I didn't have much confidence at all pre-transition. I didn't transition for 13 years post-puberty because I was worried that my body was unfixably masculine. I was large-built, 6'2" tall, had very large arms, a huge upper body, a big sloping guyish forehead, a receded hairline, a large chin, a large nose, and a strong jaw.
Transition timelines on Youtube gave me hope. People who looked just as masculine as I did, with enough time on hormones, eventually started looking feminine.
When I finally decided I was going to do it, what convinced me wasn't so much a belief that I could do it, it was realizing that at age 27 I was still at an age that these things could hypothetically change. If I waited any longer, though, it might be too late, and I'd definitely need surgery to correct them if they progressed any further. It was the fear of masculinizing any more than I already was that gave me the drive.
In terms of physical attributes that gave me some degree of hope, my shoulder bones were about the same width as my hip bones, I had a relatively low waist-hip ratio for someone of my weight, smallish hands and feet for someone of my height, and my frame size as measured with the classic wrist trick and elbow trick were only in the small-medium range. So even though I was overweight in all the wrong places, I realized that my bone structure wasn't as bad as I thought it was, so it gave me some glimmer of hope that the bulk was just muscles and fat, and thus hormones and dieting could work a miracle and melt all of that male bulk away.
