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Start a new character when it feels like u can't progress with your current one. It makes you realize how much better at the game you've gotten, is a good training and helps you find everything you might have missed in previous playtrough.
Also very few bosses are actually mandatory. The first boss is optional.
Learn bosses weaknesses and abuse them. Wether it's elemental weaknesses, AI glitches or limited moveset; they can make farming unnecessary.
Don't forget chalice dungeons, they give nice loots which will help you run trough the main game.