I spent at least half my childhood drawing. By the time I got to college and signed up for my first drawing class, I was pretty comfortable with a pencil. My teacher was a brilliant draftsman named Will Reimann. To impress him, I fired up all my best tricks: lots of varied lines, fade-outs, soft gradients. One day while I was drawing, something landed on my sketch pad. It was a mechanical drafting pen.

“Use that from now on,” said Mr. Reimann. And he smiled the smile of a man who has hatched an evil plot.

Oh, how I hated that damn pen! It drew a stark black line of unvarying thickness, making all my faboo pencil techniques impossible. You’d think my teacher would’ve been helpful, or at least forgiving. But no. He’d glance at my awkward ink drawings, groan “Oh, God,” and walk away holding his head in his hands, like a migraine sufferer. My art grade plummeted. I writhed with frustration. A few weeks later, as I sat in another class taking notes with the Loathsome Pen of Doom, something happened. Without my intention, my hand started dancing with that horrible pen. Together, they began making odd marks: hatches, overlapping circles, patches of stippling.

The next drawing I completed won a juried art show. “How did you figure out a drafting pen could do this?” one of the judges asked me.

“I failed,” I told them. “Over and over again.”

Since then I’ve had many occasions to celebrate failure, in myself and in others. From my life-coaching seat, I’ve noticed that the primary difference between successful people and unsuccessful people is that the successful people fail more. If you see failure as a monster stalking you, or one that has already ruined your life, take another look. That monster can become a benevolent teacher, opening your mind to successes you cannot now imagine.

The Optional Agony of Defeat

My dog-groomer friend Laura breeds and shows prizewinning poodles. One afternoon she arrived at the off-leash dog park looking thoroughly dejected.

“What’s wrong?” I asked her as our pets gamboled about.

“Ewok,” said Laura, nodding mournfully toward her well-coiffed dog. “He didn’t even place at the show yesterday. Didn’t…even…place! And he just hates to lose!” Her voice was so bitter I winced. “He should have been best in show,” she said. “Look at him—he’s perfect!”

I looked at Ewok. He looked fine—but perfect? Who knew? To me, saying a poodle with long legs is better than one with short legs seems absurd. A poodle’s a poodle, for heaven’s sake. I think Ewok would’ve agreed. He certainly didn’t seem to be the one who hated losing. He’d discovered a broken Frisbee and appeared to be experiencing the sort of rapture Saint Teresa felt when visited by God.

Laura’s desolation stemmed not from what actually happened at the dog show but from her ideas about success and failure. Lacking such concepts, Ewok was simply enjoying life. Going to dog shows and winning, going to dog shows and losing, going to the park and scavenging—from Ewok’s perspective, it was all good. Meanwhile, Laura’s thoughts about losing had tainted all these experiences. Thankfully, she’d managed to avoid a pitfall even worse than failure: success.

“Success is as dangerous as failure,” said Lao-tzu, and any life coach knows this is true. I can’t count the number of times people have told me, “I hate the job I’m doing, but I’m good at it. To do what I want, I’d have to start at zero and I might fail.” Dwelling on failure can make us miserable, but dwelling on success can turn us into galley slaves, bound to our wretched benches solely by the thought, “I hate this, but at least I’m good at it.” This is especially ironic because researchers report that satisfaction thrives on challenge. Think about it: A computer game you can always win is boring; one you can win sometimes, and with considerable effort, is fun.

With time-killing games, where the stakes are very low, pretty much everyone’s willing to risk failure. But when it comes to things we think really matter, like creating a career or raising children, we hunker down, tighten up, and absolutely refuse to fail. Anyway, that’s the theory. The reality is, we are going to fail. Then we make things worse by refusing to accept this.

Tammy came to me distraught because her 17-year-old son, Jason—her perfect son, whom she’d raised with perfect love, perfectly following every known rule of perfect motherhood—had been arrested for public intoxication.

“I’ve failed,” Tammy sobbed. “I’ve failed Jason; I’ve failed myself!”

“Yup,” I said. “You got that right.”

Tammy stared at me as though I’d slapped her. Clearly, that was not my line. I shrugged. “You’ve failed a million times, and you’ve succeeded a million times. Welcome to parenthood. Do you know any mothers who never fail their kids?”

“Sure,” Tammy said, nodding. “A lot of my friends at the country club are perfect mothers.” She wept even harder. “And they say horrible things about the bad mothers. Now they’ll judge me, because Jason…” She dissolved in sobs.

“Tell me,” I said, “do you actually like any of those women?”

