The Legend of Heroes: Trails in the Sky
Still very early in the game. Did the training mission and then there was the first "real" mission.
You were supposed to go west, but I thought you were supposed to go east.
The monsters to the east hit quite a bit harder than he ones to the west, so I spent quite a bit of time grinding until I could mostly get through unscathed. You don't get money for encounters, so there's no opportunity to upgrade equipment either...so, lots of grinding.
Finally made it to the end of the path with most of my HP and EP in tact only for the guy to not let me in (apparently, the mines are closed and the moose out front should've told me).
Figured out my mistake, went west, and discovered that the so-called boss fight was very easy.
It was the first mission of the game so I doubt it was intended to be a challenge in any event. But a couple of hours of unnecessary grinding really sealed the deal.