This week was Yom Kippur, the Jewish holiday of repentance and atonement. Every year on Yom Kippur, my wife says to me, “I’m sorry for all the things I have done this year that have hurt you.” I respond with the same message. The message matters—not “If I’ve hurt you,” but the presumption that we have hurt each other. None of us are perfect, and this simple ritual begins from that truth. Small slights and bigger miscommunications are an inevitable part of any relationship. The practice pushes us toward humility, instead of focusing on another person’s flaws or on how we’ve been wronged, we start with our own shortcomings.
This is the opposite of our instinct. When we wound someone else, we often don’t even notice, but when we feel wronged, the sting is sharp and memorable. This imbalance leaves us seeking apologies and recognition for our own hurts while remaining blind to the pain we’ve caused. It's easier to feel victimized or indignant or angry at the slights we endure than it is to acknowledge our own role and feel repentant and remorseful.
The irony is that the people we love most are often the ones we hurt most—and who hurt us most in return. That is not what we want, but it is how closeness works: proximity magnifies both the good and the bad. The discipline of saying sorry—without excuses, without conditions—resets the emotional ground of a relationship.
Saying sorry first assumes that this is a universal human fallacy, and participation is a universal requirement. It does not wait for the other person to go first. Often, when we fight, we hold back, waiting for the other to admit fault before we relent. Here, the expectation is that each of us must take the first step. Accountability is not dependent on the other person’s willingness or readiness—it is our starting point.
We all overestimate the harm done to us and underestimate the harm we cause. If we know we are imperfect and prone to mistakes, why not act on that knowledge? The truth is not controversial. What is remarkable is how our behavior rarely matches what we know. I keep looking for strategies to close the gap between our understanding and our actions. Presumed error—leading with the assumption that we have fallen short—is be one way to bridge it.
When we refuse to acknowledge mistakes, we push others further away. But when we admit fault, we invite them to do the same. Responsibility begets responsibility, apology begets apology. As a leader, walk into a complicated situation where lots has gone wrong and assume responsibility, and watch everyone else start to own their contribution. Walk into the same situation and start blaming people, and watch the accusations fly and buck get passed. Acknowledgment opens space for others to speak honestly. This cycle has real power: it draws us toward reconciliation, it clarifies what went wrong, and it strengthens connection.
Recognizing that we both wound and are wounded keeps us humble and connected, rather than self-righteous and alienated. The challenges of being human– the errors we naturally make and the ways we all fall short and suffer– are hardwired into our brains as much as our innate compassion and kindness are. Religious rituals and practices are often rooted in this reality, and are tailor-made correctives to help us turn towards our better selves. This practice is not really designed to be an annual exercise, but rather to point the way towards a way of living that allows us to live with greater love and intimacy.
Most of the people that read this know me, in one way or another. And for those of you that don’t, you still read what I write. I’ve made mistakes this year. For many of you, I’m sure I’ve hurt you. I am sorry.
My hope is threefold. One, that you will also forgive me. Two, that you will take this as an opportunity to say sorry to the people you care most about for hurting them. And three, maybe try to use this message and this practice to help reset the rifts that are all around us. It is a small, concrete step to maybe make the world we live in a little bit kinder, a little bit better, a little bit less fractured.
Love,
Doc
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