I saw this day a countless amount of times in the last two months. Typing this blog post after passing the exam, is a surreal feeling. Forecasting a goal, envisioning its completion, and driving it home is the things fairy-tales are made of. How the air smells at that time? What does it taste like? Why I deserve it? How all the countless hours of study I am willing to endure would eventually lead to pay-dirt and once again, me on top! Triumphant. How relieved I’d be? How much elation I’d be feeling. Like having a superpower to force anything I want into existence. Gotta have that vision!

I’ll get to what studying looked like, felt like, exam review dialogue and such soon. Yes! This post is LONG. But guess what I’m the one who had to write it. I didn’t do it for myself, I did it for you. The length was dictated by however many words I needed to produce a post with the context of what I would have wanted in hindsight after passing the exam. Most of the blogs I see are humble brags of people looking for everyone to kiss their feet since they passed it. Some are really good like the ones at the end of the post. Some are long and list out key things you should be on the lookout like CMMI or BCP without any other context. Continuing by saying how it was the MOST difficult test of their life, they felt like they were going to fail when the test ended. I just don’t think this is or has to be the typical case. Anyone can pass CISSP – keep reading and I’ll detail how to study and why most of the practice materials are broken. You could extrapolate something out of that too (if you only use the recommended study materials you will fail).

The point needs to be restated that I think the journey is the most valuable portion of attempting certifications not the actual cert. This one for instance, proves you are not only familiar with all the content from the 8 domains, but also, able to synthesis and apply it to scenario-based situations using sound risk management principals acting as an Information Security Manager. Not only do I want to provide a valuable resource for exam preparation but also give you insight and texture into my life during the entire process.

Part-1: What’s My Motivation?

Time: Late December 2019

Self Introspection (self observation) – is important as it’s a kind of regular check on self development which helps you to know what we have achieved so far.

I was promoted in December 2019 to Application Security Manager 😛 (for context). Christmas is a really special time in the Caribbean so I try to be there every year during that holiday period. (That’s how you end the year baby 👊🏽) So literally the next day after getting home from the trip (still having a week off before I go back to work) I start to get the feeling. Anybody know what I’m talking bout? The thirst? Watch TV for maybe a few hours, go out a day, chill then it’s like “What am I doing with my life? What’s all this idle time I have? How do normal people do nothing for most of their lives? Happens to me every time 💯

I had preconceived thoughts about CISSP honestly. “It’s typical to fail on first try” … “It’s a management exam” … “It’s an inch deep mile wide” … “Reddit horror stories” … “Folks literally studying on average 6 months some 1 year”. After doing some research I decided it was the one for me. Not only would it give some sort of legitimacy to my new position, it would, in addition, significantly broaden my understanding of Information Security and Risk Management.

I ordered the following studying materials the same day based on research from CISSP sub-reddit:

Major S/O to that sub it’s a trove of information! That’s part of why blog. As to keep this process continually flowing. Provide helpful materials to those after you. We have to realize 90% of the time we’re acting as consumers not producers. I think it takes a certain level of appreciation for the field overall to be devoted to giving back in whatever form you can. We all have something we can contribute ‼

Life happened and I wasn’t able to start studying immediately. Shame because I got a free same-day delivery of the books. I never even opened the package when it came. Put it in my office and it sat there for most of January.

Part-2: What Was The Preparation Like?

Time: End of January 2020

Thinking about sports and basketball in particular – How many free throws might a average player shoot per day when trying to improve their percentage? 50 free throws per day? 100? 500? That number may actuality be well around 2 thousand or more. Now lets abstract that a little and dumb it down for a second. It’s not going to be anything novel. You need to consistently be shooting your free throws. In this case it all the practicing, reading all the materials from different sources, doing more practice questions, flashcards it’s all apart of the process. You can’t go a weekend without studying, or even a day. Consistently & repeatedly!

You guys know by now, there’s nothing special about me I just feel like when I really want something there an insatiable thirst to quench and borderline obsession maybe for me to get it. I guess what I’m trying to say is I know how to “Lock In”. I literally had hundreds of unanswered LinkedIn messages, DMs, text everything. I cut everybody off and focused at the task at hand. It would need my upmost attention at all times. There’s absolutely no going out, minimal TV, if I’m commuting I’m reading, if I’m on break I’m reading or researching, when I get home I’m getting settled at say 5 pm and then grinding till I’m dosing off. In bed i’m reading. When I wake up before I get out the bed I’m reading. Around this time is when you realize you could live with someone and be a complete stranger to them in the same house 😂 So some of the attributes that describes someone in this stage is consistency, dedication, resolve, discipline, resiliency.

