THE PRODUCTIVE ART OF F***'ING UP

Epic Failures

Let me tell you why wrong has never felt so right. Because we live in a world where failure, at one point or another, is inevitable, and we’re finally arriving at a place where we can talk about it. We still wince, yes, but we’re getting there. It’s a tough topic. Failure usually involves a pretty sizable f-up, plus pain and embarrassment, but when we come out on the other side of it, there’s something more. Hopefully, a lesson. And one that sticks.

I really believe failure is a rite of passage, with no off-ramps, for anyone. At least, most. I don’t know anyone who hasn’t experienced failure in life. In fact, rarely do you hear the story of a successful person who hasn’t experienced multiple failures.

Failure isn’t something I’d wish upon anyone, but the fact that we all go through it somehow makes me feel better. I think it confirms I’m not alone and that none of us have it all figured out.

Yesterday I rattled off a few rather spectacular examples of failure stars. Steve Jobs was famously fired from the company he founded. J.K. Rowling was rejected by publisher after publisher before Harry Potter found a home. Oprah Winfrey was taken off the evening news early in her career after being told she wasn’t right for television.

Today, those stories sound almost unbelievable. Of course Jobs went back to Apple. Harry Potter became Harry Potter. And well, Oprah became Oprah. We know their endings. There are so many greats like this, it’s impossible to list them all. But they inspire me every. single. day. I hope they inspire us all.

As hopeful as these stories are, it’s tough to hold tight to the inspiration of others who’ve come out the other side because, well, they’re on the other side of it. It’s a lot less inspiring when you’re the one sitting smack in the middle of failure’s threat, or you’ve arrived.

And why is this seemingly universal experience such a lonely one anyway?

I can only speak for myself, but I’ve got to believe you’ve experienced failure in some shape or form too. First, it’s personal. It’s something that usually reflects poorly on us: a miss, a fail, a wrong call. When things go sideways, you just want to suffer the indignities in hiding.

I’ve experienced my share of failures, and I still don’t know whether I’m entirely over them. But here’s what I’ve learned: the real regret isn’t the failures themselves. It’s the time, and in my case, years, absolutely wasted being embarrassed by them, hiding from them and, worse, the theft of confidence they created and the opportunities I may have missed because of it.

That’s the peculiar thing about failure. It never feels safe. In real time, there’s no guarantee that a particular failure is eventually going to become part of a success story, or that you’re even going to be okay.

The very notion of failure is daunting because it represents the unknown. It doesn’t tell you whether you’re going to succeed. It tells you you’re attempting something whose outcome isn’t guaranteed. And that is lonely business indeed because no one, including yourself, has this answer.

Maybe this is why great failure stories matter. When we hear them from the other side, failure becomes triumph. Over the unknown. Over fear. Over the possibility that things might not work.

We logically know trials, challenges and failures are part of life. But emotionally? It’s an entirely different story. I found that out yesterday when I tried to talk about my own failures on camera and, despite everything I want to believe about failure, found the words, the story, remarkably hard to say.

I have tremendous pride. I like dignity. I don’t want to hang my personal laundry out for everyone to see, but I want to be able to talk about my failures with a sense of objectivity and openness. Maybe even pride. A sort of survivor’s pride. I want you to talk about yours too. Maybe it’s time we started wearing failure as a badge of honor rather than a scarlet letter.

Because a failure-free life isn’t necessarily a successful one. It may simply be a life in which we never risked enough to find out.

So maybe the better question isn’t How do I avoid failure?

It’s How do I get better at having it?

IT’S NOT YOU. WELL, ACTUALLY…

Why Failure Is So Damn Personal

The problem with failure is that it rarely stays neatly attached to the thing that failed. It tends to stick to us like glue. A business fails. A relationship fails. You don’t get the job. The project bombs. You make a terrible financial decision. Somewhere along the way, this failed slips into I failed. And if we’re not careful, I failed becomes I’m a failure.

That creep and then leap matters.

Researchers Lauren Eskreis-Winkler and Ayelet Fishbach have found that people often learn less from failure than from success, even when failure contains useful information. Why? Failure threatens the ego. We disengage, stop paying attention or look away from the very information that could help us improve. Fascinatingly, their research also found that we can learn perfectly well from someone else’s failure. In fact, we may learn better. Apparently failure becomes considerably more educational when it isn’t ours.

