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Another format experiment
Hello friends,
Starting this week, I’m experimenting with another format: A weekly issue linking to new writing I’ve recently published and Interesting Stuff I came across that week.
This newsletter started in October 2019 as a way to write about uncertainty outside of the confines of my book. For most of its existence, each issue has focused on publishing an essay that tries to unpack a single idea or concept.
Now that format feels too confining. I have several writing and work projects simultaneously underway that take my work on uncertainty in different directions — on strategy misunderstandings, on not-knowing, and on meaningmaking. I also want a way to publish small and big things, half-baked drafts and more fully baked pieces, parts of series and standalones, and both more and less frequently. And I’ve been meaning to put as much of my writing as possible onto my own website. Decoupling the publishing from the newsletter seems like an idea worth testing. So I’ll run this experiment for at least 8 weeks — your comments along the way will be very welcome (just reply to this email).
Recent writing
Structured messiness and urban innovation. This month, I’ve spent a lot of time in strata title malls. They’re seedy, non-prime, largely illegible buildings with a retail/commercial mix that no self-respecting property manager would actively seek out. Because, not in spite, of that kind of structured messiness, they provide homes to niche or untested business models and become incubators for an unfashionable but essential type of innovation. I wrote about how structured messiness leads to good spaces in which to live, work, and play.
The tensions and misunderstandings of strategy. For two engagements I’m working on, the core problem appears to be that different people in the same org have different ideas of what strategy is. The result: Failures of both communication and execution despite good intentions. So I’m building management tools for solving the problem of misunderstanding strategy. As a byproduct of this work, I’m writing up a series of articles exploring seven strategy tensions and misunderstandings. The first three are on why strategy is not the same as planning, on why good strategy must be embedded in operations on the ground (instead of only speaking abstractly to the boardroom), and why good strategy must engage with feelings and emotions (not just with cold cognition). If you’d like to talk about this in the context of your own organisation, just reply to this email and we can set up time to chat.
Forwardable introduction requests. Suddenly, it is the season of introduction requests — I received 6 introduction requests in the first half of March. Introducing people properly is a lot of work. The more of that work you can do for the introducer, the more likely they are to agree to introduce you, and to introduce you effectively. Which is where forwardable introduction requests come in. I explain the logic of forwardable introduction requests and how to write good FIRs.
Work featured
idk, the world’s first tool for productive discomfort, showed up in la mutante and at Hurae. The idea behind idk is: Uncertainty is intensely uncomfortable. We avoid discomfort because we’re not used to dealing with it, so we avoid uncertainty even when it could be generative. idk is designed to build your capacity to be productively uncomfortable.
Interesting stuff from elsewhere
LLMs and established knowledge. John Willshire and I had an exchange about when using LLMs to write seems to help — my observation was that LLMs always slow me down when I use them to articulate novel ideas, and sometimes speed me up when all I want is summaries of established thinking. To explain this, John came up with this 2x2 which makes a lot of sense to me:
Blandness and high-signal environments. At dinner last week at a well-regarded (by Michelin) but ultimately extraordinarily mediocre local zichar restaurant, we asked for grouper head stir fried with bittergourd. This much-prized, delicately flavoured fish arrived coated in a thick brown sauce that had been overseasoned with everything, but especially with black bean paste. This made me reflect on how everything needs to be Intense and Amped Up to succeed today — maybe because of the increasingly high-noise, low-signal content environment we float around in. How can we get back to demanding high-signal, low-noise stuff again? On this topic, I especially enjoy François Jullien’s In Praise of Blandness.
The absurdity of ultrarationality in an obviously uncertain world. I’ve written before, obliquely, about how silly I find Effective Altruism’s risk-based approaches to choosing actions under the uncertainty of futurity. Then, mid-week, I accidentally had a coffee meeting with an Effective Altruist moments after seeing this comic by Zach Weinersmith.
Speed isn’t everything, especially when doing meaningmaking work. Julian Lehr wrote an excellent essay about how conversational interfaces act as a bottleneck limiting the speed of data transfer. I experimented recently with writing some new exploratory work in conversation with an AI system (ChatGPT) by talking to it and having it ask me clarifying questions. Conversational dynamics compelled me to fill gaps in the conversation with plausible-sounding but meaningless words. These eventually got synthesised into readable prose output that, on deep reading, turned out not to say what I mean because I didn’t know what I meant while I was having the conversation. (Here, “meaningmaking” = the act of making inherently subjective decisions about relative value.) When I’m doing meaningmaking work, what I need is for my tools to enforce slower data transfer and give time for meaningmaking.
See you next week,
VT
I like this format: many paths of thinking to choose from and get lost :)