Learning Resources
Hacker Culture & Hackerdom
To stay on top
Steps to follow
- learn
- learn some more
- keep all that up to date
Tools
Too many to mention. You need to already understand your systems, their internal commands, then find maybe more suitable systems for pen-testing. Then you need to build your knowledge of your target systems. Then you need to look for tools.
Famous things you'll come across: Nmap, The Metasploit Framework, Wireshark... but that's really just a start.
Next...
If you need more specific information... it really depends on what you want to do, what type of systems you want to pen-test, etc... But basically just read a lot, and experiment. There are some learning platforms / playgrounds available online for this.
Learn about low level software development, operating system programming, or anything really that gives you an understanding of how things tick and how to break them down. Breaking things is essentially what penetration comes down to. If you're good at breaking things, you're already gifted :)
You have the whole WWW to learn. Lots of free resources out there available. Strangely, not as many (relatively speaking) and not as easy to find as they used to, but you have tons of options: wikis, blogs, books, tutorials, open source projects to have a look at, etc...
Have a look at some security-oriented platforms as well, like BackTrack Linux. (btw, I assume you know how to use something else than a vanilla Windows or a vanilla Mac, right? If you don't, then start by learning how to use a GNU/Linux, a BSD and expand to others...)
If you have some money to spare, you can have a look at taking training courses and aim for pen-testing and ethical hacking certifications, like:
Security is a very multi-faceted thing, it encompasses a lot of areas. Your question is very vague at the moment to point you towards something specific, so there are very generic pointers for you to build up on.