I've been in the IT world for a few years now. I've basically learned everything from work experience. But the people here aren't the brightest. I would imagine there are some really good podcasts or blogs somewhere for security. I want to learn more. I want to make my own personal stuff more secure. I'm talking firewalls, VPNs, the latest hacks. I'm pretty much coming from some basic knowledge of managing a domain, VMware, and SQL. I was a consumer level technician for a few years so I've got your typical laptop/desktop hardware/software stuff down nicely.
Books... are pretty good sauce: Hackers Playbook 2, RTFM (Red Team Field Manual), BTFM (Blue Team Field Manual), Twitter (yes, twitter.. the infosec comunity is very active there), BlackHat, Defcon, CCC, Hak5, ...
Security Now is a weekly podcast that covers all kinds of issues and tools. Schneier on Security is a useful blog. Neither of these will give you the in-depth training of books, but can point you down useful avenues and help keep you up to speed. I'm on my phone, but will post links when back at the pc.
I'm trying to put together a modest security blog-wiki thing for the community, as I'm seeing a lot of security-related questions, and it would be nice to have a more permanent place to aggregate all of this useful information. Keep an eye out for it in the next few days, and please consider contributing.