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vaughn

@vaughn.bsky.social
321 followers 187 following 538 posts

idk tbd \\ marseille \\ pizza \\ grouchy www.vaughntan.org

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vaughn @vaughn.bsky.social · 04/05/2026
I wrote a strategic map of four types of AI business. One example of type 3: a developer built a bespoke court submission tool in a single afternoon, using no AI at runtime. Hours of manual work done in minutes. This is what AI has done to the economics of custom software. vaughntan.org/ai4ways
vaughntan.org
4 ways to build an AI business - Vaughn Tan
tl;dr: Most people use “AI business” to mean one of two things — building the AI itself, or building products that call AI at runtime. There are
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vaughn @vaughn.bsky.social · 02/05/2026
i hear that there is an appropriate mindset for this
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vaughn @vaughn.bsky.social · 12/04/2026
yea i know — it's rare that the distinction is made, even though it is currently the most important distinction to make. i know a good book about it :-)
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vaughn @vaughn.bsky.social · 26/02/2026
This week's newsletter: My project on building a practical understanding of not-knowing now has a coherent home. One annotated contents page organised by what the essays do, from motivations through theory to practical tools for four distinct types. uncertaintymindset.substack.com/p/gbw92026
uncertaintymindset.substack.com
River crossing (wk 9/2026)
Here and there; navigation, many games; slop, possums, agency, immaturity.
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vaughn @vaughn.bsky.social · 23/02/2026
🫡
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vaughn @vaughn.bsky.social · 24/01/2026
i look forward to your findings
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vaughn @vaughn.bsky.social · 20/01/2026
not yet but at least the blurb sounds like it is trying to have the right idea what did you think of it?
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vaughn @vaughn.bsky.social · 14/01/2026
Reviewed my writing from the past year vs 5-10 years ago. Recent stuff is worse despite decades clarifying the concepts. Problem: machine-generated prose appears so finished I've become insensitive to when the substance misses the point I'm trying to make. uncertaintymindset.substack.com/p/gbw32026
uncertaintymindset.substack.com
Writing with machines (wk 3/2026)
Tacit knowledge, motivation, and negotiation; writing with machines; Smart Bricks, being kinded, and specs.
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vaughn @vaughn.bsky.social · 11/01/2026
i have recommendations for champagne ...
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vaughn @vaughn.bsky.social · 11/01/2026
There are two types of discomfort: 1) Execution discomfort has immediate payoff. 2) Innovation discomfort has delayed and uncertain payoff. People resist the second type. The way to get over this: make innovation discomfort unavoidable through productive desperation. vaughntan.org/desperationd...
vaughntan.org
Desperation by design - Vaughn Tan
tl;dr: Innovation requires uncomfortable unfamiliar work, but people instinctively resist discomfort. Incentives and motivation programmes don’t
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vaughn @vaughn.bsky.social · 11/01/2026
finding problems in real life
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vaughn @vaughn.bsky.social · 11/01/2026
Most organisations respond to tacit knowledge problems by trying to write better documentation, style guides, brand books, training programmes. None of this works. You can't learn tacit knowledge by reading descriptions of it. Instead, try the 3 mechanisms here: vaughntan.org/learnwhatmat...
vaughntan.org
Learning what matters - Vaughn Tan
tl;dr: The most important knowledge in any organisation—what makes your work distinctively yours—can’t be written down or taught through training
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vaughn @vaughn.bsky.social · 08/01/2026
Businesses need cheap small-scale automation which is already feasible. But mindsets and procurement systems built for around expensive-to-build software can't figure out how to buy these Boring Tiny Tools. Imagination failure, not technical barrier. vaughntan.org/bttparadigm
vaughntan.org
A Boring Tiny Tooling paradigm - Vaughn Tan
tl;dr: Small-medium businesses are missing a huge opportunity because of three imagination failures: they believe digital transformation must be big
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vaughn @vaughn.bsky.social · 08/01/2026
Spoke today with an editor at a press. We talked about how the gravitational pull of high-certainty books and books which are illusory in their high certainty of success. The big effort investment for getting books to mkt is what makes publishers grasp for certainty that the investment is worth it.
uncertaintymindset.substack.com
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vaughn @vaughn.bsky.social · 05/01/2026
This week's newsletter focuses on building judgment from the ground up. Organisations reserve subjective decisionmaking for senior people, but critical thinking develops through practice—you can't wait until someone is senior to start teaching them. uncertaintymindset.substack.com/p/gbw012026
uncertaintymindset.substack.com
Multiples (wk 1/2026)
Judgment from the ground up; labour-intensive and industrial foods, prompting as teaching; maintenance and replacement; Boring Tiny Tools in India, Chinese peptides, shoveling snow.
