I Took My Former Boss, Gayle King, To Lunch & We Talked Breakups, Career Goals, & Yes, Oprah 2020

I asked my former boss Gayle King about everything from how to ask for a raise to whether long-term marriages are truly possible for career-oriented women — and, yes, whether or not her BFF will run for president in 2020.

Squiggly Line
On my first day as an intern at O, The Oprah Magazine in 2009, my supervisor immediately commented on my outfit. “That is such a Gayle King look!” she said with a smile. I looked down at my sleeveless sheath dress and long beaded necklace and realised she was right. And I was mortified. There I was, looking like I was trying to copy the style uniform of O's editor-at-large. As soon as King walked in, I cringed, waiting for her to notice and give me a Miranda Priestly-style up-and-down. Instead, she gave me a huge smile and said “Hey, I love that necklace! Where did you get it? I need to find it!”
That was my first glimpse at the natural instinct King has to make everyone from 20-something interns to her big-name guests on CBS This Morning feel at ease. I went on to become her assistant, and over the next four years I'd marvel at the way her energy immediately lifts the mood of a room. She’s endlessly sunny but not inauthentic, with a contagious, almost girlish giggle that comes out only when something is really funny, and a penchant for poking fun at herself. (Don’t miss her recent attempt to recreate her 20-something niece’s beach photoshoot on Instagram.) Still, life hasn’t always been rosy for King: Her father passed away when she was a psychology major at the University of Maryland, and she lost her mother when she was 40 years old. When her daughter, Kirby, and son, Will, were seven and six, King’s marriage dissolved due to her husband’s infidelity.
And now, more recently, she’s grieving a different kind of loss: her CBS This Morning co-host and friend, Charlie Rose. A few days after we sat down to lunch for this story, the Washington Post reported that the 75-year-old journalist had been accused by multiple women of sexual harassment; more allegations followed, and he was swiftly fired from both PBS and CBS. A week after a visibly shaken King said on air that she was “reeling,” I asked her over the phone how she’s feeling; neither of us knew this follow-up conversation would be just one day before the “sickening deja vu” she would experience when she learned Today Show host Matt Lauer had also been fired.
“I am still trying to process it all to be honest with you, because I think that the thing that made the show successful was the chemistry among the three of us, so I feel a tremendous sense of loss,” said King, adding that the show is only just now beginning to think about who Rose’s replacement might be. “I felt and still feel very close to Charlie Rose; you know that I was always Team Charlie Rose with my pom-poms high. I admired him greatly and really saw him as a friend and a partner. It’s extremely difficult to come to grips with the fact that someone that you cared about could potentially be capable of the things we read in the Washington Post. But as painful as that is, I’m still a woman, so I am glad that if there’s anything good that’s come out of this, it’s that women finally feel emboldened to speak up, and that they now have the language to do so.”
Photographed by Krista Schlueter.
Still, through all the rollercoasters life has thrown her way, King has always managed to maintain that signature sunny disposition; pity party is not in her vocabulary. I can count on one hand the number of times I ever heard her complain — and surprisingly never about her 3:22 a.m. wake-up time. (Yes, 3:22 specifically, so she can read the papers and catch the news on various channels before her 4:30 a.m. car arrives to take her to CBS.) After starting her career at WJZ in Baltimore — where she met her best friend, Oprah — King later became an Emmy Award-winning news anchor at WFSB in Hartford, Connecticut, and hosted her own Sirius XM radio show. That's all before becoming the co-host of one of the most-watched national morning shows in the country in 2011, and taking on the aforementioned O role in 2000. And she’s juggled all of the above while raising two incredibly well-adjusted, down-to-earth kids, now in their 30s.
