One Long Swim

If you haven't seen any comics from asofterworld.com, I highly recommend you take a quick peek- and then begin revisiting the site, regularly. They're often funny, sad, and a little fed up, all at once- which is probably why I enjoy them, so much.
I've been meaning to take a long swim, for a while, now- but I often find myself frozen in an indecisive purgatory of confusion and uncertainty. However, I have recently hatched a plan to begin a controlled drift to various cities, over the next decade. Currently living in Chicago (the biggest move of my life, to date), I am counting this as my first city. At the end of next summer, I will be moving to St. Louis, MO. It's still fairly safe: not terribly far from family, with a small group of good friends in the area and many more who pass through for family who still live there. But it will move me out of Illinois, for the first time in my life. This is exciting, for me, if in a muted fashion.
Beyond St. Louis, the plan is rather vague. A friend living overseas has expressed interest in having me join him in South America, two summers from now... which is tempting. Almost two years to work on language skills, figure out what avenue to pursue for employment, figure out passports and visas (wholly foreign to someone who's never stepped a foot onto land claimed by another government). A foreign world, peopled by many multitudes of strangers speaking another language and one amazing friend... potential adventures abound.
Other cities I'm considering include: Los Angeles (college friends), Seattle (maybe college friends?), Boston (no one!), somewhere in Hawaii (no one!), and Orlando (a high school friend). Discussing this with a few loved ones, aside from a quick note that a career would no longer be an option (was it ever?), there was a common response that this will serve me well when I finally get around to writing a book. The possibility of such an undertaking is far more overwhelming than the thought of living in ten cities in ten years... but I have often fantasized about being an actual writer (if only for one, brief, publication)... and I find myself considering it a real potential. Who knows what could happen in so many zip codes? How many stories might be hiding behind the door of a new apartment? How many plays lurking? Perhaps a few poems impatiently awaiting the chance to pounce?
That is all just fancy, at this point... but I am moving to St. Louis, next summer. And from there, who knows? It feels good. Not knowing, doubting, being uncertain- these are often unpleasant experiences, wrapped around so many aspects of existence that they become a series of waves crashing around me, slowly ebbing into a background roar, contemplating it's next rush for shore. This uncertainty feels good. This not knowing feels like an infinite potential for action. This doubting, maybe one day knowing for sure.
As I toss around ideas for new cities, I welcome any opinions and explanations the world may have to share. Let me know your thoughts on the matter, if you have any. Happy Monday. :)