Caitlyn Jenner reflects on transitioning to a woman: Part 1

Jenner talks about her bombshell Vanity Fair cover, giving her ESPYs speech in front of her peers and family and how she feels today.
8:39 | 04/22/17

Coming up in the next {{countdown}} {{countdownlbl}}

Coming up next:



Skip to this video now

Now Playing:


Related Extras
Related Videos
Video Transcript
Transcript for Caitlyn Jenner reflects on transitioning to a woman: Part 1
Two years ago, this is where it began. Bruce Jenner, athlete, famous dad on a reality show, waiting to stun the world by announcing inside he'd always been a woman. He greeted me at the door, 6'2" tall, welcoming and anxious. We'd never met before. How are you doing, baby? It's going to be an emotional roller coaster, but somehow I'm going to get through it. Reporter: And when we sat down for the interview -- It's been really tough. But here I am, I'm still here. That's the good news. Reporter: So Bruce Jenner is -- through tears, telling about the secrecy and confusion that had locked him into a kind of fortress his whole life. At a symbolic moment -- We're talking about all this stuff -- Reporter: The ponytail came free. Are you a woman? Yes. For all intents and purposes. I am a woman. And that's very hard for Bruce Jenner to say, because why? I don't want to disappoint people. Bruce lives a lie -- she is not a lie. I can't do it anymore. Reporter: In that moment, the anguished, uncertain man we knew as Bruce said farewell. And two years later, as we pull up to a door at a house in malibu, someone very different comes out to say hello. Welcome. Reporter: Remember me? I do. Two years. Reporter: Casual, still welcoming, and this time, excited. We have so much to talk about! Reporter: So what has it really been like, two years on the path living as a woman? Is the rumor of doubt and regret true? We start with that question from two years ago, slightly rephrased. So let me start with the same question. Caitlyn Jenner is? Happy. Peaceful. Peace in my soul. All of that confusion has left me. Reporter: You told me two years ago that a feminine side was a part of you. Mm-hmm. Duh. Reporter: Do you ever have doubt that you did the right thing? Never. Never had a doubt. I did the right thing. Reporter: Do you miss being Bruce? No, not at all. Not -- not even, not even close. Not even close. Reporter: She says in the old days Bruce would look in a mirror and feel the anxiety of a body in a kind of duel with what was true inside. And when you look in the mirror now, you get up in the morning and look in the mirror? I'm excited about the day. For so many years I isolated myself. I wasn't -- I couldn't care less about the next day. Now I do. Reporter: What have you learned about being a woman that you didn't know before these last two years? I think I've learned a lot about compassion. Caitlyn, have a great day. Same to you! Bye-bye. Reporter: She'd always said her dream was an ordinary day, an uneventful hello. I kind of come around the corner. And this guy goes walking by. And he just goes, "Morning, ma'am." "Morning," kept walking. And I just go, "How wonderful is that?" It's so simple. All right, we're going with the macaroni salad. Big one. And I'll go with the potato salad. How are you today? Reporter: You can see her two times a week at the supermarket, turning strangers into friends. This may be their only encounter with a trans person. I want it to be a good, joyful experience. Hi, I'm so sorry to bother you. Can I have a picture? My name is Linnea. 1, 2, -- I probably take, you know, 20, 30, 40 selfies every day. I can't tell you what an inspiration you are to me. Well, thank you. I appreciate that. What's your name? Matthew. Matthew. Get the camera out. Let's do it. Reporter: She says some people look at her because of her celebrity, but there are others who seem confounded or wary. I always wonder why they're staring. Reporter: The transgender community has a word for it. When you feel someone is staring and singling you out, - it's called clocking. I had a guy actually ask for a selfie and said, "Oh, Bruce, could you give me a selfie?" And I looked at him. Nobody's called me that in two years almost now. And? I said, "No problem." I want them to walk away saying, "Oh, Caitlyn Jenner was so nice," you know? That trans people, yes, are approachable. And they're a vital part of our society. Reporter: It's been her mission since that first magazine cover seen more than 3 billion times around the world. The cover that made your mouth drop. Okay, the cover of "Vanity fair." Reporter: What do you say about that picture? Now, my feeling on that picture, I know, my kids that thought, "You know what? It's a little too much." But from my standpoint, I had suffered for 65 years, okay? To have a beautiful shot of my authentic self was important. And the shock value. Reporter: You wanted the shock value? Yes. I wanted to end the old Bruce, my old life. And that picture did it. Reporter: Then she did it again four months later, in a room full of 6,000 people. Including superstars like Lebron James, Derek Jeter. It's the espys -- the academy awards of sport and she's getting the Arthur ashe award for courage. And in this room there are a lot of people who remember Bruce Jenner, the 1976 king of the decathlon. A man of unmatched strength and speed, mastering the ten olympic events that are the highest test of human endurance, and raw masculine power. Flying over the hurdles, heaving the shot put, so fast his competitors go down in agony, but he takes a victory lap for the usa. And now that same person is walking down the aisle in a long white dress. I'd like to thank my family. Reporter: There in the audience, the Kardashian stepdaughters and his six Jenner children. The biggest fear I've always had in coming out is I never wanted to hurt anyone else, most of all my family and my kids. I'm so, so grateful to have all of you in my life. Thank you. Reporter: Also there, looking up at the person on stage, thousands of the toughest competitors of every sport. What were all of them thinking? These are my peers. These are, I'd been to the espys so many times. Kind of a scary place to go. Reporter: You said you wondered if they're looking at you trying to be supportive. But thinking, "This" -- "What a freak." And I still wonder about that. Some guys can accept it, some guys can't. Reporter: Did you look at their faces? Or would it have been -- Oh, I couldn't look at their faces. Reporter: Too daunting. She says she made it through this moment by thinking about the thousands and thousands of transgender people around the world, living in fear from bullying, homicide. In the largest national survey of transgender adults, 40% have attempted suicide. All those kids just trying to live in a world of discrimination and ridicule. If you want to call me names, make jokes, doubt my intentions, go ahead, because the reality is, I can take it. But for the thousands of kids out there coming to terms with being true to who they are, they shouldn't have to take it. Reporter: A promise to be their champion. And two years ago telling me she was setting out to create an inclusive world. What I'm doing is going to do some good. And we're going to change the world. Reporter: Back when Bruce first emerged as Caitlyn and the path ahead seemed sure. Optimistic then? Too optimistic? I was hoping then, okay? There was a lot of hope there. Have I, in the last two years, had a bigger dose of reality? Absolutely.

This transcript has been automatically generated and may not be 100% accurate.

{"duration":"8:39","description":"Jenner talks about her bombshell Vanity Fair cover, giving her ESPYs speech in front of her peers and family and how she feels today.","mediaType":"default","section":"ABCNews/2020","id":"46948874","title":"Caitlyn Jenner reflects on transitioning to a woman: Part 1","url":"/2020/video/caitlyn-jenner-reflects-transitioning-woman-part-46948874"}