Three thoughts on leaving:

1.  Adam Moss, the longest serving editor of New York magazine, is leaving after 15 years. He says, "I want to see what my life is like with less ambition." Here's a reaction by someone who worked for Moss about that being one of the most quoted lines of the New York Times article about his departure. In learning of his departure, she says, "There’s nothing quite like stepping off the treadmill to teach you which direction you want to go."

2.  Elizabeth Gilbert discusses what to do when you know it's time to leave here. The whole conversation is worth a listen, but the conversation shifts to ending at minute 39. Further reflection here.

3.  This piece by Amy Poehler in the New Yorker in 2013 contains the greatest wisdom I've ever read on the subject: "It’s important to know when it’s time to turn in your kazoo."