John Koenig is the author of The New York Times' Best Seller Dictionary of Obscure Sorrows, a dictionary of made-up words for emotions that we all feel but don't have the words to express. We talk about his book, identity and individuality, contradiction, writing, the human experience, fatherhood, and more.

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(00:44) Why use "sorrows"?

(02:51) Did he ever expect the dictionary to be what it is now?

(05:48) Existential wonderment and loss

(08:50) Truth, internal dialogue, and contradiction

(14:00) Contradiction of definitions

(17:02) Is introspection valuable? Can you know who you are?

(20:43) Not focusing on the present

(24:18) Self-actualization vs. contentment

(30:26) How you perceive people vs. how they really are

(35:57) Next book: Sonder

(39:03) Does sensitivity make life more difficult?

(41:54) Career identity & pigeonholing

(44:24) Writing vs. video

(47:32) How fatherhood changes work & focus take on his work; finding meaning in community & ritual

(51:25) Where does meaning reside?

(53:27) Creative process takeaways for kids; self-expression and art

(55:15) John's final questions for listeners

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John’s Twitter: https://twitter.com/obscuresorrows

Dictionary of Obscure Sorrows (Amazon): https://www.amazon.com/Dictionary-Obscure-Sorrows-John-Koenig/dp/1501153641

YouTube: https://www.youtube.com/c/obscuresorrows

Spencer’s Twitter: https://twitter.com/SP1NS1R

Spencer’s Blog: https://spencerkier.substack.com/

Dylan O’Sullivan is a curator, editor, and writer at O'Shaughnessy Ventures and Essayful. Dylan and I talk about writing, taste, discipline vs. inspiration, timelessness vs ephemerality, boredom and solitude vs. the internet, inciting a digital renaissance, not lying to yourself, and more.

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(00:45) Curating & editing vs. writing

(05:39) Fear of never writing quality work or living up to your idols

(08:32) Discipline vs. inspiration

(15:49) Balancing technology & ephemerality with the timeless

(17:44) Solitude, getting better at the craft, and having a "normal" life

(21:09) Boredom

(26:32) Short attention & the effect on art & mediums

(29:54) Lack of original works & risk taking

(36:43) Digital renaissance; timeless stories & works

(44:15) What is timeless & what will become timeless

(48:17) Creativity & the subconscious

(52:08) Long form writing vs memes

(55:00) Above all, don't lie to yourself

(01:00:29) Books he’d have in his bookstore window

(01:03:38) Three favorite directors & their three movies

(01:05:34) Final question for listeners

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Dylan’s Twitter: https://twitter.com/DylanoA4

Essayful: https://www.essayful.co/

O'Shaughnessy Ventures: https://www.osv.llc/

Spencer’s Twitter: https://twitter.com/SP1NS1R

Spencer’s Blog: https://spencerkier.substack.com

Steve Schlafman is a venture capitalist turned transition coach. We talk about lostness, transformation, curiosity, mindfulness practices, his new Downshift program, being a husband and father, and more.

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(00:59) Lostness, navigating liminal identity space, personal transformations

(18:31) Head and heart, mind and body; intellectualizing emotions & feelings

(25:52) The role of curiosity; people, world, self

(29:52) Using practices as a means to an end

(34:21) Is downshifting antithetical to the history of humanity (advancement)?

(41:32) When to upshift

(46:27) Stillness & silence

(52:43) Renewal, rediscovery, experimentation

(57:39) Spouse support during transformations

(01:02:35) Balancing ambition & being a father

(01:06:54) Final question for listeners: what stops you from being at your best

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Steve’s Twitter: https://twitter.com/schlaf

Personal Site: https://www.schlaf.co/

Downshift: https://www.downshift.me/

Spencer’s Twitter: https://twitter.com/SP1NS1R

Spencer’s Blog: https://spencerkier.substack.com

Matt Clifford is a co-founder of Entrepreneur First and leads their AI efforts, as well as chair of ARIA, the UK’s Advanced Research and Invention Agency. We talk about EF, talent investing, ambition, why we don’t have more Thiel Fellowships, his new focus on AI, and AI safety concerns.

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(00:59) Talent matters most

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Matt’s Twitter: https://twitter.com/matthewclifford

Entrepreneur First: https://www.joinef.com/

Personal Site: https://www.matthewclifford.com/

Spencer’s Twitter: https://twitter.com/SP1NS1R

Spencer’s Blog: https://spencerkier.substack.com

Joscha Bach is a cognitive scientist and AI researcher. We talk about our relationship with & models of reality, creativity and curiosity, animism and self-organizing software, stages of development, and more.

