The problem though, is empathy is going to be really hard for men -> women or women -> men; both sexes are remarkably different culturally.

What you see is a large number of socially awkward and inept people flocking to industries where being socially tact is less valued over intellectual prowess. Women have always been more socially tactful than men - it's how our society is set up, women are treated as a valued commodity.

If you want a "close" approximation of figuring out what it's like to be the other gender in a "x dominated field", you should go the route of the author of this book: http://www.amazon.com/Self-Made-Man-Womans-Journey-Manhood/d...

She did a remarkable job of actually experiencing what being a man in our society is like. I would be very interested if someone of the male sex were to do something similar and write a book about it, this article doesn't cut it IMHO.

Self-Made Man is a tale similar to Black Like Me, where it was a writer's experiment, rather than a transgender exercise.

http://www.amazon.com/Self-Made-Man-Womans-Journey-Manhood/d...

There are also a lot of interesting works by transgender people, but the perspective there is different, since they usually report that they never felt comfortable in their birth gender.