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 :-)

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

🫡

i look forward to your findings

not yet but at least the blurb sounds like it is trying to have the right idea

what did you think of it?

Writing with machines (wk 3/2026) Tacit knowledge, motivation, and negotiation; writing with machines; Smart Bricks, being kinded, and specs.

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

i have recommendations for champagne ...

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...

finding problems in real life

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.

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.

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

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.

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...

feels very AI 😑

"the one piece of data..."

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

Going online (wk 48/2025) Online workshops; finding books in space with situated memory; headlessness, 3D-printed boats, AI energy usage, climate models, mendacity.

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...

🙏🙏🙏

moatiness may not matter so much if the market is small enough that it is a natural deterrent to new entry

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 ...

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

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

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

Reasoning scaffolds (wk 43/2025) Infrastructure for human subjective reasoning; walking in a forest; dynamic moulds, San Francisco malls, Kryptos, television; coloured water.

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...

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.

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

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 ...

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