buybuydandavis comments on Be a little bit more trusting than most people think sensible - Less Wrong
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I've got trust issues.
It helps me to clearly identify the potential cost involved should the trust be betrayed. "Ok, that's the loss, I'll live." I also try to inject some priors for the person I'm dealing with - not what they could do, but what they are likely to do.
I've concluded that I've missed far more in opportunities than I've made up for by avoiding betrayal. Life isn't so hard. I try to remind myself of that.