Maybe Software Can Really Eat Anything

Venkatesh Rao wrote a very long personal reflection called “King Ruinous and the City of Darkness”, which sprawls over both ancient and modern stretches of Indian history. The text is difficult to summarize in a couple of sentences, because it’s an expansive overview of how Rao came to think in the way that he does. But here are two quotes that jumped out at me:

“There are no real reasons and motivations in Indian politics. As with the rest of the world, politics in India is the art and science of the possible. You do what you can do. You spin the story whichever way you can spin it. The perception problem and the action problem need have no relation to each other, so long as you have solutions to both.”

“One does not simply exit the caste system, but one can sure as hell scramble it beyond recognition and render it unusable by having software and urban modernity eat it. This, incidentally, has been the single most positive development I’ve witnessed in my life. If software can eat the Indian caste system, it can eat anything.”

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Remote Mentorship

I read a lot. And I learn a lot from what I read. When I discover a writer I really like, whose work is particularly insightful, I glom onto them — I’ll tear through their whole archive, or if they’re particularly prolific, read all of their classics (defined as the pieces they themselves reference the most).

The internet’s casual and iterative blogging culture encourages this behavior in a way that the offline world doesn’t. Sure, you can read every book an author has written. But what about doing that and following their life on a day-to-day-basis? Social media lets you get to know someone in real-time even when they have never registered that you exist.

Map of the internet via Bill Cheswick. Remote mentorship is possible because of this technology.
Map of the internet via Bill Cheswick.

The term I use for this process is “remote mentorship” — it’s similar to traditional mentorship, but without the constraints of time or place. The mentor doesn’t have to be interested in the mentee or pay any specific attention to them. There’s no need to meet for coffee or exchange letters. In fact, this is scalable mentorship: someone can post once and influence many, without having to dispense one-on-one advice to each enthusiast.

I maintain a public list of people who shaped my intellectual growth. Some of them have mentored me in the traditional sense, and some are friends, but the majority are busy professionals who have maybe acknowledged me once or twice on Twitter. It’s not the same as dedicated hands-on mentorship, but I get just as much out of reading Slate Star Codex as I have out of personal coaching relationships.

Remote mentorship is a combination of the intellectual hero-worship that’s been around forever (boosted by the printing press), and today’s burgeoning influencer economy. It’s like the nerdy version of lusting after Instagram stars.


I’ve been thinking about this for literally years, but I owe a hat-tip to Venkatesh Rao’s “Cambrian Explosion of Consensual Realities” for the immediate inspiration. Guess what Rao qualifies as 😉

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What If History But Darkly Amusing

“The writing down of history turned out to be a self-perpetuating activity. Anytime kids asked questions, adults would yell, ‘READ THE FUCKING MANUAL!’ (later shortened to ‘BECAUSE I SAID SO’). These kids, when they grew up, tended to reproduce this behavior. This was called culture.”

“Armed with priestly justifications, and supported by good people, political leaders could finally begin going beyond mere intentions and retcons and actually begin inventing history. They were no longer limited to merely encountering it in the form of unpleasant surprises, and reacting to it on an improvised case-by-case basis. The ability to separately define ‘good’ and ‘people’ allowed history writing to become truly predictable, proactive, scalable and deployable to large populations. Sometimes history could even be written before it happened.”

Quotes from Venkatesh Rao’s very entertaining satirical history of history.

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People Who Shaped My Intellectual Growth

I came across Tracy-Gregory Gilmore’s list of people who have influenced him, and I found the idea really charming. Exposure to a few different people’s ideas has been incalculably valuable to me, and I want to publicly thank them in the same way Gilmore did.

These are people I consider “remote mentors” (a concept I wrote about in August, 2016). Two writers in particular have profoundly shaped how I see the world: Scott Alexander of Slate Star Codex and Ben Thompson of Stratechery. Their names are repeated on the list below, but they deserve special recognition.

In chronological order:

  • Vladimir Nabokov, who penned the infamous novel Lolita, is my favorite author. That book in particular turned me onto postmodernism and moral complexity.
  • Ben Thompson of Stratechery is a business analyst who writes about the tech industry. Reading his articles got me interested in business and economics, and I learned a lot from his commentary on incentives and the structure(s) of markets.
  • Scott Alexander of Slate Star Codex is… well, professionally he’s a psychiatrist, but online he’s sort of a cultural philosopher. His essays on identity, community, and politics have been very illuminating. Everything is virtue-signaling!
  • Venkatesh Rao, creator of Ribbonfarm and Breaking Smart, is a writer in a similar vein to Scott Alexander of Slate Star Codex. The label “cultural philosopher” once again feels like it fits. His area of expertise is breaking people’s mental models and then helping reconstruct them.
  • Meredith Patterson and Alice Maz are both programmers who wrote essays that helped me become more empathetic. Patterson wrote “Okay, Feminism, It’s Time We Had a Talk About Empathy” and “When Nerds Collide”. Maz wrote “Splain it to Me”.
  • Adam Elkus and David Auerbach are two polymath scholars who incisively understand the meta-politics of the cyber age (which is only just dawning, I might add).
  • Lou Keep’s Uruk Series is a phenomenal tool for understanding modern discontent and the failure cases of social control systems. Start with the essay on Seeing Like a State and then skip to the essay on witch doctors.

Last updated 8/13/2018.

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Ambiguity = Opportunity

Venkatesh Rao wrote an essay for his Breaking Smart newsletter about uncertainty versus ambiguity:

“High uncertainty tolerance requires you to develop analytical skills. High ambiguity tolerance requires you to develop insight skills. […] The risk of uncertainty wrangling is being wrong. The risk of ambiguity wrangling is seeing something where there is nothing, or vice versa.”

If we roll with Rao’s implied definitions, uncertainty is being unsure about facts, whereas ambiguity is being unsure about interpretation. (This is perhaps beside the point, but I’m not sure the distinction between the words “uncertainty” and “ambiguity” is actually so clear-cut.)

My guess is that most of Rao’s readers work in tech and probably a high proportion of them are aspiring startup founders (I’m not excluding myself from either of those categories). I can easily see how this uncertainty and ambiguity matrix applies to either investing or entrepreneurship.

Let’s say you’re examining a market. You don’t know how many people have XYZ characteristic. That’s an uncertainty problem. Or maybe you do know how many people have XYZ characteristic, but you don’t know what to do about it. That’s an ambiguity problem.

Rao’s proposed solution is free-form intellectual play — he encourages, “it’s not wasted effort because there is no concept of waste in true play.”

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