Why We Must Fail (Rosh Hashanah 5779)

Rabbi Joel Mosbacher | September 10, 2018

Special thanks to Rabbi Michelle Pearlman of Beth Chaim Reform Congregation of Malvern, PA, with whom I collaborated on the ideas for this sermon.


When she was growing up, Sarah Blakely’s father would sit her down at the kitchen table every Sunday night and ask Sarah and her brother, “What did you guys fail at this week?” If they had nothing to report, her dad would become upset.

After years and years of failure, Sarah Blakely went on to create a little company - perhaps you’ve heard of it - called Spanx. Forbes eventually named Blakely the youngest self-made billionaire in history.

Sarah Blakely’s father’s question, “What did you guys fail at this week?” turns the usual parenting question, “what did you accomplish this week?” on its head. Sarah credits her dad with granting her the freedom to explore. For her, failure would never be about inadequacy, but instead, about searching out  bold new opportunities. Through the freedom to fail, Sarah Blakely gained the independence and self confidence to take risks.

So, what did you all fail at this week? I love that question, not only for parenting but for Rosh Hashanah, as we stand on the precipice of the new year.

What does failure look like, and what might we learn from it? I’d like to share some stories with you this morning, and then, I’d like to invite you to join me in making 5779 a year of failure. But more on that later.

A story comes to us in the form of a letter written by Rabbi Yitzchak Hutner, who was the head of a yeshiva in Brooklyn in the 1960’s and 70’s. The letter was addressed to a former student who was experiencing spiritual struggles.

The student wrote, in part, “I will never forget the desire that I once had to succeed and to climb ‘from strength to strength,’ but now, my hope is lost.”

Rabbi Hutner writes back to his student, saying, in part, “It is a terrible problem that when we discuss the greatness of our [ancestors like Sarah and Abraham and Moses], we actually deal only with the end of their stories.

“We tell about their perfection, but we omit any mention of the inner battles which raged in their souls. The impression one gets is that they were created with their full stature. This is, of course, not the case.”

Hutner points to a lesson in the book of Proverbs, where it teaches, “The wisest of all men, King Solomon, said, sheva tzadik yipol v’kam. ‘The righteous person will fall seven times and will rise.’”

Rabbi Hutner continues, “the unlearned [person might] think that [this saying] means, “Even though a righteous person falls seven times, they will rise.” [But a] wise [person] know[s] well that the [true] meaning is: “Because a righteous person falls seven times, they will rise.”

Hutner seeks to comfort his student by assuring him that the experience of failure can make him stronger in the end.

The next anecdote about failure comes from my favorite singer songwriter, David Wilcox - I urge you to check him out. He’s an incredible guitarist and an even better storyteller. I saved up money for a long time so that I could afford to play the same kind of guitar he plays. Over the years, he has really become one of my spiritual rabbis.

I had the privilege some years back of attending a songwriting workshop with Wilcox. Towards the end of the session, there was time for questions and answers, and one woman raised her hand and asked, “how do you write such truly amazing songs?”

Wilcox thought about it for a moment, and then responded. He said, “when I decide to write a really great song, I buy a new notebook and some great new pencils which I sharpen on my old pencil sharpener - you know, the kind that suctions onto the table? So I sit with that notebook and those pencils, and I say to myself, ‘I am going to write a truly amazing song.’

Wilcox pauses for a long second, and we’re left thinking, “that’s it? That's all it takes for him? I guess there's no hope for us."

But we wait.

And then Wilcox continues. “I say to myself, ‘I am going to write a truly amazing song. But first, I am going to write about a hundred really bad songs.”

David Wilcox gave me hope that day, because, after 34 years of playing guitar, I’ve written a total of 2 songs. One was a terribly cheesy love song to a college crush, and the other was a truly lame effort at a tribute to first responders after 9/11.

I have failed miserably as a songwriter. But maybe I just need to write 98 more bad songs in order to write 1 good one!

