Two of Pentacles
Just a silly guy playing? I don't think so.
Definition
On the one hand it is represented as a card of gaiety, recreation and its connections, which is the subject of the design; but it is read also as news and messages in writing, as obstacles, agitation, trouble, embroilment.
Reversed: enforced gaiety, simulated enjoyment, literal sense, handwriting, composition, letters of exchange.
Detail
Immediately I am drawn to the two ships in the water behind the juggler. It is precisely the position that stuck out. Is this person juggling and playing a game, that never ends? I am not really sold. I see this person that is juggling all that they have to; never-ending. Always juggling, yet, life's ups-and-downs (two ships going in the same direction, one up, one down) are behind him. He has left them behind.
Do what you must, left the up and downs behind you.
Day
This card speaks to me a bit; I might be pushing into it, rather than drawing from it—but it is the energy I am getting. Keep doing the things I that I need to do; work or play matters not, just that the ups-and-downs stay behind me.
Easier said that done obviously. There are some other items from this card's imagery that sticks out to me; the head looking down; and the barren ground he is walking on. Food for thought.