I recently was asked by some colleagues how an IT admin can get into infosec. It’s a tough question for 3 reasons: 1) Most administrators are not wired to be security professionals. The goal of admins is to provide services to users. The goal of infosec is to limit services to only authorized users. These goals often conflict. 2) Most admins specialize in a single technology; good security pros need to be fluent in a wide range of technologies. 3) Security requires a deep knowledge of computing and networking theory, which many admins lack. Modern operating systems provide a high level of abstraction from issues such as the proper format of TCP headers. I know some very skilled systems engineers who do not fully understand a 3-way handshake, nor do they need to. But for a security engineer, understanding this process, how to exploit it, and how to recognize when someone else is exploiting it is critical.

My best advice for those crazy enough to desire a career in infosec is always to start with the technology they already know, learn how it works at a low level and how to break it, and then learn how to protect it. After that, security is a non-stop learning process. The best security guys I know spend hours reading, surfing, and studying every night. Sleep is for the weak!

I compiled the list of books below as a representative sample of the books on my shelf that I reach for regularly. In my (never) humble opinion, every infosec professional should own (and read) each of these, or others in the same category. Originally, I intended this to be a Top 10 list, but I had too many books on my list. 20 is the shortest I could get it and still be representative.

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