We book holidays as if another location contains a calmer, happier and more interesting version of ourselves. Then we arrive and discover the weather is real, the queues are real—and our personality came through baggage handling completely unharmed.

In this episode, Oldmate and Josh unpack Alain de Botton’s The Art of Travel: a philosophical look at why we travel, why the imagined holiday can feel better than the real one and why even paradise eventually becomes Tuesday. We explore anticipation, airports, bucket lists, exoticism, nature, photography, social-media performance and whether AI-generated itineraries are quietly removing curiosity from the journey.

Are we travelling to experience the world, escape ourselves, collect evidence—or simply remember how to pay attention?

Listener question: What is the greatest travel experience you’ve ever had that would still matter if you had no photographs and nobody knew you went? Leave a comment, send us a message or email oldmateandjosh@gmail.com.

Apologies for the publication-feed weirdness. Caleb is too sick to function and Oldmate’s brain has melted into a warm, unusable paste—so naturally, both were given access to podcast-distribution software. Welcome to Episode 99.2.

Website: https://www.oldmateandjosh.com
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Spotify: https://open.spotify.com/show/67lmDK0OJwdjKzCfrMEW41
Apple Podcasts: https://podcasts.apple.com/au/podcast/oldmate-and-josh-the-podcast/id1745812861

Music by Pity Lips.