Qiaochu_Yuan comments on The Wrongness Iceberg - Less Wrong Discussion
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Several ideas and techniques from the CFAR workshop are relevant:
The workshop included a practical session on comfort zone expansion (we went to a mall and did mildly uncomfortable things involving strangers) which I found helpful, mostly because it helped me internalize social pressure in the direction of comfort zone expansion. At the workshop this was abbreviated as CoZE and there was a half-serious idea floating around of awarding "CoZE points" to people whenever they expanded their comfort zones, which is the main technique I used the last time I tried asking for advice. (The other technique I used was a social commitment mechanism, but explaining how that fit in would make the story too long.)