A few years back Rob Donoghue posted a Cortex+ hack for playing Lieber-y rogues staying one (or fewer) steps ahead of their mistakes. I’m working on fitting it to DW, so here’s a more broadly-applicable preview:
Scenario Starter
After character creation is complete, either ask the PCs the following questions, or roll 2d6:
A) What crime have you most recently committed, and was it intentional or accidental?
2: Regicide
3: Trespassing
4: Murder
5: Fraud
6: Kidnapping
7: Theft
8: Arson
9: Assault
10: Treason
11: Blasphemy
12: Littering
B) Who is pursuing you as a result of this crime?
2: Avenging Angel
3: Restless Spirit
4: Jealous Spouse
5: Inquisitors
6: Royal Guardsmen
7: The City Watch
8: Thieves’ Guild Thugs
9: Agents of an Aggrieved Noble
10: Sorcerer’s Familiar
11: A Parade of Bounty Hunters
12: Vengeful Orphan
C) What circumstances are making the situation worse?
2: They have allies (roll again on B)
3: You were set up and you don’t know it yet
4: Haven’t slept in days
5: Headed somewhere Even Worse
6: They’re catching up quickly
7: Had to leave one piece of Gear behind
8: One of you is already wounded
9: Both of you are currently wounded
10: Left something Important behind
11: Your safe house isn’t
12: Currently naked