In the first episode of Season 4, Caitlin talks with Cheryl Strayed about how tending to humanity’s toughest quandaries has become her calling, and the three central questions that keep us all up at night.

Through years of listening deeply and sensitively to others’ experiences as well as her own, Strayed has unlocked what makes a good advice-giver and friend: sincerity, listening without judging, and connection. This—paired with her straight-shooting style—is why thousands of people have trusted Sugar with their deepest secrets. In all of her work, from memoir to advice to fiction, she teaches us all to listen deeply to our own inner voices for the truth we already know.

Get comfortable and tune into this episode with Cheryl Strayed to ponder how to move on after a deep loss or a heartbreak and reflect on the three major questions people struggle with throughout their lives.

Stick around after the interview for when Ben Schuman-Stoler joins Caitlin Schiller to talk about the main takeaways from the conversation with Cheryl Strayed and helps put together a book list for further reading on how to better communicate your needs and listen to your inner voice.

For more info, including links to everything we discussed in the episode, go to

Let us know what you thought of the episode, or just give us some book recommendations on Twitter—we’d love to hear from you! Find Caitlin at @caitlinschiller and Ben at @bsto.

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That excellent music you heard is by Nico Guiang. You can find more of it on Soundcloud and Facebook.