Beating AI on Yom Kippur – Parshat Ha’azinu/Yom Kippur 5787

by LEIBY BURNHAM | September 18, 2026 7:53 pm

Recently, my daughter was driving me to the airport, when she told me about a frustrating customer-service experience she had that day. The person on the other end of the phone clearly was not a native English speaker, and understanding her was a challenge. The representative also couldn’t quite understand what my daughter was asking, the solutions she offered didn’t really match the problem my daughter described, and as the conversation went on, she seemed to become increasingly annoyed with my daughter. By the time my daughter hung up, she had lost a half hour of her day, she still had the exact same problem, plus the exciting bonus of now being aggravated.

I told her, “You know, I don’t think this problem is going to exist much longer.” We are rapidly approaching a world in which most customer-service calls will not be answered by someone sitting in a giant call center in the Philippines. They’ll be answered by artificial-intelligence agents. These agents will sound remarkably human, they will have the equivalent of 140 IQs, they will understand our requests much better, solve our problems much faster, and offer us alternative solutions that we weren’t even looking for.  

The AI agents won’t get tired. They won’t become irritated because you’re the 273rd customer who called that day with the exact same problem. They won’t be annoyed because their boss expects them to resolve 15 calls an hour, and you’re already on the phone for six minutes. They’ll have instant access to every company policy, every previous conversation you had, every product manual and probably the answer to your problem before you finish explaining it. And they will never wake up in a bad mood.

The company employing them will be happy to have them. They won’t need to step out for bathroom breaks, they won’t play on their phones while talking to customers, they will work 24 hours a day, seven days a week without charging for overtime. They won’t expect health insurance, or yearly raises. The companies won’t have to pay employee taxes, Social Security and Medicare, unemployment or worker’s comp, and won’t have to give them two weeks of paid vacation.

They will never sue the company for making a “hostile work environment,” they will never harass their coworkers, and they will never show up late to a shift. They won’t talk smack about the company at the water cooler with other employees, or complain about how little they are getting paid when the company is making so much money. And they can be trained on entirely new categories of services or products in a matter of minutes not months.

As we continued driving, the conversation broadened. What is going to happen when AI can do more and more office jobs that currently require human beings? Obviously, if your job is replacing a sewer line or rewiring someone’s house, you’re relatively safe for the moment. Eventually someone will probably build a robot plumber too, although based on what plumbers charge, I assume the robot will arrive wearing a Rolex.

But today, there are millions of jobs where the primary tools are a computer, a telephone and a human brain. Customer service. Scheduling. Basic accounting. Sales support. Tech Support. Insurance processing. Reservations. Those jobs are ripe for the picking, by millions of AI agents that you’ll be able to hire for fractions of the cost of hiring humans.

Already today, companies like Retell, offer 100,000 minutes of AI Generated customer support, using an AI model that reasons at the level of a person with a masters degree, for about $8000. They help you build the training and simulation testing until you’re satisfied with their competence.  You don’t pay for any time the AI agent isn’t actively working, so no bathroom breaks, no “I just need to call my daughter’s school back”. The AI can handle 20 calls at the same time, so you don’t need to hire extra workers to handle calls during the busy season. 100,000 minutes is far more productivity than you can get out of any employee in a whole year, and $8000 is a fraction of the cost.

That doesn’t necessarily mean companies will eliminate every human employee. In fact, I think some human beings will become much more valuable. But which ones?

If I own a company and have a choice between an AI agent that will enthusiastically help every customer twenty-four hours a day and an employee who acts like I am personally violating the Geneva Convention every time I ask him to answer the phone when it rings and respond to emails within 24 hours, that is not going to be a terribly difficult decision.

The people I’m going to fight to keep are the people who bring something to the job that the machine cannot bring. The customer-service rep who genuinely wants to solve your problem. The tech-support person who takes real satisfaction in figuring out why something isn’t working and helping you fix it. The salesperson who enthusiastically believes in what she sells. The reservations agent who makes you feel like helping you is an honor instead of an interruption. The employee who wakes up thinking about how to make the business better because, for some strange reason known only to him and possibly his therapist, he really loves his job.

AI may be able to imitate enthusiasm beautifully. But it cannot actually care.

And I think there is something in that distinction that helps us understand Yom Kippur.