You have to REALLY want it. When you do you are laser-focused. As random as this is I see myself in my head as i’m typing this as heat-seeking missile. I’m coming in hot and I will not miss! I care about accuracy and precision. You get the picture. Whatever it means to you – “Lock In” that’s the mode you need to be in – keeping in mind it’s a marathon not a sprint. Life will happen some days you’ll be much more motivated than others – but anything in your control better be related to CISSP.

Sybex Official Study Guide 8th Edition (8/10) – This behemoth took me about 2 weeks to finish. I didn’t read it intently but more skimming and identifying what I absolutely don’t know, or if I know something’s right for the wrong reason. You can register the Sybex book along w/ the practice test on the Wiley test bank. It allows you to take the chapter questions in the exam atmosphere instead of writing in the book as well as practice exams. All your work is tracked and saved. After I finished reading the book I registered it and proceeded to go thru each domain’s chapter questions. I would say my average was in the 60’s for most of them. Bunch of new material, definitely vast amount of knowledge you need for every single domain. I was familiar with the SDLC / Security Testing / IR domains from work related experience. Gets two dings for being so damn big. Very useful but again it’s not something you can use alone to pass exam despite it being the “Official Study Guide” 🤔

– This behemoth took me about 2 weeks to finish. I didn’t read it intently but more skimming and identifying what I absolutely don’t know, or if I know something’s right for the wrong reason. You can register the Sybex book along w/ the practice test on the Wiley test bank. It allows you to take the chapter questions in the exam atmosphere instead of writing in the book as well as practice exams. All your work is tracked and saved. After I finished reading the book I registered it and proceeded to go thru each domain’s chapter questions. I would say my average was in the 60’s for most of them. Bunch of new material, definitely vast amount of knowledge you need for every single domain. I was familiar with the SDLC / Security Testing / IR domains from work related experience. Gets two dings for being so damn big. Very useful but again it’s not something you can use alone to pass exam despite it being the “Official Study Guide” 🤔 Kelly Handerhan’s (9/10)

Boson Test Engine (8/10) all the study material test.

the study material test. It’s now about mid-February and a blessing falls from the sky directly into my lap. I find my MOST valuable resource.

Discord CISSP Server (12/10) . This type of forum was perfect for most of my learning when tackling technical certs so I knew it would push me here. We’re equally amazing but some unmatched wisdom in there for sure! This drastically improved the amount of information you retain as well as increase the depth of such information respectively. I think this is the case because you’re not just you in your head alone in your room with a book. You’re now defending your argument on a particular question, or understanding why you’re wrong, this goes on 24/7 since the group is global. 4 pm EST or 4 am there’s going to be active discussions ALWAYS going on. There’s a psychological aspect to this as well. Feeling like you’re alone in a fight is depressing. Having an active army of mission-oriented soldiers all ready to fight, defend and operate 🔫 ?! Oh now this is a whole different story! Don’t underestimate the power of a topic being explained to you by a person instead of a blog post. I’ll forever be apart of this channel – definitely my new brothers and sisters. Blame most of me passing on them!

valuable resource. . This type of forum was perfect for most of my learning when tackling technical certs so I knew it would push me here. We’re equally amazing but some unmatched wisdom in there for sure! This drastically improved the amount of information you retain as well as increase the depth of such information respectively. I think this is the case because you’re not just you in your head alone in your room with a book. You’re now defending your argument on a particular question, or understanding why you’re wrong, this goes on 24/7 since the group is global. 4 pm EST or 4 am there’s going to be active discussions going on. There’s a psychological aspect to this as well. Feeling like you’re alone in a fight is depressing. Having an active army of mission-oriented soldiers all ready to fight, defend and operate 🔫 ?! Oh now this is a whole different story! Don’t underestimate the power of a topic being explained to you by a person instead of a blog post. I’ll forever be apart of this channel – definitely my new brothers and sisters. Blame most of me passing on them! I start to do a million practice questions from anything I could find books, practice sites, old materials. I guestimate I did over six thousand practice questions. I can remember off hand doing 1300 in a 2 day hiatus 🧾At this point I’m at about 5 hrs a day on weekdays and at least 12+ hrs on weekends #overdrive

Sari Green’s CISSP (9/10)

Mike Chapple LinkedIn Learning CISSP (9/10)

After I finished all those I started from domain one and did the following for all 8 domains Read Sybex chapter summary Read 11th hr chapter summary Watch Sari domain summary Do Mike Chapple practice questions for associate domain



We’re at about 2 weeks out now time wise. I started to read all the NIST documents related to the major processes in the various domains. These actually were well written and I learned to love them. Every night I would open them and try to relate everything I was doing back to risk management. I’m still doing practice problems but maybe like 10 a day at this point. Most of my time is spent trying to understand the SDLC in depth, the IR process in depth, the BCP/DR process in depth. You not only need to understand the order of the processes but all the details & outputs that come from each.

