Yom Kippur: A National Celebration of Failure
As a recovering perfectionist, I never truly allowed myself to connect deeply with the Al Chet prayers. Sometimes, I would say the words but wonder: Do I really struggle with these? Admitting failure felt overwhelming—too final. I was too focused on maintaining an image of perfection, too afraid to confront the gaps in my own character.
This year, I made a conscious shift. Instead of seeing failure as something to avoid, I embraced it. I took each Al Chet and wrote out what greatness could look like if I truly embodied the positive side of that failure. It was a transformative experience. Suddenly, the gaps between who I am and who I could be became clear—and instead of feeling shame, I felt empowered. The language of positivity energized me, opening my eyes to a world of possibilities I had been too fearful to see.
Here’s an example of how I flipped the script:
- For the mistakes we committed before You under duress and willingly. I reframed this as: I avoid compromising situations and make proactive choices.
- For the mistakes we committed before You in business. I flipped it to: I am scrupulously honest with my clients, competitors, employees, and vendors.
By reframing the negatives, I began to see how much room there is for growth. This exercise wasn’t just a tool for me to feel better—it was a way to start living better.
Yom Kippur and Israel’s Current Moment
Reflecting on Israel’s current challenges, I couldn’t help but feel the relevance of the Al Chet prayers for our nation. Yom Kippur isn’t just an individual journey—it’s a national one. As I repeated each confession, I didn’t just focus on my personal failures, but on our collective struggles as a people.
For example:
- For the mistakes we committed before You by being arrogant.
I gut-checked myself: I practice humility and don’t feel superior to others. Right now, humility is something our nation desperately needs. - For the mistakes we committed before You by being stiff-necked.
I asked myself: Yes or no? Am I open-minded and do I cherish constructive criticism? Unity only happens when we stop being so stubborn. - For the mistakes we committed before You through baseless hatred.
I had to pause here: I unconditionally love all Jews and am actively unifying our nation. Baseless hatred is hurting Israel’s soul, and we can’t ignore it.
Why Didn’t Chazal Use Positive Expressions in Our Prayers?
My Rabbi, Rabbi Berkovits, shared something that completely changed how I view Yom Kippur: Yom Kippur is a national celebration of failure.
This day isn’t just about repentance—it’s about recognizing that greatness lies in confronting our flaws. It’s about standing face-to-face with our weaknesses, owning them like a deer caught in headlights. We don’t hide. We don’t shrink. We don’t cower. Instead, we embrace our shortcomings because, in that ownership, we create the space for true growth.
Yom Kippur teaches us that failure is not something to fear. In fact, it is the key to greatness. Our national identity as Jews is deeply tied to the willingness to embrace challenges. Saying the Al Chet prayers with a negative focus isn’t about wallowing in guilt—it’s an emotional, national celebration of confronting our weaknesses, fully embracing the raw emotional disappointment of where we currently are.
And it’s precisely this confrontation that paves the way for forgiveness and a brighter future. Letting go of the past and focusing on the present is not just healing—it fuels the future we are determined to build.
A Simple Yet Powerful Exercise
In this spirit, I’ve developed a simple exercise to help you transform your Yom Kippur reflections. You can access the document here, make a copy, or print it out for your personal reflection.
Here’s how it works:
1️⃣ Step 1: I Am…
For each Al Chet, reflect on a positive affirmation that corresponds to it. Then, ask yourself: Am I living this positively?For example, if the Al Chet is about dishonesty, ask: Am I truly honest in my daily life?
No gray areas—just Yes or No. This binary reflection forces us to confront reality and strip away excuses.
2️⃣ Step 2: If “No”—Do I Know How to Fix This?
If the answer is “No,” the next step is self-reflection. Do I know what needs to change? If not, I’ve identified an area for growth, an opportunity to improve.
The Power of Yom Kippur
This process forces us to be brutally honest with ourselves. It bridges the gap between past failures and future commitments to greatness. Our failures don’t define us—they’re simply guideposts pointing us toward improvement.
Our tradition has long embraced this mindset. Yom Kippur is not just a day of repentance; it’s a day of transformation. By confronting the parts of ourselves we often ignore, we can begin the real work of growth. And it’s in this work that our true potential emerges.
Our weaknesses don’t define us.
We can repair them.
We can grow from them.
This mindset is central to why we were gifted the Torah. We have the potential for greatness when we face our imperfections head-on. And the beauty lies in the power of these ancient prayers.
Final Thoughts
If this exercise resonates with you, or if you have any questions, feel free to contact me. The spreadsheet is dynamic and will generate personalized questions based on your responses. The final column focuses on the future commitment you can make to yourself—an added bonus as you work toward your own greatness.