My shoes are Specialized Motodiva and the soles seem pretty stiff.--

Loosening the straps sounds like a good thing to try. I have the same problem with toes going numb after running for about 45 minutes - I asked a podiatrist about this several months ago and he said he had no clue what would cause that (?). Since I land on a different part of my foot when running vs. the pressure point on the bike pedals, the feet swelling over time might be a common denominator.--

Deb