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So, you know that special brand of squelched eye-roll/mini-smirk you trot out whenever you find yourself cornered by your Positive Thinking-evangelizing sister/friend/coworker? Turns out, raining on her parade might be the best thing you can do for her.

In a comical opinion piece in Sunday’s NYT that’ll make the cynic in you chuckle, Oliver Burkeman lays out a solid argument for being an Eeyore. The impetus for his piece was last month’s debacle involving 21 Tony Robbins devotees who wound up being treated for burns after “Unleashing the Power Within” (read: attempting to walk across hot coals).

(Quoth the fire captain: “We discourage people from walking over hot coals.”)

Schadenfreude aside, Burkeman lays out a pretty solid argument for leaving the power alone, and instead unleashing the grouch within.

He quotes social critic Barbara Ehrenreich, cites The Stoics and principles of Buddhist meditation, debunks the power of visualization:

Consider the technique of positive visualization, a staple not only of Robbins-style seminars but also of corporate team-building retreats and business best sellers. According to research by the psychologist Gabriele Oettingen and her colleagues, visualizing a successful outcome, under certain conditions, can make people less likely to achieve it. She rendered her experimental participants dehydrated, then asked some of them to picture a refreshing glass of water. The water-visualizers experienced a marked decline in energy levels, compared with those participants who engaged in negative or neutral fantasies. Imagining their goal seemed to deprive the water-visualizers of their get-up-and-go, as if they’d already achieved their objective.

Interestingly, elsewhere in the paper (O, glorious Sunday on the couch!), in a (much-emailed) piece titled “Raising Successful Children” Madeline Levine, practicing clinician and author of “Teach Your Children Well: Parenting for Authentic Success,” takes down not just helicopter parents and tiger moms, but “overparenting lite.” It’s a topic we’ve covered before, but Levine mentions an interesting study:

In a typical experiment, Dr. Dweck takes young children into a room and asks them to solve a simple puzzle. Most do so with little difficulty. But then Dr. Dweck tells some, but not all, of the kids how very bright and capable they are. As it turns out, the children who are not told they’re smart are more motivated to tackle increasingly difficult puzzles. They also exhibit higher levels of confidence and show greater overall progress in puzzle-solving.

Interesting, huh? Taken together, the two certainly got me wondering. How much positivity is too much? Exactly how deeply rose should our glasses be colored? Where does healthy stop and delusional begin? And, maybe more to the point: why does this kind of stuff feel, in some (albeit slightly uncomfortable) way, like a relief?

We write often about the importance of embracing failure, how it is not only surmountable, but a teacher. We also write often about the crushing pressure of great expectations. How they can turn out to be more paralyzing than empowering. (And how the message so many of us are fed, that you can do anything you want, is internalized with the pressurizing conclusion: so it better be something really freaking good.) And so I wonder: how much better off would we all be were the pressure to be positive ratcheted down, even just a tad? And not just because the pressure would be off: because failure, imperfection, moments of (gasp!) mediocrity are kind of a fact of life.

In her piece, Levine notes that becoming who we are (and being allowed the space to accomplish this deceptively simple task) is kind of the most important work at hand for a fledgling human being (or the people tasked with raising said human being). I’d agree. And accepting and getting to like that person is pretty important work, too. And accepting and liking ourselves is considerably easier if we’re not expecting perfection, not least because people–all people–are inherently imperfect. (And through no fault of our not thinking positively enough.)

Here’s a little more from Burkeman:

Buddhist meditation, too, is arguably all about learning to resist the urge to think positively — to let emotions and sensations arise and pass, regardless of their content. It might even have helped those agonized firewalkers. Very brief training in meditation, according to a 2009 article in The Journal of Pain, brought significant reductions in pain — not by ignoring unpleasant sensations, or refusing to feel them, but by turning nonjudgmentally toward them.

From this perspective, the relentless cheer of positive thinking begins to seem less like an expression of joy and more like a stressful effort to stamp out any trace of negativity. Mr. Robbins’s trademark smile starts to resemble a rictus. A positive thinker can never relax, lest an awareness of sadness or failure creep in. And telling yourself that everything must work out is poor preparation for those times when they don’t. You can try, if you insist, to follow the famous self-help advice to eliminate the word “failure” from your vocabulary — but then you’ll just have an inadequate vocabulary when failure strikes.

Everything’s not always going to be great. And that’s perfectly fine.

