@InspectorCaracal Agreed. There's also "have we made this thing *too* %$&#*@ hard to win?"
@skquinn I like the attitude that the FATE RPG system takes when advising you on when to roll for challenges: losing should be an interesting option to play.
But the originating thought was, if your gameplay isn't fun enough to still be fun when you lose, then maybe it isn't actually a fun game.
@skquinn I dunno, there's also the completely viable design direction of Failbetter Games, which is essentially "progressing in the game is to lose less badly and in different ways".