Three Great Books, Two Holy Songs, Five People You Meet on Earth, and the One Idea Behind It All
I missed number Four. I think I was supposed to.
In Mitch Albom's The Five People You Meet in Heaven, we meet Eddie, a maintenance man at an amusement park who spends his life feeling like a nobody. He dies convinced that his life was pointless. In heaven, he learns that his humble, unnoticed work had saved lives, brought joy, and created safety for generations. His purpose was real, even though it wasn’t seen.
In The War of Art, the author Steven Pressfield, argues that simply showing up every day to do your work, especially when it feels invisible or thankless, is an act of spiritual resistance. The artist (as well as anyone else engaged in meaningful labor) must confront and overcome “Resistance,” the inner force that tries to stop us from doing the work that matters. Regardless of recognition or acclaim, the key is to do the work that our souls are here to do.
We’ll continue to the third book later. Before that, let’s explore five remarkable individuals, two holy songs, and the single idea that weaves them all together.
Dovid HaMelech
Dovid HaMelech, the progenitor of Mashiach, wasn’t born into a throne. He was born into doubt.
According to Chazal1, Yishai, Dovid’s father, was one of the greatest tzaddikim of his generation, even serving as the head of the Sanhedrin. A direct descendant of Boaz and Ruth, Yishai harbored a halachic uncertainty: Was Ruth’s Moabite lineage permissible? Did the Torah’s prohibition of “a Moabite shall not enter the congregation of Hashem” apply to women as well as men?
Fearing his lineage might be flawed, Yishai separated from his wife. He had already fathered many sons who were considered legitimate and upstanding. Then came Dovid.
Yishai had planned to enter a relationship with a maidservant. She, however, shared the plan with Yishai’s wife, and they conspired to switch places, much like Rachel and Leah had done with Yaakov. Yishai’s wife, still deeply connected to him, disguised herself and approached him in secrecy. From that concealed, halachically complicated union, Dovid was conceived.
When he was born, his brothers wanted to kill both him and his mother. The circumstances of his conception, intended to be with a maidservant, somehow influenced his red-haired appearance, a marker that Yishai interpreted as a sign to leave the child alone. Dovid was sent to shepherd the family flock, tucked away from the public eye.2
Later, when Shmuel arrived to anoint a king from among Yishai’s sons, Dovid wasn’t even summoned from the field. He wasn’t considered. He wasn’t counted. He was rejected3.
“כִּי אָבִי וְאִמִּי עֲזָבוּנִי, וַה׳ יַאַסְפֵנִי”
“My father and mother abandoned me , but Hashem gathered me in.”4
From the beginning, Dovid carried the weight of not being seen. Yet, it was he whom Hashem chose. He, the youngest and most disregarded, was anointed to be king. He, the child of a hidden and misunderstood union, became the foundation of the eternal dynasty of Israel.
This isn’t a footnote. It’s a blueprint.
The mekubalim explain5, when a soul is too great, too luminous, to enter the world through ordinary channels, it must arrive through hidden back alleys of reality. It must descend through concealment, sometimes even controversy. The greatest light often enters from the places we least expect.
“כאשר הנשמה גדולה מאוד, אי אפשר להוציאה אלא על ידי מרמה ותחבולה.”
“When the soul is exceedingly great, it cannot descend except through cunning and concealment.”
Dovid, the son of that hidden reunion, becomes the one who writes Tehillim, who defeats Goliath, who unites Klal Yisrael, and who gives the world its ultimate hope: Mashiach. Rather than coming through the front door, Holiness slips in through the cracks.
Rebbe Akiva
Rebbe Akiva, the towering pillar of Torah Sheba’al Peh, began as an outsider. He was born to convert parents, illiterate until age 40, a shepherd, unknown, unlearned, and seemingly insignificant. Yet his neshama came from deep, hidden places.
Chazal teach that Rebbe Akiva descended from Sisra, the Canaanite general who terrorized the Jewish people during Devorah’s time. Sisra was ultimately killed by Yael, who lured him to sleep and then drove a tent peg through his head. The Gemara calls this act an aveirah lishmah, a transgression for the sake of Heaven. From that complicated encounter came descendants, and from them, Rebbe Akiva.
