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What do you want to be when you grow up? Parshas Toldos

What do you want to be when you grow up?

…is a question I ask boys and girls before their Bar or Bat Mitzvah. But really, as I heard Rabbi Moshe Hauer point out at a recent lecture, it’s a question I should be asking all of you, all of us adults. When was the last time we asked ourselves that question? When we were 20? 12? Never? We made that decision of who we are and what we do, either consciously or just fell into it, and for the rest of our lives, this is me. I sit at this desk, I do these tasks, I volunteer in this way, and that’s who I am. But is that it? Are we really done? I hope not. 

There’s a man who’s stealing all the headlines these days, who is anything but a role model in terms of his morality or kindness, but when it comes to this question of ‘what do you want to be when you grow up’ he’s worth paying attention to. Elon Musk is relentless in his pursuit of new frontiers of accomplishment. In 1999, Musk co-founded an online bank which ultimately became known as PayPal, changing the way we transfer money. In 2002, he founded SpaceX, a space transport company that among other things has ambitions of bringing people to Mars. In 2004, he was an early investor in Tesla, eventually becoming its CEO. In 2006, he founded SolarCity, a solar energy company. In 2015, he founded OpenAI, a nonprofit artificial intelligence company. In 2016, he founded NeuroLink, a company that explores the interface between our brain and technology. In the same year, he founded the Boring Company, a company that bores holes underground to solve traffic issues. And in 2022, he bought Twitter (which he probably shouldn’t have done, but that’s another story for another time).

Now none of us have anywhere near the amount of money that this man, the wealthiest man in the world, has. But to never stop, to constantly ask oneself, what do I want to do next? What’s my role to play in this world? That’s a question we should all be asking.

The greatest impediment is not the fact that we are not worth 181 billion dollars like Elon Musk. The greatest impediment is a lack of self-awareness and a fundamental lack of understanding of our role here on earth.  


Yaakov and Eisav – I can’t think of two more different brothers in the Torah. One a man of the field, a hunter, a brute. The other, a man of purity who never leaves his tent. And yet, the Medrashim inform us that before they reached teenagehood, their parents treated them in exactly the same way. Yitzchak and Rivkah were oblivious to their differences and educated them with one identical style, not differentiating whatsoever in how they treated the worldly, physical, tough Eisav and the spiritual, sensitive, kind Yaakov.

Rav Samson Raphael Hirsch suggests that had they picked up on the characteristic differences of their children, had they custom-tailored their education, had they cultivated the unique gifts that each one of their sons had, history would have been radically different. Eisav, the man who is out to murder his brother, Eisav, the grandfather of our arch enemy Amaleik, Eisav, the godfather of the Romans and all subsequent antisemitism, none of that would have happened. Eisav’s strong character should have been nurtured, channeled, developed in a healthy fashion, but alas – his parents were oblivious to who he was. Instead, says Rav Hirsch, we have thousands of years of violence, pillage, rape, and bus bombings.

It’s quite the accusation. Many took issue with Rav Hirsch’s harsh criticism of Yitzchak and Rivkah. Be that as it may, the point stands – each person is born with unique characteristics. They need to be understood, they need to be cultivated, they need to be utilized.

Rav Moshe Chaim Luzzato, in his magnum opus, Derech Hashem, takes this idea one incredibly important step forward. He explains that G-d created each individual in the world with unique characteristics, this we know. But then he explains the Kabbalistic reason why. Every human being has unique characteristics because every human being has an utterly unique role to play in this world. Personal and collective redemption will only come about when each of us figure out what role we have to play in society.

And it sounds so simple, but it’s not. If you were to ask a career counselor what you should do for a profession, they would tell you to do a SWOT analysis. Strengths, Weaknesses, Opportunities, and Threats, or some other analysis of one’s personality and qualities. What the Ramchal is teaching us is that an analysis of self is only step one. Step two is to do a SWOT of your family, of your community, of the world-at-large. To figure out what you should do with your life, you need to not only figure out who you are, you need to figure out what the world around you is missing and then how you can fix it.

Imagine a graph with your talents on one side, and the needs of your family, your friends, your co-workers, your community on the other side. Where those two lines meet is why you’re here on this planet, why G-d imbued you with a soul. Creating this graph is the most important thing you can do. Because it answers the most fundamental existential question – what am I doing here? We believe there is a purpose. What is mine?

And those things change. The needs of our surroundings change, and we change. This graph needs to be revisited all the time. If we want to fulfil our role here on earth, we need to constantly be asking ourselves, as difficult as it may be, what do I want to be when I grow up?

