There is a local cable television station run by the University of Washington.  On it there airs a show called Information Technology Leaders hosted by a woman named Laura Shildkraut.  On the show, Laura spends an hour interviewing, you guessed it, leaders in the information technology field.  The guests are CEOs, CIOs, VPs, COOs, CTOs, etc.  Topics covered include not only what they are doing now but what they did in the past and how they got to where they are.  Laura gets some interesting guests.  For instance, she interviews all three Renegades of the Empire (Alex St. John, Eric Engstrom, and Craig Eisler), John Connors, Rick Devenuti, etc.  I find the stories fascinating.  There is also a lot to learn from people who have "made it."  If you have some time, I recommend you check out the streaming video version of the show at http://www.informationtechnologyleaders.com/video.html.