Hang on a second. One of the smartest things I ever read on the topic had nothing to do with tech - it was a female psychologist who also happened to be a private pilot, and she was talking about getting more females interested in flying. (I don't think somebody could write such a candid article about tech, unfortunately.)
Her basic premise was that females need more encouragement from other women who've "been there" in order to feel comfortable taking that path. Basically, the "odd one out" thing you mention. But males are more apt to do something even in the face of active discouragement. I've certainly observed this in myself and other males, barely (if ever) observed it in females, and it makes sense from an evolutionary standpoint as well (intuitively - I don't know if there are any studies that explicitly show this, but if risk-taking is on a bell-curve like most traits, in general the standard deviation in males is greater than in females). In professional flying, there's a lot of discouragement - it's hard, pretty thankless, the pay is crap for a long time despite needing a lot of expensive training just to start, and you're away a lot. Most pro pilots I know are in it for some version of prestige, which we know motivates women less than men.
In other words, to use your language, women are "herding creatures" to a greater extent then men (though I'd probably say "social creatures"). Men are more likely to find a niche in which they can excel, while women are more likely to stick to a "tried and tested" path. Note that I said "more likely", not "will always" - there are plenty of men who go into some boring average field, and plenty of women who don't, but on a societal level the averages and characteristics are important. And I don't think either of these characteristics are necessarily bad, or desirable to change. Both approaches to live have substantial downsides, and it's probably better to have a mix.