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vaughn @vaughn.bsky.social · 23/12/2025
This week my newsletter is about deliberately pushing into the discomfort of learning to build software with AI coding tools. Tiny projects with low stakes. Each small success building capacity for slightly more uncomfortable next steps. uncertaintymindset.substack.com/p/gbw522025
uncertaintymindset.substack.com
Boring and uncomfortable (wk 52/2025)
Why Boring Tiny Tools are good; what to do when there's nothing to do; being uncomfortable; billionaire babies, moneymaking, choosing deviance.
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vaughn @vaughn.bsky.social · 22/12/2025
Digital transformation fails when you buy software built for millions to serve dozens. The economics have inverted. You can now build tiny, highly specific tools that fit seamlessly into existing workflows—if you know how to think about product development differently. vaughntan.org/boringtinyto...
vaughntan.org
Boring Tiny Tools - Vaughn Tan
tl;dr: This essay is about Boring Tiny Tools—why they’re the way forward for digital transformation. Generative AI coding tools now enable
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vaughn @vaughn.bsky.social · 22/12/2025
feels very AI 😑
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vaughn @vaughn.bsky.social · 21/12/2025
"the one piece of data..."
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vaughn @vaughn.bsky.social · 21/12/2025
The comfort trap: modern life is comfortable → you become unable to handle discomfort → you avoid it more → you become more fragile. idk breaks this vicious cycle: it's a structured, intentional, repeatable practice for productive discomfort. EU shipping now available: productivediscomfort.org
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vaughn @vaughn.bsky.social · 15/12/2025
i wrote a reading list for learning how to do nothing vaughntan.org/doingnothing
vaughntan.org
Doing nothing: a reading list - Vaughn Tan
For 3 years during Covid, I lived in crumbling houses in depopulated hamlets on two different mountains in the Haute-Loire, one of the departements
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vaughn @vaughn.bsky.social · 29/11/2025
this week my newsletter is about redesigning workshops for online-ness; finding books in space (with situated memory); headlessness, 3D-printed boats, AI energy usage, climate models, mendacity. uncertaintymindset.substack.com/p/gbw482025
uncertaintymindset.substack.com
Going online (wk 48/2025)
Online workshops; finding books in space with situated memory; headlessness, 3D-printed boats, AI energy usage, climate models, mendacity.
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vaughn @vaughn.bsky.social · 28/11/2025
Online workshops rarely work; we do them because in-person is too expensive. Wrong framing. Right framing: redesign online workshops from the ground up to be more effective _because_ they're online. vaughntan.org/onlineworksh...
vaughntan.org
Making online workshops great … from the ground up - Vaughn Tan
tl;dr: Online workshops rarely work well, and we keep on doing them because they would be too expensive/infeasible to do in-person. This is the
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vaughn @vaughn.bsky.social · 20/11/2025
🙏🙏🙏
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vaughn @vaughn.bsky.social · 20/11/2025
moatiness may not matter so much if the market is small enough that it is a natural deterrent to new entry
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vaughn @vaughn.bsky.social · 18/11/2025
I'm back from a brief hiatus with a new newsletter issue about: Public value and public strategy; what I've been up to; electric anxiety; Rupertness in polyhedra, rewritable pads, tape clips, zip ties; trees, cats, dogs. uncertaintymindset.substack.com
uncertaintymindset.substack.com
The Uncertainty Mindset (soon to become tbd) | Vaughn Tan | Substack
On not-knowing—what it is, how it affects us, and how to relate to it—and other stuff. Click to read The Uncertainty Mindset (soon to become tbd), by Vaughn Tan, a Substack publication with thousands ...