When I asked this question to our Bar Mitzvah boy, Asher Pensak, I was blown away. He knows who he is. He is not a school guy. He goes to school, but to quote him, “School teaches you to memorize dots, not how to connect them.” He is ambitious and good at doing research – when he wants to know something, he will spend hours reading up on it, and then do it. And that’s why this young man over here is an unpaid consultant to his uncle’s landscaping company. But more than just an unpaid consultant with keys to the company’s excavators and other such vehicles that he should not be driving, he also has ambitions to take over the company. Lunch at the Pensak’s today is going to be so awkward…

Asher, you may just be the next Elon Musk. (And just in case, you know how maser works, right? 10% of 151 billion would go very far in our shul…)

But honestly, I think you’ll go further than Elon Musk. Because you not only know yourself and your skills – one important line on the graph. You also have parents who model for you daily the importance of the second line of that graph; the importance of looking around to see what the community needs, and then taking every one of your skills and using them. Your parents both are probably in this building more than I am; making golf tournaments, volunteering with the youth, cooking meals for the entire shul and more.

Who am I and what does the world around me really need? Those are questions we need to ask ourselves always.

May we recognize our unique talents and qualities and the exclusive role that each of us play in history. And may we never stop asking ourselves, what do I want to be when I grow up?    


Those Who Choose to Stay Parshas Chayei Sarah

There is a video on YouTube called the Awareness Test. It begins with a group of people standing around, and a voiceover asking you to count how many times the ball will be passed from one person to another. And then they start passing the ball. They’re moving quickly and it’s a little difficult to keep track. But while this is going on, a person in a full-length gorilla outfit moonwalks across the screen. Most people, including myself, miss it entirely. We’re so focused on counting how many times the ball is getting passed that we completely miss something as glaring as a gorilla dancing across the screen.

I was thinking about this video as I read through this week’s parsha. The bulk of our Torah portion describes how Avraham’s servant, Eliezer, finds a suitable marriage partner for Yitzchak. It describes how Avraham gives instructions to Eliezer, how he travels to the land of Padan Aram leading donkeys filled with gold, silver, and jewelry, how he prays to G-d to assist him, how he finds a suitable match, Rivkah, how he has to persuade Rivkah’s family to have her come with him, and finally, how he returns to Yitzchak. 67 verses describing the very first matchmaking in Jewish history. Why? Why so much ink spilled over this tale?

The classic answer to this question is addressed by the Medrash. It suggests that the unique length of this episode is to encourage us to study the text carefully so we can learn lessons from Eliezer’s actions; his faith, his wisdom, his tenacity. The great detail is there because not only are our forefathers incredible models, but even their servants have what to teach us.

But something else occurred to me this year which I subsequently found a version of in the Sefas Emes, and that is – there is a gorilla walking across this screen. I have been so busy watching Eliezer that I didn’t notice the intense drama playing out right before my eyes.

You see, there is another Medrash that wonders why Avraham forces Eliezer to take an oath that he would find a wife for Yitzchak from Padan Aram. Eliezer is his employee – you don’t typically ask your employee to take an oath. “Swear to me that you will get me that report by the end of the week! Take an oath!” It’s strange. The Medrash suggests that there was some underlying tension in this interaction. Eliezer was committed to Avraham and Sarah. He dedicated his life to them and their cause. He fought with Avraham against the four kings, he traveled with Avraham to the Akeidah, he himself was circumcised. He was so dedicated that at one point, before Avraham had any children of his own, Avraham thought that Eliezer would be the next leader of the nation that he was forming. Of course, once Yitzchak was born it became clear that Eliezer would not be the successor.

But all was not lost. Eliezer had a daughter, a special, kind, thoughtful, spiritual daughter, who was well-versed in Avraham’s way of life. She, like her father, was dedicated to the cause. Eliezer had spent the last decades assuming his daughter would marry Yitzchak. He held off on marrying her to anyone else, knowing that she was destined for greatness.

And then, one day, Avraham calls Eliezer into his tent and says that he wants to speak about Yitzchak. This is it! Finally! I will take my rightful place in the development of this new and wonderful nation! But instead, Avraham instructs Eliezer to travel to another country, to find a woman they don’t even know, that his daughter has no chance of marrying Yitzchak. And all of his dreams come crashing down.

Avraham senses Eliezer’s disappointment. Avraham is concerned that Eliezer, independently wealthy, shrewd, and knowing that his master, Avraham, doesn’t have much longer to live, may manipulate the situation, and so he makes Eliezer take an oath that he’ll follow through with these instructions.

And now with that understanding, read the next 67 verses and tell me, do you now hear a thousand nails scratching on a chalkboard? Do you now sense the weight that Eliezer is carrying? Do you now appreciate how at every turn, Eliezer could have and maybe should have taken the donkeys filled with gold and silver and walked off into the sunset? Think about the disappointment, the frustration, the rejection that he must have felt.

And yet, he carried on. He put on a brave face. He fought against every feeling in his body. Despite the heartbreak he had to deal with at every step of that journey, he went forward, with poise, with faith, with joy, and ultimately, returned to Avraham.

That’s why the story goes on and on. The Torah wants us to feel the intense emotion that is bubbling up right beneath the surface. The Torah wants us to open our eyes not only to Eliezer’s invisible pain but to the invisible pain that so many carry and struggle with each day. And perhaps most importantly, the Torah wants to present a role model for the many people who will need Eliezer to look up to; for the people in our communities who feel rejected, dismayed, ignored, and through him will somehow find the strength to carry on.

