The Conversation You Keep Putting Off—And How to Start It

from Between Now And Next Podcast · host Tessa Shahid

In this episode, I share my experience trying to have these (health, aging, end of life) conversations with my parents: what made them hard, the cost of not having legal documentation, and how to approach them imperfectly.Key Takeaway: Pick one conversation prompt this week and try it to open the door with your loved one or even friend (if you want to try it on someone else, non-family first). This episode is for anyone hesitant to start or who tried, and it didn't go as well as you'd have hoped.

What this episode covers

In this episode, I share my experience trying to have these (health, aging, end of life) conversations with my parents: what made them hard, the cost of not having legal documentation, and how to approach them imperfectly. Key Takeaway: Pick one conversation prompt this week and try it to open the door with your loved one or even friend (if you want to try it on someone else, non-family first). This episode is for anyone hesitant to start or who tried, and it didn't go as well as you'...

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The Conversation You Keep Putting Off—And How to Start It

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This episode is 34 minutes long.

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This episode was published on March 10, 2026.

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