OPRAH ‘5 moments that changed my life’
A global force for more than 30 years, the star looks back at her pivotal forks in the road – and considers how life might have been very different
‘My strength comes from a spiritual knowing that I’m part of something bigger than myself ’
Few have lived a life more examined than Oprah Winfrey, who has shared her triumphant climb from poor Mississippi schoolgirl to billionaire media mogul during her decades in the public eye. So when she sat down to discuss the crucial moments of her journey, she was initially faced with a very un-Oprah-like predicament: She wasn’t sure she had enough to say. But then came this question: What if she had zigged instead of zagged? What if key moments had gone the other way? “OK, that’s something that reads to me,” she says. “The what-ifs.” Since signing off from her iconic talk show in 2011, Winfrey has continued to ask herself, and her fans, bold questions while taking new risks: A year ago she announced a new multi-year deal with Apple to create original programming, and in January she’ll embark on the motivational 2020 Vision Tour. The woman who introduced the goal of ‘living your best life’ continues to change lives around the world, including lifting 1000 girls out of extreme poverty through her Leadership Academy in South Africa, while donating millions to charitable causes. Reflecting on the paths she didn’t take, the 65-year-old opens up about the age she never thought she’d live to see, her relationship with longtime partner, Stedman Graham, and why she’s still learning. “There is not a moment that can’t turn out to be useful later,” she says. “Life is a huge classroom, and when you learn one lesson, you get to move on to the next one.”
1 / Moving from Milwaukee to Nashville as a young teen
Born in tiny Kosciusko, Mississippi, to Vernita Lee and Vernon Winfrey, Oprah lived with her mum and two half siblings in an impoverished Milwaukee neighbourhood when she was in primary school. Then, as a teen, she was sent to Nashville to live with her father.
“I used to have this dream that I was going to be dead at 56, so the year that I turned 56 I was filled with dread. I had only told one other person that I had a number in my head when I was going to die, and that was Gayle [King, her best friend]. Gayle said, ‘What’s the number?’. I said, ‘I’m not going to tell you, because you will drive me crazy and then I will end up dead’. So when I got to 57, it was like, ‘Why did all my life I think it was going to be 56?’. At the time I started having this vision of 56, it was when I was in Milwaukee and I was trapped in a world where I could see how dire it was. Had I not gotten out of Milwaukee, nothing would have been the same. I do believe I would have been dead at 56. I believe I would have been almost 200 kilograms. I would have had diabetes. I would have had high blood pressure. I would have suffocated knowing that things could have been different.
“So for me, the big ‘zag’ was being sent to live with my father. If that had not happened to me, I would have been one of those people who would forever have been looking through the windows of other people’s houses wondering what that’s like. What is that warmth? What is that laughter? What is that feeling of comfort? I feel so deeply for people who are trapped and they know there was once a part of them at 10 or 12 or 15 years old that was smart and vibrant and hopeful. That thing got smothered and overwhelmed. And so, because I was just a zig away, I have great empathy, feeling and compassion for those people. I am always, through all of my work, also speaking to those people who feel like they got left behind, because a lot of people did get left behind.”
2/ Leaping from Baltimore to Chicago – and finding a boss willing to take a risk
In 1983, after seven years at Baltimore’s WJZ TV, Winfrey auditioned to host the local show AM Chicago.
“I interviewed for AM Chicago on September 3, which was Labor Day weekend. That was the only time I could get off, and everybody from that station, WLS, including [general manager] Dennis Swanson, came in on the holiday to audition me. He told me then I had the job. At the time [the show was airing] against Phil Donahue, who was national. I said, ‘I don’t know if I can beat him’. Dennis said, ‘We’re not asking you to beat him, because we know you can’t. We’re just asking you to go on the air and be yourself’, which was the greatest gift. When they asked, ‘When can you start?’, I had said, ‘Certainly by October 1’. When I went back to Baltimore, my boss said, ‘Well, your contract isn’t up until December, and we’re not letting you out’. But Dennis Swanson said, ‘We will wait for you’. Suppose he’d said, ‘Sorry, we have to find a host sooner than that’?”
3 / Deciding not to marry or have children
Winfrey met Stedman Graham, now 68, an author and business consultant, in 1986 at a charity event. After six years of dating, the couple announced their engagement. Fans waited … and waited for a fantasy wedding that never took place.
“At one point in Chicago I had bought an additional apartment because I was thinking, ‘Well, if we get married, I’m going to need room for children’. Doing the Oprah show allowed me to see the depth of responsibility and sacrifice that is actually required to be a mother. I realised, ‘Whoa, I’m talking to a lot of messed-up people, and they are messed up because they had mothers and fathers who were not aware of how serious that job is’.