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(01:25) The dream world; how we interact with & perceive reality

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Joscha’s Twitter: https://twitter.com/Plinz

Joscha's Substack: https://joscha.substack.com/

Personal Site: http://bach.ai/

Spencer’s Twitter: https://twitter.com/SP1NS1R

Spencer’s Blog: https://spencerkier.substack.com

Gabe (@VividVoid_ on Twitter) is a writer and coach, and former Marine. We talk about inferiority, art, nothingness, spirituality, courage, fear, alignment with The Void, representations of reality, exposure therapy, Quality, and more.

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(00:52) You’re not inferior to anyone else

(06:14) Art is the byproduct of a spiritual practice

(09:28) Authentic expression; anger & competition

(16:55) Do nothing, seek wisdom: space for contemplation & rest

(20:31) What is The Void?

(25:57) Microdosing honesty & better representations

(33:27) Courage & fear

(37:48) Exposure therapy & yin-yang

(41:35) Going from conditioning back to freedom; critical thinking & being a “combat medic”

(48:30) Direct experience; understand your behavioral loop & where you can intervene

(51:53) Taking practices & ideas from ideologies; being identity-less

(59:51) Poetic writing

(01:02:48) What is Quality?

(01:04:50) Gabe’s final question for listeners

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Gabe’s Twitter: https://twitter.com/VividVoid_

Gabe’s (Old) Blog: https://vividvoid.substack.com/

Spencer’s Twitter: https://twitter.com/SP1NS1R

Spencer’s Blog: https://spencerkier.substack.com

Nathan Baugh writes fiction and the World Builders newsletter. We talk about writing, non-fiction vs. fiction, storytelling and world building devices, Kurt Vonnegut and other authors, getting the most out of technology and the internet, and more.

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(00:47) Why writing

(02:46) Loops & closing the curiosity gap

(04:05) The combination of short form non-fiction & long form fiction

(09:54) Storytelling & world building; Virgil Abloh’s 3% Rule

(14:30) Tradeoffs of traditional publishing vs. self-publishing; going direct-to-audience

(21:54) Tech and magic; AI

(28:26) His most influential authors

(31:08) Favorite opening sentences

(34:25) Vonnuget’s shape of stories & promise, progress, payoff

(49:11) Why not go all in on fiction?

(44:41) Writer’s self limiting beliefs

(52:54) Biggest fear as a writer: not living up to expectations

(55:33) Balancing technology and the internet with deep work

(59:58) What's one work of fiction that has stuck out?

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Nathan’s Twitter: https://twitter.com/nathanbaugh27

Nathan’s Newsletter: https://www.worldbuilders.ai/

Vonnegut’s Shape of Stories: youtu.be/oP3c1h8v2ZQ

Spencer’s Twitter: https://twitter.com/SP1NS1R

Spencer’s Blog: https://spencerkier.substack.com

Billy Oppenheimer writes the Six at 6 newsletter, and has been a writing and research assistant for Ryan Holiday, Robert Greene, and Rick Rubin. We talk about research, naive optimism, working for legendary writers and creatives, boredom, his newsletter, curation and creation, how “the work is the win”, and his first book.

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Billy’s Twitter: https://twitter.com/bpoppenheimer

Six at 6: https://billyoppenheimer.com/newsletter/

Spencer’s Twitter: https://twitter.com/SP1NS1R

Spencer’s Blog: https://spencerkier.substack.com

John Coogan is the co-founder of Soylent and Lucy, an Entrepreneur-in-Residence at Founders Fund, and a YouTuber and podcaster. We talk about AI, pioneering vs. wire-heading, identifying problems to solve, the need for more risk takers, satisfying curiosity, techno optimism, YouTube and podcasting, and his next venture.

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(00:53) “Benevolent murdering” AI, wire heads vs. pioneers

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John’s Twitter: https://twitter.com/johncoogan

John’s YouTube: https://www.youtube.com/@JohnCooganPlus

John’s Podcast: https://open.spotify.com/show/2JcCU31J07hCMxw99RWVRk

Spencer’s Twitter: https://twitter.com/SP1NS1R

Spencer’s Blog: https://spencerkier.substack.com

Sasha Chapin is a writer, coach, and the co-founder of a fragrance line. We talk about his book, awakening, meditation, Deep Okayness, coaching, writing, fragrance, and more.

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(00:54) Writing a book on meditation & awakening

(49:25) What’s the uncomfortable thing you want to do?

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Sasha’s Twitter: https://twitter.com/sashachapin

Sasha’s Site: sashachapin.com

Sasha’s Substack: https://sashachapin.substack.com/

Spencer’s Twitter: https://twitter.com/SP1NS1R

Spencer’s Blog: https://spencerkier.substack.com