Having recently turned 30 myself, I couldn't think of anyone better to kickoff my series in search of life and career advice. So I took my former boss to lunch at Emily’s in New York’s West Village, a burger-pizza joint that’s become a favourite since she visited the Brooklyn location before a Jay-Z concert. While we devoured wood-fired pepperoni pizza and dripping burgers as two kale salads looked on sadly, I asked her about everything from how to ask for a raise to whether long-term marriages are truly possible for career-oriented women — and, yes, whether or not her BFF will run for president in 2020. And this time? Lunch was on me.
Photographed by Krista Schlueter.
I have so much to ask you about, but let’s start with work and your career. What do you think was the biggest lesson you learned on the job when you were just starting out?
“My first on-air job was in Kansas City in 1980 when I was 24. When I arrived to WDAF-TV for my first day, the moving van hadn’t gotten there yet with my clothes and furniture. I had to go to work with no clothes, no nothing. I called a fellow reporter, Bruce Johnson, to tell him about it, and I remember expecting he would say ‘It’s okay, don’t worry, I’ll help you!’ But instead he just said ‘Grow up!’ and hung up the telephone. I just stared at the phone like, ‘Uh, hello?!’ That was a very seminal moment for me, because he was someone I counted on for advice, but it forced me to have to figure it out myself. So I went to Walmart and bought some clothes and did my live shot that day and then waited for the rest of my things to come. At the moment, I didn’t appreciate it, but looking back, I realised Bruce was throwing me in the pool to teach me how to swim. That was my newsflash that sometimes, you just have to count on yourself. And it forced me to grow up very quickly.”
Fast-forward a few decades, and you have not one, but two major jobs. What do you look for when you’re hiring someone at the beginning of their careers, like I was?
“I want someone who’s organised, because I’m very disorganised. As you know, I’ll get in the car and go ‘Where are we going again?!’ But I really want somebody who gets me, who’s a self-starter, who anticipates — and somebody who thinks outside the box. I don’t want someone who’s sitting there looking at the clock and doing the bare minimum. Someone who won’t wait for me to give them suggestions and instead will give me some suggestions.”
At Refinery29, we’re always encouraging our readers to ask for the compensation they deserve. What’s your advice on asking for a raise?
“I always say a promotion or raise is something you earn, not deserve. Just because you’ve been somewhere a long time doesn’t mean you deserve it. You have to prove to your boss that you’re invaluable and you add something to the work environment. And then when you feel you’re ready, you can lay out everything that you’ve done and build your case. You might think if you just do a good job that you’ll be noticed, but it doesn’t always work that way. Sometimes you have to point out ‘This is what I’m doing,’ because if you’re really good, your boss will have no idea how many fires you’ve been busy putting out. As women, we’re taught not to toot our own horn, but if there’s ever a time to be full of yourself, it’s when you’re going to ask for a raise.”
The Gayle King I know is very opinionated. How do you remain so un-biased as a CBS This Morning co-host?
“I’m very mindful that nobody wants to hear my opinion; they’re tuning in to see the news. That said, it is hard. When there are stories like Bakari Henderson, a Black kid who was beaten to death on vacation in Greece...I interviewed his family, and they’re heartbroken, and it’s hard to keep my cool and not get outraged. But our audience is very smart, and my job at CBS is to report the facts and let them decide how to feel.”
Do you ever feel, as one of the few Black women at the head of a major news show, that you have to represent for Black women?
“I never feel I have to represent. But I am very mindful that I’m a drop of cinnamon in a dollop of caramel. That puts me in a position where I can pitch and encourage stories that might get overlooked. Like when the Trayvon Martin story first happened, CBS was covering it, but I felt it deserved even more coverage than it got. I was very passionate about it, and because of that we were one of the first outlets really going hard with that story. I think my biggest responsibility is introducing people to topics or stories they might not be familiar with and educate them. And that’s why I think it’s important for women and minorities to have a seat at the table.”
Obviously with the reckoning happening in media and entertainment, we’re all talking about sexual harassment in the workplace. I know you and Harvey Weinstein used to be friendly. What was your reaction to the news about him?
