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I don't know if this is a silly question, but I am a little confused about Journeys. Some characters have specific tasks to complete in order to check off one of the tracks, but some don't. At the end of a Chapter do they count up their individual leftover tokens and trade each one for a track segment? 

Yep! Those are leftovers, and that's exactly how it works, if they don't have checklists.

Awesome thank you :)