The key to successful non-conformity is to find your tribe later. If you look at people who’ve done this now, they seem like conformists, because they do what their peer-group does. But they’ve fit their peer-group to their personality, rather than trying to fit their personality to their peer-group. They’ve had to move through local minima of non-conformity.
Here are some examples of where I’ve made what have at the time been socially brave choices that have paid off big. This is exactly all about asking “what is the best thing I could be doing”, not “what is the thing to do”.
Decided to accept and admit to my bisexuality. This was very uncomfortable at first, and I never did really find a “home” in gay communities, as they conformed around a lot of norms that didn’t suit me well. What accepting my sexuality really bought me is a critical stance on masculinity. Rejecting the normal definition of “what it means to be a man” has been hugely liberating. Being queer has a nice signalling perk on this, too. It’s much harder to be straight and get away with this. If you’re queer people shrug and put you in that “third sex” category of neither masculine nor feminine.
Decided not to pursue any of the “typical” careers. I was getting top marks in English and History in high school, and all the other kids with that academic profile were going into law. I chose to just do an arts degree in linguistics, with an eye on academia. This turned out to be a very important decision, as I’m very happy with my academic career in computational linguistics. When I meet people, they’re amazed at how “lucky” I am to have found something so niche that fits me so well. Well, it isn’t luck at all: I decided what everyone else was doing was not for me, and had to suck it up when people called me a fool for leaving all that near-certain law money on the table.
Decided the “school” of linguistics I’d trained in all through my undergraduate was completely wrong, requiring me to abandon my existing professional network and relearn almost everything. It was kind of a scientific crisis of faith. But I think I’m happier now than I would’ve been if I hadn’t.
Decided to become vegetarian. This benefited me by reducing my cognitive dissonance between the empirical facts of the meat industry and my need to feel that I was making the world a better place, and wouldn’t do something I had believed caused great harm just because it was normal. Now I have a network of vegetarian friends (not that I abandoned my old one, mind), so it doesn’t feel like lonely dissent. And I did only “convert” after meeting a rationalist vegetarian friend. But the non-conformity pain was still there when I did it. I had to deal with feeling like a weirdo, which is unpleasant.
Hired a domestic cleaner. Domestic help is fairly socially unacceptable in my champagne socialist slice of Australia. How bourgeois! Well, yes—we are totally bourgeois. Champagne socialists are very uncomfortable about this. This exchange of goods for services is very high utility for me, though.
So I disagree that “non-conformists” are worse off, for this definition of “non-conformist”. People willing to make socially brave choices stand to gain a lot; people who are completely craven in the face of any social opprobrium wind up trapped in circumstances that don’t suit them well.
Often I hear guys complain that an advance is deemed “creepy” if it’s unwelcome, but not if the same thing were said or done by an attractive man. I also see a lot of emphasis on “confidence”. Guys are often advised to “be more confident” in the way they approach or “escalate” with women.
The problem is, sexual advances are often gambles where the potential downsides are paid by the party approached, not by the one who does the approaching. When you think of it this way, complaining about unwanted advances is perfectly justified, and telling guys to “be more confident” is totally upside-down.
Take this example of a highly upvoted piece of advice on how a guy should try to kiss a girl for the first time: http://www.reddit.com/r/dating_advice/comments/1bymdq/never_datedbeen_in_a_relationship_i_m21_want_to/c9bu81j
The advice here is in general very “high risk”: if the girl didn’t want to be kissed and the guy grabbed her and moved in suddenly in that way, that would really suck for her. Often these types of risks are also high-reward: a welcome advance of this type is often hotter than a more timid one. Being pressed against a wall and kissed is awesome if it’s welcome, and horrifying if it’s not.
What’s truly valuable is a well-calibrated and highly accurate model of how your advances will be received. That lets you carry off these high risk, high reward advances. But time and again I see people advocating confidence—as though just predicting that every advance will succeed were the solution. Wishing does not make it so.
To avoid being creepy, the focus should be on keeping your model well-calibrated, and on being fairly risk averse. If you think your advance is unlikely to succeed, you either shouldn’t make it in the first place, or you should be careful to give the other person a graceful way to decline.
So, in the example of kissing that girl for the first time from before, I’d be suggesting he get verbal consent. He’s having trouble predicting whether she wants to be kissed from the non-verbal interaction, so he has to take the lower risk option, even though it comes with a lower reward.
This idea of a well-calibrated model is also behind my objection to a lot of PUA advice. It often sounds to me like the negative externality is “priced out”. Guys are advised that they have nothing to lose from approaching a lot of women. Well, that might be so, but the women do have something to lose, even if it’s only a mild discomfort, and it’s totally unethical to not care about that. The fact that the downsides are external should strongly encourage risk aversion.