"What is it about your environment, history and values that encourages you to surpass limiting social expectations?"
Asking in a non-specific way leaves the answer open. A warning, when you ask the question of a woman if you happen to be another woman, take replies with the awareness that women tend to "tell their troubles" to bond with other women.
(To understand much more of how all this happens and more about what the issues are concerning women and those who do not match the current social trends in their conversational style, I recommend the very conversational but content-rich books written by linguistics professor Deborah Tannen, PhD - especially her book "Talking 9 to 5.")
Stereotypes and trying to be "right" by using mind-reading affects us personally, as well as affecting the culture in general. It took me a great deal of thought about this question to find the answers in myself. There were three pivotal experiences for me as a young person.
What made the biggest difference motivating me to think for myself happened when I was only five years old. My idol, which was my elder brother of eight years, gave me a snake for a pet - sanctioned by my parents. It was 1959, and in that era, snakes suffered from many social misconceptions about their nature. At a crucial stage when I was going to transfer my family's authority toward the authority of school&a greater social world - there was this serious mis-match. People I did not know or trust mistakenly thought snakes were dangerous, contradicting what I knew to be true according to my family and the San Diego Zoo. This experience encouraged me to think for myself and put out effort to learn the true nature of things before I accepted societal norms. It inoculated me against cigarettes as well as sent me to college.
Of course, the most obvious solution to free the minds of young people would be world travel. Becoming an exchange student during middle or high school is the most socially acceptable way, but spending at least six months in another culture works just as well. Once you have been a young person in a radically different environment, you return and realize how self-absorbed your peers are.
The other pivotal issue was attractiveness and the accidental social authority that went along with it. It upset me that, according to society, women were expected to be helplessly manipulative to get things done. The social fact that an attractive female asking for a "favor" gets it from a male who has temporarily lost his reasoning - this bothered me. For me as a young girl, there seemed no way to "opt out" of that game gracefully. I did not want the power men handed me to deny or accept their attention. Because of the accident of birth making me coincidentally attractive, I had to deal with this issue early on. Only later I realized that this was a social reality for almost every girl. If you're a straight guy reading this, imagine if you had to deal daily with attention from people you did not want - from other guys, for instance. This is the environment young women find themselves.
What eventually remedied this issue for me was learning about body language. After this education, it was indisputable that how I behaved was evident for anyone to see. What sort of a person I was, my values, showed beyond my physical features. A person's character is expressed in their walk, how they move, where their attention goes & the quality of attention used. After learning about body language, I had to accept there were, in me, obvious additional desirable qualities of character, in addition to matching social definitions of beauty.
So I would recommend to teach body language as part of a relationship communication class as a solution for the common desire for membership and bonding - in high school or earlier. (For me, studying Alexander Technique in a classroom situation worked.)
There are many reasons why there is a sudden drop in confidence when girls (and boys) reach middle school age. They realize how they do not match the social norms, and there is the tendency to envy what they are not. This is when they first must grapple with social questions about how they are going to deal with sexual attention. A desire to for membership and to belong becomes important, as well as trying on what roles might suffice for gaining membership.
The last pivotal experience for me was when I discovered creative thinking skills at around fifteen. Not just the result of thinking creatively by making things artistic, or modeling creative people I admired... I'm talking about the actual nuts and bolts of how to do problem solving in any situation of decision-making. Creative thinking skills taught me HOW to think for myself. Wanting to think for yourself in spite of societal norms and actually doing this thinking constructively are two very different things. Edward de Bono has a series of proven simple but effective creative and strategic thinking skills designed for middle school aged students and older. Again - not What to think - but How to think. Young people have refreshing bullshit detectors. These natural talents can be fostered into effective and constructive rebellion.
Nobody is going to take my word for it...but I say if creative thinking skills and relationship classes were taught in high school (instead of so much of what is ridiculous mind-reading for "correct" information that is taught now,) society would experience a big jump in social responsibility from all young people.