His origin was beyond the outside of the camp. It was outside comfort and expectations, including outside the categories we usually call “Tahor.” From that fierce and ambiguous energy emerged a man who would forever reshape Jewish destiny.
Rebbe Akiva didn’t simply learn Torah. He reimagined it.
In the aftermath of the second Beis HaMikdash’s destruction, while others mourned the end, Rebbe Akiva saw the beginning. When he and his colleagues walked through the ruins and saw foxes running through the Kodesh HaKedoshim, they wept. Akiva laughed.
“Why are you laughing?” they asked.
He answered: “Just as the prophecy of destruction has been fulfilled, so too will the prophecy of redemption.” Where others saw tragedy, he saw promise. Where others saw an ending, he saw the unfolding of something larger.
My father, Rabbi Yaacov Haber, teaches: “To Rebbe Akiva’s companions, the game was over, Judaism was finished. But Rebbe Akiva saw the bigger picture. He widened the frame. He understood chronology. This wasn’t the end, it was the turning of a page.”
His mission became more than teaching Torah, it was about preserving Torah for the unknown future. Every teaching of Rebbe Meir, every Mishnah redacted by Rebbe Yehuda HaNasi, each traces back to Rebbe Akiva. He built the scaffolding that allowed Torah to survive exile.
In order to do that, he had to come from outside. He had to carry the raw, transformed energy of Sisra, take the very force that once destroyed, and flip it into something redemptive. As the mekubalim say, the same koach that can destroy a nation, when refined, can rebuild it anew.
Dovid HaMelech and Rebbe Akiva
Although Dovid HaMelech and Rebbe Akiva lived centuries apart, their stories mirror each other. Both were excluded, questioned, mocked and dismissed. Both descended from ambiguous unions, born of acts that hovered between righteousness and scandal. Both came from the margins and finally, both became foundational figures in Jewish eternity.
Dovid was overlooked by his father, unrecognized by his brothers, and nearly forgotten by his nation, until Hashem said, “That’s the one.”
Rebbe Akiva was a shepherd at forty, a descendant of Israel’s enemies, and written off as an ignoramus, until he became the man through whom Torah would survive.
Dovid's vision of the world was poetic and prophetic; his Tehillim resonated with longing and closeness to Hashem.
Rebbe Akiva saw the world through eternity, his laughter amidst ruins was not delusion, it was clarity.
This illustrates that concepts in life are more than about where we come from, they are also about how we perceive. They saw beyond what was, they saw what could be and what would be. Their story is not a personal biographical sketch. It’s the blueprint of redemption.
Mashiach will come from contradiction, rather than comfort. The holiest figures may have the most complicated beginnings. Greatness may not always be born in light, but it always brings light with it.
Shlomo HaMelech
If Dovid HaMelech represents the voice of longing, and Rebbe Akiva the vision of redemption, then Shlomo HaMelech is the paradox of perfection born from imperfection.
Shlomo was the wisest man to ever live. The author of Koheles, Mishlei, and Shir HaShirim. The king who built the Beis HaMikdash, the dwelling place of Hashem on earth.
Shlomo was also not born in a palace of purity. He was born in the aftermath of an apparent sin.
His mother, Batsheva, was the wife of Uriah, a soldier in Dovid’s army. Dovid saw her, desired her, and brought her into his home under a cloud of moral and halachic controversy. The child from their first union died. After repentance, heartbreak, and public scandal, Shlomo was born from their second union.
And not just born, but chosen.
“וַתֵּ֣לֶד בֵּ֔ן וַיִּקְרָ֥א אֶת־שְׁמ֖וֹ שְׁלֹמֹ֑ה וַֽה׳ אֲהֵבֽוֹ” , “She bore a son and called him Shlomo, and Hashem loved him.”6
Despite, or perhaps because of, the messiness of his beginning, Shlomo was blessed. He wasn’t hidden away like Dovid or ignored like Rebbe Akiva. He was affirmed by God Himself.
Yet the pattern is the same: His birth was morally ambiguous, his origin forged in pain and teshuvah, and from that space, holiness emerged.
