Soledad O'Brien On Storytelling, Feminism's 'PR Issue' & Not Taking 'No' For An Answer

NEW YORK, NY - DECEMBER 10: Soledad O';Brien attends 2013 Billboard's Annual Women in Music Event at Capitale on December 10, 2013 in New York City. (Photo by John Lamparski/WireImage)
NEW YORK, NY - DECEMBER 10: Soledad O';Brien attends 2013 Billboard's Annual Women in Music Event at Capitale on December 10, 2013 in New York City. (Photo by John Lamparski/WireImage)

What does it take to get to the top -- without losing your center? Our “Making It Work” series profiles successful, dynamic women who are standouts in their fields, peeling back the "hows" of their work and their life, taking away lessons we can all apply to our own.

Soledad O'Brien has a lot going on.

She's the CEO of the Starfish Media Group, a production company and distributor she founded in 2013 with a focus on "life's untold stories." Alongside her work there, she's reporting for HBO's "Real Sports" and Al Jazeera America and producing her two documentary series, "Black In America" and “Latino in America." Oh, and she's raising four kids, too.

The 48-year-old broadcast journalist started her career in 1987 as an associate producer and news writer at WBZ-TV in Boston -- and she's come a long way since. She's co-anchored NBC's "Weekend Today" and CNN's "American Morning," and anchored CNN's "Starting Point." She's won awards for her coverage of events ranging from Hurricane Katrina to the Haiti earthquake to the 2012 elections. And in 2011, O'Brien and her husband Brad Raymond started the Starfish Foundation, which helps send young women to college.

Watching O'Brien at an AOL BUILD interview on Feb. 5, it was clear that she thrives in her different roles. While answering questions about social media and race relations, she talked about how her experiences as a journalist, a businesswoman, a mother and a woman of color inform the work she's doing -- and the work she hopes to do next.

O'Brien sat down with The Huffington Post to talk about advocating for herself, raising feminist girls and how people will surprise you when you ask for help.

How would you define success?

I think success changes as you change. Success before you have kids has a different definition than when you become a mom, than when you send your kids off to college. So for me, success is multifaceted. At one point it was about, “what’s my job title?” “How much money am I going to make this year?” Then you start thinking, “What’s the job I’m actually doing? What’s the quality of the work I’m turning in?” And then you think, “Well, what is my life like?” I think right now where I am -- with four kids who are all in the 10 to 14 range -- success for me is trying to figure out how to balance all the things that are important, and to balance them well. In a way where you’re not shorting yourself, or your work, which is something I’m very passionate about -- but you’re also not shorting your children, and your spouse. For me it’s about getting all these things to work in harmony.

Would you consider yourself successful?

Most days. I don’t think anyone is 100 percent successful. I think I am mostly successful, which is sort of what you aim for. You get up, you try to go to the gym, you try to eat well, you try to get your kids to school, help with homework and do good work and work on a project. And now I’m a CEO, so I'm growing a business. If you can make most of those things happen during any given day, then yeah, I think you’ve been pretty successful.

Why do you do the work that you do?

I have always been driven by telling good stories. Part of what drives me is to just tell stories about people whose lives fly under the radar -- that no one seems to necessarily care about. I think those stories can be incredibly interesting.

I also have four kids, and I’m really driven to be as good a mom as I can be. I long ago gave up on pureeing baby food, I don’t really cook very well, we have comforters so we kind of make beds like -- swoosh, cover it up. So I feel like I have figured out the parenting thing at this moment in time, and it could change tomorrow. When my youngest son was diagnosed as deaf, we had two responses. One, we were very grateful to know what was going on, because he had been struggling a lot. And two, it gave us a real perspective on how bad things could be. Because he was happy, and he was healthy, and he is doing well in school, and he has lots of friends, and he’s a happy kid. And it is very easy to not have that. Covering stories as I have for NBC and CNN over the years, when you cover real disasters, it gives you the healthy sense of -- well, this is not a disaster. So I know that whatever little drama that’s happening is not a disaster, and we will get through it. Having that perspective on life is incredibly helpful.

If you weren’t a journalist, what would you be doing?

I used to tell people that I’d be doing hair... because for any girl who grows up with a lot of big hair, learning how to work a flat iron would be a really good thing. I don’t know, I can’t imagine doing anything else. I was pre-med in college, and I really thought I’d be a doctor. And then I left school and decided not to go to medical school, and I didn’t really know what to do, and I started working at a TV station and I was just good at it. It’s now been 28 years or something. I would love one day not to have 10 jobs -- kids and running a company and running a foundation and running around like a maniac -- but I love storytelling. So I really think I’d be involved in telling stories about people in some capacity.

What advice would you give to young women starting to decide what they want to do in life? How do you encourage and guide your own daughters?

