My journey to OSEP
So if one was to search terms like “OSEP journey” or “OSEP review” on any search engine he will be ending up with at least a dozen blog posts explaining how it is to train for and become an OSEP. I want to give you some insights the people don’t tell you. Or at least those are the things I experienced throughout preparing for the OSEP and especially taking the exam.
And although I cannot talk about any technical aspect of my exam, as this clearly violates Terms & Conditions with Offsec I sure enough can give you an impression what you will be up against mentally.
Well, you all sure enough already know that you will be provided with a course pdf and some exercise machines, as well as some challenges to solve before you attend the exam.
And for this task you will either get 30, 60 or in my case 90 days. I was buying the long time frame, because it was clear to me that I will have to train for this whilst doing a 9 to 5 job, having a wife and two children and basically having a live outside of what is in front of the screen.
But to be honest. My time management is quite good, so I finished the first run of doing the course pdf and the challenges after just about 30 days. There was plenty of time to do it over again, which I did - twice.
Taking notes is crucial in this phase, because everything you have notes of and everything you have ready-made code snippets of will relax your exam a lot. And frankly, I did an average job at this. Later on in time I wished I would have taken this more seriously.
But to conclude this section - OSEP did not yet influence me and my private life that much at this phase.
Playing the waiting game
This is where OSEP hit me a little the first time. And all of this was my major mistake again. My training schedule and lab time ended right before Christmas (23rd of December 2021 to be precise). And I scheduled my exam to start on the 12th of January 2022.
I mean, I am a chill person most of the time, but when it comes to exams I might lose my mental strength quicker than usual. This happened to me in a time when you are supposed to enjoy yourself and everything and everyone around you.
Waiting for the exam to happen is in fact having a bad time. So my recommendation is:
Schedule your exam right after your lab time ends
But, oh well. I dragged through doing the best not to let others feel, what I felt in this time span before the exam.
Now comes the serious part. I bet that everyone would be nervous taking an exam. And this is perfectly okay. So it was no wonder to me that I was not able to sleep the night before and that the morning until the exam started (8 am) was hell of nerve-wracking to me.
But eventually the mail from Offsec arrived, and I was instructed to attend the proctored session, which I did. So it started.
I was working my way through the objective of the exam and failed at first. Miserably. Just to clarify. The objective is either to reach a segmented machine and find a file or to pwn enough machines to get 100 points. And after 24/48h I just had opened one machine and gained 20 points.
Imagine sitting in front of your machine and hitting a wall for about 24h. This is where family and friends came into play. If it were me I would have ended that exam right at this point. My mental health decreased to an unhealthy level. I did not sleep the first night although trying and my body was already shaking. But my wife and friends encouraged me to go on.
To give you more context I will tell you how I fight this problem of having too less self-confidence from time to time since I was a child. Ever since I was a little child I was having the habit of giving in too soon. I was cycling through a lot of different hobbies. But none of them I did longer than an average of one year. Every time I was reaching a point where the hobby would get too hard for me I was just quitting. I already hear folks saying:“How can you survive as a pentester in your daily job with this quitter-attitude?”. I tell you, that I am working on this everyday for 34 years now and that most of the time I can just beat that condition by dragging through it.
So now that you have a little more context I can tell you, the OSEP exam triggered that condition of having too less self-confidence really quick and I fell into old habits of wanting to quit again. This is where Offsec will tell you to try harder (to be honest I cannot here this phrase anymore). But it is true, you just have to. And I did.
The second morning of the exam my established sessions got so wacky that I decided on starting over and resetting the complete environment. At least I already had notes and an idea on how to proceed.
And this was the point where everything clicked into place. This reset was like resetting my mental state. I did the second half of the exam without any pause. My wife and later on even our guests were bringing me food. They were bringing me little plates of sweets like dextrose, gummy bear, bakery, … just to get my brain kicking again. They were handing me coffee to stay awake and they were handing me water and drinks just to stay hydrated.
My wife kept the kids away from me and managed to have my work environment as quite as possible. And every reader who is a mom or a dad too will know what hard task my wife managed here.
All in all everyone around me was supportive which I appreciated, more than I could show at the time being. To be honest during exam I was a dick to everyone around me. I could not help but to show how bad my mental condition really was.
But eventually after 44 hours into the exam I reached a point where it was clear to me that I might pass. And this was the biggest relief to me I felt my whole life. I am telling you that I already did exams like OSCP and CCNA. I attended two childbirths and gone through several strokes of fate in my family. But this relief was the biggest one I ever felt this far.
So I went downstairs, picked up I beer (which I really earned at that time) and sat down on the couch. I sat there, shaking, my vision was blurry and my eyes were tearing up, I was cold and hot at the same time. I remember sitting there 1 hour not moving, not even drinking the beer I held in my hand. I tell you, this was surreal altogether.
After I recovered from that state I drank my beer and tried to sleep, which I did manage at 4 am.
You might assume I slept in. I did not. My eyes opened at 9 am again (after sleeping for 5 hours). Still, I had not really recovered from the stress the exam puts on you. But there is no time for recovering, because you still have to hand in a report.
So again I sat in front of my machine and wrote the report. This part was easy to me. As a pentester you are used to writing reports like this. So I finished early and handed it in at 5 pm. There was still plenty of time left, which I didn’t need.
They tell you that you will hear from them within 10 business days. So my mind was set to not hear from them any soon’ish.
But as I was standing in my kitchen, cooking the dinner the day after handing in the report, suddenly a mail arrived. I remember looking at my phone and seeing “Offensive Security” flashing on my screen. This instance my heart dropped. The first thing which came to my mind was, that I clearly would not have passed the exam because of some kind of violation of terms or anything comparable. Why else would they get in touch with me so soon?
So I read the first sentence of the mail and I read it again and over and over again. It took me several attempts to recognize they just told me that I passed the exam. At this time we had guests and everyone around me was just staring at my, waiting on what happened. I must have looked like someone was telling me my mom died or anything like this.
So finally I read out the first sentence loud and this was the moment all hell broke loose. Everyone was celebrating, the kids were running around screaming in cheer and everyone had tears in their eyes. This moment will go down into my life history as one of the most enjoyable moments so far.
At the next evening I was talking to my wife, and she was telling me how she have felt throughout the exam. She had a really hard time, too. She was not sleeping well either and had to manage the kids and our daily life. And for this period of time she had to do it herself without any help. This I can image was at least as hard as doing the OSEP exam.
So there you have it. This is what becoming an OSEP feels like. It is going through a lot of pain, feeling miserable but then feeling invincible at the same time. It is a roller coaster of feelings. And keep in mind that this will not only affect you but everyone around you, as well.
I hope you enjoyed a different view on the journey of becoming an OSEP.