The whole road biking position is pretty awkward, really. I'm still getting comfortable. When I got my bike fitted the position that I *wanted* to be in was a little too stretched out in my LBS' opinion. Being new, I was more than willing to follow their suggestions but have readjusted things for me when I've gone back. I like my bike shop.

In regards to the pain on the outside of you foot, some people get insoles. I purchased Superfeet insoles for my road shoes pretty early on when I got setup with my beautiful road bike, so I don't know if its just a muscular adjustment or it really was fixed by the footbeds. I have different insoles for my casual shoes and wear birkenstocks otherwise.

Of course, my big toe goes numb when climbing in spin class and on hills on the road. The sports medicine podiatrist says that its a matter of strengthening my back muscles, but its nice to be sure (the xrays they took to rule issues out are pretty spiffy). Again, to that, I've both loosened my straps and kept exercising and its not as evident as before.

And those mental suggestions for better, more efficient pedaling helps, too!

Hope your efforts to avoid pain work out!