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

This story first appeared in The Hollywood Reporter‘s Women in Entertainment Power 100 issue.

It’s an unseasonably warm November day as I wind my way through the roads of Montecito, Calif., to an estate tucked behind an imposing gate. A security guard checks my credentials as I arrive. I’m a bit tense, but who wouldn’t be? In a matter of minutes, I’ll be interviewing the most famous woman in the world.

The iron rails open to reveal grounds so exquisite, they could be confused for a five-star resort. The guard has hopped on a golf cart and now is leading me through manicured greens that stretch 42 acres. For a second, I catch a glimpse of the property’s main house, a neoclassical edifice in the distance. Scurrying about is a sea of workers, who are a year or so into a remodeling project still months from completion. We take a sharp left, meandering down a long cobblestone road toward another property, this one shielded by a wall of bricks. I park my car and am ushered through a door that leads to a modest, multibedroom cottage — and suddenly I see her, Oprah Winfrey.

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She’s dressed casually in calf-length khakis, a white button-down shirt and a pair of Jimmy Choo flats she’ll soon lose. Her soft curls are pulled off of her face, and she radiates the warmth for which she is well known. I have spoken to her by phone only a handful of times and still she pulls me toward her for an embrace that puts me at ease. Then she steps back and assesses my sartorial decisions for the day. Her eyes fall to my feet, wedged into 5-inch heels, which now I see were overkill.

“Girlllll!” she teases, with bellowing laughter, before leading me to a patio table where a lunch of root vegetable soup and lobster Cobb salad will be served.

Welcome to the world of Oprah, a mix of grandeur and simplicity, the huge and the humble. She’s one of the richest women on the planet (worth a reported $2.9 billion, she is the first African-American female billionaire and one of few self-made women at that level). She also is one of the busiest, with her own from-the-ashes TV network (OWN), production company (Harpo), magazine (O, The Oprah Magazine) and a hit film (Lee Daniels’ The Butler) that is generating serious awards-season buzz. (Winfrey was nominated for a Screen Actors Guild award Dec. 11.) But you’d never know it on this afternoon.

There are no phones in sight, no evidence of handlers or assistants. She laughs readily and easily and makes clear her afternoon is mine. If she launches straight into interviewer mode, eager to know who ranks among my favorite subjects, it is to be expected. She is Oprah, after all, whose daily talk show ruled the airwaves for 25 seasons. The only time edge creeps into her otherwise relaxed demeanor is when I ask about the near “nervous breakdown” she reportedly suffered in 2012. “I never had a nervous breakdown,” she insists, noting how Access Hollywood had taken an interview she gave about her overwhelming workload out of context. “I thought that was such sensational exploitation.”

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It is clear that her memories of that incident — and the emotions surrounding OWN — are still raw. And she’s the first to admit it.

At one particularly low point in April 2012, Winfrey succumbed to the media’s decidedly negative narrative about her then-struggling network. While seated beside longtime friend Gayle King and co-host Charlie Rose for a segment on CBS This Morning, she said, “Had I known it was this difficult, I might have done something else. … If I were writing a book about it, I could call the book 101 Mistakes.”

The bout of self-pity infuriated David Zaslav, Discovery CEO, whose company had poured $312 million into the network. Three days later, the executive pulled her and her two top staffers, OWN presidents Sheri Salata and Erik Logan, into a room at the Mandarin Oriental in New York following the channel’s upfront, and said: “We are going to change the f—ing narrative. Enough of the ‘how hard this is’ and ‘boy, is this difficult.’ It ends now.”

Zaslav was right, and Winfrey knew it. She describes a “come to Jesus” talk she had with herself: “What did you expect would happen? You were going to end the Oprah show, go on a little cruise and then step in and everything was going to be fine?”

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If anyone is a living, breathing embodiment of “Live Your Best Life,” the Winfrey it’s-never-too-late-to-improve mission on which OWN was founded, it is Winfrey herself. Rather quickly, and at her direction, the network — previously a punching bag in media circles — began to take shape.

In July, Zaslav announced in an earnings call that OWN, a 50-50 partnership between Winfrey and Discovery, was in the black. Headlines such as “Oprah Winfrey isn’t quite holding her OWN” gave way to “Oprah Winfrey’s OWN becomes profitable faster than execs predicted.” The channel, buoyed by a handful of Tyler Perry shows and a collection of Winfrey-fronted series, registered a ratings uptick of 20 percent in its key female demo thus far this year, and cable and satellite operators agreed to pay millions in fees to carry the network going forward. “It makes it sweet,” says Logan. “Going through what we went through, we really appreciate where we are today.”

