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Surviving The Great Reshuffle - Jim O'Shaughnessy | Modern Wisdom Podcast 326

Jim O'Shaughnessy is an investor and the founder, Chairman, and Chief Investment Officer of O'Shaughnessy Asset Management. Time, space and geography are collapsing. The richest people on the planet are no longer in charge of labour or buildings, they're symbol manipulators. The skillsets we need today are completely different to what was needed 50 years ago, let alone 500. Jim is here to give us some advice on how we can survive this catastrophic reshuffling. Expect to learn why 2020 was the best thing to happen to talented people in the developing world, the danger of grade-inflation in top flight universities, why we both have a man-crush on Rory Sutherland, why Isaac Newton was a dick and much more... Sponsors: Get over 37% discount on all products site-wide from MyProtein at http://bit.ly/modernwisdom (use code: MODERNWISDOM) Get 20% discount on Reebok’s entire range including the amazing Nano X1 at https://geni.us/modernwisdom (use code MW20) Extra Stuff: Check out Jim's company - https://www.osam.com/ Check out Jim's Podcast - https://www.infiniteloopspodcast.com/ Follow Jim on Twitter - https://twitter.com/jposhaughnessy Rick and Morty and The Meaning Of Life 1 - https://hackernoon.com/rick-and-morty-and-the-meaning-of-life-6640df17e263 Rick and Morty and The Meaning Of Life 2 - https://medium.com/@dan.jeffries/rick-and-morty-and-the-meaning-of-life-part-ii-screw-enlightenment-become-an-adult-instead-e1b2ec832e4e Jim's Superthread - https://twitter.com/jposhaughnessy/status/1343371350493319169 Another Jim Superthread - https://twitter.com/antilibrary_vk/status/1164959690234593280 Get my free Ultimate Life Hacks List to 10x your daily productivity → https://chriswillx.com/lifehacks/ To support me on Patreon (thank you): https://www.patreon.com/modernwisdom #greatreset #greatreshuffle #finance - Listen to all episodes online. Search "Modern Wisdom" on any Podcast App or click here: iTunes: https://apple.co/2MNqIgw Spotify: https://spoti.fi/2LSimPn Stitcher: https://www.stitcher.com/podcast/modern-wisdom - Get in touch in the comments below or head to... Instagram: https://www.instagram.com/chriswillx Twitter: https://www.twitter.com/chriswillx Email: modernwisdompodcast@gmail.com

Jim O'ShaughnessyguestChris Williamsonhost
May 26, 20211h 22mWatch on YouTube ↗

At a glance

WHAT IT’S REALLY ABOUT

Great Reshuffle: Thriving In A Digital, Post-Certification, Probabilistic World

  1. Jim O’Shaughnessy and Chris Williamson discuss what Jim calls “the great reshuffle”: a rapid shift from a physical, credential-driven economy to a digital, proof‑of‑work, talent‑driven one, massively accelerated by COVID.
  2. They explore how geography and traditional gatekeepers (universities, legacy media, corporations) are losing power as online reputation, curiosity, writing, and non‑linear thinking become key advantages.
  3. The conversation ranges through memes, media polarization, cults, behavioral biases, Enlightenment thinkers, and the dangers of rigid belief, repeatedly returning to personal agency, intellectual humility, and lifelong self‑education.
  4. They close by outlining how a younger person can “prep” for the reshuffle: read broadly, think like an owner, learn to program, publish your work, avoid catastrophic zeros, and optimize for learning and autonomy rather than money alone.

IDEAS WORTH REMEMBERING

5 ideas

Build a visible digital proof-of-work instead of relying on credentials.

Hiring and opportunity are shifting from paper CVs and elite diplomas to long‑running, publicly visible work (Twitter threads, blogs, podcasts, code, Substack), which show actual ability over time.

Cultivate non-linear thinking and broad curiosity to thrive digitally.

The physical world rewarded linear, stepwise thinking; the digital world rewards people who connect disparate ideas, learn across domains, and stay endlessly curious, because opportunities now emerge from unexpected intersections.

Treat media as propaganda and seek independent, at-risk thinkers.

Legacy outlets on both left and right optimize for outrage and fear; following people whose positions cost them social capital (e.g., Sam Harris in the middle) is a useful heuristic for finding more honest analysis.

Hold beliefs lightly and assume you’re easy to fool—especially if you’re smart.

Dogmatic certainty “brain‑deads” you; recognizing that narratives, biases, and identity attachment make you the easiest person to fool pushes you toward probabilistic thinking, updating, and intellectual humility.

Write by hand and articulate your thoughts to expose fuzzy thinking.

Forcing ideas into clear language on a page (or via long-form conversation) quickly reveals where you don’t actually understand something, and helps reprogram your own “operating system” and self‑story.

WORDS WORTH SAVING

5 quotes

COVID was the best thing to happen to talented people in the developing world, and the worst thing to happen to talentless people in the developed world.

— Chris Williamson

We’re deterministic thinkers living in a probabilistic world, and that world just got a fuck ton more probabilistic.

— Jim O’Shaughnessy

If I know one of your perspectives, and from it I can accurately predict everything else that you believe, then you’re not a serious thinker.

— Jordan Peterson (quoted by Chris Williamson)

The first rule is you must not fool yourself, and you are the easiest person to fool.

— Richard Feynman (quoted by Jim O’Shaughnessy)

Following your passion will be the hardest thing that you will do in your life. You will have to lift the heaviest weight that you have ever lifted, but the tools will feel light.

— Tim Cook (relayed by Chris Williamson)

The Great Reshuffle and collapse of time, space, and geographyShift from credential-based status to digital proof-of-work and online reputationMedia polarization, propaganda algorithms, and heterodox voices (Substack, podcasts)Belief systems, dogma, cognitive biases, and ease of fooling smart peopleEnlightenment, historical context (Newton, Deutsch, Bostrom) and existential riskWealth, happiness, and optimizing for learning versus chasing moneyPractical preparation: skills, curiosity, writing, agency, and avoiding catastrophic decisions

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