Spiral on the Glove
The blue gloves have three straight lines - seams from construction or decoration - either way it reminds me of linear thought. Early in any practice, mundane or spiritual, the student stays within the marked lines, follows the established pattern. Our young man is communicating with someone with a different pattern - a spiral - someone who is not contained by linear thinking, but also someone who will watch something evolve - crossing it's path again and again, possibly seeing something new with each crossing. Someone who is willing to go out of his way to experience something as opposed to the laser-straightness to a goal.
I see in this potential for exchange, a decision being made to leave behind established patterns and move into something new, something that may not seem so well established (fewer oak leaves on the staff).
I see the sphere as his companion/advisor either as a pearl of wisdom or scrying sphere. Only he can see into it, but he has to remember to look. it is unclear in the Two of Wands that he has looked. His gaze is to the person off-stage, so to speak.
In the background there appears to be a green field, it could be water, an ocean calm and ready for sailing. So our young man is choosing from a place of prepared land (acres ploughed and planted) and clear skies.
As I take my last look, it occurs to me that perhaps our young man is looking for this change and is bartering for admission rather than being courted by some unknown person. Perhaps our young man seeks change and is out to get it.