230: Anna Sale: Cultivating Courage to Talk About Hard Things, like Death, Sex, and Money
No Small Endeavor with Lee C. Camp
Why Hard Conversations Feel So Difficult
Anna and Lee discuss shame, pain, and fear as barriers to speaking up during uncertain life transitions or value clashes.
When Anna Sale launched Death, Sex & Money in 2014, she was 30 years old, newly divorced, living alone in a studio apartment in New York City, and trying to figure out what her life would become. She had covered politics as a reporter, but her personal world was unraveling. So she started asking strangers to talk about hard things, the questions she herself was desperate to explore: How do people rebuild after loss? What do we do with grief, shame, money, or fractured relationships? What does it mean to live with honesty when the easy script disappears?
Over the past decade, Anna Sale has become one of the most trusted voices on how to have hard conversations—the ones we often avoid but need most. Her hit podcast has been named Podcast of the Year by The Atlantic and Apple Podcasts, and her book, Let’s Talk About Hard Things, has been embraced as a guide for meaningful living.
In this conversation, Anna and Lee explore the important difference between "let's talk about HARD things" and "yes, LET's! let's talk about hard things." And why talk about hard things might be, potentially, among the most life-giving conversations. They discuss shame and grief, the ways our families teach us what not to talk about, and the habits that help us listen well. Anna reflects on her own divorce, her Unitarian Universalist upbringing, and how practices of honesty and vulnerability help us build flourishing relationships even across cultural divides.
Along the way, Anna shares wisdom on navigating sex and intimacy without shame, why money conversations trigger so much discomfort, and what facing death can teach us about authentic human flourishing. Her insights blend psychology and happiness research, theology and culture, and a deep faith in the inherent dignity of every person.
A beautiful conversation about being human, and about what becomes possible when we have the courage to ask hard questions and the patience to really listen.
Please be advised that this episode contains details that may be upsetting to some listeners, including reference to suicide. Additional resources are available at:
Show Notes, Resources, and Transcript for abridged episode with Anna Sale
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No Small Endeavor: An award-winning podcast that asks what it means to live a good life. Through conversations with leading thinkers across theology, philosophy, psychology, politics, and the social sciences, we explore human flourishing, meaning and purpose, faith and culture, science and religion, virtue and character, community, and the practices that help shape a good life grounded in truth, beauty, and goodness.
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Host Lee C. Camp: Lee has worked as a professor of theology & ethics for more than 25 years, teaching and writing on topics of faith & politics, inter-religious dialog, and human flourishing at the intersection of theology, moral philosophy, and social sciences. Follow @leeccamp
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