About 2,700 years ago, the prophet Isaiah delivered his inaugural prophecy, one of the strangest messages imaginable to a religious population. People were bringing sacrifices to the Temple. They were observing holidays. They were praying. You would think G-d would be pleased. Instead, Isaiah begins speaking in G-d’s name and says (Isaiah 1:11-15):

“What need do I have of all your sacrifices? I am stuffed with burnt offerings of rams, and the fats of fatlings, and blood of bulls; And I have no delight in lambs and he-goats. That you come to appear before Me – Who asked that of you? That you should trample My courts?

No more! Bringing meal offerings is futile, incense is offensive to Me. New Moons and Sabbath, proclaiming of solemnities! Assemblies with iniquity I cannot abide. Your new moons and holidays fill Me with loathing; they are a burden to Me, I cannot endure them!

And when you lift up your hands, I will turn My eyes away from you; Though you pray at length, I will not listen.”

That is an astonishing passage. G-d Himself commanded the sacrifices. G-d Himself established the holidays and commanded us to come to the Temple! So why was He now telling them to stop?

Because they had apparently confused religious activity with a relationship with G-d. In other words, the problem was not that the sacrifices were wrong. The problem was the absurdity of thinking that G-d wanted the sacrifice while being indifferent to the person bringing it. They were giving Him the output, G-d wanted them!

Isaiah immediately tells them what G-d actually wanted (Ibid. 1:15-19):

“Your hands are stained with crime! Wash yourselves clean; put your evil doings away from My sight. Cease to do evil; learn to do good. Devote yourselves to justice; aid the wronged. Uphold the rights of the orphan; defend the cause of the widow.

Come, let us reach an understanding,- says G-D. If your sins be like crimson, they can turn snow-white; if they be red as dyed wool, they can become like fleece. If, then, you agree and give heed, you will eat the good things of the earth.”

That distinction becomes especially important as we approach Yom Kippur.

We sometimes think about Yom Kippur primarily as spiritual tax season. We go through our records, discover some uncomfortable discrepancies, file an amended return, promise the Auditor that next year our books will be cleaner, and hope to avoid penalties.

I did this wrong. I shouldn’t have said that. I need to be more careful about this. I need to improve that.

All of that is important. Yom Kippur is certainly about repentance and changing our behavior. But there is a much bigger question hiding underneath all of it:

Do I actually want this relationship? Do I want to be on G-d’s team? Do I want to be like Him? Do I want to spread His light and goodness to the world?

Because if all G-d wants are perfectly obedient servants carrying out His instructions without distraction, complaint or failure, He does not need human beings. He already has angels.

Jewish tradition describes angels very differently from the cute winged babies decorating greeting cards. The Hebrew word malach literally means a messenger. An angel has a task from G-d and carries it out. Classical Jewish thinkers contrast angels with human beings precisely on the issue of free choice: the angel executes its mission; the human being can choose whether to do so. Some even say that this is what it means that G-d created humans and only humans in His image. He is a chooser, and we are choosers. Everything else in the universe, from anteaters, to angels, to oak trees, to mountains just do what they’re programmed to do.

Accordingly, viewed purely from an efficiency standpoint, we are a terrible upgrade. An angel does not oversleep and miss morning prayers. He does not take out his phone in middle of services. He doesn’t mouth words of prayer while thinking about how the Lions can improve their defensive line, or how they can juggle their daughter’s doctor’s appointment with the Costco run.

An angel does not know perfectly well that gossip is wrong and then begin a sentence with, “I really shouldn’t say this, but…” An angel never yells at his kid, an angel never knows that G-d is watching him, but acts in a way that seems to indicate that G-d left the room.

If G-d needed perfect religious machines, heaven was already fully staffed. What human beings bring to the relationship is not perfection; we bring choice. We can say no, and therefore our yes means something.

This idea is expressed clearly by Maimonides. In Mishneh Torah, Laws of Repentance 10:1-2, he describes two ways a person can serve G-d. A person can do what G-d wants because he hopes to receive reward or because he is afraid of what will happen if he does the wrong thing. That is a legitimate starting point, but Maimonides says it is not the highest form of religious life. The higher level is serving G-d out of love.

That person does the right thing not because he is calculating what G-d will give him for it and not because he is terrified of punishment. He does it because he loves G-d and believes that G-d’s way is true. He wants to be closer to G-d, the Sustainer of all life, and he wants to act like He acts.

That changes the entire conversation about Yom Kippur. Of course there is judgment. Of course there are consequences. The Yom Kippur prayers do not exactly hide that fact.