“I do know Harvey and was friendly with him. He’d been on the show many times and invited me to lots of fun things. Listen, I thought and heard he was a bully about his movies, but I never knew about the kinds of things that came out. When they say it was an open secret and everybody knew, I wasn’t one of them, because I had never heard anything like that about him, ever. But I do worry now that everything is getting lumped into one category where we’re calling everyone a Harvey Weinstein. They’re both disgusting, but there is a difference between a guy who says inappropriate out of line things and someone who is a sexual predator. They are both wrong, but we need to be careful with that language, because there are fine lines.”
Is sexual harassment at work something you’ve ever personally dealt with?
“I wouldn’t say harassment, but there was one time where I was sitting in the newsroom on my typewriter, I was like 23. And this guy comes up to me, he was a photographer, and goes, ‘You know what I would like to do to you? I would like to lick know.’ And I’m like ‘What?!’ And then he repeated it! All I could do was laugh awkwardly. I was so thrown! Looking back at that now, I should have said ‘What the hell?’ It was just something very ew, and it didn’t have an affect on my career, but having been there I can see how young women would be so afraid of losing their job, or worrying about anyone believing you, or thinking ‘What did I do to make him think he can do that to me?’”
Photographed by Krista Schlueter.
Obviously things aren’t just a mess in media and entertainment right now, but in politics, too. What do you think 2020 is going to look like? Is there any truth to the rumours that Oprah might run?
“This is the thing: Donald Trump has got a lot of people who never thought about running for president or politics thinking about it. I would have never thought that in this country, you could be president of the United States with no political experience. I would’ve never thought that was possible! So I’m glad to see more people are considering it. But Oprah has said no, and I don’t think that’s happening.”
Well, I think Oprah would be amazing as president...
I do too actually...why do you think she’d be amazing?
I think she’s already been a leader for our country in a lot of ways, especially for women. But people of all races relate to and respect her as a journalist, a healer, and a businesswoman. There’s not even a single negative that I could think about.
“What I like, and I know I’m biased, but as someone who’s known her for so long, I know that Oprah always does the right thing, even when no one’s watching. What you see publicly and what you see privately, she always does the right thing. Something as small as, when she first started out, her publicist had made a deal with Us Magazine, but People was ginormous compared to Us back then, so when the publicist got an offer from People, she said ‘I’m so sorry, I made a mistake, People is calling, I’ll get you out of the Us deal.’ But Oprah said no, we can’t back out. We gave them our word, so we are going to do it. And sure enough, today you can probably find that Us cover and there she would be in that black and gold!”
How do you think Melania Trump is doing as first lady?
“I think she has a very difficult job because she’s following in the footsteps of Michelle Obama, who many people feel was the epitome of the perfect first lady. But I think Melania is doing a good job as first lady because she plays it just right. Donald Trump is so full and big, and she’s not trying to compete with him. She’s very focused on her son and being supportive and doing what she can. And I’ve met Melania, I know her, and I like her.”
What about Ivanka? You interviewed her earlier this you feel she’s complicit in her father’s actions as president?
“I think she has her father’s ear, but I get the impression that she picks her battles carefully with him. Because at the end of the day, it does seem that the president of the United States seeks his own council. And I think we can never expect her to ever say anything negative about her father, and I get that. But she does have the ability to walk into the Oval Office and say ‘Dad, what the heck?” I think she does that, but we can’t know what happens behind closed doors.”
Photographed by Krista Schlueter.
Okay, let’s shift gears a little, because aside from your career, I’ve also learned so much from you personally. You were married for 11 years, but I never knew: How did you and your ex-husband meet?
“I met him in Kansas City at the Safeway store! He was standing in line and I was buying some bananas, and the lady opened up a new line and said ‘I’ll take you over here.’ But he says that I cut the line, and I’m like ‘I didn’t cut the line!’ Then he was glaring. So I said ‘How come you never smile?’ And he said ‘You could make me smile…’ Obviously, the marriage didn’t work. But I have Kirby and Will, so that first meeting was so worth it.”