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The other day after I got home from my run (I use the term advisedly), I got a call from the local NBC affiliate asking for a quick interview on the overall impact of “girl power”  in this year’s Olympics.  Within ten minutes, the reporter and her cameraman were on their way.

While dashing around the house trying to figure out what to wear — no white, no black, no patterns — and ruing the fact that I never mastered the art of applying makeup, I did some power thinking about what the so-called “year of the woman” means to those of us who have never done a cartwheel and who were always the last to be chosen for volleyball.  (Both would be me.) And what I realized is that the Olympic Games are a good metaphor for a lot of what we call real life.

Wherein we find some real lessons, especially for us women.

Lesson one:  You go for the gold, girl.  First, there’s the good old-fashioned inspiration of the goose-bump variety.  Whenever a woman excels at anything, I’m inspired — even if it’s not my field.  Gabby or Missy or Kerri and Misty?  Talk about motivation.  And yet it’s a message that goes far beyond the pool or the (faux) beach or the balance beam: set yourself a goal, work hard, try your darnedest and anything is possible: You never know what you can do until you take that leap of faith.

For all of us, there’s joy to be found in getting into the Zen of it all, of being totally absorbed in our passions, whether it’s poetry or pole vaulting.  Put yourself out there, throw yourself into your dreams one hundred percent, and the message is this: you just might bring home the gold.

Lesson two:  Fail well.  Or maybe you won’t: put yourself out there, give it your all — and you still might fall flat on your face.  But even if you fail spectacularly, you still win. We write about this a lot:  one of the surest indicators of future success is how good you are at failing. In fact, this year the New York Times reported on some cutting edge school programs based on something called the character strengths inventory that is proving that kids who move through failures with a mindset of looking at them as learning experiences are much more equipped for success in life. (Look no further than world gymnastics champion Jordyn Wieber, who failed to qualify for the individual all-around final yet came back to nail her floor exercises.)

Which leads to …

Lesson three: Take the risk.  In other words, failure can often be the world’s best teacher. First, there’s the satisfaction of knowing that you’ve taken a risk and lived to tell the tale. And then there’s this: That whole process of trial and error is likely to bring you closer to figuring out your own goals and how to get there.  Maybe you’ll learn from what you’ve done wrong and do it better the next time – or just maybe you can use that failure to rule things out.  If you can see that failure for what it is, just one more step in the never-ending process we call life, you may well learn something that can propel you forward. Or, as psychologist Ramani Durvasula told us back when we were reporting our book: “You’ll always get over a failure. But regret? It’s not recoverable.”

That risk-taking, the idea of allowing ourselves the courage to fail?  It’s especially important to today’s women who are often navigating uncharted territory, especially in the workplace.  As Elizabeth Gilbert once wrote, “We don’t have centuries of educated, autonomous female role models to imitate here (there were no women quite like us until very recently), so nobody has given us a map.”

And speaking of running without a roadmap …

Lesson Four: Dispense with the shoulds.  That’s Gloria Steinem’s line, not ours.  More in a bit. I was once asked for advice from a very earnest twenty-something who wanted to know what women trying to make their way into high-stakes careers should do. And my answer was this:  I don’t have any advice — not because I don’t like to dish it out – but because there are no clear cut, one-size fits all answers.   For us, I told her, it’s all too new.  And then I quoted Gloria Steinem, who once told a group of college women: “Dispense with the word “should.” Don’t think about the way women should fit into the world.  Think about how the world should fit women.”

Which brings us back to my soundbyte on the nightly news and perhaps the best lesson of all from the year of the woman.  The reporter asked my take on those women who were owning the non-traditional sports like Judo and weightlifting, breaking through the stereotypes, and what I said was something like this:  “Every time a woman does something a little above and beyond society’s expectations, it opens doors for all of us.  And I think that’s fantastic.”

I was overshadowed, of course, by an interview with a poised young tween in a leotard at a local gymnastics center.  What she said she has taken away from this year’s Olympics is the belief that women can do whatever they want, that they can do just as much as men can.  “I’m motivated,” she said, looking straight at the camera, “to do better than I think I can.”

Girl power, indeed.

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This being graduation season, the other day I asked the over-achieving rockstars in my senior journalism capstone class what they’d most like to hear from a commencement speaker.

