Keeping the Edge, Even When You’re a Billionaire

Anyone who’s ever found themselves in the middle of a true-life personal, physical or professional adventure, where the outcome is uncertain and the edge of the cliff is disconcertingly close at hand, might wonder how anyone would envy their tenuous position. Most of the people who say they envy adventurers haven’t spent too much time seriously doubting how they’ll pay the rent or how they’ll get through a bad weather situation in the wild. It’s not really as much fun as the movies make it sound. Envy the reward, sure. But the uncertainty at the cliff’s edge? You’ve gotta be kidding.
And yet, without the cliff’s edge, the rewards of challenge and learning and in-the-moment vitality fade, as well. I remember a conversation I had once with a highly successful entrepreneur who told me he envied my adventurous life somewhat. He’d taken daring risks at times in his career, so he knew what being on the edge felt like. But it had been a long time since he’d been there. Success had softened what he was putting at risk. He now had financial security and an entire firm to back his investments and calculated risk-taking. “I change clothes and roles often now,” he said. “But I’m not ever really naked anymore.”
If memory serves, I told him that nakedness was highly overrated. But even though I’d still desperately like to have a few more pieces of clothing at my disposal, I understood his point. I’ve never had the luxury of being in his particular position, of course, but even without the financial margin, I’ve learned that too much comfort takes the edge off of life. Not to mention the amount of growth you experience.
And while I haven’t actually talked to her about it, I think Oprah Winfrey would agree.
Oprah’s recent announcement that she was leaving her fabulously successful talk show in two years took a lot of people by surprise. Why on earth, the buzz went, would anyone give up such an incredibly successful and known power base? She’d likely lose the ability to create a bestseller overnight or boost a presidential candidate’s chances of election. Not to mention the financial windfalls that could keep coming her way, without her changing anything.
Oprah is an interesting entrepreneur and adventurer to watch … for many reasons. I wrote a piece for The Atlantic web site last week about why Oprah’s success should be studied … and yet would be hard to teach. Deep authenticity, and what Kleiner Perkins’ John Doerr would call “missionary” entrepreneurial drive—two of the strongest forces behind Oprah’s success—are not things that can be created as a strategy, or through model or method.
But Oprah is also an impressive role-model in terms of continuing life education. She was in an enviably comfortable position. And she may end up giving up power and influence by leaving. But then again … she may not. She may end up more powerful and influential by half, by running her own network and whatever other associated ventures she’s now throwing herself into. Only time will tell. Right now, even Oprah doesn’t know the answer to that one. But to find out, she has to get back closer to the edge and risk failure—or at least a loss in stature and influence.
Some might argue that a woman who’s so wealthy that she put $50 million into a “bag lady” account in case her fortunes turned one day isn’t risking anything with a new business venture. Financially, she’ll be fine, no matter what happens. But I would argue that for someone in her position to completely retool her golf stroke, as it were … leave the platform that made her so successful for the unmapped territory of a new and unpredictable venture … is a courageous move, indeed. Nobody wants to be known as the woman who used to be the most influential woman in America.
But that’s why I admire the move so much. Win or lose, she’s setting an example for the rest of us, and telling us that comfort isn’t all there is in life. She has more to learn … and she evidently decided that the only way to learn it was to shed some of her comfortable clothing and tread a little closer to the edge again.
John W. Gardner, who served as President Johnson’s director of the Health, Education and Welfare Agency and was the founder of Common Cause, said once that you don’t want to die with the music still in you. For all she’s accomplished, Oprah obviously believes she still has some unwritten or unsung music inside of her. So she’s setting out, at the age of 55, on a new adventure that might allow her to bring more of it into the world.
Her travels are worth following.
 
Lane Wallace is the Editor and Founder of No Map. No Guide. No Limits.