Sometimes, as with David Wilcox, we have the luxury to fail in private, like an artist who struggles behind the closed doors of the studio before revealing a finished product for public consumption.

Michelangelo made sketches, wax models, terracota models, stucco models, and more wax models before he even touched the marble block that became his sculpture of David.  Often, by the time we reveal ourselves and our work to others, our efforts contain, visible or not, a host of failed efforts.

Not so with the Great Chicago Fire Festival. This story of failure is not about self-expression or inner, personal truth. The goal of this festival in the fall of 2014 was to create a platform where the city of Chicago could celebrate its spirit of grit and renewal.

This was a project whose designers sought to reveal the city at its very best, and it was to culminate with a dramatic display of buildings on fire as they floated down the Chicago River.

The task for putting the festival together was given to Jim Lasko, the founder and co-artistic director of Redmoon Theater in Chicago.

The throng of tens of thousands of people that lined the streets along the river jostled for good vantage points as dignitaries gathered for a celebration of the city's rebirth after the legendary 1871 blaze that left it in ashes.

But instead of roaring flames, the fires sputtered and guttered. The model Victorian homes floating down the river failed to ignite as planned. A public announcement blamed the difficulties on a problem with the electrical system.

After several failed attempts to light the fires, the spectacle's crew moved on to the fireworks finale. Thousands of people were witness to an event whose highly promoted conclusion fizzled. Literally.

Jim Lasko wrote a beautiful and poignant piece about the event in the Chicago Tribune a few months later, in which he shared the experience of speaking to his children about his failure. They had seen the newspaper headlines and read some of the social media posts, and had been teased at school, and Lasko was left to explain it all to them.

“The way that we gleefully heap scorn upon failure is misguided at best,” Lasko wrote. “Failure is the foundation of success. Without question and without exception. No great thing has been accomplished, no life-changing invention has been made, no bold new art form has been created that was not preceded by a string of unhappy failures.”

“No great thing has been accomplished” Lasko wrote, “that was not preceded by a string of unhappy failures.”

Boy, does this theme speak to us on this first day of the New Year!

It is our season of reflection, a season that began in earnest with the first day of the month of Elul, 29 days ago. This is the time when we are called upon to think about our own failures. It could be a mighty depressing season for those of us who fail as often as we succeed!

But we have spiritual teachers with us this morning - Sarah Blakely, Rabbi Hutner, David Wilcox, and Jim Lasko - who are calling us to a different perspective on failure. They call us not to discount or disavow our failures, but in fact, to grow from them, to embrace them.

And more, these teachers  would not want us to only make safe and secure choices so that we don't fail in 5779.

In fact, I think they'd ask us to be willing to fail,
because it is often only by falling that we learn to get up;
it’s only by writing 100 bad songs that we get to write a truly great one;
it’s only by failing in our efforts sometimes that we learn to light a fire that needs to be lit.

Sheva tzadik yipol v’kam, King Solomon said. Because a righteous person falls seven times, they will rise.

Jim Lasko told his children, “it is not failure or the frequency of failure or even the scale of failure that is the deciding factor in the arc of a career or a project, but the response to it. How one absorbs and assimilates the failure is the crucial measure.”

In this sermon, I am going to issue you three failure-related challenges. The first challenge is just for you, but for the last two, I am going to ask you to make yourself vulnerable to another person.

The first challenge for you to reflect on for a moment is: What do you consider your biggest failure from the past year? Think big. What risk did you take - in a relationship, in a business venture, or in some other field, that blew up in your face, that went south, that went wrong somehow?

I know this might be difficult or even painful to do. Who among us relishes dredging up our own personal failures? But that’s what this time of the Jewish year is all about.

Think about what you learned from that failure, if anything. How did you grow or change as a person because of the nature of that failure?

