Freelance pentester, the only way for me to understand something has always been to take it appart entirely.
This naturally lead me to security/ethical hacking, where I try unorthodox and creative ways to accomplish my hacks.
My favorite topics are web serv/client pentesting, exploits(appsys), reverse engineering and cryptography.
My experience & knowledge into security wolrd will help you to find the weaknesses of your application (there always be ;) )
I am invested in several hacking communities such as Root-Me (Top 50).
Have a try, you might be surprised !