Thankfully, I heard no references to roads not taken nor endings-versus-beginnings.  (Though I would have enjoyed a quick reference to that four-word piece of advice from the iconic film about post-grad angst, The Graduate:  “In a Word: Plastics”)

But anyway.

The best answer came from a young woman who said she’d like to hear from someone who has failed – and was still okay.

Now, I suspect this is a young woman who, herself, has never failed.  And yet: she may have tapped into one of the biggest fears of young women who have been raised with great expectations, high aspirations and the message that they could do it all and have it all: What happens if they can’t?

If you’ve been following this space, you probably know that one of our key messages is the need to embrace failure, to put yourself out there, to take some risks – even when said risks might end in a big fat fail.  In most cases, if you can see that failure for what it is – just one step in a life-long process of trial and error – you may well learn something that can propel you forward.  Or, as psychologist Ramani Durvasula told us back when we were reporting our book: “You’ll always get over a failure.  But regret?  It’s not recoverable.”

In other words, to borrow a quote from another movie classic, you’ll always wonder if you “coulda been a contender.”

And so, as a nod to my student, and to graduates anywhere, here’s a short list of successful women who failed famously – and still, one way or the other, ended up on top:

Emily Dickinson:  Regarded as one of America’s greatest poets, she wrote over 1700 poems.  Only a handful were published in her lifetime.

Lucille Ball: The winner of four Emmys and a Lifetime Achievement Award was told by one of her first drama teachers that she should try another profession.

Marilyn Monroe: When she was just starting out, modeling agents told her she should go be a secretary.  Why?  She wasn’t attractive enough.

Kathryn Stockett:  Her manuscript for “The Help” was rejected by 60 literary agents over a period of three and a half years, before being picked up by an agent named Susan Ramer, who sold the book to a publisher three weeks later.

Oprah Winfrey:  At 22, she scored a gig co-anchoring the evening news in Baltimore, and eight months later, was fired.  Because she still had a contract with the station, they shuffled her off to a talk show, which ultimately launched her career.

Hilary Clinton:  The Yale Law School graduate failed the D.C. bar exam – but passed the Arkansas bar and moved there to be with Bill.  The rest, as they say, is the history of one of the most influential women in the United States, if not the world.

The list goes on, or could, but the point is this: while we all fail at one time or another (be sure to ask me about some of my own personal doozies) the only real failure is letting the fear of it hold us back.  Or, as former New York Times editor Anna Quindlen once said: “The thing that is really hard, and really amazing, is giving up on being perfect and beginning the work of becoming yourself.”

By the way, our commencement speaker this year is Steve Wozniak, co-founder of Apple Computer, who has experienced a few failures of his own.

Let’s hope he doesn’t fail to mention them.

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The other day, I ran across an interview with Susan Sarandon over there at ontheredcarpet.com that reminded me once again that good things are often born of chaos.  Or, as we so often write: We are our failures, those blips in the road that can propel us forward.

But only if we let them.

Back to Sarandon, I’ll confess that she has been one of my favorite actors ever since Bull Durham, so I am predisposed to find anything she says to be both witty and wise.  Currently, she is starring in “Jeff, Who Lives at Home” — playing a frustrated mom whose loser son lives in her basement while he searches for the meaning of life.  She told OTRC that she “could actually relate to Jeff’s plight of not knowing what his path should be in life”.  Which might come as a surprise, considering that she is, after all, an Oscar winning actress.  But what she says is this:

“Even if you don’t believe in a higher power, there’s clearly something that happens out of the chaos. My whole life has been totally serendipitous and everything that’s been important to me has come out of the blue and oftentimes against the odds,” Sarandon told OnTheRedCarpet.com. “And my daughter says, ‘You know mom, it doesn’t look good on paper’ and I go, ‘You know what, I’m just going to jump, I’m going to do it.’ I don’t mean being reckless, but I think you have to give life the benefit of the doubt sometimes because it’s got far more imagination than you do.”

In other words, you never know what might be waiting for you just around the corner until you take that leap of faith.  It’s a pretty hopeful message, yes?  But what we’ve found is that it’s a tough one, too.  Because it means you have to be willing to take a risk, to live life without much of a net, and, in so doing, accept the fact that there’s a chance that you’ll fall flat on your keister.

