How Will You Fail?

In My Humble Opinion: Harriet Rubin on living dangerously.

Just yesterday, one of the new filthy rich — a consultant with a great stock portfolio — told me that his new goal was to become a billionaire. At a time in his life when he could do anything — explore the jungle, help the sick, start a business that’s been his passion — he wanted only a bigger bank account. Some goal: The 1990s have been so good to us that we think danger means putting real cream in our coffee — instead of the fat-free stuff. When did risk become limited to how we invest our money, rather than how we spend our lives?


Every other year, which is roughly how often I find myself stuck in some safe routine, I spend time with a great teacher who reminds me that danger is the only way to live. John Tarrant is a Jungian therapist in Santa Rosa, California who is also a Zen master. That’s the black belt equivalent of kicking the shit out of what “isn’t” there. (You think it’s hard to kick the shit out of what is there?) The last time I saw John, he told me: “We go on a journey in our youth that we are called on to repeat in our forties. But this second time, the journey is different; it’s not one of discovery but of power and danger. We can either accept the invitation, or turn toward safety.”

Danger is everywhere today, if you look for it. Increasingly, it’s the only game in town. The definition of acceptable risk has changed in the last two years. Find me an angel who’ll invest in a sure thing. To be a leader in this new economy, you have to love risk — which means patterning your life on the heroic, not on the strategic. Acting boldly is better than acting knowingly.

I saw this new truth in action recently at Sun Valley, at the famous annual summer retreat organized by investment banker Herbert Allen. There, the top 100 media moguls make deals and raft down the chilly Idaho waters. All week long, the retreat participants put together companies and realign the media world. Everything is about risk. Stock markets used to reward companies for being safe and secure. No more. Now when a company shows a profit, the market punishes it. Play it safe, and your stock price falls.

Jeff Bezos of, Jay Walker of, Steve Case of AOL are all there as living proof. They make the old profit seekers — Mel Karmazin of CBS, Sumner Redstone of Viacom, even Barry Diller of U.S.A. Networks — seem small and dull by comparison. At one point, NBC news anchor Tom Brokaw kids Bezos, whose company turned a modest profit one quarter, a while back: “Jeff,” he asks, “how do you spell ‘profit?’ ” Without missing a beat, Bezos says, “p r o p h e t.” In this high-altitude atmosphere, the old prophets’ appetite for danger and outrageousness is what’s called for.

On the last night, at dinner in the Sun Valley Lodge, a few of us begin discussing the best definition of leadership. Jack Valenti, head of the Motion Picture Association, remembers a line on a soldier’s tombstone outside of Arles: “Leadership is wisdom, courage, and a certain carelessness with the self.” You can argue that carelessness is what killed that soldier. But you can also recognize that most people define “great” as the image of the high-risk leader: At the level of international greatness are liberators like Nelson Mandela and Vaclav Havel, and on the corporate front is Apple Computer’s Steve Jobs who keeps coming back from failure, testing himself, pushing his wits to the limit. Valenti, who had been a special assistant to President Lyndon Johnson during the Vietnam War observes that, “Presidents today don’t want simply to govern anymore. Rather, they want to be remembered as great. So they try to model themselves after Franklin Roosevelt or Teddy Roosevelt or Abraham Lincoln. They study these men who were careless with self. We see this in Bill Clinton, of course. In him, we don’t like the narcissistic way his carelessness displays itself. But we admire his sense of danger that’s missing in Bill Bradley and Al Gore.”

Carelessness with self — risk. Five years ago, I’m sitting in John Tarrant’s office while he leads me in a guided meditation. I have just started writing The Princessa and have been steeped in the stories of women warriors. I feel as if I am a warrior too. I have taken a bold step: leaving Bertelsmann and putting in peril a job my friends say is the best in publishing. I am risking my reputation on whether a book editor can write a book herself. I have come to John to make sure that I know just how far to go in that new pursuit.


John says, “Close your eyes. Imagine that there is no light but one small beam. Follow it into the darkness of your imagination. What do you see?” I see myself rushing through the jungle at Mach speed, unafraid and unstoppable. Then I look closer. The whirring air conditioner in John’s room has vanished. Up close, I see that my speed and bravery aren’t mine at all but rather those of a tiger’s. I see myself being carried in its jaws. I’m not running or even standing on my own. I am contained by invisible but real limits — limits on how much I can risk, how far I can go if I open my heart to bravery. I thought I was brave. I’m not even close. I’m the tiger’s dinner.

“What brings us out of comfort and fear is imagination — creativity,” John says. “Those who truly love danger aren’t extreme athletes, triathaloners, or mountaineers. Creative people plunge into disaster every time they do something new. Because every time they try something new, they risk everything that’s familiar to them. They have to confront their incompetence and stupidity, feelings that all of us carefully avoid. That’s the journey of power and danger.”

When danger ends in disaster, that usually means that we are taking things too literally or are seeking oblivion. An adventure can be concocted in any number of ways — from an assault on Everest to an ill-advised airplane flight — that amount only to faulty decision making or excessive ego. Heroic danger, John Tarrant tells me, is to descend into the imagination. That gives the plain — the flat — things of life an opportunity to be bold. What are those flat things? The wrong choices, the bad diagnoses, the boredom.

I think about this constantly, because today there is always the opportunity to work primarily for money. For security. For that BMW roadster. For the chance to go from being filthy rich to being a billionaire. But who are you when it’s all over? Can you turn away from risk once and think that you’ll ever be able to be “careless with the self” the next time? The new economy is a dangerous place. It is unforgiving, and it measures human life in dog years: Three years wasted on the wrong pursuits, or, just as bad, in avoiding the right ones, leaves you 21 years older and farther off track. There’s never a time for comfort. Now, asks John, can you act as though you know that?

At some point, we all have to decide how we are going to fail: by not going far enough, or by going too far. The only alternative for the most successful (maybe even the most fulfilled) people is the latter. The interesting challenge is to know that if you don’t go far enough, you’ll never know how far you can go.

Harriet Rubin is author of “The Princessa: Machiavelli for Women” (Dell, 1998) and the forthcoming soloing (HarperCollins). Her Web site ( debuts in November. Contact John Tarrant by email (