I recently read a book called, Unmatched. It’s a well-written memoir by a Jewish Orthodox woman describing her attempt to get married. It’s raw, funny, insightful, and terribly sad. The author is smart, accomplished, funny, thoughtful, attractive, and yet, she is consistently set up with bozos. There was the guy who makes her travel across New York for a date, shows up 45 minutes late even though he lives a block away. There was the guy who kept on making passes on her, which she rejected because of her observance, only to be dropped by him because “she was not religious enough for him.” There was the guy who started the date by looking her up and down and saying you’re not very pretty. There was the guy who came to the first date with a list of 100 questions, which he drilled her on. There was the guy who kept on reaching out to her to talk and hang out but was consistently dating others at the same time. There was the guy who slammed the door in her face upon meeting her. And on and on and on.

And while she continues to date dud after dud, she gets bombarded by friends, rabbis, strangers – “You’re too old. You’re too ugly. Are you straight? Why don’t you do this? Why don’t you do that?” She receives endless attention from her community – but it is only about her singlehood. Her interests, her successful career, her talents – all of them are unnoticed. She lives in the Jewish community, she attends shul, social functions, greets her neighbors every morning, but feels utterly rejected and ignored. The pain of rejection – rejection by friends, by rabbinic leaders, and most hurtful, by G-d, all of that explosive pain is not visible to anyone who interacts with her, but it’s hidden right beneath the surface.

Like Eliezer, she should run. But like Eliezer, she stays firmly put. And that’s what I was moved most by from this book. She never ran. She never let go. Sure, she slipped. She did things that were beneath her standards. She flirted with ideas that would take her well out of our faith. But ultimately, she held on.

Reading Unmatched and processing some of the disturbing news affecting our community this past week made me appreciate just how many such people we have in our midst. Whether it’s people who are single, divorcees, widows, people who have been through a tragedy and did not receive the support they needed from their community, people who have been abused and did not feel believed, people who due to their orientation or any other reason are meant to feel like outcasts, there are no shortage of gorillas moonwalking all around us. Only that they’re not gorillas, they’re human beings. And they’re not moonwalking, they’re falling apart.

And yet, like Eliezer, such people are here in our community, in this shul. They somehow hold on.  

By describing the story of Eliezer with such detail, G-d is trying to wake us up to the Eliezers’ in our midst; to open our eyes and be more attuned to pain that we may not be able to appreciate. By utilizing 67 verses, G-d is conveying to us that He can see beneath the surface, that He sees that pain, that He cares. But most importantly, by taking so much space up in our precious Torah, G-d is conveying to us how heroic such an existence really is. To practice a way of life that seems to not fit with your life circumstances, to live in a community that is not always attuned to your needs, to engage with a G-d who seems, at times, out to get you, that is a story worthy of all the holy ink in the world.

The book concludes – spoiler alert – with this woman in her 50’s and still ‘unmatched.’ Allow me to read to you the final paragraphs:

“We are stronger than we think. We come from a chain of strong women starting with our own mothers and grandmothers, going all the way back to our Biblical foremothers and all the ordinary Jewish women throughout history who faced extraordinary challenges and met them with bravery and faith.

Perhaps wider society ridicules and casts us as pathetic. Perhaps those who are happily married would never choose to trade places with us. But we are ordinary women doing something very extraordinary. Each time we put our faith before ourselves, each time we hold on to G-d rather than turn away, we are erecting another spiritual skyscraper unequalled by any of the wonders of the world.

We are unmatched. We are strong. This is our challenge, and we will meet it.”   

Avraham & Sarah in the 21st Century Parshas Lech Lecha

I’ve been wondering what would happen if Avraham and Sarah lived in the 21st century. This is how I envision it:

It would all start with a TikTok of Avraham smashing his father’s idols. Anti-establishment, anti-authority, this man is cool. He’d get a gazillion followers and the hashtag #breakstuff would be trending for weeks.

Then, he’d get a book deal writing a memoir called, Leaving Charan. It would describe the challenges of leaving home, parental rejection, being an immigrant, and how to start a new life. It would probably make it to Oprah’s Book Club. 

And finally, the tent Avraham and Sarah set up would be more popular than Burning Man. Anyone looking for an experience of radical inclusion and unconditional gifting would flock to them. They would be wildly popular, attracting a diverse following ranging from heroin addicts from the streets of San Francisco to royalty like the Duke and Duchess of Sussex.

And that’ll be about when things go south. The downfall will start with a Twitter account, under the handle, Lot, a disgruntled relative of theirs, who claims that Avraham and Sarah are not heroes, they are cult leaders. This account will share snippets of conversations that allegedly take place with guests, demonstrating how the chesed that Avraham and Sarah perform are contingent on the guests becoming monotheists. Of course, this will set off a Twitter war, with the many Avraham-Sarah stan accounts sharing pictures and stories of unbridled kindness and accusing Lot of jealousy.

