Today's question is:
Do you feel being trans holds you back from your career choice?
This is a somewhat complicated question for me because building my career has in some ways spanned through a "pre" and "post" period: The "pre" being back when people viewed me as a butch woman, and the "post" being after I "passed" and people began viewing me as a man.
As for right now? Not really. The only time it affects me is when I have to deal with a background check that is actually seen by somebody making hiring decisions, and rarely has it actually posed a problem. Documentation is a bigger problem than transphobia. And that makes sense: I am a relatively privileged individual. I'm white, I'm educated, I'm male, people don't really read me as queer, I don't have a particularly non-standard gender presentation.
When I was going to school for Information Technology, though, then it was a bit of a problem... before hormones. I'm reasonably good at figuring things out myself, and my teachers were more than willing to help me out, but in my classes I was surrounded by dipshit cis male libertarian capitalist pieces of shit. When I wasn't on hormones and people read me as a butch woman (despite already having male documents and a male name), it was a regular occurrence that cis men would cut me off or wouldn't allow me space to speak, and since I didn't speak they assumed I didn't know computers very well. And I know what any dipshit cis dudebro reading this probably will say: "Well you just weren't assertive enough."
But after hormones, it just "magically" stopped happening. People let me talk, they didn't cut me off, and people suddenly trusted my understanding more. It was surreal and it was really gross. And I'm certainly not the only trans man who has had that experience. A great number of feminist-minded trans men got that way specifically because we recognized the huge differential of privilege that came with people suddenly seeing us as men.
This is the sort of experience that informs my perceptions when people try making the case that masculine women have privilege compared to other women, as well as people who desperately try to maintain that trans men as individuals have always had male privilege throughout our whole lives. There are some respects where this might change the way we behave; for instance, during high school I deliberately changed a lot of behavior because people called it "feminine," and having a masculine-sounding name is likely to help a woman land an interview. But it really isn't as simple as "masculine privilege."
In a nutshell, most of the issues career-wise I've experienced from being trans were due to misogyny, not necessarily transphobia.