This article previously appeared in Forbes.
Oprah Winfrey is one of the most successful entrepreneurs of her generation. Raised by her grandmother in rural Mississippi until age six and then by her mother, who worked as a maid in Milwaukee, Ms. Winfrey was an unlikely candidate to become one of the most dominant media personalities of modern America.
The tremendous challenges she overcame make Oprah’s career especially inspiring. The fact that she has handled her success so adeptly, despite her impoverished childhood, is astounding.
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When I began gathering examples of Oprah’s wisdom, I expected to identify a handful of quotes relevant to entrepreneurs. To my surprise, I identified dozens of worthy bits of wisdom. From these, I collected 23 insightful missives of interest to aspiring entrepreneurs. Oprah’s thoughts are group into four general categories: Fear, Failure, Success and Humility.
1. Fear – Channel It
“The thing you fear most has no power. Your fear of it is what has the power. Facing the truth really will set you free.”
Ms. Winfrey’s big break was an accident. An accident which Oprah’s hard work and dedication had more than adequately prepared her to exploit. Channeling the Roman Philosopher Seneca, Oprah later characterized her lucky break by saying, “I feel that luck is preparation meeting opportunity.”
In 1982, Oprah was the co-host of the local television news in Baltimore Maryland. As part of their job search efforts, one of the station’s producers created a montage tape of their work and sent it to a number of major-market stations, including WLS in Chicago. Coincidentally, one of the on-air personalities on the tape was Oprah Winfrey.
The WLS executives were immediately impressed with Ms. Winfrey and asked her to audition for A.M. Chicago, a glorified cooking show. Did Oprah know anything about preparing food on live television? Heck no. Did this slow her down? Of course not.
It was natural for Oprah to be apprehensive about assuming an unfamiliar role in the US’s third largest media market. However, she balanced her trepidation with a lifelong desire to face and conquer her fears, later stating, “I have a lot of things to prove to myself. One is that I can live my life fearlessly.”
Contrary to conventional wisdom, entrepreneurs are typically not blind to risk. However, they tend to view what most people consider to be “risky situations” as opportunities to be exploited. Oprah description of risk is typical of entrepreneurs: “I believe that one of life's greatest risks is never daring to risk.”
2. Failure – Refuse It
Oprah’s biggest failure was ultimately her greatest success. Her WLS morning show was well received from its outset. Within a few months of its launch, she was consistently beating Phil Donahue, the then-current national king of daytime television.
Her show’s local success led to a meeting in Los Angeles with several ABC network executives. The network owned Oprah’s AM Chicago show, as it was created under the auspices of her contract with WLS. Thus, in order to expand beyond Chicago, she needed to negotiate the terms with ABC.
After a brief meeting, the ABC executives told Oprah, (paraphrasing), “You have a great, local cooking show, but it has no future beyond Chicago.” Oprah was understandably disappointed.
Some young people would allow rejection by “industry experts” to short circuit their dreams. However, Oprah’s healthy balance of humility and self-confidence caused her to be undaunted by the network executives’ poor judgment. In the midst of her disappointment, she no doubt took the advice she has since shared with her fans, “Think like a queen. A queen is not afraid to fail. Failure is another steppingstone to greatness.”
On the return trip to Chicago, Oprah realized that by rejecting her local show, the network had effectively freed her from her contractual obligations, allowing her to own all aspects of her show; from the studio, to the syndication rights, to the hiring and firing of the show’s employees.
Like all entrepreneurs, Oprah’s career has included multiple failures. “Nobody's journey is seamless or smooth. We all stumble. We all have setbacks. It's just life's way of saying, ‘Time to change course.’” If you are not intermittingly failing, you are not trying hard enough. Oprah encourages entrepreneurs to expand their comfort zones by “Do(ing) the one thing you think you cannot do. Fail at it. Try again. Do better the second time. The only people who never tumble are those who never mount the high wire.”
One of Oprah’s setbacks was the 1989 television show Brewster Place. The ratings were poor, the writing was uninspired and Oprah did not have enough time or energy to devote to the show. As such, she elected to “change course,” despite the fact that she had already been paid a sizable bonus.
