Ep. 19 Comedy and Compassion

Today’s guest is a comedian and actor. She lives in Chicago and she is the co-host of the comedy and politics podcast Sit Still, Look Opinionated. Part of the show is discussing how to have productive conversations around “taboo” topics and hone critical thinking skills.

Welcome, Claire Malkie.

Claire is smart, funny, and ready to have hard conversations that aim to make us all better. I admire her for that and hope you enjoy this episode.


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Lots of things have become politicized and the best way to engage with someone is to understand where they are and why they believe those things.

- Claire Malkie


Where to find Claire online


Tips for Hard Conversations

  • Start by asking “why?”.

  • Look at history. Everything is cyclical.

  • When talking with people who have a different opinion, meet them where they are. Again, ask why they have the perspective they do and then present another perspective that solves their problem.

Is Claire optimistic?

She sometimes gets into a doom spiral (like me!) but having a conversation with one person and seeing a small change gives her hope.


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