Photo: Rob Howard

That's the question the women here asked themselves at a point when their days were filled with the same old, same old. And then they jumped—sometimes without a clue as to where they were heading. The upshot was that each found herself one step closer to connecting wholeheartedly with the person she was meant to be.

→ From publishing executive to sailor and author

→ From marketing executive to stationery store owner

→ From corporate fashion executive to clothing company founder

→ From nonprofit staffer to nonprofit founder

→ Attorney and bakery co-owner

→ From executive recruiter to renovation and design manager

→ From stay-at-home mom to adventure-travel company owner

Plus: How a style maven fell into real estate development