(edited freewrite from Dec. 22, 2014)
Today, my thoughts begin with hats. I'm wearing one other than my usual today.
Hats, in fiction and to some degree in real life, externalize your core self. You choose to wear a hat, in a way that you do not choose to need glasses, but also in a distinctly different way from which you choose your wardrobe. Glasses can mean 'cool' or 'nerdy' or 'smart'; they represent constant, immutable traits. Clothes give a shorthand method for determining a person's choices; you can change your choices, if you dislike them. As surely as you must wear clothes, though, you must make choices. On the other hand, few situations truly require a hat; in everyday life you only put on a hat to do hard work or make a statement about yourself. It's the symbolic equivalent of wearing your heart on your sleeve.
An iconic character like Indiana Jones without his hat would be unthinkable; in fact, leaving their hat behind usually signifies that they've given up on their deepest drives. Royalty and clergy alike top themselves with the most extravagant hats as an external symbol of their power and calling. Hacking culture differentiates good and evil hackers as 'white hat' or 'black hat'.
I make it a habit to wear cool hats, as it makes me happy to look as awesome outside as I desperately hope I am inside. At the moment, I'm wearing a straw hat; I worry it signifies silly anime pirate than super-cool rationality master.
Perhaps that describes me better. I enjoyed being a pirate, back when I was pastafarian. Pirate rules pose few restrictions—I just do what I want, since the rules are more like guidelines anyways. A "rationalist" might insist on the doing the sensible thing, for a particularly rigid definition of 'sensible'.
Amidst the rationalist community, it sometimes looks like only certain wants really count. For example, I want a pie. A pirate would just eat the pie, and not share it. The picture of a rationalist in my head decides to eat something else. When I picture my picture rationalist's reasoning, it's because they genuinely want their long-term health more than they want the pie.
However, I have only spotty access to True Rationality(tm). If I decide to not eat the pie, I'm probably just ignoring my desire because Rationality said so. I feel wary of this strategy; ignored desires have a way of coming back at you with a vengeance. I vaguely sense that if my brain could envision quantities well enough to compare desires directly, I would, in fact, want my long-term health more than I want pie. If I try to think about it in terms of health points, I might like eating pies less—but probably just enough to make eating the pie less enjoyable, rather than preventing me from eating the pie.
Does my tendency to reduce rationality itself to a static model make me not a rationalist? These questions haunt me late into the night, and all because I'm wearing a different hat today.