So I've worked for this place for several years and am the senior dev (small place). I only just emailed him a few minutes ago to let him know I'm trans and will also be out for over a month in January - February for surgery.

Peak anxiety, man. AMA.

Edit: he's cool with it! He said he did pick up on some cues so...yeah! He offered to help tell my coworkers too, which is something I have to think about (but seriously awesome too). Looks like I'm keeping my job!

what do you think theyll say? and will you update us on what they say?

I have no clue. I hope it’s not a “you’re fired” reaction, but I’ll be ok even if I’m let go.

I’m hoping he’s picked up on the few clients over the years who thought I was a woman (not a lot of them, but still) and that it might soften the shock.

I’ll update everyone here once I get a response.

He's cool with it! He said he did pick up on some cues so...yeah! He offered to help tell my coworkers too, which is something I have to think about (but seriously awesome too). Looks like I'm keeping my job!

What employer would fire you for being trans? Of course you're gonna keep your job. It would be discrimination to fire someone for being trans or becoming trans man.

Not in my state. It’s also a small business, so there’s not federal protection either (from what I managed to Google).

Do you have any idea of what his reaction will be, or is it a complete shot in the dark?

Read update. He was cool with it. I had no idea if I was going to keep my job when I sent it, though.