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Concurrently, Winfrey was at work on The Butler, only her third feature film as an actress in nearly as many decades. The $30 million drama in which she plays the alcoholic wife of a longtime White House manservant has earned $116 million at the box office and made Winfrey the subject of Oscar talk (she was nominated for her debut role in 1985’s The Color Purple) — not bad for a film she had serious doubts about making. She had turned down previous roles director Lee Daniels had offered her in The Paperboy (the part went to Macy Gray) and Prisoners (it moved forward without him), arguing that both were too dark for her liking. “Acting is about going into the space,” she says, “and there are just some places that I’m not willing to go.”

Though she claims she’s “never loved” any experience more than she did Color Purple, she felt the timing was all wrong when Daniels came knocking, just as she was wrestling with all the challenges plaguing OWN. But the idea of being part of a film that could educate audiences about the role women played in the civil rights movement, coupled with Daniels’ relentlessness, convinced her to accept, “I went from screaming to crying to pleading and then I caught her at a very calm moment [at her home in] Hawaii,” the director says, “and I went straight for the kill.”

The result was well worth it. “Winfrey is a full-throttle wonder,” wrote Peter Travers in Rolling Stone, “filling her role with heart, soul and a healing resilience.”

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.”

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.”

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.”

The story of Winfrey’s rise from poverty and abuse in rural Mississippi by now is well known.

By the time she entered elementary school, she had decided she wanted to be a missionary. She’d save her lunch money and urge other kids to do the same. “I’d collect it in a little cup and take it back to church on Sunday to give to the starving children of Costa Rica,” Winfrey recalls. “I always felt that whatever you have, you have to share it.”

It was that philosophy that inspired OWN many years later. When she and Zaslav first sat down in April 2007, she was struck by the idea of launching a network of higher consciousness. But Winfrey, who watches little TV (exceptions include ABC’s Scandal), misjudged the audience. The series of disappointments came fast.

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The early days were marred by delays, management upheaval and reports that OWN might not survive. A year in, Discovery had nearly doubled its initial budget, and the ratings — like the press surrounding it — were dismal. After decades of unremitting success, failure hit Winfrey hard: “I had become so accustomed to succeeding that I no longer even remembered what it was like to fail.”

The turnaround began when Winfrey redefined what the network needed to be. “We were too earnest,” says Zaslav. OWN has since broadened, pushing into other genre’s with Perry’s shows (The Haves and the Have Nots, Love Thy Neighbor, For Better or Worse), embracing the African-American audience and welcoming eye-catching programming such as a Lindsay Lohan docuseries and a two-part Lance Armstrong interview.

At this stage of Winfrey’s life, she has several decades’ worth of wisdom to share — and legacy, it seems, is top of mind.

One of the more valuable lessons she has tried to pass along to the girls, many from impoverished beginnings like hers, is one of managing success — and the wealth that can accompany it. “When you’re the most successful person in your family, in your neighborhood and in your town, everybody thinks you’re the First National Bank,” she says, “and you have to figure out for yourself where those boundaries are.”

What Winfrey learned is that people’s needs were in direct proportion to what they thought she had. “I got to the point where nobody ever asked me for anything less than $5,000. I felt pressured for a long time to say yes, because I thought, ‘I can’t lie and say I don’t have it. My salary is printed in the paper,’ ” she laughs, looking back at all her charity: “I’ve bought more houses and cars than I can even tell you.”

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Despite everything she has achieved, Winfrey is aware nobody can have everything. Her work in The Butler, for instance, hasn’t led to a deluge of other offers, and she surmises: “That’s the reality of being 59 and female, not to mention a woman of color.”

Still, she is thinking about Broadway next, trying to determine when she’d have the time. “It’s something I would like to do, but I’d like to get settled in my house, have a life and then make the next move,” she says. “I’d just like to be in the space where I really feel like I have nothing to prove.” Is she close? “I think I’m just about there.”

She readily admits to disappointments — not least how quickly people wrote her off when she left her daily show. She describes Graham as her foundation of support and, at times, her reality check. “He would say, ‘You think you’re going to rest on your laurels? You think anybody cares about 25 years?’ And I’d go, ‘Yeah, I kinda felt people did. Twenty-five years means nothing?’ “

In fact, it was Graham, not Winfrey, who kept track of all that was said in the press. “The other day I said to Stedman, ‘I hear it was bad,’ and he goes, ‘Oh no, no, no, it was worse than bad,’ ” she says. “Same thing happened with Gayle. I said, ‘I heard people were counting me out.’ And she goes, ‘No. You were counted out.’ “

But she refuses to dwell on such things. She is, after all, America’s embodiment of optimism. As Obama said in awarding her the Medal of Freedom, the highest civilian honor a U.S. president can bestow: “Oprah’s greatest strength has always been her ability to help us discover the best in ourselves.”

As for Winfrey herself, she’s still on the path to getting there. “This has been the great climb of my life,” she says of the past three years. “But I still have a long way to go.