I don’t have the ability to compartmentalise the way I see other women do. It is why, throughout my years, I have had the highest regard for women who choose to be at home [with] their kids, because I don’t know how you do that all day long. Nobody gives women the credit they deserve. I used to think about this all the time, that I was working these 17-hour days, and so were my producers, and then I go home and I have my two dogs and I have Stedman, who’s letting me be who I need to be in the world. He’s never demanding anything from me like, ‘Where’s my breakfast? Where’s my dinner?’. Never any of that, which I believed would have changed had we married.
“That’s why I had not just cold feet, I had two feet in a block of cement – because my feeling was, he is a traditional guy, but this is a completely untraditional relationship. If it remained a relationship, I can manage it. If I become the wife, now I’ve got to play by the rules of whatever that is, and that would not have been pretty. Both he and I now say, ‘If we had married, we would not be together’. No question about it – we would not stay married, because of what that would have meant to him, and I would have had my own ideas about it.
“Gayle used to say to me, ‘Oh God, I think you’re going to regret [not getting married and having kids] when you get older’. I have not had one regret about that. I also believe that part of the reason why I don’t have regrets is because I got to fulfil it in the way that was best for me: the Oprah Winfrey Leadership Academy for Girls in South Africa. Those girls fill that maternal fold that I perhaps would have had. In fact they overfill – I’m overflowed with maternal.”
4/ Swearing off sensationalist TV in 1989 after two pivotal episodes
After just three seasons of her talk show, Winfrey took a big chance
– she declared she would be producing only shows with inspiring and positive content. In an era when Morton Downey Jr and Geraldo Rivera brought in big ratings with shock television, it was an enormous risk.
“I was making the intentional effort to be a good force in people’s lives. If I hadn’t, I would have been out of television much sooner. It was the KKK skinhead show [during which fights broke out repeatedly and one guest was kicked out for profanity] and then the show with a man, his wife and his mistress. At the time, the producers thought this was one of the greatest bookings we could ever get. We thought, ‘He’s agreed to come on with his girlfriend? This is unbelievable’. Then there was a moment when the man says to his wife, ‘You know what? There’s nothing you can do about [the affair], because [my mistress] is pregnant’. We were live, and I didn’t know he was going to tell her, nor did the producers know. It’s one of my greatest shames, but a shameful act that allowed me to make the shift, because I go, ‘Never again will I do that to somebody. Never is that going to happen on my watch again’.
“When I [made the shift away from sensationalism], the ratings dropped at first, and I had affiliates who said, ‘What are you doing?’. We had said we were going to take the higher road, and the affiliates were saying, ‘Even if you’re going to do that, don’t tell anybody you’re going to do it!’. I had affiliates saying, ‘Well, why can’t you have Trash Fridays? Why can’t you just do it once a week?’. Then there were a lot of critics accusing me of trying to create the Church of Oprah. This was at a time when there weren’t so many voices. Now it’s hard for anybody to get heard saying anything meaningful. Somebody needs a curator out there to help you figure out what is and what isn’t meaningful. That’s what I’m doing for books. [Winfrey’s wildly successful book club, responsible for launching dozens of bestsellers, is relaunching via Apple.] But it’s hard to find somebody who doesn’t have an agenda and is focused on your best interest and not just their own.”
5 / Ending her talk show after 25 years to launch the Oprah Winfrey Network
After 4561 episodes, Winfrey wrapped her talk show in 2011.
“The most afraid I’ve ever been is after leaving the Oprah show and the struggle with [my network] OWN. That’s as close as I’ve come to feeling defeated. Even in the middle of that defeat, I knew that it would pass. I would say, ‘I’m going to admit this is bad right here. But this isn’t your whole life’. I didn’t know how long it would last, but in 2012 I took a beating. Everybody was saying, “You should have kept your day job, Oprah. It’s over’. People were essentially saying, ‘You are cancelled. What a mistake’.
“I questioned whether I made the right decision … Did I do it the right way? Should I have worked harder at doing a weekly show for ABC? Because that’s what I was working on.
“You know who was the best for me during that time? Stedman. He was saying, ‘You didn’t come this far to have your whole life discarded because of a decision to own a network. And whether that works out or it doesn’t work out, you still have a life’. It was also really, really helpful to meet Barry Diller [former Paramount and Fox CEO]. What I learned is that I’m the only one out here internalising every move, like it’s defining who I am. Men are like, ‘Invest in that business. If it works, invest [more]. If it doesn’t, move on’. Look at how many businesses Barry’s had – some more successful than others – and he doesn’t define himself by that. “Now we’ve turned it around, and I couldn’t be prouder of Greenleaf, Queen Sugar and the fact Tyler [Perry] created the foundation for our scripted programming, saying, ‘I’m going to help you out’. For me it’s the great reward.