What’s your relationship like now?
“We have come to a place where we can actually get along. He sends me a joke every day. I’ve realised, you can spend your whole life bitching and moaning about ‘Girl, you know what he did?’ But you do have to get to the point where you choose between being a bitter person or moving on. It does take a minute to get there when you’ve been betrayed, though. But the bottom line is, and I say this to Kirby all the time, no matter how much you love somebody, you don’t want to be with someone who doesn’t want to be with you. You don’t want to have to convince somebody ‘You know, I’m really wonderful!’ And you know, I would be open to marrying again. Everyone sure is always setting me up!”
Was there anything you wish you had known about motherhood before you became a mum?
“No. And I never fell into the trap of beating myself up for being a working mother, either. I refused to do that. I remember my-ex husband was at home when he called and said Kirby just took her first steps, and I had just gotten off the air. I told everyone at work ‘Kirby just took her first steps!’ And someone said ‘You must’ve been so sad you weren’t there to see it!’ And I was like ‘Well, I’ll be home at 6, and I’ll see it’s not like she ran a marathon, and he videotaped it!’ I just refused to guilt myself. I think we have these self-imposed ideas, but are we really supposed to see everything? Go to every game? I say no. I think you really should just enjoy motherhood. And work gives me joy too. If you’re satisfied and happy with what you’re doing, it only makes you a better mother.”
Photographed by Krista Schlueter.
I’m someone who’s very career-oriented, and I think about your story, or someone like Oprah who has a partner, Stedman, but never married, and wonder if it’s really possible to be a successful woman and also have a husband who won’t be intimidated by that.
“I absolutely think so. You just have to be with the right person. I even look at the breakup of my marriage: That was a very painful time, but I wonder if I would be able to do what I’m doing if I were still married. I think my ex-husband had a lot of resentment about me and my position, which he might deny, but I felt that. So if that marriage hadn’t ended, would I be at CBS? I don’t know. But I believe with every fibre in my body that you can find the right person that celebrates you and encourages you. Because I don’t think it’s an either or for men. Man, woman, you want to be with someone who’s proud of you and cheers you on.”
What do you think is the biggest misconception about you?
“I guess that I’m just Oprah’s best friend. But I don’t get hung up on that. Because even when people say she’s just Oprah’s best friend...well, that ain’t a bad thing! I’ve never felt like I had to justify my existence, because the truth of the matter is, that’s how most people did get to know me, as Oprah’s best friend. I don’t think that’s a misconception, because that is what I am. You know what is funny is that when I started at CBS, people would say ‘Where did you learn how to do that, you’re really good at reading the news!’ And I go welp, I was working in Kansas City and then Hartford for 18 years...some people didn’t even know I had a job! They just thought I lived off of Oprah! How did you think I supported myself, people? I’ll be in the airport and people will say ‘What are you doing here? You don’t have a plane?’ And I’m like, yeah I do: It’s called American Airlines!”
You’re 62 and kicking ass. Where do you see yourself at 70?
“I don’t see myself on TV at 70, but never say never! I would like to have grandchildren, but I don’t think I’ll be the stay-at-home, babysitting kind of grandma. I’m thinking I would want to kick back. Maybe I’ll be in California with another radio show and some outdoor space! But right now, I have no intention of slowing down.”
As you know, I turned 30 back in August. If you could look back at your 30-year-old self, what would you tell her?
“That the things you’re getting all worked up about will work themselves out. The job you didn’t get, or the flight you missed, or the guy that did something to you; soon, that will all be a distant memory. The relationships with your family and friends are the most important things to focus on. One day, we’re all going to be a trivia question. Even Barack Obama, it’s going to be ‘What was the name of that first Black president?’ But you never want to be a trivia question with your family. If you can get things right with your loved ones, that’s the most important thing you can do. And looking back so far, I think I’ve done pretty good.”
Special thanks to Emily West Village!