Rabbi Volpe, in the way only he can, broke down the essence of Yom Kippur to how all people deal with screwing up and asking for forgiveness.
Here’s the core idea:
Life is too short to not fight for what you want today. If you screw up, and you will, there’s no magic fix. Apologize and mean it. Reflect on what went wrong. Remember, sorrow isn’t a strategy, but it is a vulnerability and a promise to be better. Then, move forward.
Life is messy. Clean up what you can. And keep moving forward, because the fight that matters is today.
Here’s the passage that hit me the hardest (and do read the full essay if this hits you too, “A Rabbi’s Guide on Making Amends and Letting Those Grudges Go“),
Judaism offers a series of ideas and guidelines for how to cope with offense and foster forgiveness. On Yom Kippur, it’s traditional to wear white, not only because white shows the slightest stain, but to remind us of the shrouds in which we will one day be buried. We do not have forever; we must struggle to right our souls now.
If you have caused offense or harm, Yom Kippur does not magically buy you absolution. But the traditions surrounding the day do offer guidance for seeking forgiveness. First, you must apologize to those you’ve hurt, sincerely, as many as three times. The apology should not come weighed down with justification, but rather should acknowledge the other person’s hurt and express sincere regret.
Second, serious, sustained reflection is required to try to change who you are. The Hebrew word for repentance, teshuvah, also means return. To repent is to return to what once was, what became hidden through coarseness or impulse. It is also to return to God and to the community. But slow, careful restoration takes time. The one who is sorry today and expects to stride right back, unblemished, is naïve or conniving.
Third, you must change your ways. The sage Maimonides teaches that one who says to himself, “I’ll sin and then, repent” cannot be forgiven. Sorrow is not a strategy. It is a vulnerability and it is a promise.
h/t Brian Portnoy (more insights from Portnoy here and Volpe here too)