Oprah Talks O Magazine, Life Lessons, and Her Bestie Gayle at Hearst Tower

by Kristen Heinzinger

When Oprah comes to town, you make sure your schedule is cleared. Yesterday, a group of lucky Hearst editors got to witness the media mogul dish out some of her most divine Oprah-isms and lessons learned on her journey to becoming the mononymous marvel she is today at an intimate Q&A at Hearst Tower. Naturally, her bestie Gayle King was in the audience, as was O, The Oprah Magazine’s creative director Adam Glassman. Below, a few gems from the Hearst Master Class led by O Mags EIC Lucy Kaylin. Take it away, Oprah! 

Why she’s not a dreamer…
When I first met my best friend, Gayle, we were working at a TV station in Baltimore. I was making $22,000 a year and I was 22. I remember Gayle saying, “Imagine when you’re 30 and you’re making $30,000! And when you’re 40, you’re making $40,000!” My dream used to be to make the salary of your age. And then I stopped dreaming my own dreams, and realized that I would be more powerful if I stepped into the dream that creation had for me. If you can live the dream that’s already been dreamt for you, you don’t have to dream anymore.

How she keeps calm when fans freak out…
I was in Australia with the prime minister walking down the street—for some crazy reason we thought that was a logical thing to do—and I saw security pushing people back. I got really still, hands to the side, and I said not one word, and waited for everyone else to stop. You have to do that emotionally within yourself. That’s my greatest piece of advice for anyone who has a challenge going on in their life. It’s about being still so that you can know yourself.

On her decades-long friendship with Gayle King…
In our entire friendship, I can honestly say there’s never been a jealous moment. When I left Baltimore and I was moving to Chicago, and I went to tell my bosses that I was leaving, they told me that they were not going to let me out of the contract. They [said], “You’re going to fail, you’re going to walk into landmines, it’s a racist city.” Gayle is the one and only person who said, “I think you can do it.” I was going to be up against this guy Phil Donahue, who was number one for years. Not even I thought I could beat Phil Donahue. I went on the air, was myself, and beat him. There’s nobody else more shocked by that than myself and Phil Donahue. If you look back at the pictures of me, I was overweight and I had a Jheri curl. I did my own makeup, I shopped for myself at the local department store, I had on white stockings…everything possibly wrong. But I was myself. And that is the secret to any success in any work.

Why she bought herself a plane…
One night, I was sitting in an airport in Chicago, minding my own business. My plane had been delayed, and I was leaning over, trying to sleep. This woman comes up, and I can see her feet. I look up and she says, “I know who you are. You’re sittin’ here tryin’ to be all incognito. But you’re not actin’ the way you do on TV. On TV you’re huggin’ everybody. I want a hug.” I go, “…You want a hug?” She goes, “I want one of those hugs like you do on TV.” So I got up and hugged the lady, called my lawyer, and said, “I think it’s time.”

Her life lesson learned from “The Wizard of Oz”…
One of my greatest spiritual teachings is “The Wizard of Oz.” When Glenda the Good Witch says to the Wicked Witch of the West, “Go away, you have no power here,” that is profoundly true. You only have power in your own energy field. You have no power in anyone else’s territory.

Why she started O Magazine
The purest intentions that I ever had [were] the magazine and the talk show. Several people came to me about doing a magazine before I said yes—Anna Wintour, Conde Nast, Time Warner, Essence—but every time I would say no. When [former Hearst editorial director] Ellen Levine came to me, she had the key words. She said, “I know you love words, and with a magazine people get to hear your words.” Now you have my attention. I did this magazine because I want to spread the word. I want to spread the message of hope and beauty and insight and information.

On transforming OWN from struggle to success…
When I was in my deepest struggle with OWN, that was the saddest and most troubled I’d ever been. And then I realized it was the language I was giving it. I was calling it a struggle. I turned my own narrative around. I started speaking to myself differently about it. I came from a porch in Mississippi all the way to having a network with my name on it—what’s a struggle about that? I changed to seeing it as an opportunity. I literally had a “come to Jesus” moment with myself under my oak trees, just quietly praying, writing, meditating, reflecting on how I had gotten to that point. And I got still enough to feel what the answer would be.

How she balances authenticity with celebrity…
In my most recent partnership with Weight Watchers, they called me—obviously there was a problem [Laughs]. I said, I will not join because I don’t need it just to lose weight. I thought, How can I be of service for something that’s bigger than myself? Over the years, my producers would get so frustrated with me, because I’d say, “I can’t use that word. I don’t believe that world.” Even for a promo, they’d want me to say, “Please meet my friend.” And I said I couldn’t use that word, because the word “friend” is real for me. I’m not going to call them a friend because I met them a couple of times or met them at a dinner.

Who she would invite to her dream dinner…
Nelson Mandela, Maya Angelou, and I would ask Jesus to come by. I would probably have Harriet Tubman and have a conversation with her about that Underground Railroad.

Her little-known talent…
It was little known until Gayle Instagrammed it! My little-known talent is spot removal.

The biggest misconception about her…
That I’m an extrovert. I’m really not. I’m a combination of both, because you have to have some extrovert-ism to sit on television. But you all would be stunned to know the parties I turn down! I would rather be at home in my tub or sitting under my trees.

Chai tea or tequila…
[Long pause] What about a little tequila in the chai? They serve different purposes!

President Trump or President Kanye…
Oh lord. Don’t even imagine it.

26 or 62…
62, definitely.

An eight-hour lecture on revisions to the tax code or an eight-hour road trip with Gayle and she’s picking the music…
Did you say lecture? I might take that. You can at least zone out. I have never known anyone else with a range of music that could last for 11 days and likes to sing to it all.

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