Maya Watson’s Journey from Teen Mum to Oprah’s Right-hand Woman

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Hard work and smarts really do go far.

From teen pregnancy and single parenthood to a shaky career trajectory that culminated in an Emmy win, Maya Watson, vice president of marketing and social media for the Oprah Winfrey Network (OWN), has learnt the hard way that self-belief really can take you places.

It started when Maya was a young girl – her parents decided to forfeit the great American dream and move from their house in the suburbs. Instead of being upset, Maya was impressed by her parents’ gumption and the honest conversations they had as a family.

“[The] six of us had to move out of our nice four-bedroom house in the suburbs and into a two-bedroom, one-bathroom apartment,” says Maya, who grew up in Minneapolis, Minnesota. “They told us, ‘The next few Christmases, birthdays, they’re not going to be as nice as they were, but we’re investing in our future.’”

More than 20 years later, Maya is still inspired by her parents’ candour and believes being honest and transparent is crucial in her role at OWN. And while Maya says she’s not an entrepreneur, she does describe herself as entrepreneurial. “I work within an organisation, but I see things differently. Anything can be done if you’re honest and transparent with your team, your family, or whoever you need to rally behind you.”Maya’s post high-school life got off to a bumpy start; her rebellious streak saw her move across the country from the Midwest to study public relations and marketing at the University of Miami.

Wait…what? #lifeyouwantsj

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“I wanted to be as far away [from home] as possible. It was a big cultural shock. I had a great time, but I definitely lost myself, my direction and my intention,” explains Maya of her life in Miami’s infamous South Beach. “I partied and wasn’t going to school. I ended up in a relationship, I was 18, and I became pregnant. The day I found out, I was hysterical. I thought, ‘Oh my god, what have I done?’” Maya flew home to her family that day, and they rallied around her. “It was that reminder of when we were all living in that tiny apartment. We had each other’s back.”

She returned to college when she was seven months pregnant; her daughter Michelle was born in 2005. “It changed everything,” says Maya. “Once I got out of that toxic environment [in Florida], I remembered what I’m here to do. I’m not here to be a f*ck up, I’m here to actually get sh*t done. [Michelle] was the catalyst for getting my a*se in gear. The first time we made eye contact, it was like, ‘I get it. This is so much bigger than me.’”

When Michelle was just two weeks old, Maya returned to her studies at a nearby university, going home to breastfeed between classes. During that time, she landed an internship at ESPN and started cold-calling Harpo Studios in Chicago, Illinois – the home of Oprah.

“I remember my dad saying, ‘You need to work for Oprah if you want to work in entertainment,’” says Maya. “This was before social media, so I just started calling. I was calling and not getting any replies, so I decided to drive to Chicago and turn up unannounced.”

Maya sat in the lobby of Harpo Studios for hours before someone from human resources appeared, handed her a business card, and left. It was all the motivation Maya needed. Over the next six months she maintained contact and, eventually, an internship became available. “It’s like the stars aligned, putting me so close when I was mission-driven and had purpose again in my life.

“They wanted interns who had just graduated and I hadn’t yet – I had one more semester – so I lied, and started the following Monday,” she says. “My university worked with me so I could do independent study, but my schedule was ridiculous. I’d wake up in Indiana on east coast time, take my daughter to daycare, drive 90 miles [140 kilometres] to Chicago, switch time zones to central time, work all day, then drive home in time to tuck her in for bed and stay up all night doing papers for class. I did that for a year!”

For those 12 months, Maya was working 12-hour days at just US$10 an hour, but loved every minute of it, not least because Oprah had been a staple in the Watson household while Maya was growing up. “My mum would say, ‘We’re going to watch this show together, then we’re going to have a conversation [about it].’” And so the seeds were sown for Maya’s dream to one day work for the star.

“It was exhilarating!” she says. “The Oprah [Winfrey] Show was at the peak, she’d just started campaigning for Barack Obama, had announced the Oprah Winfrey Network, and produced her first feature film, The Great Debaters… there was so much happening, and so fast. The people were so smart and creative and passionate about what they were doing… it was something to be proud of. On day one, I was like, ‘This is going to be such a crazy ride, but let me put on my seatbelt. I’m ready!’”

Understandably, when it came time to say goodbye at the end of her internship, Maya was devastated. In an attempt to stay on at the company, she fronted up at the desk of every department head – including Winfrey’s – but was met with the same response: there was nothing available. “I ended up leaving really disappointed and discouraged, because [the internship] had ignited something in me.”

Maya says that staying motivated and positive while she was out of work was only possible because she knew she’d done everything that she could. “I’d walk away knowing I put myself out there and took some risks. You don’t think, ‘I wish I did that or maybe I could’ve done that.’”

But then fate intervened. In 2008, Maya was campaigning for Obama in the battleground state of Indiana, knocking on doors seven days a week with her daughter in tow, trying to recruit voters. Eventually hired as Indiana’s regional field director for the Obama For America campaign, Maya was filmed by 60 Minutes for an election segment. When Obama won the election, one viewer noticed Maya on TV – Oprah Winfrey herself.“Obama won that Tuesday, November 4. But what was crazy is, I got a call from Harpo [the next] day, and they offered me a position.

“I trust and believe there is an architect of my life,” she continues. “That moment that Harpo called? You can’t choreograph that. By letting go and wrapping myself in something new, it gave me everything. Dots will connect, and doors will open you can’t even see.”

Maya quickly rose to the role of director at Harpo and was part of a team that won an Emmy for social TV in 2013. And when Harpo’s Chicago headquarters closed in 2015, and Oprah created her own network, Maya went along for the ride and at the age of 30, landed her current vice president role.

“I think because I was so young, people were like, ‘Can you do [social media]?’. I was able to gain expertise over a short time, and social media became a really big component of marketing. It was a combination of my talent, people believing in me and having the courage to speak up and say, ‘I can do this, I can handle this.’”

Read More: Oprah Shares The Unique Secret to Her Success With New Graduates

Since becoming OWN’s youngest executive in 2016, Maya has found strength and guidance in her working relationships, and believes it’s important to surround yourself with people who you can “be real” with: people who understand that striving for career progression, entrepreneurship and personal development can mean facing seemingly insurmountable challenges. “One of the things that drives me crazy is when you tell people you’re really upset about a situation and they try to talk you out of being upset. They’re like, ‘Oh, no, you should think this and be grateful.’ Well, yeah, that goes without saying, but I just need a moment to keep it real! And having people around that’ll let you keep it real and let you lament for a second, but still support and back you up, is really important.”

“It all starts from the top down,” says Maya, who now lives in Los Angeles with her daughter. “We have a great culture of transparency, candour, trust and honesty [at OWN]. It’s a masterclass in how to be a good human being, and how to run a company with integrity that’s mission-driven, validates your experience, and puts out content that changes people’s lives.”

Reflecting on her turn last year as a guest speaker at Wanderlust’s Amazing Women Entrepreneurs event, Maya says, “One of my favourite things to do is to be around women. You walk away feeling better, you sit a little taller. You feel in your power. Women, in particular, we don’t allow ourselves to feel everything. Being disappointed that something didn’t work out is okay; it’s natural and normal.

Read More: How to Master the Art of Self-Promotion

“We haven’t really created a culture that allows people to be human and not superhuman. I wish, as women, we were more accepting and not each other’s harshest critics. If you’re fortunate enough to have one person you can be super real with, and they accept you and love you through it, then you’re really lucky.”

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