I missed the deadline for this essay. I’m sorry about that. It’s just one of the daily mistakes I make, the imperfections I try to own and learn from.
If “perfect is the enemy of the good,” as attributed to Voltaire, might we infer that “imperfection is the friend of the great?” As the Jewish High Holy Days approach, many of us engage in a practice called cheshbon hanefesh—literally, an “accounting of the soul.” It’s time for our annual performance review, on a personal level and not just at work, a time for honest self-reflection, acknowledging our failures and charting a path forward. While this tradition is deeply rooted in Jewish practice, its lessons are profoundly relevant to corporate and nonprofit leaders of all stripes who are navigating how best to drive meaningful change while maintaining the trust and credibility essential for lasting influence.
From an early age, we are taught that failure is a bad thing and that we should do everything we can to avoid it. What this causes is a tradeoff: it creates a culture focused not on succeeding but on not failing.
Our fear of our imperfections also holds us back from learning and growing. As Rabbi Elimelech of Lizhensk noted: “Only G-d is perfect. Man’s actions must be basically defective in part. If one believes his good deed or holy study to be thoroughly pure and perfect, this is a sure sign they are thoroughly bad” (Louis Newman, The Hasidic Anthology [New York: Scribner, 1954], 315).
The prophet Michah stated (7:8): “Ki nafalti kamti—though I have fallen, I rise again.” How might we adopt this mindset and shift our focus toward success rather than merely avoiding failure? And how might we embrace our imperfections so that we may achieve even greater heights?
In a digital-first world that often seems to revolve around touting our accomplishments and announcing our successes, perhaps the most important assumption underlying this season is that it’s not about all we’ve achieved in the past year. Quite the opposite—it assumes we’re imperfect and have accumulated failures, mistakes and missed opportunities.
The question, then, isn’t whether we’ve fallen short personally or professionally. Rather, the challenge is facing the reality that we have all inevitably fallen short.
The Three Pillars of Embracing Imperfection and “Failing Forward”
From my experience as an imperfectionist and a nonprofit leader, I’ve identified three steps for transforming personal and organizational mistakes into growth opportunities.
1. Pushing to and through failure: if at first we don’t succeed . . .
I’ve missed more than 9,000 shots in my career. I’ve lost almost 300 games. Twenty-six times I’ve been trusted to take the game-winning shot and missed. I’ve failed over and over and over again in my life. And that is why I succeed (Michael Jordan in a Nike commercial).
Whether on a personal level or organizationally, growth and innovation are often elusive. This is especially so in a culture built on self-protection, process and fear. When fear of failure holds us back, we never fully push ourselves to next-level thinking, bold action and, ultimately, success. When we exercise, we actually break down muscle. The process can be painful, but we must achieve that failure in order to grow. We need to establish a culture that not only allows for but even encourages failure so we can create space for the learning opportunities that spring from the failures, the imperfections, the misses.
In a recent training with a group of intrapreneurs at the OU—talented employees across departments and levels—I asked them to “please fail.” The best way to learn your limitations is to sail past them!
2. Embracing imperfection: accepting limitations and owning mistakes
Fay Vincent, who served as Major League Baseball commissioner from 1989 to 1992, famously said: “Baseball teaches us, or has taught most of us, how to deal with failure. . . . I also find it fascinating that baseball, alone in sport, considers errors to be part of the game, part of its rigorous truth” (Ernest Kurtz and Katherine Ketcham, The Spirituality of Imperfection [New York: Bantam, 1993]).
When you’re managing complex operations and multiple stakeholders, mistakes are inevitable. Perfectionism isn’t just unrealistic—it’s counterproductive. Baseball is a milieu where if you fail seven times out of ten, you’re a hero. As organizational leaders, we must embrace this kind of imperfectionism—although perhaps not at that rate! In The Spirituality of Imperfection, the authors write that this kind of spiritual wisdom isn’t about knowledge—it’s “a spirituality of not having all the answers.”
When fear of failure holds us back, we never fully push ourselves to next–level thinking, bold action and, ultimately, success.
Imperfectionism isn’t about lowering standards or accepting mediocrity. It’s about creating a culture where failure becomes a catalyst for growth rather than a source of shame. As Shlomo Hamelech writes in Mishlei (24:16): “Ki sheva yipol tzaddik vakam—Seven times the righteous man falls and gets up.” If this is true for the righteous, then how much more so for me?
What that looks like can vary from small, personal examples of imperfection to bigger, more institutional ones. One instance of imperfection I experienced recently was in expressing my support to our 200 staff members huddling in bomb shelters across Israel during the recent Israel-Iran war. While each person I was writing to was in my thoughts, I incorporated some of the same language in multiple messages, and at one point I copied and pasted a note to a different staff member with the wrong name in the subject line.