When she attempted to return the prepayment to ABC, the executives told her to,“forget it.” They were astounded, as no one had ever returned a prepayment. However, Oprah felt she had failed to deliver a quality product. After ABC rejected Oprah’s check, she suggested they give the money to charity, which they subsequently did.
Oprah realized that failing is a part of succeeding and that much can be learned when plans go awry. In her words, “So go ahead. Fall down. The world looks different from the ground.” You can never fail if you refuse to lose, especially if you have the necessary self-awareness to, “Turn your wounds into wisdom.”
3. Success – Envision It
“I had no idea that being your authentic self could make me as rich as I've become. If I had, I'd have done it a lot earlier.”
After being rejected by ABC, Oprah left WLS, formed Harpo Productions and launched a national show. Owning her show in its entirety also allowed her to be truly authentic, in a way that hosts controlled by large networks were unable to emulate.
She did not have to host B-level celebrities to cross-promote the network’s shows, work within arbitrary budgets, hire mediocre network employees or accept sponsors recruited by the network. Soon after she launched her national show, a major diet soft drink brand asked Oprah to promote their product. She did not drink the product and was able to refuse the company’s lucrative offer.
Saying “No” to certain advertisers was a cornerstone of her authenticity, which ultimately led to her global popularity. Her fans knew that she was not “for sale.” If she promoted a book, product, movie or diet, it was because she was a fan, not because she was earning a promotional paycheck.
Oprah’s message about success is empowering because she reiterates that success is not “something that happens to other people.” Success is a choice and the path to success is to identify your passions, define significant goals and then work your butt off. As she once said, “The big secret in life is that there is no big secret. Whatever your goal, you can get there if you're willing to work.”
Work = Fun
“When you're doing the work you're meant to do, it feels right and every day is a bonus, regardless of what you're getting paid.”
“What I know is, is that if you do work that you love, and the work fulfills you, the rest will come.”
“Forget about the fast lane. If you really want to fly, harness your power to your passion. Honor your calling. Everybody has one. Trust your heart, and success will come to you.”
Significance Is Significant
“The key to realizing a dream is to focus not on success but significance - and then even the small steps and little victories along your path will take on greater meaning.”
“How do I define success? Let me tell you, money's pretty nice. But having a lot of money does not automatically make you a successful person. What you want is money and meaning. You want your work to be meaningful, because meaning is what brings the real richness to your life.”
Change Is A Choice
“I believe the choice to be excellent begins with aligning your thoughts and words with the intention to require more from yourself.”
“The greatest discovery of all time is that a person can change his future by merely changing his attitude.”
4. Humility – Exude It
“Be thankful for what you have; you'll end up having more. If you concentrate on what you don't have, you will never, ever have enough.”
Oprah remained the most watched daytime television host for over two decades. One of the reasons she was able to maintain and grow her media empire over such an extended period was her ability to maintain an emotional and personal connection with her audience, despite her tremendous wealth and power. As she said on numerous occasions,“I still have my feet on the ground, I just wear better shoes.”
Another reason Oprah retained a solid connection with reality was because she surrounded herself with a team who worked with her from the outset of her venture. A wise leader, Oprah was loyal to the early members of her successful startup, understanding that her success was shared by everyone who contributed to Harpo’s growth. As she once said, “Lots of people want to ride with you in the limo, but what you want is someone who will take the bus with you when the limo breaks down.”
Having It All - Eventually
It is no secret that Oprah has struggled since she launched the Oprah Winfrey Network (OWN). As usual, the popular press has been quick to decry OWN a failure. As Oprah once said, “You CAN have it all. You just can't have it all at once.” The lack of instant success is not equivalent to failure. As with any new venture, it takes time to hire the right team, define a viable value proposition and create a winning product.
As long as she can draw upon an adequate store of energy, my money is on the humble girl from Mississippi, the planet’s first African American Billionaire.
Follow my startup-oriented Twitter feed here: @johngreathouse. I promise I will never tweet about daytime TV hosts, dogs on skateboards or that killer burrito I just ate.
Photo by cliff1066™ on Flickr