Episode 55: The Heartbreak Road Trip

Featuring Ali Powell

Breaking up with a partner on the road is—to say the least—a unique way to leave a relationship. But for all the turmoil that breakups can bring, there are also amazing opportunities for growth tucked within such a transitional and often painful chapter. Solo traveler and photographer Ali Powell took the pain she felt from ending her last relationship and decided to do something with that energy, and she calls it The Heartbreak Road Trip.

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In this episode, you'll hear:

  • How Ali’s project, The Heartbreak Road Trip, got started

  • The reactions Ali has received online to her project

  • A few of the items Ali received for the project that stand out in her memory

  • What it’s like to destroy someone’s once-treasured personal belongings

  • The reason Ali doesn’t travel full-time, and why it doesn’t matter

  • What Ali has learned from taking on The Heartbreak Road Trip

  • Our stories and responses to being told by exes we couldn’t do road travel on our own

  • How you can get involved in The Heartbreak Road Trip

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Ali with her van

Ali with her van


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Music is by Josh Woodward.

WOTR podcast cover artwork designed by Dani Opal.

Hailey Hirst