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gwern comments on Harry Potter and the Methods of Rationality discussion thread, part 15, chapter 84 - Less Wrong Discussion
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I don't actually go to meetups, but Harry's comments about anti-conformity training made me wonder if it'd be worth trying.
You could retest the original experiment, see if lesswrongians can avoid it through knowledge of the effect.
You could mock obviously true statements to practice withstanding opposition.
You could practice the ability to do harmless but nonconformist things to gain the ability to do so if the situation called for something unusual, but you might otherwise be too conformist or embarassed. (each meeting attendee shall order a coffee whilst wearing the ceremonial tea-cosy!). I suspect some of this overlaps with PUA a little and easily veers into general confidence building.
I don't know if rehearsals would do any good, but you could go through the motions of not complying with the Milgram experiment, making people handle little fake emergencies...
You could wonder if EY is planning things like this for the Center for Modern Rationality.
Based on my own experiences being a lone dissenter, the main thing that has allowed me to stand up and maintain my position consistently in the face of uniform opposition and derision, was not expecting much of everyone else in the first place.
For example, in an introductory logic course, when the professor made a mistake, which everyone else in the class agreed with, and I was the sole person to disagree, and attempt to explain it in the face of the entire class brushing me off and laughing about how I thought I knew better when the answer was so obvious to everyone else, it didn't seem weird to me at all that every other person would make the same mistake and I would be the only one to notice it. It wasn't confusing to me, and my success in showing the professor in a couple minutes after class that she had been mistaken after all confirmed for me that my expectations were on track.
Conforming to the beliefs of the crowd is perfectly sensible behavior, in domains where you have no reason to expect yourself to be more accurate than anyone else. Learning to disregard conforming instincts completely is a bad idea, because a lot of the time, it really will be everyone else who's right, and you who's making a stupid mistake which will make you feel like an idiot when you finally realize it. Refusing to conform is both achievable and proper when you have a palpable expectation that other people are going to be stupid.
Unfortunately, it's rather easy for one's expectations of other people's intelligence and rationality to become poorly calibrated.
Having an experience of being right where everyone else is wrong, is good for breaking the fear of nonconformity.
When I was a child, I participated on a science olympiad and on one question I gave an answer that seemed trivially wrong, but in fact it was correct. (There were two objects of different size, made of same material, balanced on a lever, then both immersed in water. How will the balance chance?) Everyone thought I was wrong, and the official solution confirmed it. Then the organizers realized they made a mistake, and confirmed my solution.
Since then I knew (also on emotional level) that it is possible to be right, even if everyone else disagrees. Sometimes it is wise to keep quiet, because the social consequences of nonconformity are real, but being alone does not make one automatically wrong. It was a good lesson.
On the other hand, the fact that you were comfortable being the lone dissenter while untrained in resisting conformity may indicate that your social wiring is atypical. Some people in some situations may interpret that difference as a socioemotional flaw.
It might be that my own experiences won't generalize to other people, but in domains where I haven't developed an expectation that everyone else really will make mistakes that I didn't, if everyone else is saying I'm wrong, I'll tend to conclude that I'm probably wrong.
I wouldn't exactly say I was untrained though. We learn from our life experiences. I was smarter than the great majority of my peers growing up, and fairly precocious, a stage ahead through my childhood, so seeing people around me believing things that seemed head-in-sand stupid, because the things they believed were actually stupid, as the products of less developed minds, was simply the way of the world as I grew up.
The hard part, which I see reflected among many other people who grew up ahead of their peers, was developing a sense of when you really should expect other people not to be any less sensible than you are.