The kabbalistic model plays out again. A soul too great to enter through clean, well-lit doors must descend through brokenness. The Beis HaMikdash, the ultimate dwelling place of God in this world, built by a man born in tension rather than purity.
Shlomo teaches us that Hashem doesn’t merely use broken vessels. He chooses them. He took the longing and laughter, pain and prophecy, and turned it into construction.
Shlomo HaMelech famously wrote in Koheles that there is a time for everything: A time to weep and a time to laugh, A time to tear down and a time to build, A time to mourn and a time to dance.
What he didn’t list explicitly, because it exists within and between them all, is the time for shirah, the time to sing.
Sometimes Shirah is musical, but not always. It’s what happens when something too deep for ordinary language finds its way into expression. It can come as a whisper, a cry, a melody, or a tear. It’s the voice of the neshamah when it refuses to remain silent.
It was for this that Shlomo wrote Shir HaShirim, the Song of Songs, a text of love, longing, union, and exile. A song of ache, in place of answers.
Mendel Roth
Let’s meet a contemporary Jew: Mendel Roth.
Mendel Roth was born into legacy. He is the grandson of the famed Shomrei Emunim Rebbe, the son of a rebbe, raised in the heart of Mea Shearim. His path, however, was never going to be conventional.
From a young age, he displayed a creative and spiritual individuality that didn’t conform to the expectations around him. When he picked up a guitar in yeshiva, it wasn’t rebellion, it was yearning. A search for something real. For a way to give voice to the ache inside. He was expelled.
Later, he was pushed into a marriage he didn’t choose, and eventually divorced. His friends were banned from his wedding. He had become, in the eyes of some, a dangerous influence.
Mendel wandered, spiritually, emotionally, existentially. Instead of looking for a new truth, looking for his truth.
Over time, he became a voice for the disillusioned. Writing haunting songs, raw, beautiful, unpolished. He spoke publicly and privately with countless young adults who felt they no longer had a place in the system and yet still yearned for G-d.
He became a rebbe, not by inheritance, but by honesty. For the struggling. For the seekers. For the ones who thought their questions disqualified them.
Still, he remained. He wears the levush. He lives in Yerushalayim. He carries the tension of staying rooted while breaking norms.
Recently, Mendel joined the Chashmonaim Unit of the IDF, a new initiative for Charedi soldiers. At 33, older than most recruits, he enlisted, out of conviction in place of pressure.
His vision of Geulah is one of integrity and quiet courage. No slogans. No protests. Just doing what’s right, even when it’s hard.
In a recent post, Mendel opened up:
“I don’t know. Suddenly I just want to let it out… Not the version of me that inspires people on Instagram, the one that shows everything is fine. I want to share the version that is tired. That misses love. That lies awake at night wondering if he’ll ever find someone to build a life with. That runs through training drills all day, wondering what Hashem wants of him…”
Even those who seem brave on the outside carry unseen weight.
Mendel is, in many ways, a Shir HaShirim Jew. He sings from the ache. He shows up with honesty and devotion. He still questions. He still serves. He is still becoming.
And maybe that’s what being a rebbe really is.
The Ropshitzer
This leads me to the fifth person you meet on earth, and perhaps the outlier.
There was another Rebbe, the great Ropshitzer.
He, too, was a singer of songs. Songs of elevation in place of wandering.
The story is told that near the end of his life, he was in incredible pain, caught in a state where his neshamah couldn’t seem to leave his body. Those around him recited Viduy, said Shema, davened with intensity, but he remained in this in-between space. Then the B’nai Yissaschar came and said Az Yashir with him. As the words were sung, the Ropshitzer’s neshamah ascended --- That was the shirah that matched his soul.
Interestingly, his writings on Az Yashir aren’t flashy. There isn’t a single teaching that explains the power of that moment. Yet something in that song, the simplicity, the clarity, the unfiltered expression of redemption, carried him to where he needed to go.
The Duality of Shirah
Lately, I’ve been drawn to the idea of shirah, as I explored in my Purim post. On Pesach, we read two of the most powerful shiros: Az Yashir and Shir HaShirim. They couldn’t be more different — in tone, in energy, in structure — but somehow, they bring us to the same place.
