Yom Kippur Doesn't Cover What You Did to People

You know that apology you’ve been carrying around for months? The one you’ve rehearsed in the car, at a red light, maybe four separate times, and never once said out loud?

Yeah. That one.

Yom Kippur starts at sundown on Sunday, September 20 this year, which means we’re sitting in the ten days right now. And I hate to be the guy who brings this up with a week to go, but the fast doesn’t cover that apology. It was never going to.

The Loophole That Isn’t

A lot of us grew up half-understanding this holiday. We treat it like a reset button. Fast, show up, beat your chest a few times, walk out clean.

The Mishnah closes that door in one line. Mishnah Yoma 8:9 says that for things between a person and God, Yom Kippur atones. For things between a person and another person?

It doesn’t. Not until you go and appease the other person yourself.

No asterisk. No workaround. No “but I felt really bad about it in my heart.”

The holiest day on the Jewish calendar has a carve-out, and the carve-out is other people.

The same Mishnah adds a line I think about more than the famous one: whoever says “I’ll sin and repent, I’ll sin and repent” doesn’t get the chance. The system notices when you’re gaming it. (Which feels like something written by a person who had met other people.)

“Sorry You Feel That Way” Is Not an Apology

Now let me bring this into my day job, which is mostly Zoom calls with business owners who are nervous about their websites.

I run the custom websites division at DoorLoop, and I’ve written before that roughly 75% of that job is emotional, not technical. Which is a polite way of saying I get a lot of chances to be short with somebody, miss a detail, or answer a question in a tone that lands harder than I meant it to.

So I’ve heard every flavor of the corporate non-apology. You have too:

• “Sorry for any confusion.”
• “Sorry you feel that way.”
• “We apologize for the inconvenience.”

Notice what all three have in common? Nobody’s in them. No person did anything. A confusion simply occurred. (Where does a confusion come from, exactly? It just rolls in off the bay, like the afternoon rain.)

An apology without a subject in the sentence isn’t an apology. It’s a press release.

When’s the last time you said sorry to someone without sneaking an “if” in there? That’s the actual standard the Mishnah is setting. Go to the person. Say the thing. Out loud, with your own mouth, in a sentence that starts with “I.”

The Rambam Wrote You a Script

Here’s the part I love, because it reads like an escalation policy somebody’s ops team would build.

In Hilchot Teshuva 2:9, the Rambam walks you through it step by step:

Five steps, and the whole thing fits on an index card. (No slide deck, no offsite.) It’s tighter than most conflict training I’ve sat through, and I’ve sat through a few.

The Part That Stings

Step five has a twist I completely missed the first time I read it.

Once you’ve genuinely gone three times and the person still won’t forgive you, the Rambam says you stop. And then he adds something I didn’t see coming. The one refusing to forgive is now the one sinning.

The obligation transfers.

Turns out the person holding the grudge has homework too.

Which is inconvenient, because most of us are far more interested in the apology we’re owed than the one we owe. (I’ve been on both sides of this in the same week. Possibly the same day.)

There’s one exception, and it’s a good one. If the person you wronged was your teacher, you keep going. A thousand times, he says. Some relationships don’t get a three-strikes rule.

So. Eight Days.

I’m not going to pretend I’ve got a tidy list of calls to make and a color-coded schedule for making them.

But I keep landing back on something I wrote about Heschel: the showing up is the practice. And notice that the confessions we say on Yom Kippur are written in the plural. We betrayed, we robbed, we spoke badly. Not I. We.

The whole liturgy assumes you’re standing shoulder to shoulder with people you’ve got unfinished business with.

So before the sun goes down on the 20th, make the awkward call. Send the text that makes your stomach drop a little. Use a sentence with a subject in it: “I did this, and I’m sorry.”

Worst case, they say no, and the obligation isn’t yours anymore. Best case, you walk into Kol Nidre with a shorter list and a lighter chest.

Either way, you’ll have done the one part of the day nobody can do for you.

G’mar chatima tova from Miami. If there’s a call you’ve been working up to this week, go make it before the fast starts.