Explore every episode of the podcast The Philosophy of Giving - Rav Dessler Podcast

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If everything will be clear, and the world filled with divine truth, what will happen to our ability to choose? What’s the point of life without choice? In this episode, we explore the nature of free will in the Messianic era — and what that means for us now.

Bikurim celebrates the first fruits , the power of new beginnings. But Elul comes at the end of the year. Or does it? In this episode, we compare Bikurim to Elul to ask: is Elul the closing chapter of the year, or the first step toward something new? The answer may change our approach to this month

Why would the Torah tell a soldier to carry a spade to coverhis excrement - even in the middle of a war? In this episode, we delve into the filth itself to uncover its kabbalistic meaning and why we are naturally repelled by it.

What’s the link between the negligent killer in exile and the death of the Kohen Gadol? In this episode, we uncover a surprising connection — and how it reveals not just Hashem’s strict justice, but His deep love for every Jew.

Adam was a vegetarian. Noach was not. In this episode, we take a macro look at history to see how society’s relationship with eating meat has shifted — and whether vegetarianism is ideal, permitted, or discouraged.

The sages say everything is in Hashem’s hands — except the fear of Him. But what about love? And if fear is ours alone, why do we pray for help with it? In this episode, we tackle some of the biggest paradoxes about God’s power, and what they mean for our relationship with Him.

In Shema we say hayom — “today” — even though the Mitzvos were given thousands of years ago. Why?

In this episode, we will look into what it means to live fully in the present rather than riding on the ripples of the past. We'll also explore if a mitzvah once hard but now easy still earns the same reward, and discover how growth can continue in the afterlife.

God could have placed Ruth in a righteous home — so why was she born into Moab? In this episode, we explore how a negative environment can sometimes spark the strongest desire for truth. And how the same force can pull both ways.

In this episode, we explore what exile really achieves — and what it reveals about the soul after death. What happens to a person when they die? Who are they without a body? The Torah’s choice of exile holds a deep answer to these questions.

Why did the tribes of Reuven and Gad choose land outside of Israel — and why for their sheep? In this episode, we dig beneath the surface and uncover a deeper spiritual mission: the responsibility to uplift sparks of holiness hidden in the physical world. And yes — even sheep have a role to play.

When Moshe asks for a successor, God chooses Yehoshua — and the shift speaks volumes. In this episode, we explore how the leaders of each generation reveal the soul of their people. Looking at the arc of history, we uncover a deeper pattern: some generations are led by the mind, others by the heart — and their leaders reflect exactly that.

Why did people worship idols — and why was it so compelling? In this episode, we explore what made avodah zarah so attractive, how it actually worked, and what that reveals about the deepest question of all: are we serving Hashem… or just serving ourselves?

A rebbe isn’t just a wise person — he’s a vessel through which messages flow. In this episode, we explore why we need a rebbe to help us interpret life, and what happens when that relationship breaks down.

How we see life makes all the difference. From the story of Dasan and Aviram’s perspective on Egypt to understanding the deeper meaning behind current events, this episode invites you to look beyond the surface and discover the hidden layers of meaning in everything around us.

Tzitzis aren’t just ritual strings — they’re part of the Shema, part of our identity, and part of our spiritual memory. In this episode, we explore the third paragraph of Shema, what it’s doing there, and how those little threads are trying to keep us from unravelling.

Moshe knew he was the greatest leader in history — and yet the Torah calls him the most humble. In this episode, we explore what real humility looks like, and how it can coexist with absolute greatness.

Is the Nazir holy for abstaining — or flawed for pulling away? This episode explores a deeper, more analytical question: when we do something non-ideal for a higher purpose, is it still a blemish, or does the goal transform the act completely? A more nuanced discussion this week — come thinking.

We had mitzvos before Sinai — and more came after.

So what truly happened on that mountain?

In this Shavuos episode, we explore the moment we became commanded. But why does that matter? What difference does it make if we’re told to do something — or just choose it ourselves?

The answer may change how you see every mitzvah.

A relationship with Hashem is meant to be deep and genuine — but it's easy to slip into serving for the sake of reward. In this episode, we reflect on what it means to connect to Hashem not for what we gain, but for who we become.

We often think of tzedakah as one person giving and another receiving — but the Torah's view is far more profound. In this episode, we explore who truly benefits when we give, and why the act of giving might elevate the giver even more than the one in need.

How can the Torah permit slavery? In this episode, we explore the concept of the eved kena'ani and uncover the framework that surrounds it — one rooted in justice, dignity, and responsibility. Far from the cruelty of historical slavery, the Torah’s system challenges our assumptions and reveals a deeper moral structure

We usually imagine Kiddush Hashem as a public act of courage — but is that the full picture? In this episode, we delve into the halachos of when one must give up their life, when not, and why sanctifying Hashem’s name isn’t limited to grand gestures or public moments.

“Love your neighbour as yourself” — beautiful words, but what do they really mean? In this episode, we explore three levels of love.