Az Yashir is a song of clarity. It’s loud, communal, and undeniable. The sea splits, the enemy drowns, and truth is revealed. It’s the song of triumph, of collective revelation, of knowing exactly where we stand and what we’re witnessing. In this shirah, there isn’t hesitation. Everyone sings.
Shir HaShirim, by contrast, is the song of subtlety. A song of searching. It’s personal, fragmented, full of longing and missed moments. One calls out, the other pulls away. One opens the door, the other is gone. It’s the song of vulnerability in a relationship that matters — with G-d, with others, and with ourselves.
Though here’s the thing: both are called shirah. Both are songs of geulah. According to Chazal, both are holy, with Shir HaShirim being Kodesh Kodashim, the Holy of Holiest.
Why?
Perhaps we can deepen this contrast by exploring the difference between Tal (dew) and Geshem (rain). It’s a distinction we step into each year on Pesach, when we begin saying Morid HaTal.
Rain is seasonal. It arrives when conditions are right, when we’re deserving, when we explicitly ask. It is loud, visible, and timely — like Az Yashir, which bursts forth in a moment of undeniable revelation.
Dew, on the other hand, is constant. Quiet. It appears even when uninvited. The Beis Yaakov of Izhbitz7 explains that dew is drawn from the unspoken tefillos of the heart — the kind we don’t even realize we’re praying. It’s the Torah that seeps into closed spaces, into souls not yet ready to receive, into hearts too broken to open.
This is Shir HaShirim. It’s the Torah that arrives without sound or spectacle. It enters through cracks, instead of the gates. Like the Ketores on Yom Kippur, brought by the Kohen Gadol in the Kodesh HaKodashim — so fine, so subtle, it rises through fissures too small for anything else.
Holiness doesn’t always come through the front door. Sometimes it slips in through the cracks.
The Sfas Emes8 teaches that the Torah of the community — the grand, collective, public Torah — is like rain. While the Torah of the individual — the personal mission, the private ache, the quiet return — is like dew.
That's why, Chazal say, Techiyas HaMeisim will come through dew. Because even when a person seems gone — emotionally, spiritually, or literally — their Tal remains. The unspoken yearning. The forgotten connection. The soul’s whisper. And that is enough to bring them back to life.
So too with shirah.
Not all growth is Az Yashir — bold, immediate, and celebrated. Sometimes it’s Shir HaShirim — unresolved, faltering, and intimate. One kind of shirah erupts in joy, the other aches in longing. One is triumphant, the other is tender.
If we’re honest, most of us are both. We have moments of clarity — when the sea parts and we know exactly who we are. While many more moments feel like Shir HaShirim: a knocking, a pause, a door that almost opened. A whisper of something holy — even when we’re unsure.
It feels human because it is human. That doesn’t make it less holy. It makes it more real and maybe that’s the deeper point.
Just like on Shavuos we speak of Matan Torah Jews and Megillas Rus Jews, we can speak here of Az Yashir Jews and Shir HaShirim Jews.
Some of us live in the clarity of Az Yashir. We feel connected, expressive, confident in our song. Yet many of us dwell in the ache of Shir HaShirim. Our relationship with Torah, with God, and with ourselves is full of ups and downs, of longing, of trying again — even after we’ve been pushed away.
That doesn’t make one kind of song better than the other. It just means they’re both part of the same story.
We don’t always know when we’ve shifted — when we’re no longer who we were, but not yet sure who we’re becoming. That’s the in-between space. The subtle stirrings of becoming, where we feel something awakening inside, even if nothing on the outside reflects it yet.
This is where many of us find ourselves. Not broken, nor soaring. Just… becoming. And realizing that stepping more into who we are now often comes with an unexpected cost: the discomfort of those who once knew us best.
When We Grow, They Get Uncomfortable
There’s a voice inside many of us that whispers things like, “You don’t have time for this,” or, “This isn’t really necessary,” or, “No one else is doing this.” That inner dialogue, always casting doubt, is perhaps the root of impostor syndrome. And those blessed souls who don’t hear that voice? I’m genuinely curious what goes on in their heads all day, or if, perhaps, it's just a nice quiet hum in there. Must be nice.
