I'm moving to a new, more transfriendly area soon and there are a few issues regarding my transition that are coming up. The backstory is that I'm hopefully moving to attend a new university. I'm pre-t right now, but once I start school I plan to begin seeking hrt. This becomes complicated when I introduce the work and home life aspects. As far as work, ideally I want to be able to transition while at my new job, so this is something I'm considering while applying to places. The question becomes, when do I address the issue of my transition with my new employers? So many jobs I'm looking at seem to be gendered, ie, counselor positions for girls or boys. And I would rather not wear my feminine professional clothes to an interview just to turn around and begin wearing ties once I'm hired. So, how do I find a job that will accept my gender identity before my physical transition? And then, housing situations also seem to be very gendered. Because I am a poor student, I am looking for a shared living space. Many people want to live with a male or a female... I am a guy, but will my roommates see me this way before I have facial hair and the voice to match? Does anyone have any advice for finding supportive living arrangements? Sorry this is so rambling, but I'm struggling to find my way through the beginning stages of my transition.

My own experience at work totally backfired on me (interviewed as female, started taking T, then came out about two months after that and got fired), so I can't help you there. But as for housing, you can try living in a dorm/apartment complex thingy and it'll likely be okay. Yes, it's gender-segregated, but tell whoever's in charge of assigning people to rooms about your situation and they'll probably be understanding. I live in an extremely conservative place, and even here, they let me live in the men's apartments (I'm pre-op and can't bind anymore so it's totally obvious I'm trans).

Then, assuming that part works out, explain to your roommates that you're trans (or go stealth, if you think you can pass; even without T, you can train yourself to speak with a deeper voice. There are YouTube videos on how to do it). If the apartment manager/whoever is good at what they do, they'll probably put you with more open-minded people. Social proof is a powerful thing, so when guys in other apartments see that you live with other guys in the men's-only apartment, they'll be more likely to accept or at least tolerate you.

If all that's totally not what you want to do, casually mention that you're trans to someone who's subletting or whatever; the key is to not make it sound like a big deal (if you don't make it sound like a big deal, they'll automatically follow your lead and not think much of it, either; it's a weird social thing). Don't make it the first thing you say, though, if you can.

Also, when it comes to passing (if you decide to go stealth), confidence is actually more important than anything else. A few days ago, I was feeling confident as hell (not typical for me), and even though I can't bind and none of my clothes really disguise my chest, when I ordered pizza, the pizza guy got my gender right, amazingly. When you're feeling confident and if you learn how to lower your voice, it'll actually be easier to speak in a lower voice (that's how it was for me pre-T, anyway).

Good luck!

Thanks for the reply. I'm 32 and with a cat, so I probably won't be living in a dorm at this college. I think I will take your advice about confidence and making trans a non-issue, though. Maybe I will start looking at the male only apartments more seriously. I'm probably overthinking the problem, which is typical for me. I will check out the youtube videos about lowering my voice, thank you.

Is there no option to transition while in school so that you could then apply for jobs as male?

That would be ideal, but I'll need a job ASAP so I can afford rent before I transition. I guess I could change jobs once I start T?

Changing jobs is an option. I'll be transitioning during school and will have part time jobs that don't matter to me so that I can pay my bills. Once I'm passable and have my ID changed I'll apply to jobs I actually care about.

I also tend to overthink things a bit too much, lol, so you're not alone in that.
I would either tell them right away you're trans, you're going to transition, etc. or don't tell them and swap jobs if you start your transition.
If you tell them immediately it might be tricky to find a place that hires you, but IF they do you're sure to have ended up in an open minded place. If you swap jobs later when you're starting to pass in public you could go stealth if you're afraid they won't hire you if you're trans.
It's so sad that employers even LOOK at that! I mean, one's competences and skills matter, not his/her gender and whether he/she was born AS that gender (physically)! Argh! *insert lots of nasty swear words here*

Also another thing is; how many people do you tell? It would obviously be pointless and stupid to tell EVERYONE "hey, I'm trans", then you're probably just 'trans' to attention whore on people, lol, but if I would meet someone, say a new friend, when and how would I tell him/her?
How would I get them to genuinely see me as my own gender, even if I don't pass?