Eventually the Twitter war will spill over into more mainstream television. Tucker Carlson will have an episode slamming Avraham for involving himself in wars that aren’t relevant to him, and not paying enough attention to his own people. He’ll follow that with a feature on how Avraham saved the people of Sedom despite them being on the wrong side of the culture wars. Then the View will spend a full week talking about how Sarah treats, or rather mistreats her maidservant.

The straw that breaks the internet will be the front-page news, reported by both the Wall Street Journal and the New York Times – Avraham Attempts to Slaughter Yitzchak. And all hell will break loose. Avraham will be investigated by the CIA, Sarah will face a lawsuit by Yishmael, and within a short while, their popularity will plummet.

Yitzchak will go to the grave defending his parents but will be pitied by the media on the left and right as a brainwashed child, who was traumatized by his parents. Yaakov will change his last name to avoid the negative PR, and by the time his twelve sons are born they don’t even know their grandparents existed.

In the modern era, Avraham and Sarah would be scorned into oblivion. Despite their many good deeds, despite the unique path they blazed, they wouldn’t make it past the cynicism and #antihero sentiment of the 21st century. Our society is too cynical, too suspicious, and too individualistic, to allow for a nation to develop around role models like Avraham and Sarah. Had they lived today, Judaism as we know it would be dead upon arrival.

Now, one could argue that our modern skepticism is healthy. Isn’t our cynicism helpful in creating appropriate checks and balances against fraudsters? Doesn’t our society’s extreme transparency and openness ensure that we never follow people blindly? Does the Torah not want us to think for ourselves?!

Yes, yes, yes, but.

Yes, the opposite extreme, that of unchecked adoration, treating Torah leaders as infallible, and believing the leaders to be experts on everything is fraught with danger. You have probably read in the news this past week about Torah scholars in Israel or in New York telling their followers who to vote for. Are these rabbis prophets? No, they are not.

And yes, abdicating any personal responsibility in decision making is not a Jewish value. I remember a woman coming to me years ago, telling me that I have to Paskin – I have to rule – where her son should go to school. I looked at her blankly. How could I tell you where your son should go to school? She eventually left my office and found a rabbi who would.

Yes, I, and am sure, many of you here, have read stories of rabbis who, according to the biographer made a bracha before being nursed by their mother. These stories are false, and lying, of course, is prohibited in all forms.

And yes, we have all heard tragic tales of Torah scholars who have committed horrendous crimes and yet were defended nonetheless by their followers. G-d is infallible, no one else is.

But – if our society is such that an Avraham and Sarah would not succeed in developing a nation, if our society is such that these two giants would be denigrated to such an extent that no one would take them seriously, if Judaism would be dead upon arrival in 2023, then we probably have some soul searching to do.


Rav Naftali Tzvi Yehuda Berlin suggests that G-d wrote the entire Book of Bereishis so that we can learn from the yashrus, the uprightness of our forefathers. G-d wants us to have role models. G-d wants us to have lofty aspirations. G-d wants us to have heroes.

Imperfect? Oh yeah. Subject to mistakes? Yes. Infallible? Not even close. But by throwing away the baby with the bathwater, by throwing away the hero with his or her flaws, it impacts us as well. Because without people to look up to, without people that we venerate, we are left with a static society, we are left with a culture that celebrates the antihero, that highlights our imperfections – “this is me and I’m not changing.”     

Two weeks ago, Rav Hershel Schachter the Rosh Yehiva of Yeshiva University, and Rav Shlomo Amar, the former Sefardic Chief Rabbi of Israel, came to Baltimore. Have they made mistakes in their life? I am sure they have. Nonetheless, I spent about an hour with them, and I listened as they humbled me with their depth and breadth of Torah knowledge. I watched intently as they exemplified what it means to ensure that your every breath is consistent with Torah values. I was inspired by their genuine humility and kindness. I will tell you, and I don’t say this flippantly, I walked away from that meeting a changed man. It forced me to reassess and change the Torah learning that I engage in. It forced me to consider how I act in public. So tell me, is veneration, exposure to great Jewish leaders who expand our aspirations, is that not a good thing?

I’ll share more – as I mentioned, I do not ascribe to the idea that a Torah scholar is, by definition, knowledgeable on every topic. The Torah scholars I consult with will regularly tell me they need to speak to a psychologist or doctor or lawyer to better understand a particular subject. Many questions do not need to go to a rabbi. Relationship questions should typically go to therapists. Financial questions should typically go to financial advisors. Etc. etc. However, every time I have spoken to a true Torah scholar about any personal issue, I have walked away with a fresh perspective informed by an absolute immersion in Torah values. I have walked away, almost always, with a perspective that pushes me, that expands me, that I would not have come up with on my own. Is seeking out advice from people who are immersed in G-d’s values not helpful in navigating this complicated world?