But imagine approaching someone you love and saying, “I have carefully reviewed the penalties associated with disappointing you, and after a detailed cost-benefit analysis I have decided to remain in this relationship.” Try that with your spouse and let me know how it goes. A relationship built entirely around consequences is missing the best part – the relationship.

Yom Kippur gives us an opportunity to say something much deeper: G-d, I don’t simply want to behave because I have to. I want to want what You want. I want to care about the things You care about, because You are Truth, You are Reality.

I want honesty to matter to me because it matters to You. I want kindness to matter. I want prayer to become more than words I am obligated to say. I want Shabbos to become more than restrictions I have learned to navigate. I want Judaism to become more than the operating system that happened to be installed on my family when I was born. I want You inside everything that I do.

All the things that we will beat our chests and apologize for are outcroppings of living a life that is missing its G-d consciousness on some level. That’s why the culmination of the first part of our viduy confession is: we have gone astray, you have let us go astray. We realize that our actions have distanced us from G-d, and that He in response let us wander further. That is the biggest loss, bigger than We slandered, We betrayed, We have been obstinate.

G-d was making that point through Isaiah long before anyone had heard of AI.

“I don’t need your bulls and lambs.”

What exactly are you giving the Creator of the universe when you bring Him an animal? He made the animal and He made you. He made the plants the animal ate, and he made the sun that grew the plants the animal ate. Nothing you give G-d solves a supply-chain problem in heaven.

The one thing in the entire process that has genuinely been placed into your hands is you. Your choice, your heart, your willingness to say, “I could live differently, but I choose this.”

Yom Kippur is not asking us to pretend that tomorrow morning we are going to wake up overflowing with passion for every religious obligation. Human beings don’t work that way. Some days prayer will still be difficult. Some mitzvahs will still feel inconvenient. Some obligations will feel like a drag.

But on Yom Kippur we can think: What is one place where I can put myself back into my Judaism? What is one step I can take that will bring G-d more into me and my life.

The greatest thing we can say to G-d this Yom Kippur is not simply, “I’ll do better.”

It is, “I want to be here. Truly, fully, and entirely.”

Because that is one thing no machine can ever mean.

Gmar Chatima Tova!

Parsha Dvar Torah

This week’s parsha is mostly comprised of a song which Moses related to the Jewish people on the day he passed away. Melding past, present, and future, the beautiful and at times haunting song is about the Jewish people and their relationship with G-d. In the beginning of the song Moses proclaims, “Let my instruction flow like rainfall, let my saying drip like dew; like storm winds upon vegetation, and like raindrops on grass” (Deuteronomy 32:2). The Vilna Gaon asks why Moses describes his teachings, the Torah, as being like rainfall.

While falling on a field, rain will water the whole field equally. However, what the rain will cause to grow is dependent on what was put into that earth. If the person toiled and planted fruit or grain seeds, he will soon have an orchard or a field of grain growing beautifully. If he planted nothing, having frivolously wasted the planting season away, he will find his field quite empty despite the prodigious rain. Worse yet, if he planted deadly plants such as the foxglove, he will find that the rain helped secure a poisonous crop.

Torah, the Vilna Gaon explains, has the same attributes. It is an incredible receptacle of Divine wisdom that is given to humans to interact with and explore. What we get out of it however is dependent on what we put in. If we invest ourselves in the Torah and expend the necessary time, energy, and emotion into capturing its truth, if we approach it with respect, and are honest with ourselves as we study it – even when it calls upon us to make meaningful changes in our lives, the Torah will then lead us to levels of knowledge and spiritual joy we could not have imagined possible. On the other hand, if we leave our field of Jewish knowledge fallow (i.e. we take an unhealthy approach or we don’t cultivate it), we will be left bereft of the most incredible inheritance we have as a people – the Torah.

One can also distort Torah or selectively find a Torah source to find license for distorted perspectives or to justify their preconceived, inaccurate ideas. Our approach to Torah study makes all the difference as the prophet Hoshea cautions, “For the ways of the Lord are straight, the righteous shall walk in them, and the rebellious shall stumble on them.” (Hoshea 14:10)

Rabbi Avigdor Miller zt”l (1908-2001) was one of the greatest Torah teachers in America in the latter half of the twentieth century. His many books were fascinating and interesting yet taught many of the foundations of Jewish belief and philosophy. Tapes of his weekly Torah classes made their way all across America and allowed him to inspire many more than the thousands who attended his unapologetic, direct, yet uplifting Torah lectures. He even created the Telephone Torah Program, in ways a forerunner of Partners in Torah, whereby one individual would learn portions of Chumash and then would repeat them over the telephone to a partner on a weekly basis. After beginning with Parshas Bereishis and Noach, the program was expanded to include Pirkei Avos (Ethics of our Fathers) and Talmud. Where did Rabbi Avigdor Miller get his fiery love for Torah, Jews, and Judaism?

