Mid-career Traisition to Infosec #0x02

Every planning activity I like to start by taking a step back, trying to get the big picture, and defining in one sentence: what is that I want to achieve exactly. So, let's see.

"I want to shift my career from whatever I'm currently doing to something that is offensive security related."

That's at a pretty high level, but I think I could refine it a little by adding:

"Preferably, I would like this to be also related to software engineering since it's my background, and also I just happen to like it."

Ok, so that's more or less my goal. It is still high level, I know, but it's good enough for now.

Next, I will try to recap where I stand in achieving this goal. As I already mentioned, my background is in software engineering, so I'm not exactly an IT beginner. But what does that mean exactly? Again, let's try to refine it a little.

I'm a software engineer with 15 years of experience, 5 of which I spent on actual coding (mainly in C++ and Java) and the remaining 10 years working as a TPM. It is also worth noting that I spent the last few years running the same project using the same development stack. Although these were multiple projects, the software and most of its functionality are identical. So, although I picked up some software engineering, project management, and leadership skills, I'm not up to date with the latest tech. Of course, it's not like I was doing nothing all those years. Over time I picked up many different programming languages and frameworks, but it was primarily out of curiosity and by no means I'm an expert or even proficient enough in any of them.

Knowing more or less what I want and having a clear idea of where I'm currently at in terms of skills that could help in achieving my goal, let's try to narrow down the roles (or areas) of the offensive security which I could focus on. At this point, it would be helpful to have two lists, one in order of things that I like the most and the other by the least effort I think I would have to make to get good at (knowing my strengths and weaknesses).

Things I think I'd like to do:

1. Pentesting

1. Red Teaming

1. Exploit Development

1. Reverse Engineering

1. Security Researching

1. Application Security

I didn't get the numbering wrong; it is all exciting. Also, if you try to read the definitions or job descriptions of some of those roles/areas, they are super confusing; they often overlap with each other or, in many cases, at least complement one another - difficult to decide which one I like the most. For instance, regarding the difference between Pentesting and Red Teaming, I dare you to get a single, concise description from more than two people. The same goes for Security Researching and Reverse Engineering.

Not a good start, but let's continue. Let's now try to map this list to my skills and experience, and see if I can get a more precise outcome.

Things I think I'd learn quickly:

1. Pentesting

I think I'm a well-rounded IT professional, knowing some sysadmin stuff, networking, scripting, and software development.

2. Application security

since I have decent software engineering experience, I think I would "only" need to pick up some infosec practices.

3. Exploit Development

although different from AppSec, I think I could do a decent job developing something - I like and know how to code after all. I would "only" need to pick up the other bits and pieces (e.g., reverse engineering and deep dive into OS/kernel internals).

4. Reversing Engineering

I don't think anyone is doing just that, so I'd combine it with Exploit Development (of course, I could be completely wrong).

5. Security Researching

well, I'd need to be good in all of the above, wouldn't I?

6. Red Teaming

just the fact that no two people can give me a concise definition means that either I'm asking the wrong people, or it is another role that requires knowledge and experience in all of the above.

Writing those two lists down already made me realize how little I know about this field. Also, I'm almost 100% sure there are many more areas and roles in offensive security which I don't know about, yet. It brings me to only one conclusion, if I'm serious about all this, I won't be able to do it on my own. I need to get some guidance and a decent education. Time to split the plan into two: upskill and transition. Let's start with the upskill plan.

Upskill Plan

How do I get up to speed with all offsec-related stuff? Quick Google search, and I see a few things:

  • Almost no one is considering getting a degree unless it is someone 17 years old who wants to get a degree anyway (and even then, people recommend them to get a regular CS degree and pivot later to infosec)
  • Certs in infosec are huge. I initially thought it was because maybe it was just cool to have them. But diving deeper into the subject, infosec is one of few disciplines where certifications are also significant for employers. I know what you're thinking: these are for the defensive side of infosec. I remember thinking that, but I could not be more wrong.

So, it looks like the certs are very important. In fact, in the offensive security field they are sometimes more critical than a relevant degree.

In the future, I will dive deep to understand why, and I think I have an answer (it will be in another post), but for now, let's go back to building the upskill plan.


There are many to choose from, but doing some research, you can divide them into a couple of categories:

  • easy, entry-level (e.g., eJPT or CEH)
  • advanced (e.g. eCPPT)
  • industry-standard, shiny "bling bling" - the stuff that people make a tattoo of on their back (e.g., OSCP) That tattoo thing is a joke, of course (or is it?), but you get the point.

Before I continue, a few words of caution. First, there are many more certification options, but you should probably google them and see what's best for you. Second, whatever I write next is subjective and applies to my situation only. I'm not saying that my approach was the best, what I'm saying is that it was the best for me. I will describe my thought process while choosing my first cert, and I hope it will help you make your own decision, too.

At this point, I'm still focused on learning as much as possible, not on what certifications to put on my CV. So, as you can imagine, I initially thought of signing up for the easiest one and climbing my way up to get the holy grail - OSCP. However, while I was researching about it, I noticed that all those certification bodies also offer very comprehensive study and training plans. It led me to shift my approach by 180°, and instead of looking at the certs in the order from the easiest, I turned the list upside down and started with the most extensive and difficult one. My only guideline was the list of prerequisites a student should meet before signing up.

So, since I knew I could afford it and met all prerequisites, I decided to go for OSCP. Of course, I had to make a leap of faith that the requirements were accurate and that the training materials were good enough to prepare and guide me from 0 to hero, but that was it. Next thing I know, I'm a Learn One subscriber at Offensive Security - OSCP baby! Although I signed up for it before deciding to shift to offensive security, I would do the same if I had to do it again.

I also hope that this training will give me an overall idea about what other offsec areas are out there and where to go next in terms of further education/certification. Ideally, it will enable me to kick off the transition phase by either slowly shifting internally within my organization, helping find a part-time internship, or even joining a Bug Bounty program.

To summarize, apart from all the research I've done on the subject, it looks like the actual first step I should make is to complete my OSCP, and I should also use this opportunity to answer the following questions as I go through it:

1. What different areas of offensive security are out there

2. Which one of them do I like the most

3. What are the roles associated with that particular area

4. What are the next steps in terms of upskilling in the area of my choice

5. What other relevant areas are worth exploring

That's pretty much the plan I have. Note that everything I discuss in this post is related to the upskill plan. The transition, however, is an entirely different story. I already know that it is not going to be easy and a change will have an impact on both my personal and professional life. So, I think that the best thing I can do is to look at it critically and approach it the same way as the upskill plan, hopefully with a little more knowledge about the industry. I will write about it in the future. For the time being, I'll focus on hacking the OSCP!