That’s a wrap.


Hello friends and happy new year! (🤞)

This issue is about four things:

  1. A wrap-up of Year One of this newsletter:

  2. Crass commercialism: Buy my book! You can do this easily online and offline, around the world. It’s about how to think about and thrive in uncertain times—like the times we’re in right now. There are worldwide buying links here, and some recent reviews and podcasts about it (see below).

  3. Year Two of the newsletter,

  4. A preview of idk, a new project which I hope will be ready to share soon.

For a little bit more about each one of these four things, read on …

Wrapping up Year One

Over the last two months, I thought about writing a wrap-up issue or a year-end recap. But, prompted by emails from backlogged subscribers and design thinkers, I eventually did something else.

My wrap-up project for the holiday break is a set of pages which collectively provide a hacky way to navigate all 52 issues via whatever combination you would like of

  1. Short summaries of each issue for the backlogged,

  2. My idea of cool topics across issues for those who want a conceptual overlay,

  3. Links between issues and topics,

  4. Links between topics and other topics,

  5. Links between issues and other issues.

It has many elements of what people have taken to calling digital gardens and it took a lot longer than I expected (there’s an implementation note, if you care).

The process of putting this together was fascinating in terms of a) discovering unexpected patterns across a year of writing and b) thinking practically about building non-linear vats of information that can be navigated in different ways.

In the end this wrap-up project turned out to touch two areas of long-standing personal interest:

  1. Bidirectional linking in networks where nodes are differently typed,

  2. Semistructuring data. Indexing my own book was an object lesson on this, and in #11, I wrote: “Indexing is turning a book inside-out to reveal its skeleton and make explicit the logical structure of ideas on which it is built. Being able to keep this structure aloft and in view (metaphorically) while reading and annotating a manuscript and adding to the structure is a skill that takes a long time to acquire.”

Anyway. Here’s the link to the wrap-up again:

I hope you like it (because it took a really fucking long time 🛌). And if you find broken links, please email me.

Crass commercialism

Now that the season of socially conditioned consumption is over, I feel slightly less tawdry about pushing my book: you should read it!

It’s about why risk is not the same as uncertainty and—very relevant right now, let’s be real—how to cope with and possibly even thrive under uncertainty. And about cooking and other fun stuff.

There’s more information (and buying resources for every region of the world) on the book’s website:

Since October 2020, there have been reviews of The Uncertainty Mindset in the Times Literary Supplement and Strategy + Business, and a hard-to-categorise response to the book by Andy Matuschak. I’ve also done three surprisingly different podcasts about the organizational ideas in the book and about risk vs. uncertainty, with Beyond Wealth, Building Bridges, and the Wicked Podcast.

If you like the book, I’d appreciate it if you leave a review somewhere and let me know.

Year Two

Over the 70 days between the last issue and this one, I reflected on the first newsletter year. Even the pretty loose single topic focus on uncertainty was overly constraining. And the weekly schedule was too much—for everyone.

Year Two is still a work in progress, but here’s what I’m thinking:

  1. It’s time for a different name,

  2. There will be no singular topic focus,

  3. Issues will come out approximately biweekly,

  4. Some issues will be work-in-progress on two new projects—Quality Time and Productive Discomfort—which I hope will eventually become books,

  5. Some posts may combine audio and text content,

  6. There might be a paid content option (email me if you have thoughts about this).

I’ll continue to write sporadically here but Year Two will begin in February and run on a different Substack account for boring administrative reasons. You’ll receive Year Two automatically if you’re currently signed up for this newsletter on Substack. (And if you’re not currently signed up👇)

A cryptic preview

I’ve been working on idk for a few months and hope it will be ready to share in February. This is part of what it’ll look like:

More in a few weeks 🤞.


The Uncertainty Mindset is hard to categorize and probably not for everyone. But if you know people who might enjoy it, please share it with them.

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You can find me on the web at, on Twitter @vaughn_tan, on Instagram @vaughn.tan, or by email at <>. You can also find out more about my book at