Of course, there’s also a chance that you won’t: Put yourself out there to ask for that promotion, negotiate a higher salary, work out some flextime, pitch a book proposal — and you just might get what you ask for. Still, it’s a message that’s hard to hear, especially for those of us running without a roadmap, tackling new territory, new opportunities, making new choices about what to do with our lives without the kinds of historic role models men have had for generations.  It’s no wonder so many of us want to search for the magical how-to, the “ten easy steps” from here to have-it-all.

Or would rather hear that the staus quo is just rosy, and stick with it, thank you very much.

And that’s fine.  But you have to wonder what you miss when you steer clear of the cliff.  Because when you do screw up your courage and take that leap, good things often follow.  Take us, for example: mother and daughter writing a book together.  Think about that leap of faith.  It’s something neither of us could have foreseen back, say, when Shannon was a teenager.  Who knew it would work out? But work out, it did — in ways we never could have imagined.  (Plus or minus a few spats here and there. Catch us offline if you want the real dope.)

But meanwhile, back to the question at hand:  While we’re making our way through this relatively uncharted territory, figuring out our way in the world, do we sit tight?  Search for some one-size-fits all answers?  Or do we take that leap of faith and, as Sarandon says, give life the benefit of the doubt?

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Did you catch Bill Keller’s piece in the New York Times yesterday? Called “Just the ticket,” it’s a pretty compelling case for replacing Joe Biden with Hillary Clinton for second-to-the-top job when this year’s presidential election rolls around. Now, we love Biden’s faux pas and f-bombs as much as anyone, but–hello!–how could we not jump on this bandwagon? So, without further ado, here’s our top 5 reasons why we’d love to see a Clinton-Obama—I mean, Obama-Clinton—ticket.

5. She’s ambitious. And she owns it. She wasn’t content to wrap up her time as first lady and demurely step aside. In a ballsy move, she ran for NY Senator. In a ballsier one, she ran for president–and nearly nabbed the nom. When so many of us feel our ambition is something shameful, something we should apologize for or even deny, Hillary puts it front and center. She’s taken her lumps for it, but ultimately, she’s proven that a woman can be both ambitious and liked. Which brings me to number 4.

4. We like her. I mean, we really like her. According to Gallup (by way of Keller):

Hillary is the most admired woman in America for the 10th year in a row, laps ahead of, in order, Oprah Winfrey, Michelle Obama, Sarah Palin and Condeleezza Rice; her approval rating of 64 percent is the highest of any political figure in the country.

An ambitious woman is something to be admired?! I mean, the whole George Washington/cherry tree thing is cute and everything, but how’s that–ambition and likability are not mutually exclusive–for a lesson in the history books?

3. She’s strong enough to cry. Almost four years ago exactly, during a campaign stop in Portsmouth, New Hampshire, Clinton became emotional when answering a question from an audience member about how she’s able to deal with the madness of a presidential campaign–and it was in her answer, when speaking of how much she cares about the country, that she got choked up. Again, she took flak for it, but there’s another, monstrously important message in this for the rest of us: tears are not a sign of weakness. They’re often, as Elizabeth Lesser has told us, a sign that our heart is truly engaged. I personally know that to be the case for me, and I love to imagine what the world–not to mention the freaking workplace!–would be like if everyone understood that. Being emotionally invested is a strength; Clinton understands that. And yet…

2. She’s not afraid to laugh at herself. At one of the most humbling moments in her career–when she bowed out of the race and gave her support to Obama–the type of moment when some, um, lesser people might be reduced to temper tantrum (You’re not gonna have Richard Nixon to kick around no more! anyone?), she was strong enough to crack a joke–and not just any joke–one that poked fun at herself: thanking her supporters, whom she referred to collectively as the sisterhood of the traveling pantsuits.

1. She is the total package. She has the skills and the experience, the–as Keller puts it–E.Q. as well as the I.Q. She’s already made enough of a mark that when someone describes something as Clintonian, it’s as likely they’re referring to her as it is her husband, who is, you know, a former president. She handled herself impossibly well during one of the most impossible (and public!) humiliations imaginable–and, rather than opt for obscurity, held her head high and soldiered on, right into one of the most visible positions in the world. And what a tenure: as Secretary of State, she’s smoothly handled her share of dramatic world events. As Keller writes:

She would bring to this year’s campaign a missing warmth and some of the voltage that has dissipated as Obama moved from campaigning to governing. What excites is not just the prospect of having a woman a heartbeat–and four years–away from the presidency, although she certainly embodies the aspirations of many women. It’s the possibility that the first woman at the top would have qualifications so manifest that her first-ness was a secondary consideration.

