Teach Me How To Adult

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Episode 123: Teach Me How To Have Difficult Conversations | Part 1, with Anna Sale, Host of Death, Sex & Money


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Calling all our non-confrontational queens, this one’s for you! If you’ve ever avoided or put off a difficult conversation (you know the one), you’re not alone. We all struggle with confronting tough issues head-on in fear of being judged, shamed or rejected for expressing how we feel. But here's the thing – shying away from the hard, messy stuff means that we're leaving key parts of ourselves out of our most important relationships. So, it's time to learn how to navigate tough talks with confidence and grace!

Thankfully we called in someone who has literally written the book on hard conversations, Anna Sale. Anna is the creator and host of WNYC studios’ wildly popular and award-winning Death, Sex, & Money podcast, where she's been doing interviews about "the things we think about a lot and need to talk about more" since 2014. 

The New York Times dubbed her “a therapist at happy hour”, and we could not agree more. Anna and her guests have direct thought-provoking conversations about the topics we’re often too squeamish, polite, or nervous to bring up. She’s the author of Let’s Talk About Hard Things, where she dives into death, sex, money, family, and identity. 

Join us for a deep convo about: 

  • Why tough conversations are so necessary

  • What really holds us back from talking about difficult or taboo topics

  • The anatomy of a productive, hard conversation (and how to prepare for it)

  • Why good conversations don’t always lead to tidy resolutions

  • Why hard conversations with family can be so much more difficult

  • Advice for avoidant and anxious people to get better at direct communication

  • Anna’s take on radical honesty and the use of fibbing in relationships

  • How to “pick your battles” and decide when a big discussion is warranted

Be sure to tune in next week for part 2 of our chat! 

We hope this episode helps you have the honest, hard conversations that can help us connect more deeply. 


If you have a topic you’d like us to cover or a guest you want us to interview, comment or DM us on Instagram:

@teachmehowtoadultpodcast

@cailynmichaan 

@yunggillianaire


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