5 Things I Wish I Knew Before Becoming a Penetration Tester

I have been a full-time penetration tester for over a year now. It has been exciting, rewarding, and worth the grind to get here, but I will be frank, there were aspects of the job that I was not fully prepared to handle. Training labs taught me how to exploit machines, and certifications taught me how to pass exams, but nothing really taught me what it is like to test real networks with real clients under pressure.

In this blog article, I would like to discuss the top five things I would have known before becoming a penetration tester, so you can avoid the same traps I fell into.

Quick Summary: 5 Things I Wish I Knew Before Becoming a Penetration Tester

1. Practical networks are enormous. You won't be as thorough as you'd like in your engagements.

   
   

2. Environments are more secure. Locating critical vulnerabilities will be more challenging and frustrating in real-world environments than in training labs.

   
   

3. Clients can challenge your findings. Effective communication and good morals are needed.

   
   

4. Pentesting is less about Hollywood hacking and more about documentation. Red teaming can be more suitable if you desire stealth and thrills.

   
   

5. Burnout is real. The excitement fades, the grind sets in, and balance becomes critical.

   
   

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Network Sizes

You may be accustomed to a few hosts in a lab in training. Real-world networks may have dozens, hundreds, or even thousands of systems. That is too much ground to cover in the brief window of a typical engagement.

You are conditioned to be comprehensive, yet in the real world, certain areas of the network will remain unaddressed. That is why time management and task prioritization are not luxuries, but survival skills.

This is also the reason why I value the strict time limits of the OSCP. The OSCP exam is not a perfect simulation of client work, but it does require you to think strategically under pressure, which directly applies to the job.

Strong security postures

Vulnerabilities are intentionally put there in capture the flags (CTFs), training labs, and certification exams. That is not the way the real world operates.

Clients who care about security patch vulnerabilities aggressively. Before you arrive, client environments have been thoroughly tested on multiple occasions. This implies that the easy fruit is usually picked, and it takes considerable time and effort to discover exploitable vulnerabilities.

There are still critical vulnerabilities, but they are less prevalent in the wild. This fact can be frustrating to a pentester who is accustomed to rooting everything.

Clients arguing findings

This one threw me off the most. Some clients will push back even when you present valid, well-documented vulnerabilities.

Some argue severity.

Others argue that it is not a finding at all.

Others simply want the report to appear clean for compliance or public relations (PR) purposes.

This is the line you must walk: keep to your ethics. It may be reasonable to adjust the severity when a client presents you with good compensating controls, but it is unethical and risky to water down findings to make someone look good.

The integrity of your report matters. It can be used by the customers or partners of a client to determine security. Lying or minimizing problems can be a real-life issue.

The positive thing is that not all clients are like this. Many of them prefer detailed reporting and even request that you increase the severity to enable them to justify larger security budgets. Nevertheless, preparedness for conflicts is a part of the work.

Pentesting is not as sexy as it seems

Ethical hacker is a cool title, and it is glamorous on TV shows such as Mr. Robot. Reality is different.

You are not imitating a sneaky enemy as a penetration tester. That is red teaming. You are more of an IT QA: find as many vulnerabilities as you can, write them down, and demonstrate their existence.

This is not to say that you will never pop a shell, dump a database, or become a domain admin. It occurs, yet it is not the primary goal. The majority of pentests are not associated with weeks of creating custom exploits.

When you want to navigate networks quietly like a true attacker, red teaming is the way. Pentesting is more expansive: breadth rather than depth, coverage rather than stealth.

Burnout is real

I believed that burnout was overblown. I was wrong.

After eight or more hours a day of testing, the excitement finally dies. The grind sets in. Even what you loved can become just work.

Burnout to me was not just pentesting. It was a combination of graduate school, content creation, relocating several times, and life transitions. But it still included pentesting.

Your story may be different. Perhaps you are bringing up a family, or perhaps you are pursuing other ambitions. In any case, burnout can sneak up on anyone. Balance is essential.

It's not all doom and gloom

The majority of what I posted highlights the more challenging aspects of being a pentester. But I want to be clear, I still love this career. It is the best job I have ever had.

I can do something worthwhile, with good people, at home, and make a good living. Everything I used to dream of.

I am not here to gatekeep or deter you. I would like you to enter this field prepared, not caught off guard. When you are aware of what to expect, you will be better equipped to handle the challenges than I was.

One of the best decisions I've made in my life was to become a penetration tester. I would not give it up for anything despite its challenges.

If you want a clear roadmap from zero to hired, check out my complete guide on becoming a penetration tester. It is one of the most valuable resources I have put out.