And what a first that would be.

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That which doesn’t kill you makes you stronger. Crisis is just opportunity in disguise. The universe/god/buddha doesn’t give us more than we can handle. It’s always darkest just before the dawn. Scar tissue is stronger. The cracks are where the light gets in.

Blah blah blah.

Here’s an interesting question: Which is worse, coming up against one of life’s big bitch slaps only to find all of your nearest and dearest spewing some tired old cliche, or attempting to comfort a friend who has just endured an epic bitch slap of her own using the only thing you can come up with–which happens to be the very same tired old cliche? Even when you really really mean it, even when you know whoever’s saying it to you has only the best intentions, the line–“that which doesn’t kill you makes you stronger”–just feels kinda lame.

Interestingly enough, however, it turns out to be true.

According to the University of Buffalo’s Mark D. Seery’s paper in the December issue of Current Directions in Psychological Science, small amounts of trauma may help people develop resilience. Here’s the gist:

Indeed, a lot of solid psychology research shows that having miserable life experiences is bad for you. Serious events, like the death of a child or parent, a natural disaster, being physically attacked, experiencing sexual abuse, or being forcibly separated from your family, can cause psychological problems. In fact, some research has suggested that the best way to go through life is having nothing ever happen to you. But not only is that unrealistic, it’s not necessarily healthy, Seery says.

In one study, Seery and his colleagues found that people who experienced many traumatic life events were more distressed in general–but they also found that people who had experienced no negative life events had similar problems. The people with the best outcomes were those who had experienced some negative events…

One possibility for this pattern is that people who have been through difficult experiences have had a chance to develop their ability to cope. ‘The idea is that negative life experiences can toughen people, making them better able to manage subsequent difficulties,’ Seery says. In addition, people who get through bad events may have tested out their social network, learning how to get help when they need it.

One of my clients informed me during our session last week that it was the one year anniversary of her filing for divorce. “It’s been the worst and the best year of my life,” she said. It was the worst for obvious reasons, but she’s also found that she’s stronger and more blessed than she ever thought. She recalled the day one year ago, remembering how sad, angry, and scared she was. I asked her if that her, the one from a year ago, could ever have imagined the her of today. “No way!” she said with a laugh.

A divorce is a big deal, obviously. So is illness, death, job loss, foreclosure, injury. But that doesn’t stop people from forming relationships, taking jobs, buying homes, or snowboarding. The potential for disaster is there, and yet: we’re willing to take the risks.

So maybe the question is, what are we missing out on when we refuse to take a chance? And I’m not just talking about marriage, I’m talking about everything: You don’t want to make a fool of yourself, so you never audition for the community theater. You don’t want to be rejected, so you don’t ask the guy out. You don’t know if you can handle the job, so you don’t throw your hat in the ring for the promotion. You don’t want to look ugly, so you go for decades without ever changing your hairstyle.

I guess the real question is: What are we missing out on when we let the fear of failure determine what we choose to do (or not do) with our lives–and is it worth it?

As Ramini Durvasula, PhD (a clinical psychologist, professor of psychology, and director of the psychology clinic and clinical-training program at Cal State Los Angeles) tells us in Undecided:

I always say to my students, ‘You’ll get over a failure, but you will never recover from regret. That’s not recoverable. Go ahead and try a job you might fail at. Go ahead and take some chances.’ Because where these women often get frustrated is with the paths not taken. And what I tell them is that I want them to try a lot of things–and then report back. And that’s frightening, because they still feel very programmed: They want the marriage, the house, the kids, the job–but have absolutely no sense how to get all those things at the same time. And I just don’t think it’s gettable in a single package. Women need to live lives where they’re willing to rule things out. Like I ruled out marriage. But I had to do it to rule it out. What ends up happening is that if you don’t have the realization, you wonder.

And it’s that wondering that’s the killer, not least because it saps the joy out of the life you’re living today. So give that thing you’re wondering about a try. What’s the worst that could happen? Sure, you might fail spectacularly–and you might then be forced to endure some well-intentioned folks and their tired old cliches. But, at least, this time you’ll know they’re right.