When we look closer, the obstacle isn’t time, it’s fear. Fear of looking foolish. Fear of what others might think. Most resistance traces back to fear. And that’s okay. It’s human.
So name it and then punch it in the face and keep going anyway.
Fear doesn’t only live inside us. It gets mirrored by the people around us. When someone begins showing up more fully, sharing, speaking, evolving, it unsettles the equilibrium. People who were part of the “before” don’t always know what to do with the “becoming.”
It can feel like you’ve broken an unspoken contract: You’re supposed to stay who we thought you were. You’re not supposed to be this deep. You’re not the one who shares things like this. Who do you think you are? You’re embarrassing us.
The discomfort is rarely overt. It shows up in glances, silences, sideways comments. A family member who suddenly "mutes" you. A friend who used to check in and now doesn’t respond at all. At times, it feels like our own paranoia, but deep down, we know it isn’t. We feel the tension and hear the silent feedback.
It feels subtle, though it hits hard. It makes us question ourselves. It makes us want to shrink back.
It also confirms something deeper: We're stepping into who we are and not everyone is ready to walk that with you.
The Cost of Courage
The moment someone begins to step into a more authentic version of themselves, the world around them doesn’t always adjust right away. Sometimes it resists. This happens more likely due to confusion than cruelty.
Maybe we’ve become more spiritually open, more emotionally grounded, more curious or reflective, and suddenly, the old mold no longer fits. The people who knew the older version of us don’t quite recognize this new version. We may do things a little differently than someone else expects. And that’s what makes each of us the unique individuals that we strive to be.
It’s uncomfortable, for them, and often for you. It’s growth, rather than rebellion.
This shift is rarely dramatic. It often shows up in small ways, in how we speak, what we ask, what we choose not to say. The shift starts in how we begin to think differently, even if we don’t act on it right away.
This is hard. We might find that people don’t know how to respond. Some grow silent. Some sidestep. Some simply fade. It’s not always personal. Yet it is always felt. It can sting, in the tiny absences. The text that isn’t answered. The thing we poured ourselves into that’s met with indifference. The lack of acknowledgment that quietly chips away at our certainty. The silence can echo.
With time, a new truth emerges: not every silence is rejection and not every pause is a verdict. Sometimes it’s people adjusting. Sometimes it’s their own discomfort. Sometimes it’s just life being noisy.
So the task isn’t to shrink. Or to shout louder. It’s to stay aligned. To live in rhythm with our own voice, even when others haven’t caught the tune yet.
Because the work isn’t about being heard by everyone. It’s about being real and becoming yourself, fully, is worth every bit of discomfort along the way.
As Brené Brown reminds us: “You can choose courage or you can choose comfort. But you can’t have both.”
Most of us don’t choose discomfort for fun. We choose it because becoming ourselves , fully , is worth it.
Rav Kook: The Holy of Holies of Song
Rav Kook writes in Olas Re’iyah that there isn’t a day in history as worthy as the day Shir HaShirim was given to Am Yisrael. Shlomo HaMelech, with Divine inspiration, composed it as a prophetic response to the long journey of Jewish exile and return. He foresaw generations cast into darkness, estranged from their Source, but still reaching, still remembering the early closeness between God and His people that once was. Shir HaShirim became the voice of that yearning. A national teshuvah. The longing of a people not yet home yet still in love.
In Rav Kook’s understanding, the imagery of the bride and beloved is a revelation, not a metaphor. In galus, Am Yisrael is like a separated wife, aching for her husband. Hashem whispers back through memory: I still see your beauty. I still see the kindness, the connection. I will return.
That’s why we read Shir HaShirim every Friday night. Just like the nation, the neshama is called to remember who it really is. To let go of shame. To feel held, even in the quiet. Rav Kook calls it the most elevated of all writings, not because it is perfect, but because it gives voice to our most imperfect longing. It tells us: even that is holy.
When we understand Shir Hashirim as the song of imperfection, we can understand why it was received amid controversy.
The Mishnah in Yadayim9 notes it was the most debated of all Sefarim. It was Rebbe Akiva who defended it, insisting: if all the Kesuvim are kodesh, Shir HaShirim is kodesh kodashim, Holy of Holies.
Why did Rebbe Akiva see what others didn’t?
