He used to travel on foot, singing for his supper, when the King’s Road was still patrolled by the King’s Men. Now that the King has grown old and feeble the Realm is mostly lawless, and travel is dangerous.
The woman who runs the Cliffside Tavern lets him entertain her guests for hot meals and tips. It doesn’t sound like much of a living, but: there is magic in some songs if sung correctly, and he is very good. He can spellbind them, pick their pockets, and finish his song with a flourish, and they never know what hit them.