I am Lost!

Another image was done for the Dungeon Coach for his 5E compatible book "Alkander's Almanac of All Things. I loved designing the halfling bard keeping in mind that he is frustrated with directions. Not knowing what's wrong... And there is a connection with this image from a previous painting I did prior, too. (I put the previous painting for you to find.) How do you get to point A to point B? Do you ask the town and follow any leads? Do you just wander about and let fate stumble you to your destination?