I would also HIGHLY suggest learning about something called "OSINT". It's basically the initial stage of intelligence collection. In reference to hacking it spans a wide array of topics including: whois, dns lookups, google search operators, social network recon, digital forensics, website duplication/crawling, proxy recon, etc...
I recommend this because when it comes to hacking, EVERYTHING starts here, and you are only as good as your initial recon on a target. The more information you have before you start, the more attack vectors you will have, once you begin. Knowing how to research is a critical aspect of this field. I suggest EVERYONE starts there.
A couple of resources to get you there:
Ben Benivides's OSINT Toolkit, you can't say enough about this guy, he's a pioneer in the OSINT world.
http://www.phibetaiota.net/wp-content/uploads/2013/07/2013-07-11-OSINT-2ool-Kit-On-The-Go-Bag-O-Tradecraft.pdfJohny long is a major figure-head in the hacking world, known for his Google hacking or google dorking
http://rogunix.com/docs/Pentesting/Google%20Hacking%20for%20Penetration%20Testers,%20Vol.%202.pdfHe also created the google hacking database.
http://www.hackersforcharity.org/ghdb/Whether your a scout recon in an infantry platoon, a ghost on the wire, or a kid studying for an exam.
Everything starts with research/recon... never underestimate the value of that...
Some good recon tools to get familiar with:
website digger, recon-ng, httrack, whois, netcraft, harvester, google (ofcourse) and it's special operators (some of my favs: Site, Inurl, quotes, filetype, and cache), maltego, wireshark, nmap...
and as you listed python (can be a great scripting language for recon, writing your own webscrapers/spiders,
couple good books on pythong recon: python for secret agents, hacking secret ciphers with python, gray hat python, Webbots, Spiders, and Screen Scrapers, Mining the Social Web, Python for Data Analysis, Coding for Penetration Testers, Python Forensics, Violent Python
(all books listed above can be found online... I found them all using google searches for filetype:pdf or filetype:torrent)
Knowledge is power my friend.
p.s. Download Calibre (available for windows and linux) and start a library with the ebooks you find online, this site has a pretty decent library to start, but they are still limited (and quite alot of it is outdated), you always need to do your own research to stay at the top.
Some great book publishers for hacking include:
Syngress (my fav), No starch press, PACKT, Sams publishing, Wiley, and O'reilly.
Check their sites regularly for new book releases that interest you. and then do a little google hacking to find them.
Personal Training Roadmap
Areas:
Programming
Web application
Networking
Basic:
Programming
Python
Javascript
PHP
Resources
http://www.codecademy.com
http://www.python.org
WebAppSec
XSS/CSRF/DirectoryTraversal/Jsinject/SQLi
Resources:
http://www.evilzone.org
http://www.enigmagroup.org
http://www.hacking-lab.com
http://www.hackthissite.org
http://www.securityoverride.org
http://www.owasp.org
Networking
TCP/IP
Resources: http://www.tcpipguide.com/
