Pen Testing: Making Passion A Priority

Last week, one of the partners in my firm (Bishop Fox) said something that rang true: "If you want to be a real penetration tester, you have to live it."

In a similar vein, Paul Graham says, "To do something well, you have to love it. So to the extent you can preserve hacking as something you love, you're likely to do it well. Try to keep the sense of wonder you had about programming at age 14. If you're worried that your current job is rotting your brain, it probably is."

A real hacker doesn't see what he does as just a job or as just a hobby -- he sees it as a lifestyle. No border exists between work and play, the line between the two made indistinguishable by countless cans of late-night Red Bull.

We've talked about how some pen testers will use checklists and methodologies when performing scans or doing their testing. These can be useful, but a real pen tester sees them as a baseline against which they begin to explore, like a jazz musician improvising a new and better tune. This experimentation allows a hacker to gain more knowledge and experience than any textbook can provide. In fact, this is where the argument arises about the overlearned not having the right, open mindset needed to pen test. Too much structure can inhibit the dynamic nature of true penetration testing. Having all of the knowledge in the world matters only if you also know how to apply it. Reading may get you far, but there's no better teacher than real-world experience.

In his piece on "Great Hackers," Paul Graham says, "I know a handful of super-hackers ... Their defining quality is probably that they really love to program. Ordinary programmers write code to pay the bills. Great hackers think of it as something they do for fun, and which they're delighted to find people will pay them for." Now, Graham uses the term "hacker" to describe individuals with a passion for working on code, etc., but his observation rings true for penetration testers as well.

What sets real penetration testers apart is their motivation and willingness to lose themselves in something they love. Not just in hacking, but this applies to expertise in other fields, as well. From video games to photography, martial arts to musical instruments -- it's the ability to throw yourself into something entirely, no matter for work or play, which will take you to the next level.

When your girlfriend teases you that you've been ignoring her calls and texts for the past day, when you look out your window and realize the sun is coming up and you've hacked all night, when you suddenly remember you haven't eaten yet, or you let the pizza burn in the oven because you're finally hitting your stride in exploits -- that's when you know passion has taken over.

That it's no longer what you do, but who you are.