I first skateboarded in June of 2006. I have done very little skateboarding since Smiley was born. After seven years of owning a skateboard, I still can't ollie.
Smiley and Gallant love to ride in front of my on my skateboard. One at a time. At the speeds we go together, if the skateboard hits something and stops I can always avoid a fall with a few controlled running steps. So I hold a boy's hands, and this is enough to keep hims from falling if we "crash".
Today I splurged and bought a longboard. Now our ride is much more stable and smooth.
One street near our house is perfect for our needs: long, straight, only slightly steep, and recently repaved. I had the boys take turns riding on the skateboard as we walked up the street. For the downhill ride Gallant rode in the ergo and Smiley rode on the skateboard. Very fun!
As a holiday present I got softrucks. Maybe this year I will finally learn to ollie.