Rav Avigdor Miller suggested it was because of Rebbe Akiva's love for Rachel. It was a love that was selfless, loyal, and born of hardship. It mirrored the kind of love Shir HaShirim describes. The kind that isn’t idealized, rather it is tested and real. It is costly and it is also redemptive. The kind that survives rejection and misalignment and still returns stronger.10
Rav Kook expands this idea, writing that Sifrei Kodesh must capture halachah and prophecy, along with the emotional undercurrents of the soul: the longing, trembling, and unresolved desire to come home. That’s why Shir HaShirim is kodesh kodashim, because it dares to say the deepest truths out loud.
Only someone like Rebbe Akiva, who saw the Churban and smiled, who felt pain and still called it holy, could have seen what Shir HaShirim really was. Rather than only admire it, he embodied it. He lived it and he died with it.
In his final moments, as the Romans flayed his flesh, he recited the Shema. When asked how he could, he replied: “All my life I wondered: When will the moment come to fulfill the words, ‘b’chol nafshecha’, with all your soul? Now that it’s here, shall I not fulfill it?” He then said: “Echad.” He stretched the word until his soul left him.
I heard from my father, Rabbi Yaacov Haber, that had Rebbe Akiva continued and said ve’ahavta, he might have invoked the Shem HaMeforash, and reversed the decree itself.
He stopped at Echad and in that moment, that’s all there was. Unity. Oneness. The ache of love meeting the clarity of surrender.
When others saw only romance, Rebbe Akiva saw the blueprint for redemption, personal, national, and spiritual. In other words: Shir HaShirim is not the song you sing when everything is clear. It’s the song of tension, of mismatch, of longing. But that song, sung anyway, becomes holy.
Rabbi Jonathan Sacks wrote: “There is something profoundly spiritual about music. When language aspires to the transcendent, and the soul longs to break free of the gravitational pull of the earth, it modulates into song… Jewish history is not so much read as sung.”
Perhaps Shir HaShirim is the song that tells our history best.
Its shifting tones, missed connections, and moments of return and reconciliation echo the national story of Am Yisrael. From the intimacy of Yetziat Mitzrayim and Har Sinai to the heartbreak of exile to the quiet promise of future redemption, Shir HaShirim is the musical thread that runs through it all.
This applies on the national level and also mirrors the ebbs and flows of our personal lives. The moments of clarity that are followed by confusion. The longing to be seen, and the courage to show up even when we’re not.
As described in Shir Hashirim so hauntingly “Pitchi li...” He knocks. She hesitates. By the time she opens the door, he’s gone.
That’s what it feels like to share our truth and be met with silence or polite distance. Whether you knock or you risk or even speak, the people closest to you disappear, figuratively or literally.
Az Yashir and the Other Kind of Song
Az Yashir is the other shirah, the public one. It is the Shirah that ‘everyone’ joins in triumphantly. In this Shirah, there isn’t any hesitation nor tension. When we saw the sea split and the enemy drowned, we also encountered a wave of collective clarity.
However most of life doesn’t feel like that. Most moments of growth aren’t split-sea dramatic. They’re slow and quiet. Often they are lonely and unseen...
That’s where the real songs begin, in the discomfort. In the knocking. In the not-yet.
As Rabbi Ezra Bick once wrote:
“When I learn a new fact, I am not impelled to sing. Song relates not to new facts, but to a new sense of awareness of the significance of those facts, an awareness expressed best not in prose, or in learning, but in song, in exultation.”11
It’s not the information that moves us to sing. It’s the awakening.
Often that awakening happens when no one is clapping. It happens when meaning settles deep in our bones, even if we can’t quite put it into words yet.
That’s Shir HaShirim, the song of becoming.
Resistance Is Real and Predictable
Steven Pressfield calls Resistance the subtle, invisible force that rises up the moment we get close to doing something that matters. We might call it the Yetzer HaRa.
It whispers. It shows up as procrastination, self-doubt, perfectionism, or people-pleasing. It tells us: “This isn’t worth sharing,” or, “Who do you think you are?”
The very presence of Resistance is often the best sign we’re on the right path. It never shows up when we’re playing small. Only when we’re approaching the edge of change.
