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The prison of context

January 10, 2025

I’ve recently stumbled upon “Stockdale Paradox”, named after Admiral Jim Stockdale, a prisoner of war who was tortured during his eight-year imprisonment during the Vietnam War. He said that he survived because he maintained the faith that he could and would prevail in the end, but at the same time had the discipline to confront the harsh reality. He mentions that it was not the pessimists, but the optimists who didn’t make it. [1]

This reminds me of a couple of things. Firstly, this is nothing other than a concept of “rational optimism” in the form of a more neatly named “concept handle”, to use the lingo of Scott Alexander. It’s not rose-colored glasses, naive optimism, but the more realistic one, the one that still acknowledges that reality is a harsh place, but the one that encourages belief in one’s own skills to overcome the difficulties, and is optimistic in that sense. Secondly, this reminds me of F. Scott Fitzgerald: “The test of a first-rate intelligence is the ability to hold two opposed ideas in mind at the same time and still retain the ability to function.”

Stumbling upon all of this made me want to write it down into my note-taking tool of choice only to realize that I have a “Stockdale Paradox” note sitting in it for the last four years, saying this:

In order to be successful in a startup world you can never lose faith that you will prevail, while still being disciplined to confront the most brutal facts that reality throws at you. #startups

See, this note was categorized into startups, so I didn’t think about it in a broader sense, and never thought about where it comes from. In some way, this categorization of the note made me neatly file it in my mind as well. It was neatly packaged in the “startup” box, never to leave it.

All of this is another reminder of what Taleb wrote in Antifragile:

We are all, in a way, similarly handicapped, unable to recognize the same idea when it is presented in a different context. It is as if we are doomed to be deceived by the most superficial part of things, the packaging, the gift wrapping.


  1. You can read the whole story here.
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