Vaughn Tan
@vaughn_tan
uncertainty, not-knowing, open-ended goals, open-ended roles Now: http://www.vaughntan.org/now-ish Farcaster: http://warpcast.com/vt
I’m back on the newsletter game after 3 months off. From relocating back home to Singapore to using tradeoffs to navigate global uncertainty, here’s what I’ve been doing — and what’s coming next. uncertaintymindset.substack.com/p/backinthegame
a questionable take
"Americans are richer than Europeans but Europeans have nicer lifestyles" NO THEY DON'T, sweltering and suffering through 4 months of the year is non-negotiably awful.
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/uncertaintygam…
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
how does this work if errors are not patterned enough to develop representative examples and/or occur at predictable times
Error analysis is all you need. These guys literally teach us how to do it, and wrote an entire chapter on it! (35% discount: maven.com/parlance-labs/…) Analyze: This stage covers identifying erros and understanding why they occur. By collecting samples and categorizing failure…
uncertainty/not-knowing is the unavoidable condition of discovery and innovation: vaughntan.org/innovation-and…
when you start exploring a new topic, shift to a new domain, or move in a new direction you are filled with two feelings at the same time: excitement and the fear from an uncertainty void.
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
Some: “My AGI is built from a Popperian framework.” Popper: “I will mention here ten points which throw some light on the differences between the theorist’s and the instrumentalist’s approach, and between theories and computation rules.”
"delightful work" — what every insecure writer wants to see
So my "not knowing" and "ignorance a skilled practice" fans like @literalbanana and @ConradBastable have found the delightful work by Vaughn Tan, right?
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 good manufacturing. uncertaintymindset.substack.com/p/gbw2725
A friend fled the Middle East early during the last Israel-Iran flare-up—then felt foolish when it fizzled. The real mistake wasn’t leaving too early. It was treating deep uncertainty like risk, and trying to optimise. Read more about what to do instead: vaughntan.org/optfallacy
Anthropic’s AI shopkeeper failed 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/bizmeaningmaki…
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.
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/decomposablepr…