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 Last week during all the memorializing of Apple founder/college dropout/cultural visionary Steve Jobs, I found myself watching the commencement speech he gave at Stanford University in 2005 — and, in all that wisdom, one line in particular gave me the chills: Don’t Live Someone Else’s Life, he said. Actually, what he said was:

Your time is limited, so don’t waste it living someone else’s life. Don’t be trapped by dogma–which is living with the results of other people’s thinking. Don’t let the noise of others’ opinions drown out your own inner voice. And, most important, have the courage to follow your heart and intuition. They somehow already know what you truly want to become. Everything else is secondary.

Living someone else’s life? Now, I (vaguely) recall being a fresh college grad, and I’m sure such words might have just made me chuckle then, but with a few additional years under my belt, I can say I know exactly what he’s talking about. I think most of us do, if we’re honest.

So often, we make choices based on shoulds, on expectations, biases, images, maybe even out of fear. Women in particular often find our decisions are colored by worries about being judged or getting approval, and we’re often battling some deeply entrenched beliefs around it somehow being virtuous to put ourselves last — at the bottom of our own list. Sometimes we just drift. But, with each choice we make, our life picks up a little bit of steam, until, sometimes, before we know it, we find the life we’re living is one that’s being driven by inertia, heading off in some direction we never planned.

As Molly, a young Manhattanite we profiled in the book, told us:

I did everything my boss asked, I did it perfectly, I sucked up. In six months, I got promoted. It was one of the fastest promotions they’d ever experienced. I tried really hard, and I moved to the next step; I tried really hard, and I moved to the next step. And now I’ve gotten to the point where I’m like, wait a minute, how did I get this far? I just blindly tried really hard without really thinking, What’s the end? Where is this getting me?

To quote the Talking Heads: Self, how did I get here? 

Sounds familiar, no? But maybe the more important question is this: How do I take back the wheel?

Well here’s the good news: You don’t have to take back anything! You’re not powerless. It was you who made the choices that got you to this point — this job, this relationship, this roommate, this pet chinchilla — and you are not powerless to make choices that’ll take you down a different path from here. Those are your hands on the wheel — they’ve been there all along.

Once you acknowledge you’re the one in control of those hands, your next step should be to take some time to notice where they’re steering you, your focus, your time, your energy? Because here’s the thing: everything is a choice — and every choice, by definition, entails a trade-off. Whether we go into it consciously or not.

Whether or not you consciously think to yourself: this time I’m spending baking cookies for the kids’ bake sale or agonizing over which color to use in the graph on Slide 4 in this PowerPoint is time I am not spending in the garden, or researching the yoga teacher training course I’ve been thinking about since I dropped my first “Om,” you’re still making the trade. You can’t be in two places at once. And the decisions you make about what to do with your time, where to focus your energy — well, they shape your life. So if you’re feeling like you’re living someone else’s life, start going into those choices consciously — really thinking about what you are and are not choosing to do. Once you do, you might discover you’re spending your time and energy on things (and maybe even people and jobs) that you don’t really care about, letting the things you’re most passionate about slip by the wayside, while you’re on cruise control.

It can be scary — maybe our passion seems weird, our dreams too far out of reach. Maybe you’ll fail. And maybe after that, you’ll try again. But wouldn’t you rather fail at your own dreams than succeed at someone else’s? And hey, failure’s recoverable — even Steve Jobs got fired.

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What if the surest indicator of your future success–of living a happy, meaningful, and productive life–is how good you are at failing?

Brace yourselves, perfectionists, because the evidence is mounting: in order to fly, you’ve first got to fail. And (worse!) how well you fail may be one of the biggest predictors of success. Bigger even than, say, IQ. Paul Tough’s recent piece in the New York Times, entitled “The Character Test: Why our kids’ success–and happiness–may depend less on perfect performance than on learning how to deal with failure,” looks at character-development programs in two schools–one school affluent, one not; both programs inspired by the character strengths inventory developed by Martin Seligman and Christopher Peterson–which seem to show that the kids who move through failures with a mindset of looking at them as learning experiences are much more equipped for success in life. Of course, in order to move through a failure, they have to be allowed to fail. An issue about which Dominic Randolph, headmaster of Riverdale Country School–one of NYC’s most prestigious private schools–is worried:

People who have an easy time of things, who get 800s on their SATs, I worry that those people get feedback that everything they’re doing is great. And I think as a result, we are actually setting them up for long-term failure. When that person suddenly has to face up to a difficult moment, I think they’re going to be screwed, to be honest. I don’t think they’ve grown the capacities to handle that.