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vaughn @vaughn.bsky.social · 15/11/2025
just updated my now page for the first time since july. it was a lot of stuff. have a look: vaughntan.org/now-ish
vaughntan.org
now-ish - Vaughn Tan
The last time I wrote here, it was 20 July, 2025. The late summer and fall months between then and now were unusually densely packed. July I was in
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vaughn @vaughn.bsky.social · 13/11/2025
I spoke today at the Institute of Public Administration on why borrowing private sector strategic thinking and values undermines public strategy — and a practical tool that uses tradeoffs to develop more robust public strategy. Read about the talk here: vaughntan.org/publicvalue
vaughntan.org
Public value and public strategy - Vaughn Tan
tl;dr: Why borrowing private sector strategic thinking and values undermines public strategy — and a practical tool for using tradeoffs to develop
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vaughn @vaughn.bsky.social · 22/10/2025
My newsletter this week is about infrastructure for human subjective reasoning; walking in a forest; dynamic moulds, San Francisco malls, Kryptos, television; seven-coloured water. uncertaintymindset.substack.com/p/gbw432025
uncertaintymindset.substack.com
Reasoning scaffolds (wk 43/2025)
Infrastructure for human subjective reasoning; walking in a forest; dynamic moulds, San Francisco malls, Kryptos, television; coloured water.
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vaughn @vaughn.bsky.social · 22/10/2025
i wrote about what reasoning scaffolds are, why they are interesting and important, and how to develop a practical research program about them. vaughntan.org/reasoningsca...
vaughntan.org
Reasoning scaffolds: An infrastructure for human subjective reasoning - Vaughn Tan
tl;dr: Every important decision requires subjective reasoning about objective facts—deciding what matters and why. Yet we have almost no explicit
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vaughn @vaughn.bsky.social · 22/10/2025
among other things, i've been prototyping a reasoning scaffold for a couple months. a reasoning scaffold helps its user think more clearly when doing subjective reasoning. vaughntan.org/protoscaffold
vaughntan.org
Prototyping a reasoning scaffold - Vaughn Tan
tl;dr: I’ve been prototyping an AI tool that uses Socratic mirroring to build a reasoning scaffold that helps users develop stronger arguments.
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vaughn @vaughn.bsky.social · 06/10/2025
This week I'm in Japan working on too little sleep. I wrote about: Prototypes and the value of theory; Socratic mirrors, reasoning scaffolds, and AI tools; in-country patterns; closures, modern instrumentals, natural ice, pretexts. uncertaintymindset.substack.com
uncertaintymindset.substack.com
The Uncertainty Mindset (soon to become tbd) | Vaughn Tan | Substack
On not-knowing—what it is, how it affects us, and how to relate to it—and other stuff. Click to read The Uncertainty Mindset (soon to become tbd), by Vaughn Tan, a Substack publication with thousands ...
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vaughn @vaughn.bsky.social · 06/10/2025
The tool is fully functional. Testers benefit by improving an actual argument (e.g., for a class paper, a policy plan, a business model, or a strategy proposal). If you want to test the tool and/or learn more about it as it develops, please let me know: forms.gle/pnch25sXJUTj...
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vaughn @vaughn.bsky.social · 06/10/2025
I’ve been prototyping a critical thinking tool + testing it over the last few months at universities, corporations, startups, and government. The method generalises: Users doing real work with real stakes find it useful enough to want their institutions to provide it. vaughntan.org/protoscaffold
vaughntan.org
The meaningmaking lens on AI (updated) - Vaughn Tan
Meaningmaking is a simple concept but one that is counterintuitively powerful, concrete, and applicable to understanding how we think about work and
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vaughn @vaughn.bsky.social · 28/09/2025
💕 how's 🇯🇵
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vaughn @vaughn.bsky.social · 24/09/2025
this week, my newsletter is about: An AI tool for learning critical thinking while using AI tools; Tunisia and structured elicitation; various perspectives on how to use AI; developments in zippertech. uncertaintymindset.substack.com/p/gbw392025
uncertaintymindset.substack.com
An AI critical thinking tool (wk 39/2025)
An AI tool for learning critical thinking while using AI tools; Tunisia and structured elicitation; various perspectives on how to use AI; developments in zippertech.
