My take: The fool is beginning the journey of a lifetime. In fact, it’ll take a lifetime. Traditionally, the Fool is about to fall into it, completely blindly. Even the dog’s warning doesn’t catch his attention.
The way I want to see it is a little different. I want him to be willing to take the leap, thinking he’s prepared, but isn’t, fully. Instead of falling into it, completely, he’s choosing to step into it, with some excitement, but doesn’t know what he’s getting into. His wings are too small to let him be in control of his journey (or his fall), he’s self centered, and he thinks he can record his journey – make it third person.
He’s wearing a topknot, which will show up, later. His chest is locked. He keeps it with him, believing it to be full of treasure.
I’ve had trouble representing both the unreadiness and the willingness at the same time. I’m thinking of the selfies as him knowing that he’s on a journey, and the misstep as him losing control. He thinks it’s a vacation, but it’s more than that.