Well, today was my first run outside without any shoes on whatsoever! I ordered a pair of Merrell Trail Gloves yesterday, and wanted to start getting my body ready for them. I am using this page as my guide -- http://birthdayshoes.com/how-to-transition-to-running-in-vibram-five-fingers
-- for what kind of transition to shoot for.
Background on me, I live in downtown Montgomery, Alabama (the Garden District, specifically) and so there are lots of sidewalks around, but they aren't kept especially clean. I knew of one route near my house that was better than some, so I took the short route on it. In total, I think I ran/walked about a block and a half, so maybe half a mile? For perspective, I am only on week 2 of Couch to 5K and haven't had a run over 2 miles yet (and that's still run/walking obviously).
My impressions to doing this run surprised me: First, I was pretty scared when just walking on the sidewalk with only my flip-flops in my hands. I went about a quarter of a block like this because I knew I needed to cross a road and didn't want to do it running barefoot for my first time. Luckily, our roads are lightly trafficked (unlike Atlanta where I just moved from) and I got across without any issues. On my full block, I just started running, using the short stride I knew was important, and to my surprise it really felt right. I mean, I had to stare down just a few feet in front of me to watch the surfaces I was stepping on, and would occasionally get something on my foot that I had to scrape off, but mostly I felt good. I jogged at quite a slower pace than I normally would (no numbers, as I can't exactly get a Nike+ sensor on my foot and my iPod Touch 4th gen doesn't really have GPS) but didn't feel the need to push myself or anything.
Most importantly to me, for the first time ever I really felt a connection with my run. It oddly brought back memories of trail running when I was in middle school, as we had a heavily wooded park adjacent to my school and as part of our P.E. class we would run it once a week or so. I lived near the school, and like the trail so much that I would sometimes run it just for fun, although my stamina was terrible as I mostly did fast twitch type exercising (martial arts, mainly).
When I got home, only really stopping my run once because the terrain got a bit hairy and I needed to catch my breath anyway, I felt more energized than I ever have on a run and was excited to do it again in two days. I really want to thank all the people here for giving me the confidence to do this today, and I know I'll keep at it!