Which explains a lot.

We devour stories about other people losing everything, being rejected, getting fired and eventually clawing their way back. Their failure is interesting. Ours feels like an indictment. Like a glaring spotlight on us at our weakest moment.

And the more capable you believe yourself to be, the harder that indictment can hit. If part of your identity is I’m good at this, I make smart decisions, I know what I’m doing, failure doesn’t just challenge an outcome. It challenges the story you’ve been telling yourself.

Take it from me. I’ve had a few epic, somewhat public falls from grace. A small, prestigious and very social luxury brand I owned, with boutiques in Barneys stores across the country, had to file for reorganization. Our clients read like a who’s who of world leaders, society and celebrities. It was a rarefied world, and I was fortunate enough to live in it.

More importantly, I was responsible for generations of employees for whom there was no longer a job. If letting down my employees and clients wasn’t enough, I decided to leave a very long, and what was perceived as happy marriage. I discovered the financially secure life I thought we had been building together was in shambles. I moved countries and came back to the U.S.

Talk about failure. I was in the thick of every possible area of it in my life: love, family, business, financial and social.

Then came the really expensive part: what happened next.

I became insulated. I became more cautious. I hesitated at things when I had never missed a beat before. I began to overthink the easy phone calls. The next opportunity. I just wanted to feel safe.

I think that’s what we all do. We wait until life, something at least, feels safer, more certain, more guaranteed. But with this, beware. That’s where it gets you: confidence contracts. And without realizing it, we can easily start designing our lives around avoiding another failure rather than pursuing another possibility.

That’s when failure can cost us twice. The first loss is whatever went wrong. The second is everything we stop ourselves from attempting because it did. It’s something I learned the hard way. The trauma, the perceived embarrassment, cost me valuable time.

CHOOSE FAILURE WISELY

Some Are Better Than Others

Here’s where I have to deliver the sobering news about the clutches of failure, despite my positive spin that we should all try to fail forward: failure isn’t inherently productive.

Repeating the same bad decision isn’t grit. Carelessness isn’t courage. And continually running into the same wall doesn’t make the wall the problem. For failure to actually move us forward, we have to do something with it.

Harvard professor Amy Edmondson calls the failures worth having intelligent failures. They happen when we venture into genuinely new territory, where the outcome can’t be known in advance, and discover something valuable precisely because it didn’t work. In other words, getting it wrong is how we’re fed new information.

Researcher Manu Kapur has taken the idea even further with what he calls productive failure. His research suggests that struggling with a difficult problem before being given the solution can actually produce deeper learning than simply being shown how to get it right from the start.

I love this distinction because it removes the romance from failure. The goal isn’t to fail, and I don’t think any of us would make it one. The goal is not to waste a failure. To learn from it instead.

Henry Ford put it beautifully: “Failure is simply the opportunity to begin again, this time more intelligently.” More intelligently being the operative words.

Easier said than done if you’ve ever made the same mistake twice. And I certainly have. I’m not sure why deep grooves tend to form in our personal behaviors, or whether the size of a given failure determines how well we learn from it. But the goal, once your ego and heart are in check, is to look at what happened. Own what was yours. Separate what wasn’t. Extract any valuable information you can. Then decide whether the smartest next move is to adjust, pivot, quit or go again. All four can be forward motion.

Failing forward isn’t simply getting back up and doing the same thing harder. It’s getting back up knowing something you didn’t know the first time around.

ARE YOU NOT ENTERTAINED?

Welcome To The Arena

So if failure is inevitable, and some failure is productive and some of it is not, maybe there’s another way to look at it entirely: as evidence that, at the very least, we showed up.

More than a century ago, Theodore Roosevelt was speaking to Americans during a period in our history, not dissimilar to today, of extraordinary growth and upheaval. The country was rapidly industrializing, fortunes were being made, corporations were becoming enormously powerful and the very definition of progress was changing.

In 1902, he said something that feels almost uncanny today:

“During the whole period of the marvelous growth of the United States there has been a constant and uninterrupted stream of failure going side by side with the larger stream of success.”

