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

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

Writing with machines (wk 3/2026)

Tacit knowledge, motivation, and negotiation; writing with machines; Smart Bricks, being kinded, and specs.

uncertaintymindset.substack.com

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

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.

uncertaintymindset.substack.com

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

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.

uncertaintymindset.substack.com

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

Going online (wk 48/2025)

Online workshops; finding books in space with situated memory; headlessness, 3D-printed boats, AI energy usage, climate models, mendacity.

uncertaintymindset.substack.com

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

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

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

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

vaughntan.org

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

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

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

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

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

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

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

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

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!)

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...

forms.gle

Tom Loosemore @tomski.com · 11mo ago

This new course on public sector strategy has piqued my interest. vaughntan.org/newpublicstr... Am liking the embracing of uncertainty, and the need to move beyond private sector approaches to strategy. @vaughn.bsky.social

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

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

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

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

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

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