Josh Gondelman talks with caller Holly about years of Costa Rica daydreaming, decision fatigue, and the underrated magic of hiring a travel agent.

What You'll Hear

A Very Good Move: Josh recaps trading nine years in a slightly dim apartment for a new Brooklyn spot with giant south- and west-facing windows, a coffee terrace, and an honest-to-goodness view of Manhattan.

The Costa Rica Standoff: Caller Holly admits she and her husband have been dreaming about a Costa Rica trip for years without booking a single flight, and Josh confesses he's just as allergic to building an itinerary.

Enter, the Travel Agent: Together they talk themselves into hiring an expert who knows the storm season, the good waterfalls, and won't shrug and say "I didn't do anything" the way a chatbot might.

CHAPTERS

00:00 A big move and finally getting good light

04:07 Welcome, Holly!

04:52 The Costa Rica trip that's been stuck for years

09:16 Should I use a travel agent?

12:35 Instagram envy and the courage to "break the seal"

17:21 Nailing down dates and committing to go

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