For me, part of the journey has been one of self acceptance. Have I had those moments? Absolutely. Sometimes I get all dressed up, see myself in a mirror, and just hang my head and feel like an idiot.
I am not a woman. I am never going to be a woman. Even if I had all the transition surgeries, hair laserings, and voice training, I will never be a woman. A dear friend asked me if I felt like a woman especially when I crossdress, and I told her "Absolutely not!" Looking in a mirror I am trying to see a woman, and always failing. Maybe if I starved myself down to a size 6 and had a professional service spend hours trying to transform me, I might be able to just slightly begin to look like a woman, but I will never be a woman. Setting the bar of appearing as a woman is too high and I will always be disappointed.
But, though I was born xy, have no other condition that affects my genetic/health status as a male, have the appropriate bits for a male, and have fathered children... I am likewise never going to be a man. It simply isn't who I am. I can play the role of a man, society sees and interacts with me that way, and I can do a good job of it. But, I'm never going to be 100% a man. It's just not in me. So, for me to always present as male is to some degree just as much likely to make me feel an idiot.
Trying to thread that line between the two extremes is part of that journey for me. Finding where I am in between those, figuring out how to fully integrate all of me into me is the goal. In the process, I have to actively push away the "wtf?" moments. That's working against me, and I won't accept it anymore.