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Oprah Winfrey on Forgoing Motherhood, Being 'Counted Out' and the Meeting That Turned OWN Around

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There's a good chance she'll be nominated for best supporting actress and will likely be in the audience at the Oscars on March 2. Two years ago, after attending the ceremony, where she was recognized for her Jean Hersholt Humanitarian Award, she did friend Jimmy Kimmel's ABC late-night show. He recalls his surprise at how comfortable he and everyone he worked with felt around her. "[That] night, when she came to do the show, she brought a bunch of tequila and we all did shots with Oprah," he recalls. "It really was inspiring the way she treated everybody, me included. She makes me want to be a better woman."

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All joking aside, that sentiment is shared by millions. On Nov. 20, President Obama draped a Medal of Freedom around her neck, telling a roomful of dignitaries and activists: "In more than 4,500 episodes of her show, her message was always 'You can.' You can do, you can be, you can grow and you can be better."

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Only 24 hours earlier, she had shared that message with some 1,000 Discovery employees at the company's headquarters in Silver Spring, Md. -- and another 1,000 joining by webcast. "I'm looking out at all of these employees who have tears streaming down their faces as she's talking about how you're worthy because you were born and how being of service is what makes you great," says Salata. Adds Zaslav, still marveling at his partners impact, "On my way out the door that day, four different people grabbed me and hugged me for bringing her -- and one of them cried."

That same passion for self-betterment drives her Oprah Winfrey Leadership Academy for Girls, the school she opened in South Africa in 2007 and to which she has contributed more than $100 million. Its devastating scandal -- accusations of sexual and physical abuse -- is now a distant memory. Today, the academy touts a 100 percent graduation rate, and every member of the school's first three graduating classes has continued on to college.

Among the first things she does when she rises around 7:30 a.m. each day (no alarm clock needed) is exchange emails with the girls of OWLAG. "I'm responding to everything from 'I'm feeling lost' to 'I need advice about a boy,' " she says. With 16 of the academy's graduates currently at U.S. universities, including Stanford, Smith and Barnard, she regularly travels to see them on campus, organizes an annual spring break trip and opens up her Montecito home for visits, including a recent Thanksgiving dinner. Two times a year, she returns to South Africa, where she teaches classes and spends individual time with as many of the 289 students as possible.

"What I really admire is her philanthropy, in particular as she uses it to help young girls," says former Paramount chairman Sherry Lansing of Winfrey, who is set to receive the leadership award named after Lansing at The Hollywood Reporter's Women in Entertainment breakfast Dec. 11. "That is one of the most wonderful things anyone can do."

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Winfrey acknowledges how stunned she is at how much the students have come to mean to her, especially given that, unlike her best friend, being a mom held little appeal. "Gayle [now a mother of two] was the kind of kid who, in seventh grade Home Ec class, was writing down her name and the names of her children," she notes. "While she was having those kind of daydreams, I was having daydreams about how I could be Martin Luther King."

She's certain she made the right choice. "If I had kids, my kids would hate me," Winfrey contends. "They would have ended up on the equivalent of the Oprah show talking about me; because something [in my life] would have had to suffer and it would've probably been them."

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At one point during our three-plus hours together, Winfrey mentions a desire to scale back on her dizzying schedule. That's among the reasons why she's moving from Chicago to Montecito, hopeful that she'll be settled in the property's main house (worth an estimated $88 million) by her 60th birthday in January. It's also why she held a much-publicized "yard sale" in early November, when she sold off $600,000 worth of lamps, teapots and sofas for charity. "It was about making space for a new life, which is what I'm getting ready to create for myself in California," she says.

A few days before we sit down, she got a sneak peek of what that life could look like when she and her longtime love, Stedman Graham, enjoyed a dinner out with friends in Los Angeles. "I was sending an email to say thank you so much for dinner," she says, "and I realized I couldn't remember the last time Stedman and I had been out." She grows wide-eyed as she discusses a future of long dinners and fine wine.

But a quick look at her world makes you wonder if she's really ready for change. Earlier this year, she embarked on a multicity motivational tour in Canada, and now she's planning to hit U.S. arenas in late 2014. For a woman who claims to love her own bed, she's rarely in it. She logged 235 days on the road in 2012, going everywhere from Haiti (for an Oprah's Next Chapter interview with Sean Penn) to New Orleans (to film The Butler), and 2013 looks to be only slightly better.

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Winfrey keeps her followers -- 22 million on Twitter, 2.1 million on Instagram -- abreast of all of it. She is active on OWN's message boards, too, and regularly live-tweets along with her shows, including Next Chapter and Super Soul Sunday. "She's closer to her viewers -- [both] the people that like her and the people that don't -- than any executive that I've ever worked with," says Zaslav, with King adding, "Oprah doesn't half-do anything."

She may not have her daily show anymore, but she's happy to impart lessons to those who are trying to follow in her footsteps, including Queen Latifah and Steve Harvey. She spent an hour on the phone with Latifah before her show launched this fall, telling her what she tells everybody who enters the daytime fray: "Don't do it until you have 100 percent creative control to be yourself." When she sensed that Harvey was straying, she called him up and told him, "I saw you in a chocolate factory trying to do that routine that Lucy and Ethel did. That's not you. Don't let people talk you into what they think is you."

Being your authentic self, to borrow a phrase from one of her many proteges, Dr. Phil, long has been key to her own billion-dollar brand. Winfrey is as comfortable divulging details of her own struggles, be it weight or sexual abuse, as she is eliciting them from others. "The Oprah phenomenon began because there wasn't anybody on TV who was so willing to be so candid and honest about the things in her life that weren't going so well," says Salata, who has worked with her for nearly 20 years. "And all of a sudden, we all could say, 'OK, I can acknowledge that I'm not everything that I want to be in every way I want to be and I can still like myself.' "

The only regret Winfrey harbors about her decision to end her talk show -- the most successful in history, with 12.6 million viewers at its peak -- is the timing. Had she had it to do all over again, she would have bid farewell before she tried to launch a 24-hour network. But after 25 years with The Oprah Winfrey Show, she says she had reached a point at which she felt she had little left to offer the format. "When [my producers] called me in and said, 'I know, we could take the audience to outer space,' I knew it was time to go."

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