It’s a bit like the kid who eats the occasional fistful of dirt, versus the one whose every move is greeted with an anti-bacterial wipe. Sure, one will get dirty (and perhaps cooties)–but, long term, whose immune system is going to be stronger?

When it comes to failure, the trick is being able to look at it objectively: easier said than done, when you’re in the midst of being dressed down in the boardroom or rejected in the bedroom. And for women, as we explore in Undecided, there are even more complications: often we’re carrying the weight of some great expectations–whether our own, or those of our (real and proverbial) mothers who never had the opportunity we do–born of the well-intentioned message that we can do anything! (And that we’re so lucky that we can do anything.) And the kicker: we’re doing it blind! After all, as Elizabeth Gilbert once wrote,

We don’t have centuries of educated, autonomous female  role models to imitate here (there were no women quite like us until very recently), so nobody has given us a map.

You look at it that way, and it seems we’ve all been set up for failure! But might that be a good thing–if only we could figure out how to fail well? Tom Brunzell, Dean of Students at Kipp Infinity School in the Bronx, says of the “character conversations” that have infiltrated all aspects of the curriculum:

what’s going on… isn’t academic instruction at all, or even disciple, it’s therapy. Specifically, it’s a kind of cognitive behavioral therapy, the very practical, nuts-and-bolts psychological technique that provides the theoretical underpinning for the whole positive psychology field. Cognitive behavioral therapy, or CBT, involves using the conscious mind to understand and overcome unconscious fears and self-destructive habits, using techniques like “self-talk”–putting an immediate crisis in perspective by reminding you of the larger context… “I mean, it’s middle school, the worst years of their lives. But the kids who make it are the ones who can tell themselves: ‘I can rise above this little situation. I’m OK. Tomorrow is a new day.”

It’s tough not to let our ego get in the way (even when we know there are worse things than messing up or being wrong), but when we succumb to that knee-jerk defensiveness (a “baby attack,” in KIPP school parlance), we deprive ourselves real growth. What if we could just tell our ego to chill, and take a minute to observe: what can this situation teach me about the areas where I have a little room for improvement? What can I do better next time? (And then, the fun part: holy crap! Imagine how successful I could be if I could figure out a way to get better at the things I’m not as good at yet!)

The thing is, blowing it every once in a while is inevitable: we might as well do it well.

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So, here’s a scenario. You, single, lookin to meet someone. You’re perusing the offerings at Match.com when you come across an attractive stranger whose specs are all to your liking. Then, let’s say, he describes himself: “Big Ol Failure!”

…I’m guessing you’d pass?

You’d hardly be alone. Success, after all, is a virtue in our world; failure, something to be ashamed of.

But. A new book says that, “in a complex world, the process of trial and error is essential.” The book, written by Financial Times columnist Tim Harford, is called “Adapt: Why Success Always Starts With Failure.” And while the book is business-leaning, the point–that it’s the mistakes that beget the great successes–seems pretty applicable to Life In General.

Of course, failure’s scary. But, without it, what is life? If we’re here to learn, to change, to grow, to discover who we are and what we want to do with ourselves while we’re here, well–all of those things involve taking steps into the unknown. And, like someone wandering an unfamiliar town, we’re likely to take a couple missteps. We may even fall flat on our collective face. But, with every stumble, every accidental dead-end, we get a little bit clearer about the road we do want to follow.

Makes sense–but then, it’s easy to speak in metaphor. It’s a lot harder to cut ourselves that kind of slack in our actual lives. We’d prefer to never get fired, dumped, disappointed, bored, scared, angry, or lost again. But I feel pretty certain that we will. (Admit it, you know I’m right.) After all, in a way, our mistakes are our lives. They’re certainly every bit as significant as our successes.

And so imagine if we weren’t so tied to the outcomes of the things we try. When we’re making the big decisions of our lives, what if our ego didn’t give a shit whether we’d come out on top? What if we chose to believe that there are no right or wrong decisions, only choices that we’ll live with? What if we realized that failure might, in fact, be inevitable–and went for it anyway? It reminds me of this quote from Elizabeth Gilbert that I wrote about some time ago:

Let’s just anticipate that we (all of us) will disappoint ourselves somehow in the decade to come. Go ahead and let it happen. Let somebody else go to art school. Let somebody else have a happy marriage, while you foolishly pick the wrong guy. (Hell, I’ve done it; it’s survivable.) While you’re at it, take the wrong job. Move to the wrong city. Blow it all catastrophically, in fact, and then start over with good cheer. This is what we all must learn to do, for this is how maps get charted–by taking wrong turns that lead to surprising passageways that open into spectacularly unexpected new worlds. So just march on. Future generations will thank you–trust me–for showing them the way, for beating brave new footpaths out of wonky old mistakes.

