Choices, enlightenment or contentment

There are people who think they were born into the wrong body.
Consider this hypothetical scenario.
Some religions mention reincarnation.
John lives a long life and one day he dies and his being transcends to another plane.
While on this plane it is determined whether he will transcend to a higher plane of existence or be returned to earth.
If it is decided for whatever reason, he is to return to earth, he is given the choice to be re-born as a man or a woman or as another animal.
For reasons known only to John, he decides to be re-born as a woman.
However this reincarnation process obscures or omits past memories.
So John is re-born as Jane and begins a new life.
Not long on earth, Jane feels something is not right and she becomes uncomfortable with who she is. And so Jane considers surgically transitioning.
The unavoidable moral of this scenario is a person makes a choice. Not aware that they made the choice. In this scenario you got what you wanted. Buyers remorse. Depression sets in.
So Jane transitions to John. And one day John dies and the circle is repeated.
Being too attached to a material existence, John or Jane might never ascend to a higher consciousness.
In the material plane, a person is born as they are. If they never learn to accept or fail to develop spiritually or in being, they may never be satisfied or content.