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vaughn @vaughn.bsky.social · 21/09/2025
wormhole
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vaughn @vaughn.bsky.social · 21/09/2025
Seeking testers for a new tool to help students write better argumentative essays through guided reasoning scaffolds. Looking for educator contacts with students willing to test the web app (<1hr, no instructor involvement needed). More info & signup: vaughntan.org/thinkingtools
vaughntan.org
An AI tool for learning critical thinking - Vaughn Tan
tl;dr: Students now have access to LLMs that can write essays, but seem to be losing the capacity to think critically. I solve this problem by
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vaughn @vaughn.bsky.social · 12/09/2025
I'll be doing some "taster" and introduction sessions in the next few months. If you're interested in learning more or getting notified when these sessions are scheduled, please let me know using this form: forms.gle/41k1viacAFot... (🙏 @tomski1878.bsky.social for amplifying!)
forms.gle
Public sector strategy course
This form is for collecting expressions of interest in a new public sector strategy course developed by Vaughn Tan. Click on this link to learn more about the design intent and pedagogical innovations...
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vaughn @vaughn.bsky.social · 12/09/2025
i've made a working (but verrrrry hacky) prototype of an AI-powered tool for helping users think critically while using the tool to write reasoned arguments (so #meta, i know). here's a screenshot of it, dripping primordial ooze. project details here: vaughntan.org/aiux
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vaughn @vaughn.bsky.social · 12/09/2025
the only way seems to be to write (and generally make stuff) without expectation of an audience, but to write for a reasoning, critically thinking audience.
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vaughn @vaughn.bsky.social · 12/09/2025
who does not want that delightful little crackle, that alluring little craze
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vaughn @vaughn.bsky.social · 11/09/2025
This week I wrote about: A breakthrough in cases; taking the public sector seriously; the practical value of thinking about meaningmaking; dissolving vs. solving, quant knowability breaks down, materiality. uncertaintymindset.substack.com/p/gbw372025
uncertaintymindset.substack.com
Open pollination (wk 37/2025)
A breakthrough in cases; taking the public sector seriously; the practical value of thinking about meaningmaking; dissolving vs. solving, quant knowability breaks down, materiality.
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vaughn @vaughn.bsky.social · 30/08/2025
hope springs eternal
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vaughn @vaughn.bsky.social · 28/08/2025
A game for experiencing not-knowings; things that are invisible for a long time; marsupials. uncertaintymindset.substack.com/p/gbw352025
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vaughn @vaughn.bsky.social · 26/08/2025
Built an interactive construction game called FOUNDATION at MOD. in Adelaide: players don't know what materials/rules/structures they'll run into. It's a test of generating not-knowing on demand, to build training tools for orgs facing true uncertainty. Until Sat 8/30: vaughntan.org/foundation
vaughntan.org
FOUNDATION: A game of not-knowings - Vaughn Tan
What if you could experience what it’s like to make decisions when you truly don’t know what’s possible? That’s what FOUNDATION, a new interactive
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vaughn @vaughn.bsky.social · 21/08/2025
In this issue: An award nomination, AI tools that support critical thinking; not-knowings, on demand; organisational interventions for uncertainty; subliminal learning, K4, satisfying toys, cat trains, bromism, and convincing others. uncertaintymindset.substack.com/p/gbw342025
uncertaintymindset.substack.com
Thought support (wk 34/2025)
AI tools that support critical thinking; not-knowings, on demand; organisational interventions for uncertainty; subliminal learning, K4, satisfying toys, cat trains, bromism, and convincing others.
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vaughn @vaughn.bsky.social · 20/08/2025
Current AI UX tricks us into thinking we're talking to something that can make value judgments. We're not. So I tested a prototype UX for an AI that helps users learn to think critically. Students went from vague to sharp arguments in 2hrs. More here: vaughntan.org/aiux
vaughntan.org
Designing AI tools that support critical thinking - Vaughn Tan
Current AI interfaces lull us into thinking we’re talking to something that can make meaningful judgments about what’s valuable. We’re not — we’re
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vaughn @vaughn.bsky.social · 19/08/2025
wow. so cool <3 very irritated at missing it 😑
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vaughn @vaughn.bsky.social · 19/08/2025
Ran a multidisciplinary workshop to create practical mechanisms for experiencing not-knowing firsthand. We developed ideas like 'the camera of not-knowing' that teaches users how to act meaningfully even if they don't understand causation (yet). Read more about it here: vaughntan.org/nkondemand
vaughntan.org
Not-knowings, on demand - Vaughn Tan
In June, I ran a workshop with 15 researchers from diverse fields to develop practical, implementable mechanisms for experiencing different types of
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