No Small Endeavor with Lee C. Camp

230: Unabridged Interview: Anna Sale

Oct 10, 2025
Anna Sale, a journalist and creator of the podcast Death, Sex & Money, explores the importance of having hard conversations rooted in her personal journey. She reflects on her divorce as a catalyst for asking deep questions about loss and meaning. Anna emphasizes the difference between merely discussing tough topics and genuinely engaging with them. She shares insights on tackling shame in conversations about intimacy and money, highlighting how honesty can foster deeper relationships. Tune in for practical advice on embracing vulnerability and building community!
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ANECDOTE

Roots Of Courage To Ask Hard Questions

  • Anna Sale traces her comfort with hard conversations to growing up in a talkative family and Unitarian Universalist church culture.
  • Her early political reporting taught her to ask the questions others avoid and shaped her interview style.
ANECDOTE

Divorce Sparked Her 'Me Search'

  • Anna recounts marrying at 26, divorcing after nearly four years, and feeling shame and disorientation in her early 30s in New York City.
  • That personal upheaval sparked her podcast idea and turned her research into a form of self-discovery.
INSIGHT

Shame Versus Pain Changes The Conversation

  • Hard conversations often reflect shame, grief, or fear of being seen as incompetent or wrong.
  • Distinguishing shame from pain helps you choose whether to disclose or sit with sadness.
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