Maybe it's complicated by the fact that many people transition after the point where they already have ideas or plans for their future careers. One woman I talked to actually transitioned in between getting a job offer at a major tech company and starting the job.

For the record, she said that everyone was really open and comfortable with it, and one of the first things her boss did was make sure that all her IDs and employee records were updated to reflect her actual gender identity, which was awesome.