So I came out to myself in October 2015 while I was cutting the lawn.

I made up my mind to come out to my sister as I drove 750 miles (1200 km)

Yesterday I was shoveling 7 inches of snow (with a shovel, work on the abs) and realized the reason my wife is not anxious to tell people - she's embarrassed.  And to a huge extent so am I and my guess is we're not alone.

So I asked her, after a long pause she said "I guess I am."  I think the nervousness I feel "going out" is actually embarrassment.  Isn't the Guy In A Dress syndrome just embarrassment on our part?

Anyone else embarrassed about transitioning and how do you get over that?

I think it's fear of the unknown. We fear that we will be rejected. I think that is most of it. It's all part of how we learned to adapt in society. How do we get over it? I'm not sure that we ever completely get past it. But like anything else, time helps.

It's something about how much value and power we choose to give to other people's perception of us.

If people are looking at you in a positive way while you act like a man and view you negatively while being yourself then you also must ask yourself, why is it so important for me to please people who view the real me negatively?  What is the payoff in going along?  Financial success? It's easier to achieve by being Mr. Normal.  Ease of socialization by conforming to social norms? Yes.  There are a lot of payoffs.  Family?  Well that's always a tinderbox.  Going along in the old ways for their sake or demanding something for oneself.  Either way is difficult, but even complete supression of one's feelings has its own costs bubbling up to the surface in passive aggressive resentments.
But is it more important to calm other people's minds or to find peace at the center of one's own mind?  It's a daily struggle. But awareness of how often we give other people the power to determine how we feel about ourselves.  That's important.

I mentioned this subject in an earlier thread. The first transphobe you need to deal with is yourself. Until you get past that...it's going to be an uphill slog. If you feel you're a woman, what is there to be embarrassed about? Are you? or aren't you? They were questions I finally had to ask myself, once I made it okay to let him go and be me, I no longer cared what he thought. What's important now is what I want and need and I am a woman so theres nothing to be embarrassed about. I won't  make excuses for who I am. If I do, then all my motives are questionable.  This is how "I" rationalize the issue and how I make it through every day.....finally happy!

I felt that way a little before transition - I was presenting the way I was comfortable but it was obvious (to me, anyway) that I still had very gendering features, and people would still binary gender me without an embarrassed pause on their behalf (the old "sir, I mean ma'am, no, ->-bleeped-<-, sorry!" Which is genderqueer ideal for me, because they honestly can't tell).
Transition to remove gendering features helped with that and I was more comfortable.
These days I'm just embarrassed around the few people who knew me before transition, and expect me to be my birth gender, when I'm well aware that I don't look that way completely anymore. It's just a discomfort thing, as I am also usually very private about these matters and I feel like I'm being exposed being around people who knew me before, when I presented cis. Doesn't help that they're transphobic and I'm obviously trans.
But I think that as you go along and get more comfortable in general with your body, that cringe lessens.

It's just easier to not have to explain this stuff to people you know and risk potential rejection.

I thought I felt this way but my SO felt like we had to get ready to move and go incognito because he feared the worst. I don't fear the worst exactly because I hardly know anyone where I am anyway. But he seems to feel worse about it than me.

I think I am more afraid than anything else.  I'm afraid of what others will try to do to me, how they will try to hurt me, and to be honest I have really lousy coping skills - something I really need to work on, but am unsure if I will ever have.  I'm a complete push over, almost too empathetic, a people-pleaser really.  I'm far too emotional, always have been.  If someone says something mean to me, I take it to heart, and dwell on it, usually wondering what I did to deserve such treatment..

I don't know if it is embarrassment though, not at this moment at any rate.  I think if I was not so worried about things like being beat up, having my house or car vandalized, having people lecturing me out of the blue, I would be okay. 

My wife wants to tell others, she seems almost excited about it.  I had to tell her to hold off, because she works at a school and I am afraid of the repercussions she could face there.  I think at this point, right now anyway (could change any moment ) I would be okay with people knowing I am transgender, if I felt they wouldn't try to cause harm to me or my family.

Sorry for rambling on.