An anonymous reader writes I currently work for a small IT MPS in the Southern USA. Recently, my boss approached me about offering security evaluation and penetration testing to customers in our area due to the increasing number of regulations companies area are having to meet. My role in the company is that of a proactive systems administrator. I have strong troubleshooting skills, a moderate knowledge of Linux, and a strong grasp on Windows systems. My working knowledge of networks is a bit rusty, but I've started working on my CCNA again, and skill/knowledge of any kind of programming language is extremely lacking as I have slacked off in that department. However, I've been working with Powershell scripting, and have picked up some resources on Python. Where would a guy like me start? What can I do, as far as personal development, to give me a shot at building this "new department" within my company? Am I beyond hope?