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

i wrote this week about being severely overinsulated in adelaide ... and about heterodox hot air balloon conferences, ideal-typical convenings, open space, and delicious trash foods in South Australia. uncertaintymindset.substack.com/p/gbw242025

what i'm doing now-ish: vaughntan.org/now-ish (updated 5/6/2025)

this week's grab bag is about a symphony of freshness; how to make monolithic problems less so; a course on public sector strategy; what i've been up to now-ish; some Old Skool methods; sauna talk; and signs. uncertaintymindset.substack.com/p/gbw2325

i wrote about how Big Org Problems are decomposable, and how working through tradeoffs helps unblock Big Problems and make them more tractable: vaughntan.org/decomposable...

This week, links and photos about: New American pizza and general slice-nerding; what we get wrong about not-knowing, and partial light transmission. uncertaintymindset.substack.com/p/gbw2025

This week's grab bag is about how silly it is for the public sector to uncritically adopt private sector ideas of strategy — and what I'm doing about it. uncertaintymindset.substack.com/p/gbw1825

This week's grab bag is about strategic tradeoffs; Bangkok, Marseille, hype, and legibility; billionaire group chats; Japanese cooking in the 1980s; code. And a few photos of dogs. uncertaintymindset.substack.com/p/gbw1725

I wrote about 10 days in BKK, train lines that don't interoperate, food both legible and not, canalside life, and choosing between the matrix and the nodes in it. This city makes it hard to go on autopilot, and is better for it. Take a look: vaughntan.org/bkkdiary

I wrote about why good strategy requires talking about tradeoffs here: vaughntan.org/strattrad… It's part of my 7-part series on strategy misconceptions and how to fix them: vaughntan.org/strategy [Context below]

OKRs work for stable environments and well-understood problems with validated solutions. but maybe OKRs are unsuited for innovation work, building new tech, creating a new product, finding a new market, or working in structural transitions. for that you need boris: vaughntan.org/unpacking-bo...

i price work on 5 dimensions: 1. how FUN is it? 2. how NICE are the people? 3. how EASY is the work? (= i’ve done it before and know what to expect) 4. how INTERESTING is the work? (= do i think i’ll learn something new) 5. how GOOD is the work? (= value-alignment) IMPORTANT!: see next post

this week’s grab bag is about strategic uncertainty; revelations and discoveries; video blahblah; coffee, smuggling, and subaks; Swiss tools and nonreversible work. read it here: uncertaintymindset.substack.com/p/gbw1625

if you're free tonight in BKK, come by Bangkok Kunsthalle at 18h. i'll have a (hacky, duct-taped) piece in a bunch of film microfictions about a near-future Southeast Asia with patchily ubiquitous AI systems and blockchains. (this is an output of @ethereum.foundation's summer of protocols workshop)

long-overdue update to my now-ish page: vaughntan.org/now-ish contents: humidity; writing on strategy, interviewing, experiments, introductions, transformative public policy; some UNDP work; two videos where i do some blahblahblah; being in bangkok for a protocol design workshop

In this wk's newsletter — I figure out how to explain consulting work that solves not-yet-named problems. Also: – experiments gone wrong (and how to make them go right) – fixing gov’t strategy – ditch-digging as org design – protocol in Southeast Asia uncertaintymindset.substack.com/p/gbw1525

Innovation stalls when we treat uncertainty like risk. In my latest article, I share a 4-day program helping public sector teams embrace uncertainty as a strategic resource—not a threat to be planned away. Ready to transform policy work in your govt? vaughntan.org/transformpol...

just spent 5h undoing a conceptual mess: an AI-generated essay with subtly incorrect references (some don't exist at all) that had been subtly mis-"read" by the AI system. [contd]

apparently uncertainty is modelable these days 😂 (hint: people say it is, but i don't believe it is.)

Strategy ≠ planning. Efficiency ≠ resilience. Interviews ≠ casual chats. AI ≠ meaningmaking. This week's grab bag of ideas on how we get it wrong — and how to get it right. 👉 uncertaintymindset.substack.com/p/gbw1425

Uncertainty is inevitable — and also necessary for growth. IDK is a self-training tool that helps you get better at being productively uncomfortable, one prompt at a time. Because the future of work won’t wait. 🔶 productivediscomfort.org

@jburnmurdoch.ft.com gives me another opp to point out that uncertainty /= risk: vaughntan.org/uncertaintyr... and the consequences of mistaking uncertainty for risk: vaughntan.org/the-conseque... and why it's valuable to understand the difference: uncertaintymindset.org 🙏 @afrancke.bsky.social