(Maybe one month ago 2 member of the squad from Discord discovered we all have the same exam date) The day before exam I get hit up to join a conference with both of them to do so last day studying. Without this I wouldn’t have passed. We spend 10 hours going over all the major processes, ironing out our understandings and tying relate everything back to the RMF. It’s 10 pm night before exam and boy I’m thinking I probably shouldn’t have did all of that studying today in fear of cramming and losing it. I’m also pissed at myself for drinking a redbull 30 minutes earlier. Because I should be sleeping but a hr has gone by and I’m still wide awoke – I hope I get to sleep soon in fear of not getting good rest and failing.

Part-3: You Didn’t All This Work For Nothing, Did You?

Time: Mid-March 2020

When I scheduled my exam I purposely chose a Saturday morning. I did not want to deal with the variables that a “normal” morning commute might include – so I was going to be lazy and Uber to the testing center. Now being so paranoid I just drove there and paid the crazy fee to park in the garage. I listened to Kelly’s “Why You Will Pass The CISSP” video and Larry Greenblat “CISSP Exam Tips” videos before leaving the car. Crazy only seeing about 4 people when on a regular day – a low amount normally would be around 50-100 and tons of traffic at any given time – people jogging, women pushing strollers, people and their dogs, as well as tons of business folk – it’s directly across the street from a train station.

At this point, the sports reference is to boxing. Here’s my thoughts walking to from the garage to exam center – “You did not come this far to lose did you? You’ve been wrong countless amounts of time on Discord and understood why. You worked your buns off! You learned the material, the mindset, you’ve watched hundreds of videos, did thousands of questions, read tons of pages. You’ve got some of the most distinguished practical offensive certs in existence, are you going to let a multiple choice management exam that most people fail because they don’t slow down to read defeat you? You’re going to knock this exam on it’s face. You already visioned this day many times before. This is going to turn out just like all the other times – you put in the work and the results are going to prove such is true at the end. If you synthesized the information the way you think you do you’re going to do amazing” This is how I’m I’m trying to make myself feel



In reality I’m scared as shit about this exam 😂 it’s not that I don’t the material – its I don’t know what I don’t know. Most people on Reddit say when they see the first 25 questions they sometimes wonder if the proctor configured them for the wrong exam 😌 Here’s what calmed me down sorta grounded me. I had small talk with a guy as we’re walking to bathroom and we ask one another what we’re up against this morning. Turns out him along with 90% of the other people there (16 total) were taking their medical exam. It was 7 hrs! I literally said to myself “Shitttt boy you got it good!” 🤣 It’s all relative 💭 My number gets called and I get seated for the exam. They had disposable covers for the noise cancelling headphones 🤞🏽

I had this plan to write all my brain dump stuff on the pad they gave me before starting. You get 5 minutes to read and sign NDA. One of the things I wanted to write down was the forensic process. I started to list them out and got stuck after the “Collection” phase – It’s scares the living fucking daylight out of me. I said “F-This” and clicked “Start Exam” true story 🤦🏽‍♂️

Part-4: Put Up Or Shut Up!

The questions didn’t seem like they were designed to trick me. I was comfortable with the terms in most questions. The difficulty is in the subjective and vague nature of all the questions. Unlike the practice question which test if you know terms and definitions, the exam places you in scenarios where you play from the perspective of a security manager and have to apply sound risk management principals – remembering your job is to reduce risk, provide information for senior management and apply the appropriate level of protection to your assets depends on their value and classification. Most of the questions are BEST, LEAST, WORST with all the possibly choices either being all right or all wrong. On a bunch of occasions I was able to eliminate 2 off the jump. The remaining 2 choices are what’s going to keep you up at night. I got a crazy subnetting question that I attempted to start breaking down on my pad to binary and do the power of 2’s after 20 seconds I said “F – This” and clicked “Next“. There were some gimmie’s sprinkled in there as well. Don’t forget “inch deep, mile wide” it’s way too much material for every single question to be a boulder. I made sure to slow down scrutinize every word in the questions, re-read all questions and answers and reading back the answer I chose. If a question was “Blah blah blah .. Which of following feature of Digital Signatures would BEST provide you with a solution to prevent unauthorized tampering?” … And the answer is integrity … Before moving on I’d say “Integrity is the feature of Digital Signatures that best provide the solution to the problem” … Here’s what I saw most followed by question to illustrate the context for each one:

SDLC Related – What SDLC is Change Management most likely to be apart of?

