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Viliam comments on Optimizing Rationality T-shirts - Less Wrong Discussion
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I guess the first step is to decide what exactly do we want with each product (because going for mixed solutions will likely be suboptimal):
* signalling to other rationalists (including oneself)
* a short interesting message that can serve as a discussion opener
* a standalone explanation of some rationalist technique
The lower on this list you get, the more words you need, and probably the more elegance you have to sacrifice. Because generally, in design, less is better, but in explaining rationality, the inferential distances are huge. For example, for signalling to yourself and fellow rationalists, writing "LessWrong" or just "LW" would be enough.
While all those are useful, looking stylish happens to be important because we want to look well dressed when interacting with other people. The things you are listed are additional features.
I generally have a goal factoring approach to this. The aim I think should be to both signal to other rationalists and oneself, while also spreading positive memes to nonrationalists that would at the same time serve as a discussion opener. The slogans are all intended to do that - "Glad To Change My Mind," "Growing Mentally Stronger," and even "Less Wrong Every Day" - all function to fulfill both goals.