The sobbing stopped abruptly. There was a long moment of silence, and then Tammy seemed to transform before my eyes. She sat up straighter.

“You know, I don’t,” she said. “I don’t really like any of them.”

“I believe you,” I said. “I don’t know your friends, but if I had to live with someone like the person you were a minute ago, I’d start drinking too.”

“I do live with her,” said Tammy wryly. “And I’d love a drink.”

“Hear, hear,” I said. “So go home and apologize to Jason for imitating mothers you don’t even like. Try being real with him—teenagers love that. Every moment you’re real with him, you’re succeeding as a mother. Every moment you lose yourself by trying to be perfect, you’re failing. And the moment you accept that you’re failing, you’re succeeding again.”

Tammy squinted at me. “You’re telling me to accept failure as a mother?”

“Whenever you fail,” I said. “Got any other options?”

“Well, no…but accept failure? As a mother? I can’t.”

“Sure you can,” I said. “Try this: Think about the fact that you failed to control Jason. Notice how you’re all scrunched up, thinking, ‘Oh, no!’?”

Tammy nodded.

“Okay, now unscrunch, and instead of saying, ‘Oh, no!’ say, ‘Oh, well…'”

I beamed at Tammy. She waited for me to go on. I didn’t.

Tammy laughed. “I can’t believe this,” she said. “I came here thinking you could tell me how to fix my son, and the best advice you’ve got is, ‘Oh, well’?”

“Damn. You’re right,” I said. “I’ve totally failed you.” I took a deep breath, and relaxed. “Oh, well…”

Tammy looked at me for another long minute. Then she said, “Just your saying that makes me trust you.” This is the magic of accepting that you’ve done your very best but failed. Own your failure openly, publicly, with genuine regret but absolutely no shame, and you’ll reap a harvest of forgiveness, trust, respect, and connection—the things you thought you’d get by succeeding. Ironic, isn’t it?

Blasting Through Attachments

I owe my ability to accept maternal failure to my son Adam. Though I bred young, never smoked or drank, ate right, and all that, Adam showed up with an extra chromosome, mentally challenged. Oops. From the word “go,” I’d failed to make him a successful student, athlete, rocket scientist. In my mind, nothing could compensate for such massive failures.

This was when I discovered that the bigger the perceived problem, the better it delivers failure’s great gift: freedom from attachment to ideas about success. A lucky person escapes her enemies. But a really lucky person (as the poet Rumi puts it) “slips into a house to escape enemies, and opens the door to the other world.”

This can happen in tiny ways and huge ones. The day my pencil-proficient mind accepted failure and allowed my hand to start dancing with that mechanical pen, a door opened on a new way of drawing. Accepting that I’d failed to create a “normal” life for my child blasted away much bigger assumptions, bone-deep beliefs like “Successful mothers have smart children” and “My kids should never fail.”

This hurt like a sonovabitch, but when the rubble cleared, I found myself in a world where all judgments of success and failure are arbitrary and insignificant, as ridiculous (no offense) as the American Kennel Club’s definition of the “perfect” poodle. Without judgments, it’s obvious that joy is available in every moment—and never in anything else.

I can see that Tammy gets this. Jason’s rebellion becomes a gift as failure does for Tammy what I’ve seen it do for so many others: soften, mellow, calm, enrich, embolden. The poet Antonio Machado expressed it this way:

Last night as I was sleeping
I dreamt—marvelous error!—
that I had a beehive
here inside my heart.
And the golden bees
were making white combs
and sweet honey
from my old failures.

I can’t say I look forward to the failures that await me. But they’ll be along in no time, so I feel lucky to know what to do when each one arrives. It will work for you too. Unscrunch. Exhale. Let go of “Oh, no!” and embrace “Oh, well…” Then, whatever door opens, walk through it.

Failing Upward

By my sophomore year in college, mechanical pens were my favorite drawing instruments. Trial and error (and error, and error) had made me so comfortable with them that they felt like extensions of my hands. Being a masochist and a fool, I signed up for another class from Mr. Reimann. One morning while I was drawing, something landed on my sketch pad. It was a watercolor brush.

“Use that from now on,” said my teacher. “You’ll hate it. You put a mark down on the paper, and half an hour later, it decides what it’s going to look like.”

I picked up the brush. “You’re not going to help me with this, are you?”

“Well, let’s put it this way,” said Mr. Reimann. “The sooner you make your first 5,000 mistakes, the sooner you’ll get on to the next 5,000.” And he walked away smiling his evil-plot smile, having arranged yet another dance with failure, inspirer of all uninspired artists, master teacher of all master teachers.