Preparing for Vacation: The Executive Assistant's Dilemma

Diana and Mel go off-script in this unfiltered riff on one of the most relatable admin struggles: preparing for vacation while basically running a second job to get there.

Diana shares her go-to strategies: keeping Doug's calendar light while she's out, sending weekly email briefings with every document attached, and why she checks emails from the beach anyway because coming back to 1,500 unread messages is its own kind of vacation nightmare.

Mel opens up about the text that ruined a cave hike in Curaçao, Diana gets into being screamed at during Hurricane Sandy with no power and downed trees, and both admins agree on one thing: boundaries matter, and not every leader respects them. No guests, no filter, just two admins telling the truth about the vacation you earn and the job that follows you there.