Today, she has no misgivings about being a norm-breaker. “You should not look at everything with these glasses of what the norm is,” she told me. “You look at what’s right for you.”

The psychologist and philosopher Cristina Bicchieri studies trendsetters, people who violate society’s norms and set a path for others to follow. Trendsetters, she says, tend to be more autonomous and less sensitive to risk. They possess a great deal of self-efficacy: a belief that their actions won’t be in vain. Trendsetters know that if they start a movement, others will follow.

She has also observed that in order to try new things, different people require different thresholds—a set number of people they need to see behaving unconventionally in order to, say, paint their house purple, or do something else norm-violating. People who have very high thresholds are more cautious: they’ll only attend Burning Man once they hear of tech CEOs who are doing it. If someone has an extremely low threshold, meanwhile, they might wear a Beetlejuice costume to an important work meeting on Halloween, even if there’s no indication that anyone else will be wearing a costume. (Someone with a threshold of “one,” meanwhile, might make a work buddy do it with them.)

Bicchieri, for what it’s worth, has a relatively low threshold. When she was growing up in Italy in the 1960s and ’70s, women were bound by very strict social rules. They weren’t expected to have both a family and a career. But Bicchieri was active in the feminist movement. She moved out when she was nineteen and lived alone, which was unheard of. She went to Cambridge to earn her PhD. One reason she was able to go against the grain at such a young age, she told me, is that a small group of friends did it with her.

Another choice mom I spoke with, Sarah Lenti, had a much more complicated experience than Aileen’s.

Sarah is an attractive, successful political strategist who has worked for Condoleezza Rice and Mitt Romney. Still, when she was younger, she had very low self-esteem. She didn’t date in high school and she didn’t date in college. She didn’t date until she was in grad school at Stanford, in fact, and that relationship ended when she had to move to Washington for work.

Then came a three-year slog through limbo with a man who said he didn’t want to break up or get married. He would never love her, he told her. At thirty, she wrote a note to herself that if she was still single at thirty-eight,284 she would think about becoming a mother on her own.