Among the many things we’re celebrating today, we are celebrating the birth of a daughter to Simcha and Margie Gross. Their daughter’s name is Chaya Henna. Chaya is named after Rav Chaim Kanievsky and Henna is named after Henny Machlis.

If you recall, last week I shared a story about Henny Machlis – about the man who woke her up in middle of the night to ask her to remind him how to make pizza. And how she graciously got out of bed at 3 AM and patiently reviewed the recipe with him. Did that story not expand your horizons? Did that story not force you to question if you’re really as patient and kind as can be?

Today, allow me to share with you just a little about Rav Chaim Kanievsky, who passed away just a few months ago. Rav Chaim Kanievsky was blessed with many natural gifts. He had a photographic memory, and he chose to apply his gifted mind to Torah study. By the age of 13, he completed the entire Talmud, something many people don’t finish in a lifetime. From the age of 20 and on, he would complete the Babylonian Talmud, the Jerusalem Talmud, Nach, Medrash Rabba, Medrash Tanchuma, Tosefta, Sifra, Sifri, Mishnayos, Rambam, Tur, Shulchan Aruch, Mishnah Berurah, and the Zohar. Every year. In-depth. And he knew it.

I remember hearing Rabbi Hartman, a great scholar in his own right, describe searching for a source of a comment made by the Maharal, but could not find it. He finally bumped into Rav Kanievsky who was crossing a street in B’nei Brak. He asked him if he knew where it was. And as they crossed the street, Rav Kanievsky went like this: “Babylonian Talmud… no. Jerusalem Talmud… no. Medrash… no. Zohar… no. Tikunei Zohar – yes!” And gave him the exact location. All this before they finished crossing the street.

He was meticulous with his time. He barely slept, learning Torah every moment he had. And despite his dedication to Torah study and writing important works of Torah literature, he opened his home daily to a stream of visitors who came to him for advice, encouragement, or just a listening ear.

He never accepted a formal position, turned down offers to buy him a nice home, and lived a most simple life, absolutely dedicated to Torah, to the Jewish People, and to G-d.    

My children are named after family members, people that we loved, and one child was just given a name that we liked. But Simcha and Margie chose to name their children after role models, after heroes, a Tzadik and a Tzadeikis, Rav Chaim Kanievsky and Henny Machlis. And it’s not surprising that they did so. The Gross’s think big, they act big, they aspire to greatness.

With this name that you gave your daughter, she will forever be inspired to strive to be better tomorrow than she is today. She will forever be reminded that angel-like people do exist in this world, human, yes, imperfect, yes, but angel-like. She will forever be reminded that there are people who are worth associating with, people who are worth speaking with to gain perspective on personal matters.


I’ll conclude where I began – We are here today because our ancestors saw both the good and the bad and chose to focus on what would help them grow and because of that we have a Jewish People. But if Avraham and Sarah appeared on the scene today, how would we respond? Would we seek them out or would we put them down? Would we look up to them, despite whatever flaws they may have, or would our cynicism prevent us?

Because the truth is, Avraham and Sarah do exist, all around us. But to see them, to grow from them, we need to allow our hearts to be a little less biting, a little more generous, a little more hopeful.

Ambiguous Loss – Yizkor Shmini Atzeres

In 2011, a book, titled, Legacy Letters was published. It was a collection of messages written by family members of those who died ten years earlier, by the terrorist attacks on 9/11. I’d like to read to you one letter, written by Joe DiFazio, written to his father, a stockbroker, who was on the 105th floor of the North Tower on that fateful day. Joe was 13 on September 11, the day his father died.

I guess it makes the most sense to start at the end. The last time I saw you, you had a triple stack of powdered donuts piled on top of a belly that looked used to that sort of thing. Confectioner’s sugar dusted your lips, and every time the Giants’ defense missed a tackle, you pounded a chubby fist into the couch and left a phantom smudge. You were barely five-ten, bald and out of shape.

I looked at you and saw the strongest man in the world.
“All right, time for bed,” you said. It was only the third quarter, and I turned my head to argue, but you knew what was coming. “I don’t want to hear it,” you told me. “It’s your first week of high school and you’re gonna start it off strong.”
I stalked off, headed for the stairs leading to my room. No hug, no kiss goodnight. I grumbled under my breath. It’s not fair. This [stinks].
“I love you, champ,” you told the back of my head. You knew I was upset, and you weren’t really expecting an answer. You didn’t get one.
I never heard your voice again.”

There is a term that’s used when we don’t have proper closure with a loved one. Situations like those who lost their otherwise young and healthy parents or spouses on 9/11, who never said goodbye, who for some, did not even say goodnight. Psychologists call it ambiguous loss – a loss that occurs without a significant likelihood of reaching closure or clear understanding.

It’s not limited to dramatic scenarios like Joe DiFazio and his father. It happens all the time. For example, with Alzheimer patients – Your loved one is here, you’re holding his hand, but his mind is somewhere else. When do you say goodbye to someone who will likely be with you for years to come, and at the same time never be with you at all? How do you say goodbye to someone who may forget your goodbye the very next day or the very next minute?

