If you don't already know of him, John Strand is an awesome penetration tester and highly rated SANS instructor that founded and runs Black Hills Information Security. He is a huge advocate for community engagement and regularly posts webcasts and podcasts dealing with a wide range of security topics, and does deep dives on a range of topics.
This page is his "30 Things to Get You Started" list, and includes all sorts of awesome videos and articles to help you out. I particularly recommend his "Success in Infosec: Your 5 Year Path" article to help answer a lot of the questions people have here about what to study next.
