[Achlys]

I see the arrows as indicating that everything starts from the Fool and many directions are possible in this journey.
The wooden mask to me symbolizes the blind beginning of the Fool's journey. There may be danger, symbolized by the dog at his heels, but he is armed with tools to help him face these threats.
To me, I don't see the Fool being carefree as much as I see a sense of need. The Fool needs to start his journey. You can see impulsiveness in his decision.