If you feel like you're making progress at Hackthissite.org but something's lacking, you might take a gander at social-engineer.org, a site that looks at the human side of the security equation.
Unlike hackthissite, social-engineer is a work in progress, seeking the aid of others in the community to help fill in the gaps of the site. But it does have interesting and useful information. Some of the videos in the resource section look dated, but the information is still good. The most interesting parts of this site would be the blog, podcast and newsletter. The "Framework" is the most in need of information. It's basically a wiki waiting to be filled, although there is some interesting information in it.
But if you're cruising through 'hackthissite,' know everything 'social-engineering.org can teach, are ready to go to the next level, and think you might like to get serious, maybe even make a career of this security stuff, maybe it's time to look into Offensive Security, SANS, or other groups offering certification courses online and off. Depending on the certification you're seeking, courses can run a few hundred to a few thousand dollars. It seems expensive, but the amount of information in these courses is unbelievable, and well worth the price.
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