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Thanks all for a rich and engaging conversation last Tuesday, and for continuing conversation here.   My original notes are here, if anyone wants to get back to them.  And here a few general thoughts that have been bubbling around in my mind from our conversations, with a few more specific ones in response to other comments below ...

"Affirming diversity is hard" (Roughgarden) indeed seems to be so: 

"Diversity is a threatening idea" ... cmorais

"Being the (somewhat) perfectionist that I am, I like to have things in their place- with each pen in a pencil case and marker with the right cap, so I get why society wants to create these categories. I feel like without categories there would be this sense of chaos as if people would no longer know how to interact with each other." ... Alice

"It’s far more convenient to believe in a permanent truth, a set of facts, then to take a conditional approach to reality and always be ready to adjust to a shift ..." ... Karina

"people aren't always ready to accept that they are in a mould in the first place. Because accepting that they are in a mould would mean that there is a different world out there, a different way of being, living and existing which is possible. That makes people uncomfortable sometimes, because it shakes their beliefs of 'right' and 'wrong'. We compartmentalize ourselves, our society, our thoughts - it’s just neater that way." ... skindeep

What's particularly interesting to me is that the problems being pointed to are not at all specific to sex/gender.  The same problems come up in a host of other contexts, including ethnic identities, politics, and mental health.  For more along these lines, see Culture as Disability, a very rich paper arguing, basically, that  cultures necessarily create categories that make some people feel good about themselves and, in doing so, inevitably disadvantage other people.  The paper doesn't specifically address the issue of sex/gender categories, but it might well be worth thinking about them in this broader context.

There's also an interesting parallel between thinking about sex/gender categories and thinking about "science"

"we learned that there cannot exists any (T)ruths or facts, because science is constantly disproving and finding new observations and creating new stories" ... Terrible2s

"Who knew science was so interesting?  ... 'Nothing a scientist says is true' (I wish I could go to my 10th grade biology teacher now and shove that in her face, but I will refrain). ... I like to think of myself as a free thinker, always open minded. I sure am glad I am this way because "Evolution's Rainbow" is taking my mind to places it never thought it would go" ... Elephant

"I do feel like we are definitely taking a step in the right direction by asking questions ... that make us problematize the very foundation of society's structures" ... Alice

"ours and other societies could use more edgy work like Roughgarden's to start to dismantle the idea of "gender" and "sex" as natural." ... ebock

"we cannot be moved to skepticism and reevaluation of ongoing stories without also becoming skeptical of the very observations that compelled us to that skepticism in the first place. The choice of which story to keep and which story to throw out is ultimately up to us, although what is really being asked of us is to piece together our own version of the story." ... Karina

Science  creates "categories" all the time.  But, arguably, it creates them not as fixed and eternal verities but rather as tools that can be used to "problematize" not only the "foundations of society's structures" but our own deepest understandings of ourselves and our relations to everything around us.  Maybe the key to a non-"disabling" culture, with respect to sex/gender and lots of other things as well, is not to eliminate categories altogether but rather to always treat them skeptically, valuing them insofar as they help us in "taking my mind to places it never thought it would go" and discarding them otherwise?  And we could perhaps learn to value diversity in the same terms, as the grist that makes it possible to conceive new ways of being?  Yes,  "things can get really confusing when people exist (or attempt to exist) outside of binaries," but maybe we don't have to "choose between one side of a binary or the other."  Instead we could use the poles of binaries to imagine and try out ways of being that might not otherwise have occurred to us?