As reporter Leah Fessler writes in an article called, “Fail Slower,” “Failing, whether it’s your first or fiftieth time bombing a presentation, messing up a calculation, or bumbling through an interview, the sting of rejection never quite wears off. And while Silicon Valley gurus preach the importance of “failing fast”, it’s easy to take real-life, everyday failures personally.

Failure presents invaluable learning and growth opportunities, which is why the tech world finds the concept so buzzworthy. But to extract such learnings, we need to analyze not only the failed result, but also the failure itself.

Amy Edmundson of the Harvard Business School makes the case that we need to see that failure comes in three basic types - preventable, complex, and intellectual. And she urges us to see that not all failures are equal.

Preventable failures are just what they sound like - failures we have the  knowledge and ability and sole power to prevent. When we fail a test we didn’t study for, or let ourselves or a loved one, a friend, or a coworker or even God down on any of a million promises we might have made, it’s reasonable to feel bad about ourselves for this failure we could have prevented.

Complex failures [by contrast,] occur when we have good knowledge about what needs to be done, but a combination of internal and external factors outside our control come together in a way to produce a failure. Here, we have the knowledge, but not sole control. These kinds of failures happen all the time in hospital care, for example, where there’s enough volatility or complexity in the environment that things just happen.

The third, and juiciest form of failure is intellectual failure. This is what Silicon Valley entrepreneurs talk about when they promote “failing fast” or “failing forward.” Often, these types of failures occur when we’re working in areas in which we lack both expertise and control, or when we are trying things we've never tried before.

Ultimately, all failure should be contemplated, not ignored. And while feeling bad about ourselves  is sometimes warranted, it should never be a permanent state of being. If you failed in what Edmundson calls “preventable” ways in 5778, then you might spend the next ten days repenting, apologizing to the people you failed, and earnestly resolving not to fail in those ways again.

And if you failed in complex or intellectual ways, you could, instead of feeling bad, spend these days considering what you learned from those failures that can launch you forward in the coming year. More often than not, failure is a way to learn something you didn’t know before. Sheva Tzadik yipol v’kam.

I like watching Inside the Actor’s Studio, a show in which James Lipton interviews prominent actors about their careers. At the end of every show, Lipton asks each actor the same 10 questions, including, “What would you try if you knew you couldn’t fail?” This morning/afternoon, I’d like to pose to you a slightly different question for my second challenge: What are you willing to try this year even knowing you might well fail?

Perhaps you’re like Rabbi Hutner’s student; you’re someone who once had a desire to succeed or climb, but life’s experience has beaten you down. Are you ready to make a personal change?  Maybe this is the year you’re finally ready to stand up for yourself against abusive behavior you don’t deserve at home, or in the workplace.

Or maybe this is the year you’re finally going to get into treatment for an addiction. Or maybe you're going to make yourself vulnerable enough to ask for help, or finally admit that you don’t know everything.  You are finally willing to take a personal chance, even if you might fail.

Or maybe you long to be creative like David Wilcox. You have an idea for the next great American novel or a great new business model; you’ve always wondered what it would look like to paint or work in clay or quilting; you’ve always admired stand-up comedians and really want to try improv.

But you’ve already started a dozen drafts or you’ve already been told a dozen times that it’s a crazy idea. What would it feel like to try a dozen more times, believing you can get there with practice and effort and failure as your guide? What kind of notebook, what kind of pencils, could entice you to try again, to stay with it, even when it gets hard?

Are you willing to make a public leap, maybe not on the level of Jim Lasko, or maybe yes! You’re going to reactivate your profile on the dating app. Or you’re sagged down in a career that has gotten stale and this is the year you are going to begin a whole new chapter in your work life.

You’re going to go back to school. Or you’re finally going to retire and explore the world or begin a “give back” stage of your life. You’re going to run for elected office to bring sanity to a corner of this crazy world. You’re going to refocus your philanthropic giving on an institution that has the power to transform people and the world. (If you need any ideas, Barri and I might have one!)

