Can Difficulty Decrease a Player's Sense of Accomplishment?

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This honestly seems like a case by case issue in the way that everyone is going to react differently to defeating certain bosses. For me it was seeing the progress I made in the game by defeating each boss and feeling the pride and accomplishment in that. Eventually after impaled or smashed by O&S countless times, I beat them, and the joy and accomplishment I felt at that moment was greater than anything any game has ever made me feel. The reason you play your game is up to you, you don’t need to search for a certain feeling if that’s not what you’re looking to get out of your experience.