[quote=@XxFellsingxX]
At the end of each session (chapter in this case), you check to see if you've fulfilled your obligation and if you have, you erase 1 Shadow. I might homebrew some extra rules about that to make it more interesting.
[/quote]

Since it already only takes a single successful move to remove a shadow, I'd say homebrew would be needed here. Perhaps after fulfilling an obligation, you get a one time ability to turn a roll you don't like into a 10+.