Ambiguous loss is applicable to any and every person who experienced loss and does not follow the classic five steps of grief – denial, anger, bargaining, depression, and acceptance. Psychologists have concluded over the years that many do not and cannot follow these simplified or oversimplified steps. Some people are “stuck” at one of these steps, unwilling or unable to move forward. Some people are left grieving forever.

A congregant [who recently lost a loved one] asked me after the second day of Rosh Hashana, after I spoke about Jews loving dead Jews, the following: If I am so opposed to the emphasis of “death” in Judaism, then why don’t I cancel Yizkor? After all, it reminds us of death. In truth, reciting Yizkor is a relatively new custom. Sefardic Jews don’t do Yizkor. We say it on Yom Tov, it’s supposed to be a happy day? Let’s get rid of this death reminder! That was his suggestion.

But the truth is, Yizkor in particular, and Jewish memorials in general, are the greatest response to ambiguous loss –

What is Yizkor? What are we about to do?

If you read the text of the prayer you’ll see that we first and foremost, reflect on the past. We remind ourselves of our loved ones; who they were, what they stood for, what they taught us. And then, we commit. Classically, we commit to give charity in their memory, but it’s not limited to charity. We commit to being inspired by their legacy and living a better life in their honor.

Yizkor is an exercise in embracing the ambiguity of loss –

  • Yizkor is an acknowledgment that I cannot ever have complete closure, and so we return at prescribed times to reflect and relive our memories.
  • And at the same time, Yizkor reminds me to not get stuck in the past; I use memory and grief to propel me forward.

Instead of fighting ourselves to forget, we allow ourselves to hold on. Instead of fighting ourselves to leave our loved ones behind, we allow ourselves to take them with us as we move forward in life. That’s Judaism’s response to ambiguous loss. It is not meant to depressing or death-centered. It is meant to be uplifting and life-affirming. It allows us to move forward without closing our eyes or hearts to our past.

These last days of Yom Tov, Shemini Atzeres and Simchas Torah are dedicated to the concept of ambiguous loss. Sukkos is over. We should have concluded the holiday season yesterday. However, G-d instituted a new holiday, an additional day. Why? To hold us back, to make us stop. The word Atzeres comes from the word, Atzor – stop. G-d is asking us to stop before going home, before leaving the holiday season. Why does He ask us to stop?

The Medrashic literature phrases it beautifully: “Kasheh alai pridas’chem/ it is hard for me to say goodbye.” We just spent almost a month full of powerful prayers- do you remember how the room shook at the conclusion of Neilah? We just spent hours in quiet contemplation – do you remember how we stood in silence, dreaming of what life could be? We just ate countless meals filled with joy – Jewish joy! So, G-d asks us to stay just a little but longer. It’s hard to say goodbye. Closure, it would seem, is difficult, even for G-d.

Rav Yitzchak Hutner poses the following question: If it’s so hard to say goodbye, then how does adding one day help? Instead of being hard to say goodbye yesterday, it’s going to be hard to say goodbye today. It’s still hard to say goodbye! Pushing off the inevitable seems pretty small-minded?!

But this is where Simchas Torah comes in. Simchas Torah tells us that when it comes to all relationships, and certainly our relationship with G-d, we do not ever have to really say goodbye. The Torah, which we are celebrating tonight and tomorrow, is the vehicle through which we are able to hold on to some of the magic that we experienced. We cannot experience the magic of the High Holiday season all year long, but the Torah, the medium through which G-d connects Himself to the Jewish People, the Torah through which He speaks to us, that allows us to hold on.  

You know, I sometimes walk into these last days of Yom Tov a little disappointed, maybe even upset, at all the lost opportunities. Did I accomplish enough? Did I take advantage of the special closeness that we have with G-d at this time? Am I proud of how I treated my family, my friends, during this holy time of the year?

But I am reminded of a story, a Chassidic tale, of two young men dancing on Simchas Torah. We’ll call them Yanky and Berel. The rabbi in this story watches as these two young men dance the night away. After the seven hakafos, they’re still dancing. Everyone watches in awe. The rabbi turns to one of his followers and says, “Yanky is going to stop dancing soon, but Berel, he’ll keep on going.”

And sure enough, that’s what happens. Yanky eventually sat down but Berel kept dancing.

“How did you know, rabbi? Can you tell the future? Are you a prophet?”

The rabbi smiled and explained. “I had recently spoken to both Yanky and Berel. Yanky told me that on Simchas Torah he would be celebrating the many books of Torah that he completed. He learned a lot this year, he had a lot to celebrate. And that’s why he danced so much tonight. But Berel, he told me he would be celebrating all that he hoped to accomplish in the year ahead. Yanky’s accomplishments were finite, but Berel – he’s dreaming of the future. The possibilities are endless.”