BCP Related – A global pandemic of a deadly virus is on the brink. How does the BIA help you determine your risk?

IR Related – The sky is falling and something just hit you in the head. What process of IR are you most likely in?

Bunch of stuff on Access Controls – How can i best protect this if that?

One question of Encryption – Understand PPP L2TP PPTP L2F their succession which ones can use IPSEC, EAP

Bunch of Risk Management – Something just happened you need to do something. With these constraints. What’s best?

Asset and Data Classification/Security – Why do we classify anything?

Web Application Attack Recognition – Seeing and recognizing attacks described through a scenario or graphical depiction

US and Global Privacy Frameworks – GDPR – ECPA – OECD

Roles and Responsibilities – Who’s MOST important for security? CISO CEO ISM ISSO?

Communication & Network Security – What layer is LLC most likely apart of ?

I was nervous as hell clicking “Next” on the 100th question. I knew if exam ended I either did really well or really horribly also if it continued I knew I was exactly on the borderline and could still pass up to 150 but each question would have to be correct. If that was the case I wouldn’t have been pissed but I didn’t want that to occur to even have to be in that situation. The exam stops. I’m like “HOLY SHIT”. I get the TA’s attention, she signs me out and I go to the reception area to get the print-out. The receptionist was at the bathroom 😫 had to wait 5 minutes for her to come back. I was pacing so much the entire time I probably could have burned a hole in their damn carpet. The lady takes my ID and prints it out the result, peaks it, folds it and gives it to me looking me dead in the eye with a straight face. But I did notice it was one piece of paper and people said if you get one paper you pass – if you get more it’s because you failed and that’s the explanation of the domains you came up short in. I opened it and saw I had PASSED 😍 I threw the wildest air punch in history, luckily didn’t hurt myself, jump up and down a little (nobody else in reception area at this point, say “LET’S GO” as loud as I can (since the students are literally just around the corner) and notice the receptionist now smiling so said “Congratulations sorry I had to mess with you” 😂 Here’ it was guys that moment of passing that I visioned! Slaying the dragon. What a wonderful feeling 💘

Part-5: Thoughts?

If you’ve made it this far s/o to you! I’ll never write a TL/DR ever ✌🏽 The context matters … The journey matters.

My biggest advice would be to make the NIST RMF, SDLC and all the related documents your friend. These are going to help you substantially more than doing a zillion practice questions or reading the huge books. Also it sheds light on why so many smart technical folk fail this exam the first time. The day before the exam me @Beedo @Reepdeep MAJOR S/O TO THOSE GUYS – WHO ALSO PASSED THE SAME DAY studied from 1 pm to 10 pm going through all the processes from each domain, in our own words, understanding the steps to the process but understand how every single thing is tied back to risk management.

NOTE: We think the document we created could help everyone out there out as a definitive source for passing the exam. Obviously folks need to get back to the real life and people they’ve neglected since beginning the journey but it’s something we all feel strongly about and want to provide to the community hopefully soon 😎

Part-6: Things I Shared on Discord That I Think Should Be Included Here?

These are just excerpts but I figured they maybe valuable since you forget basically everything related to the exam afterwards.

Bear with me as the grammar may not be perfect it’s Discord so I’m not necessarily caring if I make a mistake to correct it. It’s conversational texting-like language. Most of it being typed from my phone.

In regards to the difference in seemingly all the practice material vs real exam:

“I see why all the practice material miss the mark. It’s because you truly need a intelligent person to be able to spend the time to make those questions and that person cost too much to write free questions on the internet for us .. Those aren’t ones you come up with based on a definition .. You understand someone thought deeply about this, so much so they knew the answer I’d immediately go for (and it’s wrong) is included as say answer A and make the right answer further down the list like D. You need to be very careful. Also saw 2 similar looking answers where you jumped immediately to the answer and didn’t thoroughly read it would have noticed the 2nd one further down was more right”

In regards to our day before exam study conference:

it was impromptu as hell I was just going each of my Boson question explanation. It lasted lot longer than expected 😵🥴 went from like 1-10 yesterday on conference, went over each process understanding it and connecting the SDLC steps BCP steps back to RMF I’m sure they’ll agree understanding how everything relates back to RMF is the way to pass. Not technical … Not all the questions … Since they’re way to technical (use em to identify and reinforce you’re weak areas) we were already studied up at that point … Sybex/Boson/AIO/All the sources questions way to hard if we talking scope for exam. You’ll be placed in a bunch of situations where you’re somebody in security what’s BEST LEAST solution for this scenario.

