In the Road to Rule, you can upgrade your job skills. Play until you can upgrade Lute Hero to level 5.
Then play one successful bar in each of the 4 main towns for this achievement.
NOTE: This did need to be done in one sitting, but it appears to have been fixed so you should not need to go back to any spots after you have played there once.
Dweller Camp - In the middle of town.
Brightwall - At the back of town next to the merchant stands.
Bowerstone Market - Behind the clock tower.
Aurora - To the right of the city entrance in an alley. (This one may not be available until sometime after you are Ruler)