Road Trip and Rollerblade Ninjas

So this is something I have seen a couple of times over the past couple of months, teenagers walking around twirling nunchucks, and then different sets of teenagers setting up small traffic cones and rollerblade around them at night.  but last week as I was on my way back from Latin, an all you can eat brazilian bbq place(it was good, and pretty cheap but not as cheap as the all you can eat sushi place I go to which is sushi, so no contest)  Anyways, so on the way home from Latin I was riding past one of the many billboards of Deng Xiaoping and in the little plaza around it I saw a group of these rollerblade kids skating around only this time they were all twirling nunchucks.  That's it, thats the story, no real moral or point just thought it was interesting.
Number two, roadtrip, the more Ive been thinking about coming back to the US, the more I am again coming to the conclusion I'm not sure what I am going to do when I get back.  Anyways, as the prospect of a job job is coming to look clearer I am thinking of all the things that I want to do that are difficult to do with a job job.  One of them is a road trip, not just a small one but a big one, specifically I have been thinking about Route 66.  Chicago to LA, so I've been looking into that some, and it seems doable but a knotty problem about the trip is how to get me and a car to one of the starting places, either way if I drive from Phoenix to LA or Chicago I would then have to backtrack most of the way, which I'm not sure would be bad or good.  So with that preamble, anyone that may read this is invited to PLEASE help me think of a solution!