On depth of question and context. Keep in mind we already knew the blocks lengths, key size ect:

For context it’s like understanding AES is a strong symmetric algorithm, DES is a weak one that shouldn’t be used. But not that 3DES EEE has a xyz length bit size and it goes through xy rounds – the latter is unnecessary .. If you know it so be it but that’s how I would scope everything. High level and how does is connect back to RMF .. I would read the RMF and SDLC NIST doc every night

On what I think is useful studying:

I’m saying you’ve read Sybex or over big book feel comfortable been browsing reddit know the sources the videos and all the questions we do here then can go through the 11th hr and understand everything then I would focus on the processes and how it relates to RM SDLC, IR, BCP knowing how those relate was my entire exam. I had a bunch of SDLC stuff lot of OWASP what vulnerability is this? Few question from domain 4 IPSec and understanding the protocol or layer.

Overall exam tips and thoughts:

“The exam was tough but I didn’t feel any point they were trying to trick or deceive me, every question was able to eliminate two answers of back. Some of the answers are similar then you figure out differences which was slightly hard in some cases some not. Felt familiar with all the terms answers. Question were clear. I didn’t even notice the experimental which I was on look out for. I think when studying we equate inch deep mile wide to difficult. In reality it’s just understanding how the domains work together. Remember every question CANNOT be a boulder. There were some gimmes… what is encryption… what is integrity for digital signatures type stuff. My best advice in hindsight with the above is DO NOT WASTE YOUR TIME doing all these questions, Boson, Ccure, Luke, Sybex. All of them! Only if you’re weak. If you can read 11th hr and notice everything nothings a shock stop. Understand how everything is bound by risk management. Btw I didn’t use the whole mgr mindset I just tried pick best 2 remaining options. There were plenty of answers that were “doing something” I threw those out automatically”

On how I would study differently:

“don’t worry and spend some time in the nist document’s 800-64 800-37 they all link to each other. So your thinking going through say SDLC is what am I doing in this step and how does it relate back to the RMF everything relates back to it. For example that in phase one of the SDLC you have your requirements and stuff but you’re also initially understanding the systems that links back to step one in RMF which is Categorize, so think does this system store transmit or processes pii, what’s the risk. Or step two Development in SDLC, you know you starting design architecture development and testing, that relates to steps 2&3 (you also do risk assessment here) in RMF you’re identified the need for the system in initial requirements, so now in development we select the controls of the system and assess them that’s in SDLC phase two but you’re always grounded by RMF. See how that relates? I think that understanding this alone is how I passed”

Are questions from sybex syllabus or out of the box?

Wayy to technical as well as all the practice questions

Some people fail who had boson?

Boson shouldn’t be used to judge readiness just identity weak areas. You could get 20% on all bosons and pass since it’s mostly thinking not technical

How’s the difficulty level?

NOT DIFFICULT – DON’T BELIEVE THE HYPE – ALL OF US COULD PASS THIS EXAM

Do we need other source of study hindsight?

Read the NIST documents on all the processes and reclaim some of your time back

You are say every in this group can pass, can you tell your experience and main domain?

Mainly offsec and I do appsec at work for like 4 years. I’m an engineer so i have the fix it mindset by default. You don’t need be expert in anything. Just think of everything in risk mgmt is enough to pass

How long you have been preparing?

Studying since 1/28

What was difficult domain for you?

Domain 2 smh – Focus on 1,3,7 thought and definitely 8.. Obviously you need to be passing in all domains but since those weighted more it more advisable

Did you face any language mixing puzzle questions means they use different vocabulary

There were NO gimmicks every question i knew exactly what they wanted.

Do you think feedback from people different industry get it more difficult than security?

It’s your understanding and mindset. Kelly and Larry tell you the mindset. I automatically threw any answer out that was “disconnect from network, make a firewall change”.

Did you feel it’s purely management?

No. Because being in mgmt although you’re not a doer you need to have a solid understanding of the underlying area no matter what it is.”

S/O to my Discord guys ALL OF YOU 💗

I’ve included a section below on the links that were most valuable to me. Good luck & NEVER give up or give in!