Unknown-a-phobia

How many people ever get past that? I was thinking on this the other day and came to realize that schedules, career plans, calendaring meetings all set you into a mundane pattern of living. Oh, I don't think routine is necessarily e-vil or any such thing. I just think that every once in a while one should do something new, if not somewhat intimidating or "scary." We get so comfortable and honestly even in our comfort is still seems that things don't go according to plan. So why is it bad to have a little randomness. I think that the random experiences we have are often the ones we talk about and relive for years.
Here's an example: Ray and I ran out of gas on a road trip between Haines and Anchorage. we were seven miles from Tok. We walked into town just as my old boss was driving down to the river to get water for his dogs. My old boss drives from Whitter back to Washington every winter with his family and his sled dogs. We ended up eating breakfast with them. My boss drove us back to the car and we went on our way. Honestly it wasn't that inconvenient and it sure is a funny ironic (yes Adam, ironic) story.
Random musings but an interesting thought...is it worse to plan everything in life or to loosely plan life so that when you're driving along and the bumps hit you can still kind of enjoy them as you bang your head on the ceiling?