vaughn
@vaughn.bsky.social
idk tbd \\ marseille \\ pizza \\ grouchy
www.vaughntan.org
www.vaughntan.org
Pinned
vaughn
@vaughn.bsky.social
· Dec 11
idk - Productive discomfort
is based on years of research on some of the world’s most innovative teams. It’s meant to help you excel when working in unfamiliar situations
www.productivediscomfort.org
idk is a tool for productive discomfort. Each of its 52 cards prompts you to do something uncomfortable that stimulates learning and growth. Users say it is "sneakily life-changing" and "unexpectedly important." idk is designed to be used indefinitely.
more here: www.productivediscomfort.org
more here: www.productivediscomfort.org
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/p/gbw432025
Reasoning scaffolds (wk 43/2025)
Infrastructure for human subjective reasoning; walking in a forest; dynamic moulds, San Francisco malls, Kryptos, television; coloured water.
uncertaintymindset.substack.com
October 22, 2025 at 5:24 PM
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/p/gbw432025
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/reasoningsca...
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
vaughntan.org
October 22, 2025 at 9:21 AM
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/reasoningsca...
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/protoscaffold
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.
vaughntan.org
October 22, 2025 at 9:20 AM
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/protoscaffold
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 ...
uncertaintymindset.substack.com
October 6, 2025 at 2:45 PM
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
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/protoscaffold
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
vaughntan.org
October 6, 2025 at 12:37 AM
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/protoscaffold
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/p/gbw392025
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.
uncertaintymindset.substack.com
September 24, 2025 at 7:12 PM
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/p/gbw392025
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
Looking for educator contacts with students willing to test the web app (<1hr, no instructor involvement needed).
More info & signup: vaughntan.org/thinkingtools
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
vaughntan.org
September 21, 2025 at 10:55 AM
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
Looking for educator contacts with students willing to test the web app (<1hr, no instructor involvement needed).
More info & signup: vaughntan.org/thinkingtools
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!)
(🙏 @tomski1878.bsky.social for amplifying!)
September 12, 2025 at 4:58 PM
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!)
(🙏 @tomski1878.bsky.social for amplifying!)
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
September 12, 2025 at 4:24 PM
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
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/p/gbw372025
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.
uncertaintymindset.substack.com
September 11, 2025 at 3:24 AM
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/p/gbw372025
A game for experiencing not-knowings; things that are invisible for a long time; marsupials.
uncertaintymindset.substack.com/p/gbw352025
uncertaintymindset.substack.com/p/gbw352025
August 28, 2025 at 3:03 PM
A game for experiencing not-knowings; things that are invisible for a long time; marsupials.
uncertaintymindset.substack.com/p/gbw352025
uncertaintymindset.substack.com/p/gbw352025
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
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
vaughntan.org
August 26, 2025 at 6:42 AM
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
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/p/gbw342025
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.
uncertaintymindset.substack.com
August 21, 2025 at 2:06 PM
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/p/gbw342025
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
More here: vaughntan.org/aiux
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
vaughntan.org
August 20, 2025 at 2:46 PM
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
More here: vaughntan.org/aiux
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
Read more about it here: vaughntan.org/nkondemand
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
vaughntan.org
August 19, 2025 at 1:13 PM
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
Read more about it here: vaughntan.org/nkondemand
Ran a multi-disciplinary workshop in Adelaide in June to develop mechanisms for experiencing different types of not-knowing. Result: ideas like 'the camera of not-knowing' that teaches how to take useful action without certain causation.
A good read: vaughntan.org/nkondemand
A good read: vaughntan.org/nkondemand
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
vaughntan.org
August 19, 2025 at 1:06 PM
Ran a multi-disciplinary workshop in Adelaide in June to develop mechanisms for experiencing different types of not-knowing. Result: ideas like 'the camera of not-knowing' that teaches how to take useful action without certain causation.
A good read: vaughntan.org/nkondemand
A good read: vaughntan.org/nkondemand
this february, i test-ran a significantly refactored version of boris, my 1-day workshop for setting much better goals by talking about tradeoffs (vaughntan.org/boris).
Boris - Vaughn Tan
What is Boris?: Boris is a service I provide for businesses, not-for-profits, and public organisations — it’s a 1-2 day workshop designed to help
vaughntan.org
August 14, 2025 at 2:43 PM
this february, i test-ran a significantly refactored version of boris, my 1-day workshop for setting much better goals by talking about tradeoffs (vaughntan.org/boris).
