The Future of Writing in the Age of AI

This week’s guest is the singular Michael Dean, who graduated from architecture school and played in a band before spending years in tech working on virtual reality, only to metamorphose into one of the best essayists I’ve ever read. With support from Humans On The Loop supporters O’Shaughnessy Ventures and Cosmos Institute, Dean is now decoding the structure of great essays and translating his framework into both a textbook and an AI-powered editing tool.

In this conversation, we explore how to cultivate human agency at the frontiers where physical reality and the metaverse fold into one another and entangled human and machine intelligences unleash radical new possibilities for reflection and creativity. By the end of our discussion we start to trace the contours of a world in which everyone has a better chance to pursue their passions without having to worry about “product-market fit” — a future in culture stages a glorious insurrection against the dehumanizing division between passion and paid work.

If this episode stimulates or triggers you, please leave a comment here or on YouTube — I would love to learn from you and this project exists as a space for thoughtful discourse!

Upcoming Events

* 3 May @ 11 am Mountain– Book Club: Prophetic Culture by Federico Campagna(patrons-only discussion)

* 13 May-14 June – How To Live In The Future at Weirdosphere(five-week online course with ten sessions)

Project Links

• Explore this project’s essay and episode archives• Join the Discord server• Browse the books we discuss on the show• Explore the conversational mind-map grown from nine years of conversations• Book me for speaking or consulting

Dean’s Links

The Secret Architecture of Great EssaysTeleportation, $97/month, coming soonLas Vegas & the MetaverseA change of heartPrepping for the Editor G*dsMega-updateSungazerLucy in the Sky of Large Language Models4 Types of Material in Every Essay

Mentioned Books & Articles

Michael Garfield – Sacred DataJohn Smart – The transcenscion hypothesisJ.C.R. Licklider & Bob Taylor – The Computer as a Communication DeviceKevin Kelly – AR Will Spark The Next Big Tech Platform — Call It MirrorworldDouglas Rushkoff – Present ShockYoshija Walter – Artificial influencers and the dead internet theory

Mentioned People & Podcasts

J.F. MartelK. Allado McDowellDanielle BassettTyson YunkaportaMitch MignanoJaron LanierPeter DiamandisWilliam Irwin ThompsonBenjamin OlsenThe BeatlesTerence McKennaGrimesHolly HerndonTimothy LearyJake KobrinSara PhinnThe Ungoogleable MichaelangeloErik HoelMichael Crichton

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