Mentoring, Women in Leadership

#MentoringMonth: Oprah’s Mentor in Literature and in Life

By Mike BergelsonJanuary 9, 2015

She grew up in rural poverty in Mississippi, wearing dresses made of old potato sacks. Now she’s a billionaire with her own TV network, a legion of fans, and a regular spot on lists of the world’s most influential women.

In this post, we’ll look at the mentor who helped Oprah Winfrey on her incredible journey, and what we can learn from their relationship.

Oprah Winfrey’s Mentor

Winfrey grew up reading the books of Maya Angelou, and found in them not only beauty but a wealth of shared experiences. The books helped her through a difficult childhood, and as she read them over and over, she never dreamed that she would one day meet the author.

But when she was in her thirties and in the early days of her TV talk show, she got the chance to go to Maya Angelou’s house. She sat at Angelou’s feet, listening to her read poetry, and they formed an immediate bond. They talked, Winfrey says, “as if we had known each other our entire lives.”

As Winfrey was telling Angelou about her experiences, she got a piece of advice that would change her life:

“I was sharing with her some of the mistakes I’d made in my twenties, and I shall never forget what she said to me: ‘That was when you were twenty, and now you’re in your thirties. When you know better, you do better.’ It was one of the great lessons of my life.”

Winfrey says the advice freed her from being weighed down by her past, and enabled her to judge herself not by who she had been, but by who she was and who she aspired to be. She has since used that phrase on her show dozens of times over the years.

Winfrey still regularly meets with her mentor: “She’s the woman who can share my triumphs, chide me with hard truth and soothe me with words of comfort when I call her in my deepest pain.”

And mentoring others is now an important part of her life as well. She shares many of the lessons through her TV network, magazine and other media ventures, but also often does in-person mentoring. This article lists Dr. Oz, Suze Orman and Dr. Phil as some of her protégés, and says she is now mentoring actress Lindsey Lohan.

She has also set up the Oprah Winfrey Leadership Academy for Girls in South Africa, to provide educational and leadership opportunities to girls from impoverished backgrounds, as both she and Maya Angelou once were.

Lessons from Winfrey and Angelou

Here’s what Oprah Winfrey’s mentoring experience can teach us:

  • As we saw in a previous post, great books can be a form of mentoring. But in-person connections are much more intimate and powerful.
  • A personal connection is vital to a good mentoring relationship. Oprah Winfrey and Maya Angelou just “clicked” on their first meeting, and that’s a hallmark of most successful long-term matches.
  • Sometimes a piece of advice from your mentor resonates so much that you not only learn from it, but also want to share it with other people every chance you get.
  • As we’ve seen with many of our other famous protégés, mentoring is about giving back, or paying it forward. People who’ve had great mentors often become enthusiastic mentors themselves.

Could you be mentoring the next Oprah? Share your wisdom with rising talent today.

Mike Bergelson

Mike Bergelson

CEO at Everwise

About the Author

Mike Bergelson is the CEO and a co-founder of Everwise, a talent development startup that connects employees to the people, development resources and experiences they need to thrive at every stage of their career.

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