Now I want to be clear about this challenge: I am not encouraging you to take an immoral risk; I am not asking you to put your life or the life of anyone else on the line. But I am asking you to imagine stepping way outside of your comfort zone. If the idea you’re conjuring doesn’t make you at least a little anxious, you’re not thinking big enough.

And I also know another thing. Some of us feel like we have tried and failed, tried and failed, again and again. I don’t mean to sound naive or pollyannaish about how hard this work can be. But I do want to challenge everyone in this sanctuary to ask yourself the question: What are you willing to fail at in 5779?

And now, for the last challenge, I want you to think about a person in your life that you would be willing to share that willingness to fail with. Think about someone - a friend, a partner, a spouse, a parent, a child, a clergy person - that you would be willing to risk being vulnerable enough to to tell them about your dream, your vision for yourself, your family, your work, your city, your country.

Who is a person who would be willing to listen to your 100 bad songs so that you can finally write the newest hit on Spotify? Who is the person with whom you could share your quiet, personal dream who will suspend judgement? Who is a person who believes in you, perhaps even more than you believe in yourself?

Think for a minute. And then I challenge you to share your particular willingness to fail with that person in the next 10 days. And if you can’t find another person, share it with me. I’d love to be able to share some of the biggest and boldest ideas, anonymously, of course, with the congregation on Yom Kippur. And if you don’t want me to share it with anyone else, I’d still be honored to listen.

What ever happened to the people in the stories with which we began this morning? We know what happened with Sarah Blakely. I don’t know who the student of Rabbi Hutner was, or what ever became of him. I hope that he heeded the rabbi’s urging to recapture his confidence and will.

I know that David Wilcox just released his 28th studio album after writing no doubt hundreds of bad songs. And Jim Lasko is opening up a makerspace in Chicago, which will house everything from an industrial kitchen and a woodworking shop to a 4,800-square-foot event venue. Lasko described it as a "social club" designed to "bring people together around the experience of making things.”

Blakely and Hutner’s student and Wilcox and Lasko all failed. Some of their failures were private, and some were very very public. But fail they did. And for at least three of them, because they failed, they rose.

I am going to put my willingness to fail out there right now, in front of all 2000 people who will fill this space this morning. I am going to do something I’ve only done twice before. I am going to write a song. And, no, I’m not willing to share the last songs I wrote, because they were so bad. But I’m going to write a song inspired by King Solomon’s words - sheva tzadik yipol v’kam. “Because a righteous person falls seven times, they will rise.”

And I am going to play it on piano, an instrument on which I had only 3 lessons when I was 10 before I quit. And I am committing that I will share this song with you by Chanukah. And no matter how bad it is, I hope you’ll be willing to listen. I promise I won’t make you listen more than once.

Here’s the thing, my friends. We might fail. Depending on the size of the risk we’re willing to take, it might be, as the kids say, “an epic fail.”

But we need to embrace failure as evidence of effort, not condemn it as sloppy, or worse, an indictment of us personally. The cultural stigma that surrounds failure is counterproductive. The big and the bold and the new are often built on a foundation of failure.

I close this morning with words from the 20th century Jewish scholar and philosopher Andre Nehrer:

“What is it to weep? To weep is to sow. What is it to laugh? To laugh is to reap. Look at this man, weeping as he goes. Why is he weeping? Because he is bearing in his arms the burden of the grain he is about to sow.”

And now, see him coming back in joy. Why is he laughing? Because he bears in his arms the sheaves of the harvest. Laughter is the tangible harvest, plenitude. Tears are sowing; they are effort, risk, the seed exposed to drought and to rot, the ear of corn threatened by hail and by storms… It is not the harvest that is important: what is important is the sowing, the risk, the tears.

Let's make 5779 a year of sowing and reaping. Let's cry together and laugh together. Let's be willing to fail, together.

Shanah tovah.