In medicine, doctors make diagnoses by ruling things out. Seems a pretty sane approach in life, too, doncha think? I mean, maybe I’m wrong about all this. In which case… great! I’ll try something else tomorrow.


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This post originally ran in April, but we thought now would be a good time to revisit it, giving the impending release of Eat, Pray, Love, based on Elizabeth Gilbert’s mega-bestseller of the same name. So, this week, when you’re bombarded with ads for the movie, the trip, or the collection, remember these words from everyone’s favorite fuck-up: Blow it all, catastrophically, and start over with good cheer. After all, if she hadn’t made some serious mistakes in her life, who knows where she’d be? More importantly, we’d all miss out on a chance to ogle Javier Bardem.

What if failure was not only an option, it was the only option? According to a recent article by Elizabeth Gilbert (she of Eat, Pray, Love fame) in this month’s O magazine, we’d all be a lot better off. In fact, “Failure is the Only Option” is the title of the piece, in which Gilbert suggests we’d be happier if we screwed up. Early. Often. And big.

Now, easy for her to say: her divorce, after all, begat one of the publishing world’s most staggering successes in recent memory (soon to arrive at the multiplex near you), not to mention an amazing round-the-world adventure and another go at the whole Committed thing. (So, it’s probably no surprise that she’d encourage failure on an epic scale: she, after all, is living one serious silver lining.) In the course of making her case for failure, she hits on one of our main theses about the overwhelm women feel in the face of limitless options, and why those options trip us up so colossally: They’re So. Damn. New.

Here’s a little bit of what she says:

We don’t have centuries of educated, autonomous female role models to imitate here (there were no women quite like us until very recently), so nobody has given us a map. As a result, we each race forth blindly into this new maze of limitless options. And the risks are steep. We make mistakes. We take sharp turns, hoping to stumble on an open path, only to bump into dead-end walls and have to back up and start all over again. We push mysterious levers, hoping to earn a reward, only to learn–whoops, that was a suffering button!

We’ve all accidentally pushed the suffering button. This new job is gonna rock! Quitting this job is gonna rock! This cheese rocks so much, I’m just gonna keep eating it! I’m totally gonna rock these 5-inch heels all night long! How can we ever know if we’re doing the right thing?

Maybe the better question is When can we know if we’re doing the right thing? To which, the only correct answer is: after we’ve done it. In which case, if it was the wrong thing, it’s too late to do anything but pick ourselves up, dust ourselves off, and try something new (or swear off cheese altogether). But until we’ve given what may or may not rock a shot, well, we’re generally operating without a map. (When you think about it, it’s terrifically ironic: women, who are so talented at comparing ourselves to others, don’t have a whole lot of comps to go by while charting our own course through this life.)

Of course, the major failures–the ones we’re afraid of making–are more significant than a blister or a day spent, uh, divesting oneself of sins of the Cowgirl Creamery variety. But the half-full way of looking at it might be that all those missteps are indeed serving a purpose: in many ways, women today are making the map. And while, one might expect the moral of a story called “Failure is the Only Option” to be something along the lines of “You miss 100% of the shots you don’t take, so you might as well go for it!”, Gilbert’s points are more charitable: stop pressuring yourself to be perfect, and every time you blow it, consider it a gift to your little sisters. Failure as philanthropy. Check it:

Let’s just anticipate that we (all of us) will disappoint ourselves somehow in the decade to come. Go ahead and let it happen. Let somebody else go to art school. Let somebody else have a happy marriage, while you foolishly pick the wrong guy. (Hell, I’ve done it; it’s survivable.) While you’re at it, take the wrong job. Move to the wrong city. Blow it all catastrophically, in fact, and then start over with good cheer. This is what we all must learn to do, for this is how maps get charted–by taking wrong turns that lead to surprising passageways that open into spectacularly unexpected new worlds. So just march on. Future generations will thank you–trust me–for showing the way, for beating brave new footpaths out of wonky old mistakes.

So here’s to blowing it. And here’s a word to the wise, from a sister who’s been there: half a wheel of Mt. Tam is too much cheese.

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