I transitioned in a few ways. One, I intentionally changed my stride for distance training while wearing Nike Air Free Everyday trainers. Two, I did short run

I transitioned in a few ways. One, I intentionally changed my stride for distance training while wearing Nike Air Free Everyday trainers. Two, I did short runs on the sidewalks barefoot to toughen up my feet. (It's gross.) Three, I started wearing the VFFs everywhere else where possible. I trained for years (12 yo+) as a middle-distance (10k) runner, so the biggest adjustment was to eliminate my "make this stride as long as possible," technique, which lends itself well to heel-striking. Now that I run on the road in VFFs, I definitely know for days afterward if I tired enough on a run to fall back into old habits. I can barely walk and have to roll my calves and shins. Mind you, I'm too close to 40, and I think I could have pulled it off pretty easily when I was 15-20.