The Torah promises life for keeping mitzvos — but what kind of life is it talking about? In this episode, we explore three levels of what “life” can mean, and how each one offers a deeper understanding of what it means to truly live.

You've probably heard it: speak lashon hara about someone, and you hand over all your mitzvos to them and inherit their aveiros. But is that really true? In this episode, we untangle the myth and explore Rav Dessler’s deeper explanation of what’s really happening when we misuse our words.

It might not feel like it, but hitting the lowest point could be the best thing to happen to you. In this episode, we explore why real growth often begins only when there's nowhere left to hide.

Cows are content, beetles aren’t—and the Vilna Gaon has something to say about that. What your lunch says about your soul.

Aharon, the Kohen Gadol, needs a warning to perform a korban eagerly—even though he has no personal stake in it. But why warn the ultimate Tzaddik about enthusiasm? Could he really fall short?

The "wicked son" at the Seder gets a harsh response—but why? His question seems fair, even sensible. In this episode, we explore the deeper wisdom hidden in this challenging interaction, revealing how the answer given to the Rasha completely flips our understanding of reality.

Explore the deep message behind this surprising halacha and how it reveals the difference between what's just a means and what's truly an end.

The Mishkan’s construction repeatedly says “as Hashem commanded”—but why the emphasis? Does Hashem want obedience over logic? This episode explores the balance between submission and reason in serving Hashem.

The sin of the Golden Calf is often seen as an outright betrayal of Hashem—but was it really that simple?

Mordechai refused to bow to Haman—but was his defiance just an act of principle, or was he deliberately provoking the most dangerous man in the empire? Why did he push Haman’s buttons so aggressively, knowing the risks?

Are clothes just about covering up, or do they reveal something deeper? In this episode, we explore the Kabbalistic perspective on clothing and how they shape our identity.

Why does Hashem onlywant donations for the Mishkan from those who give willingly? After all He’sdone, why not command it? In this episode, we uncover how this act of givingshapes more than just a sanctuary—it shapes us.

Knowing the difference between a chok and a mishpat is not merely theoretical—it determines the attitude needed when performing a mitzvah.

In this week's podcast we will redefine the distinction and explain why knowing which mitzvos fall into each category is essential.

We often navigate between formality and informality—but how do they shape our relationships? In this episode, we explore their dynamic through Yisro’s encounter with Moshe.

We often focus on our talents, skills, and natural abilities—but do they truly define us? In this episode, we explore the purpose of our strengths and why the fruit matters more than the tree.

Why do so many people feel stuck after a burst of inspiration? In this episode, we explore the hidden power of the number three and why true happiness is a three-step journey.

Why does Hashem stretch out the downfall of Egypt across ten plagues instead of ending it instantly?

Perhaps there is more to Divine justice than meets the eye? This episode uncovers the unexpected kindness hidden within the plagues—and why revenge is sweeter than you think.

Pharaoh’s back-and-forth decisions seem baffling, but they reveal a profound truth about the struggles we all face. Why couldn’t he hold firm, and what does his failure teach us about overcoming our own challenges?

Must we thank those who act selfishly? Why did Moshe delay redeeming the slaves to ask Yisro’s permission? Could this moment reveal a deeper truth about perfecting the middah of hakaras hatov? Join us as we explore the lessons in gratitude woven into the narrative of redemption and its relevance to our lives today.

Is the statement "Yaakov never died" a poetic metaphor, or could it be taken literally? In this episode, we explore the kabbalistic depth behind this idea, delving into the spiritual and mystical perspectives that suggest it’s more than just mere symbolism.

Are there really fires in hell, or is the true pain something far deeper?

In this podcast, we explore the idea of Gehenom, focusing on how shame serves as a key element in the soul’s reckoning. But what if someone feels no shame? Can Gehenom still impact them?

Ever wonder why we thank Hashem for saving us from the Greeks—when He put us there in the first place? In this episode, we uncover the deeper forces behind the clash between Greek externalism and the soul of Judaism—and how triumphing over it ignited a hidden spark that still burns bright today.

In this episode, we explore one of the most fundamental principles of Jewish life: the balance between hishtadlus (human effort) and bitachon (trust in Hashem).

How much effort should we put into achieving our goals, and when should we step back and trust in Hashem?

Should I get a job or is this a lack of faith?

Yaakov asks Hashem for a break. As a result he is challenged with strife?

Why is this so?

In this episode, we explore the tension between accepting gifts and feeling deserving of them.

Should we gratefully receive blessings, or is there merit in stepping back and saying, "Enough"?

Join us as we uncover the deeper meaning of Yaakov's request and what it teaches us about humility, gratitude, and our relationship with Hashem's gifts.

Angels: messengers, protectors, spiritual beings.

But what are they really?

In this episode, we explore the Jewish perspective on angels, peeling back layers of mysticism and diving into their role and their connection to humanity.

Are they literal beings?

Do they have an ego or are they robots?

Join us as we unravel the nature of angels in Jewish thought and kabbalistic wisdom.