I have pain on the outside of both of my feet. It's been ongoing for about six to eight months. I had previously had plantar fasciitis on my right heel but not so bad now. I swim with fins. I cycle on weekends, 40 miles a day. I used gym ellipticals and treadmills and do weights. I am not overweight. I don't know what or why this all of a sudden started but I have read quite a few of the answers to this and the tendinitis answer seems to me to be the key thing here. I am going to try the hold/cold ice therapy someone suggested, thank you for that by the way.. I will write back if it works. Most of my pain is upon waking, once I get moving it's better and in a stable shoe. I can wear flip flops, I live in Florida, that is the most common shoe here, but I don't wear them a lot, they really aren't good for the feet. Any other thoughts out there, shoot them my way. Thanks

At the gym, put a mirror in front of the treadmill and go as fast as you can. Also jump rope in front of the mirror. Better yet, have someone videotape you. The idea is to see how your feet land.
And don't wear flip flops. Find a store that sells track shoes and talk about all the features, and buy a pair, even if you don't run.
Your ankles might be turning outward just enough to put the shock on the outer edge of the foot instead of all over the sole.

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You are very active as you mentioned. I would suggest a trip to the podiatrist to have your feet properly diagnosed.