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Episode 125: Teach Me How To Have Difficult Conversations | Part 2, with Anna Sale, Host of Death, Sex & Money

We’re back with more of our conversation on hard conversations with the fabulous Anna Sale. This week we’re leaving our comfort zones behind and learning how to confront our mess head-on, for the good of our relationships and our sanity. From finances to family dynamics and grief, we’re getting all the tips on how to approach the most hush-hush topics and have the courage to admit when the status quo isn't good enough anymore.



We’re back with more of our conversation on hard conversations with the fabulous Anna Sale. This week we’re leaving our comfort zones behind and learning how to confront our mess head-on, for the good of our relationships and our sanity. From finances to family dynamics and grief, we’re getting all the tips on how to approach the most hush-hush topics and have the courage to admit when the status quo isn't good enough anymore.

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 as we dive into:

  • Why money feels so taboo to talk about

  • How to navigate financial differences with friends and family

  • Addressing family conflict in a constructive way

  • Knowing when it’s time to take a break from someone

  • How to support someone who is dealing with grief

We hope this episode reminds you that you can do hard things!

Listen to part 1 of our conversation with Anna here!


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


Related Episodes:

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Relationships Cailyn and Gillian Relationships Cailyn and Gillian

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

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!



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


Related Episodes:

Read More