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Well needless to say these remarks of yours really resonate with my own experiences. That need to belong AND at the same time to identify myself as one of the 'cool outsiders' so as to distance myself from any complicity with the system that was and after all still is delivering me so much in terms of privilege...it seemed heaven-sent at the time.
The 'cool factor' is such a huge part of this. I remember my students saying 'o Ms. G. she's so cool, rocking the dreads' and all that come with especially the ganja. I look back not so far back actually and see a really insecure person needing to put on the outside trappings of this and that in order to be considered 'cool'. When a white chooses the trappings of Rasta they are putting on black culture and the irony is that they can get away with this precisely because they are WHITE.
I now am some years into the project of making do as an anonymous middle-aged white woman, ever more invisible due to my increasing age, and it is really very interesting. Coolness, as you well know, is an existential state of being and putting on some idea of coolness as mask for insecurity only delays the real deal, the real day to day of shedding off the arrogance and finding better and better ways to be human. For me, ganja after a certain point was only delaying the necessary insights.
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