Bike riding started off much like swimming and soccer did for Will: tears, tears, and more tears. Will never wanted to ride, and when I WAS able to convince him to pull out his bike he would only ride in slow circles on the back patio.
Will overcame his aversions to swimming and soccer very, very S..L..O..W..L..Y. I required him to continue participating, and with each new day I pushed him just a little further than I'd pushed him the day before. (For example: swimming day #1 = sit on side of pool; swimming day #2 = put feet in water; swimming day #3 = walk in water up to knees.) As I'm sure you imagine, it took a very long time for Will to get to where he is now with both swimming and soccer.
Will wasn't making any bike-riding progress, even with training wheels, so one day I decided it was time to say goodbye to the training wheel safety net. I knew Will could and would eventually learn how to ride a bike if I opted for the slow-and-steady forward progress method we'd used in the past. But to be honest, I can't stand that method and wanted to see if just jumping in feet first would work.
Both Tom and I doubted it would, but I stuck to my guns, and that weekend we went to the park (the sidewalks in our neighborhood would be terrible for learning to ride a bike) to give bike riding - without training wheels - a try.
Yes, there were tears. I knew there would be. At one point both Tom and Will wanted to pack it in for the day, but drill sargeant mom made them keep trying, and you what? He did it. Just for a moment or two, but in that moment I saw him realize that bike riding was something at which he could succeed.
The next day we went back to the park, and he did this:
If you listen carefully to the end of the first video you can hear me start to cry as Tom lets go of the bike and Will takes off.
There are times when slow and steady wins the race, but there are also times when it pays off to just take a deep breath, say a little prayer, and jump.