and tapped out. Cryptography felt like reading an alien language, and the text-heavy material just wasn’t clicking with how I learn. I shelved the exam indefinitely, figuring I’d circle back one day when the stars aligned.
Fast forward to 2024
I started my Master’s in Cybersecurity that August, then landed a Red Team Operator role in September, one that required the CISSP within six months.
Suddenly, “one day” became “right now.”
But this time, I approached it differently because I had the full support of my employer and team mates.
Smart Studying: Building My Toolkit
Instead of just grabbing a book and hoping for the best, I did my homework on how to study smarter. I dove into Reddit’s CISSP subreddit (link), where people shared what worked and what didn’t.
From there, I built my own CISSP toolkit:
• Destination Certification’s CISSP MasterClass (link)
• The Concise Guide by Destination Certification (Amazon)
• Quantum Exams for realistic practice questions (link)
• Luke Ahmed’s book, How To Think Like a Manager For the CISSP Exam (Amazon)
Work-Life Balance: No Nights, No Weekends
I studied only during work hours—between 8am and 4pm.
I never studied at home or during the weekends because I value my family time, and frankly, my mind needs a break to retain anything. That boundary made my study time more focused and sustainable.
The Learning Process
I started with the Destination Certification Master Class, and it was well worth the cost. Each domain was broken down into easily digestible videos with no fluff. I actually enjoyed every minute of it. Cryptography was no longer hieroglyphics.
After completing the course, I shifted focus to practice questions. The hardest ones were undoubtedly from Quantum Exams, but their clear and concise explanations for every answer made the struggle worthwhile. If you’re scoring around 50% or higher there, you’re probably in good shape for the real exam.
I also read through Luke Ahmed’s “How to Think Like a Manager for the CISSP.” His approach reframes the entire exam, reminding you it’s not about technical deep-dives, but about risk, impact, and the business. That mindset shift was crucial.
Passing Week: November 2024
I started studying in October 2024, while simultaneously working on my Master’s degree.
• November 13, 2024 – I completed my Master’s in Cybersecurity.
• November 20, 2024 – I passed the CISSP exam..
Final Thoughts
That moment was equal parts excitement and relief. The months of disciplined focus had paid off. But even with that certification under my belt, I still felt the weight of how much more there is to learn, especially as a Red Team Operator. The CISSP gave me the framework. Now, I’m building the skillset.
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