Real Leaders

Oprah Winfrey: “I Don’t Believe in Failure”

Photo by Simon Abrams on Unsplash

Oprah Winfrey holds a fascinating role in American life, with a celebrity status that goes beyond entrepreneur, TV personality and wellness guru. Most will agree that she Is certainly inspirational. She shares her greatest lesson, her hopes for the future and what she would have done differently.


What is the greatest lesson you’ve learned throughout your life and career?

My greatest lesson came from Maya Angelou, when I first met her. After I’d known her for a while, she said, ‘Baby, you know, you need to know that when people show you who they are, you believe them the first  time. Your problem is it takes you 29 times to see the same lesson coming in a different skirt, wearing a different pair of pants.’  That has been one of my greatest wisdom teachings – to assess from people’s behavior, their actions; and not just towards me, but towards other people; who they are and how they behave. Because if people talk about other people, they’ll talk about you. So, I think in business and in personal  relationships, that’s always been my greatest lesson. Also staying  grounded, you know, has been really great for me.

You’re on top of the world right now. What humbles you?

When I was called by the Golden Globe Awards and was told they wanted me to accept the Cecil B. DeMille award in January 2018, I said, ‘I shouldn’t be the person to get it.’ You know why? I was working with Reese Witherspoon at the time, and happened to just say to her in the make-up room one morning, ‘So how many movies have you done?’ She said, ‘Oh honey child, I don’t know. It’s been so many.’ And then I  thought, ‘I hope she doesn’t ask me because I think it’s been five.’ [laughs] I didn’t understand why they wanted to give me an award. Then, they explained that it was about overall entertainment. Now, what I was able to do with The Oprah Show and the cultural statement we were able to make throughout the world, I feel very, very proud of, but I think that when it comes to films, that I’m really the new kid on the block. I always feel when I’m acting I’m out of my box. It’s the most intimidated I ever feel.

What wisdom would you pass on to future generations of people in Hollywood who want to make films?

The way to make movies is to do stuff you love. For 25 years I worked on The Oprah Show, and Stedman [Graham – her partner] will tell you there were nights when I came home and it was hard to even take off my clothes because I knew I was going to be  getting up four hours later. But I never really felt exhausted, like  depleted. I felt exhausted, but I never felt depleted. Do the work  that comes straight from the soul of you, from your background, from stories that you’ve grown up with, from stories that bring you passion. The key to fulfillment, success,  happiness and contentment in life is when you align your personality with what your soul actually came to do. I believe everybody has a soul and has their own personal spiritual energy. So when you can use your  personality to serve whatever that thing is, you can’t help but be  successful.

If you do films that come from your soul, work or art that comes from inside you, you can’t miss. When you’re doing stuff that you think might make money, that may be a hit, or you think may bring you some level of attention or success, it usually doesn’t. All the great, wonderful experiences of my life that have  brought me to this moment have come from working from the interior of myself. That’s why it feels so authentic, because it actually is.  When you do that, you’ll win.

Oprah’s Life Lessons

Work together in the service of something greater than yourself. My deepest satisfaction and biggest rewards have come from exactly that –  picking a problem and doing something about it, because to somebody who’s hurting, something is everything. Vote. Pay attention to what the people who claim to represent you are doing and saying in your name. They represent you and if they’re not doing right by you and their policies are at odds with your core beliefs, then you have a responsibility to send them packing. Remember that people died for your right to vote, so don’t let their sacrifice be in vain. Eat a good breakfast, pay your bills on time, recycle, make your bed, aim high, say thank you to people and actually mean it. Ask for help when you need it and put your phone away at the dinner table (just sit on it). Know that what you tweet and post on Instagram today might be asked about in a job interview tomorrow or even 20 years from today. Be nice to kids, elders and animals. Know that it’s better to be interested than interesting.


You’ve always given great advice to everyone else. As you review your life, what advice would you give to a seven-year-old Oprah or a 13-year-old Oprah?

Age seven, I was so sad. At seven, all of my real love came from my teachers. You have no idea of the power of noticing another human  being and what it feels like when somebody knows that they’ve been seen, truly seen. It’s the greatest gift you can give, and from all those years of The Oprah Show, the greatest lesson I learned was that after every show, someone would invariably say, in one way or  another, ‘How was that?’ I would  finish an interview with a father who killed his twin daughters, I’d finish an interview with Barack Obama, George Bush or Beyoncé. They’d all say the same thing: ‘How was that?’ I started to see this common thread in humanity – where everybody wants to know how they did. ‘Did I do okay?’ ‘Did you  hear me?’ ‘Did what I say mean something to you?’ Recognizing this in other people has helped me to become a person of compassion, a person of understanding, a person who can interview anybody about anything because I know that at the core of  them is the same as the core of me. People just want to be heard.

There has been much social activism in America over the past year. Do you feel we are moving in a better direction yet?

From thousands and thousands of interviews and watching people in their dysfunction, when something negative is brewing, the direct opposite reaction is also possible. Because for every action, there is an equal and opposite reaction. When something as big as the Harvey Weinstein scandal started to unfold, I  thought, ‘Whoa, whoa, whoa!’ With each day’s new revelation, I thought, ‘Here’s an opportunity for something powerful. How do we use this moment to elevate what is happening instead of continually victimize ourselves?’ There isn’t a culture, race, religion or workplace that hasn’t been affected by this particular issue. People didn’t feel they could speak up. There are so many women who have endured so much and remained silent and kept going because there was no other recourse. Now that we’ve all joined as one voice, I think that it feels like empowerment to those women who never had it.

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