Yeah, I think that the DM will make sure that Cory regrets the directionless flaw.
DM: Okay, so you're in a straight hallway. Roll a d6 to determine which direction you'll go in.
Cory: But the door I need to go to is right there...
DM: Directionless flaw, remember.
Cory: *grumbles* okay, I got a six, now what?
DM: You go up.
Cory: What? Up?
DM: Yep, straight up. Through the roof and everything.
Also to add to the Zoro no sense of direction moments:
"They told us to go North, so I climbed up."