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For example let's say that a demon has a cover named Jonathan. He is a 40 year old guy with no hobbies and nothing going on in his life except going to work and coming up to watch TV or YouTube. As a result anything the demon may want to do such as seeking their keys by travelling to another city or attending some meetings is an immediate breach of cover since Jonathan wouldn't do that.

Could a demon gradually leave hints of an upcoming midlife crisis, display lowered performance at work and eventually get fired or quit in order to make their actions such as investigating companies or travelling to be within cover?

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This could be a good opportunity for a patch job (D:tD pg. 116, Pacts), depending on how much of a hurry the task is. Finding someone who's in the middle of their own crisis would probably not be hard to form a pact with.

If time isn't a concern, staging a midlife crisis may even be a good source of cover beats, depending on how you play it. Caution should be advised going down this route though; actions that would push you towards that change may in and of themselves risk compromise.

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