Impossible Conversations

Searching for truth, together



Impossible Conversations is a competition to encourage difficult conversations in good faith.

Winners receive a share of $2,500 in prize money, the inaugural Impossible Conversationalist Award, publication to Areo Magazine, and invitations to appear as a guest on several podcasts.

UPDATE: The 2020 competition has been concluded - read the winners announcement here.



What is an "impossible conversation"?

A difficult, but productive, dialectic: a conversation in which correspondents hold opposing views on an important topic, and whose exchange guides us closer to truth.

Some examples of fertile topics: religion, drugs legalisation, The 2nd Amendment, climate change, the US election, transgender athletes, reparations, euthanasia, border control.

What is the purpose of this competition?

Our aim is to advance the quality and impact of conversation. Humanity has never been more connected, and yet we remain divided on many of the important matters that will shape our future. We believe that thoughtful, good faith conversation is how ideas develop, spread, and take effect in the world.

How do I start a conversation?

Sign up to Letter, ask your interlocutor to do the same, and write a letter to them.


Our Judges

Helen Pluckrose

Editor of Areo magazine, Author

Helen is a secular, liberal humanist, mother, and dog lover. Her publication, Areo, is a non-partisan digital magazine focused on Enlightenment liberalism, humanism, secularism and freedom of expression. 

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Russ Roberts

Economist, Author, Conversationalist

Russ is an economist and Research Fellow at Stanford University's Hoover Institution, the founder and host of EconTalk (a podcast where Russ engages with an eclectic mix of guests and topics), the author of How Adam Smith Can Change Your Life, and co-creator of the Keynes vs Hayek viral rap videos.

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John Wood, Jr.

Writer, Leader, Bridge Builder

John Wood Jr. is a national leader for Better Angels, a nominee for Congress, contributor at Quillette, and co-host of The Better Angels Podcast.

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Heather Heying

Evolutionary Biologist, Author

Heather is a Visiting Fellow at Princeton University, and currently writing a book with Bret Weinstein on how an evolutionary toolkit can provide insight into our past, present and future, and allow us to live investigated, conscious lives.

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Our Partners

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Impossible Conversations

Searching for truth, together

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