When Connor Hall was young, he floated through life doing exactly what he was told to do in the upper middle class. He worked hard; he got good grades; he went to a good college. But less than a year away from earning his law degree, he realized he didn't want it. Now, he's in a relationship he isn't sure about and working a job that has no future, while worrying about how far he's lagging behind his friends and family. Jack of All Trades traces Connor's attempt to figure out what comes next, asking the question "do we settle for what we're supposed to do, or do we keep searching for what we truly want?"