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17 September 2026

Rabbi Winston: Parashas HaAzinu - Shuvah

I WISH I had your confidence.” 

“Sorry?”

“I said I wish I had your confidence,” I repeated.

He didn’t know me, nor I him, and his face said it all: “What are you talking about?”

“The way you davened Shemonah Esrei so quickly on Rosh Hashanah. You obviously are not concerned about anything bad happening to you this year.”

He just shrugged his shoulders.

“I guess after years of doing the same thing and coming out just fine, it is easy to think that our tefillah doesn’t really impact our judgment, if judgment even really takes place, right?”

“What do you mean? It’s Rosh Hashanah…Yom HaDin. Of course judgment happens,” he answered.

“Then why aren’t you concerned?” 

I think I was starting to annoy him. “I don’t know. I said everything. I knew what I was saying. I did enough.”

“How do you know?” I asked him. “Personally, I’m never quite sure. I mean, I try hard, but I wonder if I can try harder…and that if I don’t, will that be what Hashem judges me on.”

“Well, you’re still here, aren’t you?” a slight smile on his face as if to minimize my concern.

“That’s the problem…” I said, obviously surprising him. 

“Why is that the problem? You’d rather die?”

“Nope. But I’d also rather keep my merits for the World to Come in the World to Come.”

He had to process that. It didn’t seem to him to follow from our discussion, so he was trying to figure out what to respond. I didn’t wait.

“Yeah, people have the wrong idea.”

“What wrong idea?” a little concern in his voice for the first time. 

“Well,” I said, “they think that because they have survived another year despite underachieving spiritually that they pulled the wool over the Heavenly Bais Din and got past them despite being somewhat unworthy.”

Unconsciously, he made one of those faces that said, “Does that apply to me?”

“What they don’t realize is that Heaven doesn’t always exact judgment on the spot despite a person’s guilt. There are other factors to be considered when deciding how to deal with a person in need of Divine retribution, like the lives of other people they interact with, and how their punishment will affect history. Sometimes people survive their judgment in the merit of others, which leaves the person in debt to Heaven. If Heaven doesn’t want to collect in this world, it takes it from a person’s merit in the World to Come…something they won’t even find out about until they get there and see how much lower their account ended up being because of all the times they drew from it in this world.”

His contorted face revealed that all of this was new to him, and that it concerned him. It hadn’t occurred to him that by ordering “free” room service, he was actually racking up a bill to be paid at “checkout.”

There was a deliberate pause to let my words sink in. Then I said for good measure, “Like I said, I wish I had your confidence.”

He just smirked and walked away, but I must have hit my mark because I noticed how next time he put more into his Shemonah Esrai. 

How do I know? Because that person was me. I could have had the same dialogue with several others in my minyan, or in shuls around the world, but I wouldn’t have the nerve. I couldn’t turn my back on myself or say, “What business is it of yours how I daven?” And, after having that inner discussion many years back, it has spurred me on to take my opportunity to stand before God in judgment seriously.

In this week’s parsha Moshe says:

You weakened the Rock Who bore you; you forgot the God Who delivered you. (Devarim 32:18)

We do this by not being real with Divine judgment, no matter how unreal it may seem. God wants to give us good, lots of it. But we can’t receive it while unworthy, which “weakens” His ability to give to us. 

So, just because we have walked away from countless Rosh Hashanahs and Yom Kippurs “unworthy,” don’t think we get away with it. Just because so many people do even worse and yet prosper even more in the upcoming year doesn’t mean they’re getting away with anything. They just haven’t received the bill yet.

If you’re not real with the judgment you can see, work on being real with the one you can’t. Because, by the time you find out what the “cheshbon” has actually become, you’ll have no other way to pay it down. Teshuvah is that miraculously amazing opportunity we have now. Use it well.

Gmar Tov,

Pinchas Winston

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