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For Oprah Winfrey, this is not the finale

Question: With her final TV show this week, Oprah Winfrey is taking up a new challenge: developing a cable network. What is the success rate for highly accomplished leaders when they move on to "second acts"? What are the usual pitfalls? And while we're at it, what has been the secret to Oprah's success as a business leader and shaper of public opinion?

The end of this week marks the first time in 25 years that the Oprah Winfrey Show won’t be kicking off the 4 p.m. hour block. In the sweep of television history, as well as for millions of loyal viewers, this is a big inflection point. After all, we’ve grown accustomed to seeing Oprah in the role of talk show host, entrepreneur, educator, life coach, leader and, for many, friend. As her “second act,” Oprah is taking on a new challenge: developing a cable network. The challenge may be a steep one, but it won’t be Oprah’s first attempt at the unimaginable.

Oprah’s life story is one of high improbability and unusual circumstances. She was born a woman in a man’s world; a black person in a white person’s world; for many moments in her life, she has been a heavy-set woman in a thin person’s world. And yet, in many ways, those anomalies became part of what has made her so authentic, so influential and—through it all—so human.

Day after day, month after month and year after year, Oprah garnered impressive ratings, creating the most successful talk show in television history. She did this by sharing a wealth of interesting people and stories with her viewers. But in the end, the most powerful, inspirational stories came from her own life, from the journey she herself was making along her life’s path. At times she let us see her vulnerability and fear; at others, she let loose a long, deep laugh at herself and her frailties. We saw her soar and we saw her gather her wings in close as she paused to consider a new direction. In each of these moments, she was both student and teacher, learning as she traveled and offering up that learning to those who watched and listened. Through it all, she has kept summoning what Abraham Lincoln called “the better angels of our nature.” And she called on us to do the same, exhorting us and cheering us on and showing us—over and over—how to “live our best life.” 

It has been five months since the launch of the Oprah Winfrey Network. A number of media observers are openly skeptical about the odds of Oprah repeating her success in this new venture. Certainly developing, overseeing and playing a myriad of roles—some onscreen—for an entire network is a more sprawling and complicated challenge than piloting the ship of the Oprah Winfrey Show. And certainly, many successful leaders have trouble achieving world-class success in subsequent acts. But as one who has been studying Oprah Winfrey’s leadership for nearly a decade, I would not bet against her. Looking back at the past 25 years, I believe there are several secrets to her success and numerous life lessons we have learned from Oprah along the way. These insights will serve her well along this new leg of her journey:

Adversity is a powerful classroom. In life, we each face difficult tasks, frustrating disappointments, disheartening failures and deep losses. What Oprah has taught us—and what she knows very well for herself—is that in tragedy and tribulation there is always redeeming possibility. Time and again she hammered that home, most powerfully in the way she walked her own path. Revealing personal misfortunes and heartbreaks, from a painful childhood to struggles with her weight, she has taught us there is always a diamond to be picked up in the thick grass—if we look for it and let ourselves learn from its light.

Admitting fault is a sign of strength. We’ve seen Oprah learn from mistakes with dignity and humor. Take the James Frey experience for example, in 2006, when Oprah admitted she had been wrong in defending him and the veracity of his memoir, A Million Little Pieces, and did so publically. (She would later apologize to Frey for being harsh with him on the air.) In this and other comparable moments, she let us see her as the student, learning from her own mistakes and in the process showing us that the higher ground is always worth seeking out and walking on.

Recognizing the importance of humor on life’s journey. Oprah has an uncanny ability to laugh at herself – whether she’s talking about buying a bathing suit, eating sweets or her relationship with Barack Obama. She taught us no matter what is going on in our lives, it’s vital to have a sense of humor.

Understanding that the big picture is important, but the little things keep life interesting. On her show, Oprah has navigated flawlessly between the smallest, juiciest details (like how to choose a lipstick and what Tom Cruise’s relationship with Katie Holmes was like when they started dating) to the big picture issues (like how to connect with God and the importance of forgiveness). She kept the show interesting because, segment to segment and season to season, we never knew where she was going to go. But no matter where she went, she kept a sense of proportion for what really matters, reminding us to look at the big picture.

Good guidance is worth listening to. Oprah’s most significant role as a leader has been that of a compass, gently guiding us toward our better selves. Fundamentally, she has been a mentor for us, and for herself. Oprah’s tagline over the years has been “live your best life.” We trust her good intentions because she’s always followed that advice herself – leading by example. We never suspected her of conflicted interests or motives, and she’s never let us down. In a world of fallen celebrities and public leaders with dark secrets, she is not for sale.

For a quarter of a century, Oprah has embodied her motto. With no one to answer to but herself and her fans, the possibilities are wide open for this fascinating, iconoclastic, joyful, thoughtful, complicated leader.

Nancy Koehn is a noted historian at Harvard Business School and an authority on the social and economic impact of entrepreneurship and on leadership in turbulent times. Nancy expands on the leadership lessons of Oprah in her latest iBooks bestseller, Oprah, Leading with Heart .

This piece is part of a discussion with our On Leadership panel of experts about Oprah’s past and future success.

Click here to see our full discussion page, or dive straight into another expert’s perspective by following one of the links below:

Marie Wilson: Oprah's many acts

Carol Goman: The secret's to Oprah's success

John Baldoni: How to succeed all over again

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Nancy Koehn  | May 13, 2011 11:45 AM

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