The media mogul talked about her career, the
Kaylin addressed the most obvious, yet enigmatic thing about Oprah, namely her relatability in the face of her meteoric, and largely unrelatable success. How did she become Oprah?
"I used to be a dreamer. I used to have this dream that I would one day live on a house on a hill, and I used to tell my father and my stepmother that I'm going to buy you a house one day on the hill, and I had this dream of making a million dollars," Winfrey said, noting that at the time, she was working with King at a local TV station in Baltimore.
Winfrey was 22 and making $22,000 as an anchor.
"I remember Gayle saying, 'Oh my God, imagine when you're 30 and making $30,000? And when you're 40 and making $40,000," Winfrey said to laughter.
"So you're making $62,000 now?" quipped Kaylin.
"Imagine!" Winfrey, now 62, said. "It used to be my dream to make your salary and your age…and then I stopped dreaming my own dreams and realized that God — by whatever name you define God, the energy force field of your life, that which is greater than yourself, the creator of all, all that is, whatever name you use — I realized that I would be more powerful if I stepped into the dream that creation had for me. I stopped dreaming and I allowed myself to be in the dream."
Winfrey, who is reportedly worth $2.9 billion, is probably the only person alive who could get away with that kind of new age-tinged talk without evoking eye rolls or sighs from the New York audience.
"If you surrender your will to a greater will, then there's a flow. There's an energy field that comes right out of you…that is connected to the energy field out of life," she said. "If you can find the current of that and live the dream that's already dreamt for you, then you don't have to dream anymore … everything that is happening to you is also happening for you."
Talk of destiny and finding that path — consciously or not — is empowering, and Winfrey knows it. She explained that she came to the realization of finding her own energy and path through meditation and taking long baths — a relatable pursuit.
"Some of my most still moments come from my bathtub," she said, noting that one of her "saddest" and "troubling" times in life was when her network, OWN was "struggling."
Battling challenging ratings and the glare of a skeptical press, OWN didn't mirror Winfrey's past high-flying success when it was launched in 2011.
The exec said she began using different language to describe the network and she reflected on why she started the company.
Kaylin then addressed Winfrey's celebrity and how she seemed disaffected by it. The editor in chief recalled riding on Winfrey's private plane and watching her prepare to interview President Obama in 2012 and then-Republican presidential nominee Mitt Romney.
"You were a working reporter," Kaylin said, noting the irony of the suggestion of a working reporter owning a private plane.
Winfrey didn't let herself get cast as a billionaire playing at a job.
"Listen, I have my own plane … and I've actually had my own plane since 1990. I haven't flown commercial since 1990," Winfrey said, before explaining that she used to drive a Chevy Chevette even when she hosted her eponymous show in order to pay off her debt. Her decision to buy a plane only came years later when she was stuck in a Chicago airport on a three-hour delay. A woman approached Winfrey and demanded a "hug" and her cheerful TV schtick.
"I hugged the woman … then called my lawyer and I said: 'It's time' [to buy the plane]," she said.
Winfrey would also address her passion for storytelling and why she decided to work with Hearst on a joint-venture magazine launch in 2000.
Winfrey said she had been approached by Anna Wintour via Condé Nast and Essence Magazine (owned by Time Inc.) to create a magazine. No one was able to convince her until she met Ellen Levine, Hearst's former editorial director, who told her a magazine would allow her to spread her message though the written word, something she treasured.
Now, 16 years later and 200 covers under her belt, Winfrey acknowledged the challenges of the magazine industry, but underscored the enduring importance and "necessity" of magazine storytelling.
Before the talk concluded, King, who sat in the front row, shouted out a question about the presidential election, asking her friend to comment on the race.
"The election is so crazy. I just got my absentee ballot for Colorado, and will be voting for her [Hillary Clinton]. I'm voting for her because it feels illogical to me — illogical — to vote any other way," Winfrey said, brushing off an old comment made by Donald Trump that she could be his running mate.
"I think he forgot me," Winfrey said. "I will say this, too — both Gayle and I know Donald and we have seen him around and have had conversations with him. Every time we see him, and we say, 'What is going on?' and he's like, 'Well, you know me,' and I'm like, 'I thought I did.'"