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I'm thinking about doing the Pilgrimage of the Ashes quest on one of my noob characters. My question is will I get in trouble if I don't follow the blessings in order? If so, what happens? For example, for the first task it wants me to go to Thais, then Carlin, etc.

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In order to complete the quest, you must stick to the right order presented by talking to the NPCs, for instance 

Guide: The first sacred place you have to travel to is the Whiteflower Temple located to the far south of Thais. Talk to the monk Norf about your mission. ...

As the NPCs mention the specific places and the right order of buying of blessing, taking another rout will result in not being able to complete the quest.