re: Startup Weekend Made Me A Better IT Leader
I think part of what you're seeing there is that when people are working on their own enterprise, they're playing with "skin in the game" - whereas at their "real jobs," they're performing one specific role within the organization. After a while, you get the blinders effect where you only see what's around you and get a narrowed field of view about the entire organization.
Although, I have to admit, working in IT and supporting all of the users in an environment, the effect lessens when you get pulled in so many directions over the course of a day or week. When you start off supporting the sales department, then the developers, then the business intelligence group - all in one day, and actually take an interest in what they're doing in an effort to help deliver better support for them - it prevents the blinders from going on.
And, as someone who has a lot more irons in the fire than just being a stellar IT guy (I'm involved in building a recording studio, I do terrestrial/'net radio and a few other things), it's a matter of staying diverse and looking at what skils from one portion of the spectrum you work in to another part.
Indeed, the key to keeping life (much less work) interesting is to keep exploring "uncharted" territory... whether it's a new technology, new business venture or just new geography.