Legendary skateboarders like Jason Lee and Tony Hawk likely come to mind.
If it helps, the best skaters we know happen to be human.
Especially the anxiousness, these are all acceptable emotions to feel.
You can't help but grit your teeth and cross your fingers as he descends the steps, fearing that he'll lose his balance and fall.
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He's dressed, maybe for warmth or to prevent him from fleeing on his own will.
Of course, every dog is different. Skateboarding with a dog who is inherently nervous is not going to end well.
Also, train your dog to stay put on the board while you push it, especially if it has shorter legs like a small Dachshund.
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