I think there’s so many times when girls and young women are told, “It’s just not gonna work out.” And if I could give anyone advice, it would be this idea that the doing it or not doing it is up to you. And you have to run around and exploit all the resources around you. Pick people’s brains, bring them lunch, buy them coffee -- and just get in there to see how people who are doing what you want to do are doing it. Learn by watching and osmosis. There’s so much of life that is being book smart, but there’s a big chunk that’s just understanding how stuff works.

I think women are often talked out of things. I remember when I had just had my twins, I had four kids under four years old. And the tsunami happened in 2004. I got a call from someone at CNN, and they said “well, we’re supposed to try to send someone to Thailand, but I know you won’t want to go, because moms don’t want to travel.” And I said to her, "Well, I have four kids under four, so Thailand sounds amazing!" And they sent me to Thailand. But it reminded me that you constantly have to challenge people’s expectations. [The caller] wasn’t trying to be mean, she just had expectations about what a new mom would do and she was foisting those expectations on to me. I said "Listen, here’s what I want to do." You have to restate it, sometimes firmly, sometimes gently, sometimes with a smile, and just constantly write your path -- and try to figure out how to get there. Hitting people up for information, help, guidance, advice, but staying on that path of “here’s what I want to do.” We’re just constantly, as women, talked out of it. “You can’t do this and that” -- but you can. You really can. If it’s something you really want to do, you can. And I think that’s a message that a lot of young women need to hear. You have to set the parameters of the experience and the success that you want to have.

Women's roles and the topic of feminism have been huge conversations in the past couple of years -- especially when successful young women come forward saying they don't identify as feminists.

I think that those women don’t know what a feminist is. Feminism needs a really good PR agency. They say, "I’m not a feminist," and then go on to describe exactly ways in which they’re feminist. That’s a PR issue, not a factual challenge. Those are just women who don’t know what it is, and maybe women who don’t understand what feminism has done for them. My daughters who are 12 and 14 would describe themselves as feminists. I’m very aggressive about it -- I show them the opportunities that they have. They’re always stunned to hear about when people couldn’t do what they can do. They just don’t know. I’m not sure that all those young women [decrying feminism] have someone drilling into their heads, "You know, the reason you get to do this is because there are a lot of people who fought for those opportunities."

Yeah, there's still this common misperception that feminists are man-haters who look down on other women for making certain choices, for example the choice to be a stay-at-home mom.

Sometimes part of the conversation is how we love to posit women against each other. Working moms versus stay-at-home mom, and somehow everybody is better than the other person. We do have these fights that are sort of whipped up and not necessarily valid. In my kids' school, my daughters are able to do a lot of things because the moms who don’t travel as much as I do welcome them into their homes and allow my daughters to have great experiences. And sometimes I can take my daughters’ friends on cool experiences because of some of the work I do. And I think of it as a sharing thing. We are all rooting for our kids and other people’s kids to do well. I think that’s more the reality than the way it’s positioned sometimes.

What do you think are the big issues women are facing? What’s holding us back from gender equality?

A couple things. I think that women have to really figure out how to advocate for themselves -- and I would add myself to that list. I was doing an interview he other day with Tamara Mellon, who used to run Jimmy Choo. And she said it really surprised her that when she started asking people for help in her business, no one said no. She got to the point where she was like, "I don’t know what to do, I’m stuck," and she turned to people and there was not a single person who said “I won’t help you. Leave me alone.”

As a new CEO, I have found that very true. I have never had a single person who I called up and said “listen, can I pick your brain about something that I’m working on,” never once has someone said “yeah, you know what, no.” And I think the same is true for the young women that I mentor, and the young women in our foundation. When they go up to someone and say, “I am stuck on a thing, can you help me figure this out?,” they always get support. They always get help. Not just from the people who are mentoring them, but from random people who are happy to take a moment to try to help them be successful. The world is really full of those people.

Women have to open themselves to saying, “I am not perfect. I am not flawless. I am going to get help, and I am going to get better.” That is a really good first step. And really trying to decide what kind of opportunities exist, and advocating for them. The whole argument about likeablilty. It matters, but at my age, you get to the point where you’re like “eh, screw it.” I’m too old. I don’t care anymore. You get to a point where you’re like, "I don’t care if you like me. You just need to think that I’m good." And that’s a very freeing thing. I just want to be good. I want to be clear, I want to be straightforward, I want to be respected, I want to have good quality work -- I don’t give a sh*t if anybody likes me. I don’t need to go and be their best friend. When I got to that point, it was really a great moment.

The last thing I wanted to talk about was your involvement with CoverGirl's 'This Girl Can' campaign.

I’ve been working on a project for them that should be launching very soon. They sent us out to go and do documentaries -- find young, amazing women who are overcoming challenges. The greatest assignment ever. When you invest in women, you can change communities. Literally.

How Amazing Women Are "Making It Work"