Side by side. Not failure first, success later. Both happening at once.

Eight years later, Roosevelt gave us perhaps one of his most famous ideas in The Man in the Arena: the credit belongs to the person actually in the arena, willing to come up short while “daring greatly,” rather than to those standing safely outside it, experiencing neither victory nor defeat.

There’s something enormously freeing about that. After all, failure is data. We must use it or lose it.

To be seen, you have to risk getting it wrong. Put your work into the world. Start the business. Change careers. Love someone. Make something nobody asked for. Reinvent yourself. You cannot choose growth while simultaneously demanding a guarantee that everything will work out.

J.K. Rowling put an even sharper point on it: “Some failure in life is inevitable.” She argued that the only way to avoid failure completely is to live so cautiously that you effectively fail by default. And what sort of life is that?

To live without risk, without trying, without facing the potential for failure, is really missing life’s point, no? To me, this is the failure we should be afraid of. Not the spectacular f-up. Not the rejection. Not even falling flat on our faces.

Sitting safely outside the arena because we were too afraid to get in.

HONEY, I KILLED THE HYDRANGEAS

The Little Stuff Stings Too

Not every failure requires losing a company, a fortune or falling spectacularly from grace. Most of us are failing in tiny ways all day long, and while it stings, perhaps that’s exactly where we should start getting better at it.

You killed the hydrangeas. Burned dinner. Bought the sofa that looked great in the showroom and absolutely dreadful once it arrived. You painted the room, hated it, painted it again. Hosted the dinner party where nothing was ready on time. Tried to wear the trending thing that looked fantastic on everyone else and ridiculous on you.

These are hardly life-altering failures. But they’re little exercises in getting something wrong, living with it, learning from it and trying again.

In design, we don’t even call this failure. We call it the process.

We designers sketch, sample, move, remove, reconsider, edit and occasionally make very expensive mistakes. A room rarely arrives fully formed on the first try. Neither does a recipe, a garden, a wardrobe, a career, a relationship or, for that matter, a life. And in design, at least, some of the very best outcomes happen by mistake. I wouldn’t say this is the norm. I’m simply saying that failure can open up the possibility for something even better.

Iteration isn’t evidence that the design failed. Iteration is design.

And that may be one of the most useful ways to think about failure in our own lives. What if we gave ourselves the same permission to edit a life that we give ourselves to edit a room?

Try something. Live with it. Pay attention. Admit when it isn’t working. Change it.

Maybe we don’t need to get everything right the first time. Maybe we were never supposed to.

FAILURE THROUGH THE REAR VIEW MIRROR

And Connecting The Dots

Perhaps the hardest thing about failure is that we’re expected to make sense of it before we possibly can.

When Steve Jobs was fired from Apple at 30, he described himself later as a “very public failure.” He even considered leaving Silicon Valley altogether. Years later, he would call getting fired from Apple “the best thing that could have ever happened” to him. He said it freed him to become a beginner again, to create NeXT and Pixar and, eventually, to find his way back to Apple.

But here’s the important part: he couldn’t see any of that when it was happening.

“You can’t connect the dots looking forward. You can only connect them looking backwards.” — Steve Jobs

Neither can we.

Some failures will redirect us. Some will teach us. Some won’t. Some will humble us. Some will simply hurt like hell and take years before we can find anything remotely useful in them. And some may never reveal themselves as blessings in disguise at all.

But perhaps failure gives us something success never can: the knowledge that we can survive getting it wrong.

Success tells us I can do this. Failure tells us I can survive when I can’t.

And there’s real confidence in that. I wince as I write this because if you’ve ever experienced failure, you don’t ever want to experience it again. But it does give you confidence. Not the kind that makes you believe everything will work out exactly as planned, but the kind that comes from knowing that when it doesn’t, you’ve still got yourself. You can adjust, rebuild, reinvent and keep moving.

Maybe that’s what failing forward, or even productive failure, actually means.

Not celebrating every mistake. Not pretending failure doesn’t hurt. And certainly not f***ing up for the sake of it. It’s just refusing to let one failure write the rest of the story.

Because in the end, the people who never fail may simply be the people who never risk enough to find out what they’re capable of.

The rest of us? We’re still connecting the dots.