Which dream is more likely to come true in the United States of America in 2016?

Tom Krannawitter writes,

Suppose there are two adult men. The life dream of Man A is to be a woman.
He knows he can never fully, truly be a woman in every way. He knows he cannot change his chromosomes, for example. He knows he'll never experience growing up as a girl and transforming physically and biochemically through puberty into an adult woman. He knows he cannot be impregnated or have a baby, and he knows that he'll never know the concerns and joys connected to that uniquely female phenomenon.

Still, he can hire a physician to alter his body. He can swallow daily hormone pills. He can wear feminine clothes and makeup. He can legally change his name to something feminine-sounding. And he can demand that others treat him as a her for typical social purposes.

The life dream of Man B is to start his own business, build it into something large and successful and influential by delivering value to many other people, and run his own business EXACTLY how he pleases.

Which dream is more likely to come true in the United States of America in 2016?