31: Ryan Holiday - Conspiracy, Manipulation & other Pastimes: Difference between revisions

In this episode, I get to sit down with author and social analyst Ryan Holiday. I wouldn't say that I know Ryan enough to consider him a close friend, but I have enjoyed every conversation I've had with him for the unique metacognitive perspective that he brings to all things on which he thinks, speaks or writes. There are two things in particular that Ryan does that make him one of the most incisive analysts and best conversationalists in the public eye working today. In many ways, the overarching lens that I feel is missing from today's hyper-partisan world is that of expecting conflicting truths to lie in super positions. After all, why would anyone imagine that the simplified childlike positions of activists would be appropriate for those who eschew hyper-partisanship in favor of nuance? Well, I can't pretend to answer that question. I can say that Ryan's ability to fully consider the validity of two or more evident truths that are at least nominally in conflict, is all too rare in today's world of public intellectuals. Well, that itself is reason enough for me to tune in to Ryan's perspective. There's something deeper that draws me towards his voice and way of thinking. All too often in my experience, the minority of social analysts who in the internet era can still properly entertain the dialectic in public, without bending to the activist mob, tend to stop there prematurely at a point of detachment. They frequently appear to be disinterested in reframing natural tensions for others, so as to facilitate progress through synthesis and reconciliation. Instead, they often prefer the entertainment value of a continuing battle to a satisfying conclusion without victor or vanquished. In particular, I've increasingly noticed a move towards studied indifference in the projection of personal apathy on the part of several metacognitive pundits, in what seems to be a mechanism of self-protection. I find that Ryan, by contrast, is fairly open in sharing that he cares about the future deeply-but always in a thoughtful and measured way, informed in an interesting fashion by his relationship to Stoicism. That combination of caring without sanctimony makes him one of my favorite conversationalists in private, and I am glad that we got a chance to try to translate this into a public forum.  

Two words in the setting of this conversation To begin with, it took place in 2020 before the stay at home orders were in place. So it feels in some sense like a message in a bottle from another earlier world. And it oddly filled me with a sense of what feels like a genuine longing for our recent past upon listening to it. With so much rapid change it feels like full on early 2020 nostalgia is actually now a thing, even though it is only April. Secondly, we discuss Ryan's book on Gawker and Peter Thiel. This is one of the first places that I've ever shared my thoughts about the episode, and it may surprise people to hear my inner conflicts about Gawker journalism and Nick Denton. To this end, I will just point out that I was later to find out about the story from Peter than many may have imagined, and that Peter actually encouraged me always to act as an independent voice of moral concern, as you may discern from the conversation. I'll let the conversation speak for itself, however.