Shmini Atzeres and Simchas Torah are an exercise in ambiguous loss. It is hard to say goodbye, it is. So we don’t. Or, we don’t fully say goodbye. We make some space, we carve out daily rituals, to hold on to the magic. Today and tomorrow, the days in which we stop to say goodbye, is the time to ask ourselves, in what way will I hold on to this enchanting experience? Through which book? Through which class? Through which podcast?  Through which text?


Allow me to conclude by quoting Joe DiFazio once again. Because he got it. He held on, he never let go, but he also used the warm memories of his father to be a better person, to build a better future. And I quote:

“I wish that someday you could have held my kids. I wish I could
stand and watch from the bedroom doorway while you sat beside
them and sang about the young cowboy who lives on the range. I know the words–I’ll do my best.
I’ve spent hours lying in bed, staring at the ceiling, talking to your memory in the dark. I ask for help when I’m confused, for strength when I’m scared, and for comfort when I’m upset. I wonder how it was just at the end–if you were afraid, if there was pain.
You never answer, and that’s okay…
But more than anything, I wish I could hear your voice again,
even just for a minute. I wish I could listen to your stories and to the laugh that lit the room. I wish I could hear you tell me that you’re proud.

I’ll always remember to look out for Mom and my little sisters, to treat women like the angels they are and to show kindness to everyone, especially those who need it most. I’ll always remember that the guy who sees it the longest hits it the best.
Thank you for showing me that laughter can cure all, but that it’s okay to cry.
Thank you for showing me how to be a man.
I love you too, Dad, and I’ll miss you forever.
Your son,

All loss is ambiguous, all goodbyes are difficult, but the future – the future is entirely in our hands. Can we take our warmest memories, our high points of inspiration, and create something beautiful for the year ahead? We don’t have to say goodbye. We can and we must hold on.




A Snowy Yom Kippur

My phone is out of memory. Again.

Every few years I buy a new phone with more memory, like, a lot more memory, assuming that this time it will have enough memory to last forever, but it never does. Invariably, I am faced with that annoying pop-up every few minutes reminding me that iPhone storage is full.

You have to understand, I don’t have a lot of apps, I don’t take a lot of pictures. But my children, especially the younger ones, when they see my phone on the counter, they know they could just slide their finger and access their favorite toy in the world – the iPhone camera.

Which by the way, it is insane that my children can so easily access my camera. Apple boasts endlessly about their phone’s security. Double verification, triple verification, quadruple verification, you name it. My iPhone is a Ft. Knox. You can’t access the phone’s calculator without facial recognition. But there is one feature that you can access without any code, without any double-checking, without anything more than a flick of your finger and that is the camera. Why?!

Okay, I’m sorry, I just had to get that off my chest.

When I see this iPhone pop-up, telling me I am out of storage, I know to go to my pictures. And this is what I see –

Four thousand pictures of Miri, that’s my two-year-old, four thousand close-ups of her nose. Then there’s a few hundred pictures of one child posing. Each pose is slightly different than the next… A few nice family photos. And then another hundred unflattering pictures of me as I try to wrestle my phone out of my two-year-old’s sticky hands.

So, I delete. And delete. And delete. Because after all, the pictures are all the same. I keep a few unique pictures, but what’s the point of duplicates?

What’s the point of duplicates?

And it made me wonder – if a photographer was walking around with me all day, all week, all year, snapping pictures, how many pictures would I end up deleting?

Probably a lot.

How many days would look exactly as the day before? Different suit, different tie. But the same old mistakes, the same old good deeds. Delete. Delete. Delete. What’s the point of duplicates?


There is a book called, Einstein’s Dreams, written by Alan Lightman. It’s a work of fiction in which the author imagines what was going through Einstein’s mind as he was developing his theory of relativity, his theory of time. The author paints for us a wide array of possibilities of what time could look like. Allow me to read you a few passages from one alternative conception of time:

“Suppose time is a circle, bending back on itself… In the world in which time is a circle, every handshake, every kiss, every birth, every word, will be repeated precisely. So too every moment that two friends stop becoming friends, every time a family is broken because of money, every vicious remark in an argument between spouses, every opportunity denied because of a superior’s jealousy, every promise not kept.

And just as all things will be repeated in the future, all things now happening happened a million times before. Some few people in every town, in their dreams are vaguely aware that all has occurred in the past. These are the people with unhappy lives, and they sense that their misjudgments, and wrong deeds and bad luck have all taken place in the previous loop of time. In the dead of night these cursed citizens wrestle with their bedsheets, unable to rest, stricken with the knowledge that they cannot change a single action, a single gesture.”  

Are we aware of how much our life is on repeat, on how the frame of each day looks exactly like the day before? Do we wrestle with our bedsheets knowing that we’re still stuck in the same ruts, still celebrating the same accomplishments of years ago, still unable to break free of the demons we have fought with forever?

Or do we blissfully snap picture after picture. Same smile. Same frown. Same today. Same tomorrow.