Good categorisation wins over pure empiricism; Singapore's 60th birthday; a low-intervention wine experiment; the concept of enlightenment in Zen/Chan, aliveness in things and humans, drone delivery.
uncertaintymindset.substack.com/p/gbw332025
uncertaintymindset.substack.com/p/gbw332025
Categorisation supremacy (wk 33/2025)
Good categorisation wins over pure empiricism; Singapore's 60th birthday; a low-intervention wine experiment; the concept of enlightenment in Zen/Chan, aliveness in things and humans, drone delivery.
uncertaintymindset.substack.com
August 10, 2025 at 5:32 PM
Good categorisation wins over pure empiricism; Singapore's 60th birthday; a low-intervention wine experiment; the concept of enlightenment in Zen/Chan, aliveness in things and humans, drone delivery.
uncertaintymindset.substack.com/p/gbw332025
uncertaintymindset.substack.com/p/gbw332025
Categories aren’t academic—done well, they’re a competitive edge. They clarify decisions, help spot bad data, and make experiments faster. This post shows why good categorisation pays off: vaughntan.org/categorywins
(Good) categorisation beats empiricism - Vaughn Tan
tl;dr: Categories aren’t academic conceits—they’re tools that enable more effective practical action. If you care about making AI work in real-world
vaughntan.org
August 9, 2025 at 6:02 AM
Categories aren’t academic—done well, they’re a competitive edge. They clarify decisions, help spot bad data, and make experiments faster. This post shows why good categorisation pays off: vaughntan.org/categorywins
This week: I put years (nearly 2 decades!) of not-knowing into 1 diagramme; stacking spaces; desert salmon, observances of death, apples and flags ranked, radioactive fruit flies, wasps, and tumbleweeds, dubious assessments of AI.
More here: uncertaintymindset.substack.com/p/gbw322025
More here: uncertaintymindset.substack.com/p/gbw322025
Rugged terrain (wk 32/2025)
Years of not-knowing in 1 diagramme; stacking spaces; desert salmon, observances of death, apples and flags ranked, radioactive fruit flies, wasps, and tumbleweeds, dubious assessments of AI.
uncertaintymindset.substack.com
August 5, 2025 at 9:22 PM
This week: I put years (nearly 2 decades!) of not-knowing into 1 diagramme; stacking spaces; desert salmon, observances of death, apples and flags ranked, radioactive fruit flies, wasps, and tumbleweeds, dubious assessments of AI.
More here: uncertaintymindset.substack.com/p/gbw322025
More here: uncertaintymindset.substack.com/p/gbw322025
coffee roaster, cafe, training facility, cupping studio. all in the same space (in barcelona). i call these “stacked spaces”: layerings of uses that keeps cities weird and adaptive.
wrote more here:
stacked spaces → vaughntan.org/stackedspaces
structured messes → vaughntan.org/structuredmess
wrote more here:
stacked spaces → vaughntan.org/stackedspaces
structured messes → vaughntan.org/structuredmess
Stacking spaces - Vaughn Tan
tl;dr: Hidden behind an unmarked doorway in Barcelona, two coffee businesses share the same small space — one roasting and selling, the other
vaughntan.org
August 3, 2025 at 4:24 AM
coffee roaster, cafe, training facility, cupping studio. all in the same space (in barcelona). i call these “stacked spaces”: layerings of uses that keeps cities weird and adaptive.
wrote more here:
stacked spaces → vaughntan.org/stackedspaces
structured messes → vaughntan.org/structuredmess
wrote more here:
stacked spaces → vaughntan.org/stackedspaces
structured messes → vaughntan.org/structuredmess
We often treat all unknowns as risk. That mindset hides deeper kinds of not-knowing—about what we could do, what could happen, how actions link to outcomes, and what we truly value.
I wrote about why naming these differences matters, how it helps us make better decisions: vaughntan.org/nksynthesis
I wrote about why naming these differences matters, how it helps us make better decisions: vaughntan.org/nksynthesis
A not-knowing synthesis - Vaughn Tan
At base, I’ve been interested in the strategy implications of partial knowledge since 2008. Back then, I was investigating how people and
vaughntan.org
August 2, 2025 at 10:17 AM
We often treat all unknowns as risk. That mindset hides deeper kinds of not-knowing—about what we could do, what could happen, how actions link to outcomes, and what we truly value.
I wrote about why naming these differences matters, how it helps us make better decisions: vaughntan.org/nksynthesis
I wrote about why naming these differences matters, how it helps us make better decisions: vaughntan.org/nksynthesis
This week I wrote about: Games of uncertainty (not risk); art thinking and generative uncertainty; veal parts; accidents of the knee and of wine; patterns in fashion, AI consultants, editable drawings, AI4HR; coffee time.
uncertaintymindset.substack.com/p/gbw302025
uncertaintymindset.substack.com/p/gbw302025
The games we play (wk 30/2025)
Games of uncertainty (not risk); art thinking and generative uncertainty; veal parts; accidents of the knee and of wine; patterns in fashion, AI consultants, editable drawings, AI4HR; coffee time.
uncertaintymindset.substack.com
July 27, 2025 at 7:21 PM
This week I wrote about: Games of uncertainty (not risk); art thinking and generative uncertainty; veal parts; accidents of the knee and of wine; patterns in fashion, AI consultants, editable drawings, AI4HR; coffee time.
uncertaintymindset.substack.com/p/gbw302025
uncertaintymindset.substack.com/p/gbw302025
I wrote about games that operationalise true uncertainty, not just simple risk, to help players become better at making decisions when facing different types of not-knowing.
vaughntan.org/uncertaintyg...
vaughntan.org/uncertaintyg...
July 26, 2025 at 10:20 AM
I wrote about games that operationalise true uncertainty, not just simple risk, to help players become better at making decisions when facing different types of not-knowing.
vaughntan.org/uncertaintyg...
vaughntan.org/uncertaintyg...