When he was in his early twenties, Rabbi Miller left the comforts of the US to go study in the famed Slabodka Yeshiva in Lithuania. There he dedicated himself to Torah study with an uncommon seriousness. During the first three hours of the day, he would talk with no one, wanting that time to be purely dedicated to Torah study. If people came to him to discuss something, he would motion to them to return later. He was busy planting his field with fertile seeds of Torah.

Yom Kippur is a day where we not only try to remove the weeds that have prevented our growth in the previous year, but a day where we plan for the future year as well. If we can commit to planting strong seeds of Jewish values and personal growth in our lives, we will surely have a year that flourishes with success.

Parsha Summary

As mentioned above, most of this week’s Parsha is comprised of a song. In the beginning Moshe calls out to the heavens and earth to hear his song, as they are witnesses that will exist forever, and they can be G-d’s messengers to reward the Jewish people with plentiful rain and bountiful crops, or punish them by withholding the bounty.

Moshe begins by talking about the greatness of G-d, in that He is out Creator, Father, and the Rock onto which we hold to maintain our stable existence on this shaky planet. G-d is incorruptible, hence the corruption we see on this world is the invention of His children. Just ask your elders, Moshe tells us, and they will tell of the greatness of G-d, and the miracles He performed while taking us out of Egypt. They will relate to you how G-d chose us and made us into His special portion.

There will come a time when the Jewish people will be living in a place where everything is working out for them, and they will become prosperous. They will then begin to kick out at G-d and deny His role in their success, and even desert Him entirely. When this happens G-d will become angry with the Jewish people and set enemies upon them, enemies that will scatter them all over the world. (If you read the history of our people, you will find this to be chillingly accurate. Every time the Jewish nation becomes too comfortable in their host nation, and they begin to assimilate and lose their Jewishness, a terrible calamity suddenly befalls them and forces them to recognize their identity. It comes in different forms, from expulsions, to Inquisitions, to libels, to a Holocaust, but unfortunately it is a pattern that has repeated itself many times in our challenged history.)

Then, the enemy will rejoice thinking they have great power. They will not have the wisdom to see that no one has been able to quash Judaism in the past, and it is only the G-d of the Jews that has allowed them the success they have had in persecuting us. At this point, G-d swears that He will lift up His sword (metaphorically of course) and take vengeance upon those who have wreaked havoc on His people. He will lovingly return His people to their land and once again they will bask in His presence.

Although this message has some frightening and sobering undertones, we have to understand that this is what makes it a song. A song in order to have real beauty must have both low parts and high parts, which when contrasted with each other form enchanting music. This is the song Moshe teaches us before he dies. It is the story of a nation that has lows, when we are afflicted and persecuted, but then rises from the ashes to take flight again and soar. No good song can be created in monotone, the challenges and lows are what make the highs so special and precious.

At the end of the Parsha, Moshe tells his prime student and successor, Yehoshua, to teach in front of all the Jews, so that everyone will witness Moshe giving the mantle of leadership to Yehoshua, and not question his authority later. The Parsha concludes with G-d telling Moshe to climb to the top of a Mt. Nevo from where he will see the Land of Israel, the land he will be unable to enter. From this vantage point, Moshe saw not only the land, but he also saw prophetically all that would transpire to his beloved flock from the time of his death until the time of the Messiah!

Random Fact of the Week: Michigan borders no ocean… but has more lighthouses than any other state!

Quote of the Week: The really great deeds are done in secret. – Samuel Fremont

Fact of the Week: In 2002, runner Tom Johnson ran an 80-Km race against a horse… and beat it by 10 seconds!

Funny Line of the week: Before you criticize someone, you should walk a mile in their shoes. That way, when you criticize them, you’re a mile away, and you have their shoes.

Have a Radiant Shabbos,

R’ Leiby Burnham

Source URL: https://partnersjewishlife.org/beating-ai-on-yom-kippur/