Isaiah, our most eloquent prophet, paints a picture of teshuva, of repentance. “If your sins are like scarlet, whiten them like snow; if they are crimson red, bleach them as wool.” Isaiah utilized two different metaphors to describe the process of change.

The second approach Isaiah references is a process of laundering, “bleach them as wool.” This is the more well-known approach to change. We’ve committed a sin, we have a characteristic flaw, and so we cleanse ourselves. We fast, we beat our chests. “Ashamnu, bagadnu, gazalnu.” As we reflect on our past, we become aware of the crimson red sins on our soul. As we beat our chests, we pour warm water on the cloth. As we beg G-d to forgive us, we scrub the sins away with soap. This is the well-known and well-trodden path of experiencing Yom Kippur – a day at the laundromat cleansing our soul.

But the first approach, “If your sins are like scarlet, whiten them like snow,” this speaks to a very different teshuva experience. What does it mean to whiten our sins like snow?

There is nothing more majestic, more beautiful, more poetic than waking up to a city covered in snow. Before the tractors start plowing, before the people on their way to work start shoveling, before the children start playing. Just white snow. A sheet of purity covers everything. The muddy path is now a white velvet carpet. The bare tree is now a glittering tower. Everything is covered in a fresh coat of white.  

A significant portion of today’s davening does not focus on cleansing ourselves from the past. It asks us to imagine a beautiful future. “V’yeiasu chulam agudah achas, and all will become a unified society.” “Uv’chein tzadikim yiru v’yismachu, and the righteous will see and rejoice.” “V’simloch ata Hashem levadecha, and You, Hashem, will reign alone.” The liturgy begs us to imagine a pristine tomorrow, a reality totally unlike the one we are living. A snowy blanket covering all our shame, whitening all of our misdeeds, erasing all of the many things that hold us back.

And we walk outside onto this virgin snow. And our foot goes, ‘crunch,’ as it breaks through the frost. What a sweet sound. And we look at the imprint of our foot. You could see all the lines, all the contours of our boot. Every step is deliberate. Every line is new. Everything makes an impression.

Imagine living life like that. Imagine living life like every step is the first step on a fresh slate. Where every gesture is the first of its kind.

Allow me to once again read from Einstein’s Dreams, this time from a very different depiction of time:

“The shoppers walk hesitantly from one stall to the next, discovering what each shop sells. Here is tobacco, but where is mustard seed? Here are sugar beets, but where is cod? These are not tourists on their first visit. They are citizens. Not a man can remember that two days back he bought chocolate at a shop named Ferdinand’s, or beef at the Hof delicatessen. Each shop and its specialty must be found anew.

When it is time to return home at the end of the day, each person consults his address book to learn where he lives. Arriving home, each man finds a woman and children waiting at the door, introduces himself, helps with the evening meal, reads stories to his children. Likewise, each woman, returning from her job meets a husband, children, sofas, lamps, wallpaper, china patterns.

Late at night the wife and husband do not linger at the table to discuss that day’s activities or the bank account. Instead, they smile at one another as when they met the first time fifteen years ago. They find their bedroom, stumbling past family pictures they do not recognize… For it is only habit and memory that dulls the physical passion. Without memory, each night is the first night, each morning is the first morning, each kiss and touch are the first.”

Do you remember when you first held your newborn child in your hands?  Would you even dream of taking out your phone and scrolling through Facebook as they cried for your attention?

Do you remember when you first held your spouses’ hand? Would you even dream of criticizing him or her and ruining the magic of the moment?

Do you remember one of your earliest memories, a hug you received from a parent when you were in pain? Would you even dream of laughing at their old-fashioned ways as they embraced you with their huge protective arms?

Imagine a world covered in snow.

Imagine a world where you got to start again.

Imagine a world where everything was fresh.

That’s what we’re doing here today. We do not have to take the same picture every single day of our life. We could live a life full of pictures worth saving. Pictures of new horizons, of growth, of change.

And yes, of course, we do change with time. I am sure we’ve all changed this year. But how much of that change just happens to us, is a reaction to life circumstances, and how much of that change is planned? Proactive?


For the next ten hours, the world, your world is covered in snow. It’s a fresh new start. What will that first step on the pristine ground look like? A tender moment with a child? An apology to a spouse? In what way will we be a better sibling? In what way will we be a better neighbor? A better Jew? What will it be? What will it look like? What will you look like? 


Yom Kippur is an opportunity for a beautiful new start. But there’s a catch. The magic of Yom Kippur wears away. The snow melts.

So, if I could suggest if we want to take advantage of this G-dly gift of a snowy Yom Kippur, what we need to do before leaving this room tonight, is make a commitment. One small, tiny commitment, a change. Something that involves a stretch, but not too big of a stretch. Something different that we can do every day or every week of this year.

Because G-d willing, we will be back here next year, and we’ll be reviewing the photos that were taken over the course of the year. Will they be the exact same or will they be different? Will we once again repeat and delete? Repeat and delete? Repeat and delete?

Or will this be the year of change?