It may have been a comparatively small-scale imperfection, but it stings to receive a note of support that’s actually addressed to someone else, and it suggests that the sender sees people as items on a checklist rather than as individuals. In this case, I immediately owned my mistake, apologized and reaffirmed my genuine care for each team member. Failure never feels good, but when we take ownership of it, it can teach us to strive to be better. A fundamental element of leadership is the willingness and ability to take full responsibility without deflecting blame or asking for special consideration. Your team is watching how you handle failure, and your response sets the organizational tone.
There’s another, darker side of this equation that has serious consequences. In “The Pain of Perfectionism” (The New Yorker, August 2025, https://www.newyorker.com/magazine/2025/08/11/the-pain-of-perfectionism), Leslie Jamison discusses the insidiousness of perfectionism that “perpetuates an endless state of striving. It’s an affliction of futility, an addiction to finding masochistic refuge in the familiar hell of feeling insufficient.”
She investigates the work of Gordon Flett, a psychologist known for his research on perfectionism, who believes that younger generations are facing an “epidemic of perfectionism.” In a survey of Canadian high school students, Flett found that 54 percent identified with the statement “I need to be perfect.” A recent Gallup poll (2024) agreed, finding that a third of teenagers in the US “feel pressure to be perfect.” Worse, Flett and Paul Hewitt, a professor of psychology, have demonstrated a connection between perfectionism and more serious forms of mental illness, including depression, anorexia and even suicide. If we are unable to acknowledge our mistakes and own them, we can lead ourselves and others down dark paths.
So how might we overcome the tendency to pressure others into perfectionism? My friend Joey used to encourage his kids—and taught me to encourage mine—every time they fell while learning to walk or ride a bicycle, or got hurt in any way. He would yell, “Safe!” as if they had just slid home with the game-winning run! His tone of voice and the smile on his face encouraged failure and changed the child’s perspective. It was magic watching my own kids smile when I did that.
3. Learn to grow: understanding the implications of our imperfections
The thing that was most helpful was when you made a mistake, you recognized it, and we got through it. When the perfectionist sees her therapist owning up to a mistake, she has an opportunity to see that imperfection “just is . . . [t]here’s no devastating consequence” (ibid.).
For both organizations and their leaders, it is often challenging to discern the valuable lessons hidden within our imperfections. Kurtz and Ketcham share this concept in a parable of a disciple who complains: “You tell us stories, but you never reveal their meaning to us.” The master responds: “How would you like it if someone offered you fruit and then chewed it up for you before giving it to you?”
Failure never feels good, but when we take ownership of it, it can teach us to strive to be better.
There is no universal template for understanding the implications of each mistake, but it is possible to learn from our errors. A personal example that comes to mind is when an organization awards a grant to the wrong candidate: we recently introduced an intensive process for internal leaders and departments to apply for strategic grants—but that doesn’t always guarantee the funding is used in the best possible way. We had a grant recipient who presented impressive goals but failed to spend the funding for a full year, despite being clearly informed that it was earmarked for a specific project. When they returned to request additional funding, we acknowledged that awarding the original grant had been a mistake—and we chose not to allocate any further resources.
Though we owned that mistake, there are additional implications that may be more complex to address. The grant recipient should consider what obstacles may be preventing them from utilizing the funding effectively—and reflect on how to either remove those obstacles or adjust their goals accordingly. For the organization, the implications include taking a hard look at our grant-awarding process and evaluating whether additional variables should be considered or whether new guardrails need to be put in place. As this is a relatively new program, we are wide open to continuing to learn how to do this effectively and responsibly.
Creativity and innovation are key elements for the growth of any corporation or organization—not only for new programs or projects but also for solving longstanding or complex issues. To take some pressure off everyone’s need to agree with the “boss,” I often introduce new suggestions by saying, “I have a terrible idea”—and in fact it often is!
Recently I was inspired by The Spirituality of Imperfection to launch an optional session called “Imperfectionists Anonymous” at our upcoming leadership retreat. The intention is to gather anyone interested in a heartfelt and vulnerable session where team members can share their stories of imperfections and mistakes. My hope is that this exercise will push us through our failures, encourage us to own and embrace our imperfections, apologize for our mistakes, and, most importantly, learn from—and with—each other so we can grow from these experiences.
And if not? I’ll apologize and, hopefully, learn something that will help us do better at whatever we try next.
Rabbi Dr. Josh Joseph is executive vice president/chief operating officer of the Orthodox Union.