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How to Have Difficult Conversations with Empathy (W/ Katherine May) | How to Be a Better Human | TED

When someone you love is going through a difficult time, what do you say? Despite your best intentions, author Katherine May argues offering help or shying away from tough conversations isn’t as effective as you think. Katherine is the author of the memoir, Wintering: The Power of Rest and Retreat in Difficult Times, and its…

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When someone you love is going through a difficult time, what do you say? Despite your best intentions, author Katherine May argues offering help or shying away from tough conversations isn’t as effective as you think. Katherine is the author of the memoir, Wintering: The Power of Rest and Retreat in Difficult Times, and its latest companion piece, Enchantment: Awakening Wonder in an Anxious Age. Chris and Katherine share how humor may sometimes be a good medicine and how to live alongside life’s difficulties.

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Host: Chris Duffy (Instagram: @chrisiduffy | chrisduffycomedy.com)
Guest: Katherine May (Instagram: @katherinemay_ | Website: katherine-may.co.uk/)

Links
Wintering: The Power of Rest and Retreat in Difficult Times (UK Bookshop / US & CAN Bookshop)
Enchantment: Reawakening Wonder in an Exhausted Age (UK Bookshop / US & CAN Bookshop)

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25 Comments

25 Comments

  1. @Jasonxbr

    August 27, 2025 at 11:03 am

    Practical in principle, but it only works if both parties are at that concenus. Unfortunately, with MAGA and the far right, the answer is no 😢😢😢😢😢

  2. @DMaintain

    August 27, 2025 at 11:15 am

    To the individual Who is reading this please quit overthinking everything every day and night. Stop obsessing over your failures. Stop doubting yourself and seeing the greatness in everyone else But you. You are better than that. You deserve more. Start showing up differently to yourself. Believe in Yourself. God wont ever hand you something you cant handle. You are a star in this world . May God Bless Whoever Sees This Amen 🙏🏾

  3. @warpigroadkill

    August 27, 2025 at 11:20 am

    Tell them to listen to Cradle of Filth, Coffin Fodder is a good track.

    • @AtronSeige

      August 28, 2025 at 3:14 am

      You have to give them the Nymphetamine album and point out the song. 🙂

  4. @NIELIS1996

    August 27, 2025 at 11:26 am

    Nice review botting

  5. @royalsaiyanelite198

    August 27, 2025 at 11:34 am

    Ted is really leaning far left these days, huh?

  6. @poleninsyt

    August 27, 2025 at 11:38 am

    有一些回音 6:12

  7. @dirkda2451

    August 27, 2025 at 12:01 pm

    So in contradiction to what is being said at first,I hear you both speaking a lot of silver linings and being better for having gone through these winterings

  8. @Luka-ec1gk

    August 27, 2025 at 12:14 pm

    So awesome! Really good insights!

  9. @Carlos-n6p4m

    August 27, 2025 at 12:47 pm

    What you’re seeing and hearing is basically pure Taoism as a talk. They even mention Alan Watts. Neither left nor right wing. I’m happy someone’s listening to this talk for the first time. It’s like 4,000 years old. That’s awesome, because the world really needs to hear this stuff!!!

    • @Rithmy

      August 28, 2025 at 7:48 am

      It is left wing. Taoism and conservatism are in direct contradiction to each other. That is my understanding from the doa dejing. It was written as a political commentary on powerhungry people. It was also written in a time where you could not openly comment on those things, so theyve hidden it. I find it very concerning that you try to say its not political.

    • @halovsbionicle

      August 28, 2025 at 3:15 pm

      Personally I’d concede that everything is political, but thats also cuz politicians always want more control, regardless of which side theyre sitting on

      Additionally in a vaccum taoism seems conservative… until you contrast it with its contemporary of confusionism. From my own research confusionism seems to preach, above all, ones duty to their fellows and the community
      I think its a hard ask to get people to believe that anything can be more right winf than confusianism
      I could be wrong though

  10. @Tobywan83

    August 27, 2025 at 1:21 pm

    I love the topic and the wisdom. But that echo makes it unwatchable for me.

  11. @juleskoopman118

    August 27, 2025 at 2:18 pm

    Really appreciated this conversation as I’m ‘Wintering’ the loss of my Mother. Along this path I encountered how difficult it was for a few people to just express condolences, sympathy & basic human support for naturally grieving.
    People are numb and on auto pilot and afraid to listen, be present and vulnerable. Thank you for sharing your lives & wisdom🙏🌟🫶

  12. @BenTrem42

    August 27, 2025 at 3:12 pm

    *_Yoiks_* … catastrophize much?

  13. @TheBestLifeMindsetWithShelly

    August 27, 2025 at 4:21 pm

    So important! Empathy in hard conversations isn’t about fixing or avoiding—it’s about presence. When we hold space without judgment, we give others the safety to heal and the courage to keep going. 💖

  14. @kotaowens6978

    August 27, 2025 at 8:41 pm

    Hearing a lot of echo

  15. @ionageman

    August 27, 2025 at 9:20 pm

    Don’t say anything .. listen , don’t talk

  16. @drumbum3.142

    August 27, 2025 at 10:07 pm

    1.) Give a Damn about Who(m) You are With
    2.) Talk “WITH” Someone; Don’t talk “To” them.. .
    🫶🫶🫶

  17. @docnightfall

    August 27, 2025 at 11:44 pm

    Everything gets easier when you take the viewpoint of a disinterested obaerver of your own suffering. Any problem looks smaller if you look at it from further away. Zoom out. The universe is beautiful. 😊

  18. @halfcelestialelf

    August 28, 2025 at 1:56 am

    Tell them “sorry for your loss” then “move on”.

  19. @neilsunderland7691

    August 28, 2025 at 7:56 am

    ❤❤❤❤❤ Asking for help is a gift of service for the other person. Let love in, invite love in… Let it be part of your practice

  20. @joecota2644

    August 28, 2025 at 9:28 am

    Listen and then say ” That’s rough buddy”

  21. @Enkeria

    August 28, 2025 at 11:43 am

    When I was grieving, I just wished someone would ask me to grab a pizza and chill. But thats me. I did take pizza though, on my own.

  22. @pizzle425

    August 28, 2025 at 12:54 pm

    Echo is too much

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