It shows up because we’re creating something real. We’re risking vulnerability and doing work that might change something, maybe even you.
So if stepping into your voice feels uncomfortable or lonely, know that you’re not off-track. You’re exactly where the real work begins.
Rebbe Nachman taught, “Kol ha’olam kulo gesher tzar me’od – the whole world is a very narrow bridge.”
And the ikar, the essence, “lo lefached klal”, is not to be afraid.12
The bridge is real, so is the fear and most importantly, is the crossing.
As Pressfield writes: “Resistance will tell you anything to keep you from doing your work. It will perjure, fabricate; it will seduce. Resistance is always lying and always full of it.”
The invitation isn’t to wait for the fear to pass. It’s to move anyway.
Redemption Takes Time (and So Does Acceptance)
Geulah is a 2,000-year process. The same goes for personal character building. We don’t owe anyone our old self. We don’t need permission to evolve.
Some people stay in Mitzrayim, even when the door is wide open. Others pretend nothing’s changed. Some make us feel like we have to justify every step.
Pesach teaches us: we walk anyway and we leave. Redemption doesn’t wait for consensus.
Maybe this dissonance, the distance we feel, the hesitation of others, the shakiness in our steps, is historical.
History isn’t only written from Above. It’s authored below, too. Hashem initiates and we respond. Sometimes we lead, while other times, we lag. Sometimes we’re the heroes, other times, we are the hesitant ones.
This is the beauty of Shir HaShirim: it doesn’t pretend alignment. It embraces the misfires, the longing, the realness of the relationship. It says: the yearning is part of the holiness.
That’s why Shir HaShirim, with all its longing and lack of resolution, is still Kodesh Kodashim. Though it may seem that it is a fantasy of ideal love, it is actually a blueprint for sacred, imperfect partnership, with God, with others, and maybe most of all, with ourselves.
Where This Leaves Us
Brené Brown reminds us, “Vulnerability is not weakness; it’s our greatest measure of courage.”
Most of us aren’t asking to be celebrated. We just want a little space. Space to grow, express and show up a little more honestly.
Yes, it can hurt when those who once felt like home now feel far or when love comes with fine print. That is also part of the process and can be holy. Shir HaShirim, with all its gaps and confusion, is still kodesh kodashim.
Rav Kook teaches, holiness doesn’t demand perfection. It welcomes yearning and honesty, along with the courage to show up in a vulnerable and unfinished state.
Rav Judah Mischel writes: “It is in the safety and confident embrace of our Beloved that we can be our true self. Here, in the private space of the Holy of Holies, we can reveal ourselves as we are, b’etzem. To be truly open and free, kemo ani, ‘as I truly am.’ Alone, together, one.”13
That’s the work - to stand before Hashem as the person we are, more than the person we wish we were.
Az Yashir didn’t come spontaneously. It came after fear and doubt, after a step into the sea that hadn’t yet split.
Sometimes, all we can do is sing anyway. Even if our surroundings don’t sing with us or they step back. That, too, is part of redemption.
Through our songs, we reaffirm our relationship with Hashem. We declare our readiness to return. To come home. To sing the Shir Chadash, a song of the present, written by the ink of our soul and the tears of our past.
The Song Beneath the Silence
“All endings are also beginnings. We just don’t know it at the time.”
-- Mitch Albom, The Five People You Meet in Heaven
Sometimes, we only understand what a moment really meant long after it’s passed. What feels like failure might be the beginning of purpose. What looks like silence might actually be a deeper kind of calling. This isn’t just a psychological insight, it’s a spiritual one.
It’s also the story of so many of our greatest figures.
Dovid HaMelech was left out in the field when Shmuel came to anoint the next king. Dovid’s own father didn’t even consider him a possibility. Rebbe Akiva was 40 when he learned to read, and he came from the lineage of Sisra, one of the fiercest enemies of the Jewish people. Shlomo HaMelech was born after one of the most painful chapters in Dovid’s life, a child of repentance and controversy.
Mendel Roth was expelled from yeshiva, pushed into a marriage he didn’t choose, and found himself caught between two worlds. The Ropshitzer Rebbe, in his final moments, couldn’t leave this world until someone sang with him, until Az Yashir was sung.
