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

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

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...

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...

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

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.

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

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

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...

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

i wrote a reading list for learning how to do nothing vaughntan.org/doingnothing

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

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...

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

just updated my now page for the first time since july. it was a lot of stuff. have a look: vaughntan.org/now-ish

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

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

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...

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

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

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

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

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

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!)

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

A game for experiencing not-knowings; things that are invisible for a long time; marsupials. 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

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

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

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

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

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

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

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

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

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

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...

the now page is a very good idea this is what i've been doing now-ish: vaughntan.org/now-ish

In Ljubljana teaching on resilience + uncertainty, and on meaningmaking and the future of work. Other bits: → “Human mRNA” → Slovenian rustication → Art thinking for uncertainty → Stovetop espresso innovation → Risk mindset and NYC floods Full post: uncertaintymindset.substack.com/p/gbw292025

This week: This week, the AI expertise conundrum plus forest fires, frosty fingers, tuna collar, etc. tl;dr: AI helps experts ask better questions but misleads novices. Use it for synthesis, not invention — keep humans central to meaning-making. Read: uncertaintymindset.substack.com/p/gbw282025

This week I wrote about why optimisation fails under true uncertainty—and why doing business is a meaning-making act, not a task to hand over to AI. Also: admin BS, heatwave fatigue, and the arduous search for good manufacturing. uncertaintymindset.substack.com/p/gbw2725

This week I wrote about why optimisation fails under true uncertainty—and why doing business is a meaning-making act, not a task to hand over to AI. Also: admin BS, heatwave fatigue, and the arduous search for good manufacturing. uncertaintymindset.substack.com/p/gbw2725

A friend fled the Middle East early in the last Israel-Iran flare-up—then felt foolish when it fizzled. The mistake wasn’t leaving too early. It was treating uncertainty like risk, and trying to optimise. Read more here: vaughntan.org/optfallacy

Anthropic’s AI shopkeeper failed not just because it was gullible, but because businesses require meaning-making. Business isn’t just executing tasks — it’s deciding what tasks matter and how to define success. Until AI can do that, it shouldn’t run businesses. More: vaughntan.org/bizmeaningma...

this week i wrote about uncomfortable questions about unknowns; building AI tools for better meaning-making; problems, learned helplessness, performance, comfort, and dissonance. uncertaintymindset.substack.com/p/gbw262025

new essay today on building better AI tools for meaning-making: vaughntan.org/meaningtools tl;dr: design tools not just to generate human-indistinguishable outputs, but also to encourage robust user meaning-making.

this week i wrote about: a workshop on meaning-making; why meaning-making is the future of education; question-value vs performance quality, the aesthetic value of uncertainty; and what happens before and after science. uncertaintymindset.substack.com/p/gbw252025