My good friend Don Donzal of EthicalHacker.net spoke at the SANS Pentest Summit recently.
his slides and audio are available on the site
Main Link: http://www.ethicalhacker.net/content/view/201/1/
He said some good things in the talk, here are two slides that bring alot of good information.
First slide I posted was on being honest with yourself about who you are, where you want to go, strengths and weaknesses, and the family concerns. Being gone alot isnt the best thing for a marriage.
Second slide was free or cheap ways to get there once you know where you want to go. I really like this slide because I would consider it the roadmap I have taken and I think its going pretty well.
The talk is about 50 minutes and worth the listen.
I had to laugh about his "flash resume" from back in the day, if someone sent me a flash resume I'd be too worried I'd be sending a reverse shell back to the guy by reading it.