At first glance, these stories seem unconnected. However they share something vital: each begins in darkness, doubt, or failure. In every case, that seeming ending was actually the doorway into something deeper and truer. Each story began in obscurity, and became light.
These aren’t just stories of success after hardship. They reveal a different kind of spiritual blueprint, one where the way forward isn’t linear, where the soul’s journey doesn’t obey logic, and where grace often hides in the mess.
These are the stories of humans, flawed, tender, resilient. From a distance, they might look like legends or angels. Up close, they’re people who embraced their humanness. Who stayed in the process, saw that life is not a zero-sum game, and that sometimes, the missing piece is what makes the puzzle whole.
In Shir HaShirim, we encounter a relationship marked by longing, missed moments, and elusive closeness. Notwithstanding all this, there is still love. There is movement and presence, even in absence.
That’s the deeper message here.
Geulah, redemption, rarely arrives wrapped in clarity. Sometimes, it begins with being overlooked. Sometimes with rejection, uncertainty, or contradiction. Often, we don’t recognize it until long after it has begun.
Rebbe Akiva’s laughter at the ruins of the Beis HaMikdash wasn’t naïve, it was prophetic. He understood that if the prophecy of destruction had come true, then the promise of rebuilding would, too. To him, history wasn’t linear or final. What others saw as an end, he saw as a turning point.
That same way of seeing applies to individual lives as well.
Some people never quite fit the expected script. They grow up inside the system, yet feel like strangers. They get cast out for asking the wrong questions, or for expressing themselves with too much feeling, or too much truth. Some leave, while others stay. In both cases, they’re reaching for something real.
There’s a certain holiness that doesn’t come from perfection, rather it comes from perseverance. From staying with the process, even when it’s messy. From continuing to speak to God, even when the words feel raw, uncertain, or unfinished.
So too, there’s a kind of shirah, a kind of song, that isn’t polished or performative. It’s sung to survive. It’s the sound the soul makes when it refuses to go silent. That’s the shirah Rebbe Akiva called kodesh kodashim, the Holy of Holies.
That’s the song beneath the silence. Beneath the kol demamah dakah.
Not everything fits cleanly into the categories of success and failure, sin and merit, exile and redemption. Shir HaShirim reminds us: the relationship continues, even when we don’t feel it. The story keeps unfolding, even when we’ve lost the thread. Sometimes, the turning point comes without answers, instead it comes with deeper presence.
We don’t always know when a new beginning is happening.
Often, when we look back, we realize the neshamah knew it all along.
Oh, and that third great book?
It’s you.
It always was.
“The greatest book that a person will ever write is the one that will never be seen in print. Rather, it is the imprint of the person they become, and the positive impression they make on others.”
Rabbi Mordechai Ginsbury, The Jigsaw Puzzle of Life
Whether you sing like an Az Yashir Jew, with clarity, conviction, and visible strength, or like a Shir HaShirim Jew, with questions, longing, and quiet courage, it all leads to the same place. Both songs move us forward.
And that missing number four? Maybe it’s the fourth voice, the one that holds the tension between the other three: the voice of becoming. Not the hero, the teacher, or the rebbe, but the person still in process. The one who hasn’t arrived, yet refuses to walk away.
So sing your song, however it sounds, just don’t stop singing.
P.S.
Maybe, in the end, it’ll be like Abie Rotenberg’s The Band.
The ones who were offbeat. The ones no one let in.
The ones who only wanted to bring joy, not perfection.
They’ll be the ones Moshiach calls up to play the final song.
Because they never stopped trying to sing.
Yalkut HaMachiri, Tehillim 118:28
See Tiferes Shlomo HaMevoar, Oz V’Hadar edition, Vol. 6, p. 117
see Shmuel I, 16
Tehillim 27:10
Shaar HaGilgulim, Hakdama 38
Shmuel II 12:24
Seder HaZmanim
Haazinu
Yedayim 3:5
Heard from my brother Rabbi Sender Haber
Likutei Moharan, Tinyana 48
Baderech Haggadah pg. 360
I don’t know what “special sauce” you have been using lately, but this is another beautiful piece. Thank you!!!