Just found this blog and the articles that i've seen so far are pretty awesome. Looks like this guy is/was one of the contributors to ethicalhacker.net and went from the OSCP to the CISSP and OSCE

then the GXPN

He describes in detail, a way, what I think is a really realistic way, to join the infosec community and indeed for those seeking to become pentesters, this is how you go about it. It'd be cool if we could get a sticky on this topic since it comes up so often.
pwnag3: My Road to Pen Testing