We instinctively look for the quickest most efficient path from where we are to where we want to be.

But life rarely unfolds in straight lines. It twists, detours and doubles back, leaving us wondering whether we've lost time along the way.

This week's parsha opens with a list: forty-two stops, forty years, for a journey Rashi says should have taken eleven days. Rashi also brings a midrash: God recounting each stop is compared not to an accounting, but to a parent narrating every stage of a sick child's slow recovery. Not a report, but something closer to a love letter.

Drawing on Pirkei Avot, the Chief takes that same tenderness and turns it toward our own lives. "Efficiency is everything in commerce," he says. "But the human being is not a product." The years you thought were setting you back may have been the years that were shaping you most.

Every stop got written down, because every stop was precious enough to be remembered.

Key Questions

• What if the years you thought were setting you back were actually shaping you?

• Is someone who takes forty years to learn something behind, or exactly on time?

• Why do the things that matter most refuse to be rushed?

• Can you trust that none of it was wasted?

Few aspects of human relationships are more uncomfortable than criticism, whether giving it or receiving it. Yet we cannot grow without it.

If we are to become better people, we have to recognise our mistakes, learn from them, and change. The question is not whether criticism has a place in our lives, but whether we know how to give it and receive it well.

This week's parsha, Devarim, begins with one of the Torah's most important moments of correction. As Moshe prepares to take leave of the Jewish people, he reflects on forty years in the desert and offers them words they need to hear, not necessarily words they want to hear.

Drawing on Parshat Devarim, Pirkei Avot and the example of our greatest leaders, the Chief Rabbi explores one of life's most difficult questions: how does telling someone they're wrong become an act of love rather than an act of harm?

Key Questions

• If speaking up risks the relationship, is silence really the safer choice, or just the easier one?

• Can criticism be an act of friendship, or is that always self-justification?

• Why does Moshe correct the people without ever naming them?

• What does a person have to become before they're allowed to correct someone else?

• Is the goal of a hard conversation to be right, or to make someone else greater?

Why do we spend three weeks manufacturing grief for a building none of us ever saw? This is the question the Chief puts directly to his audience in this year's Shemiras Halashon shiur, delivered the Shabbos before Tisha B'Av - a program he has been part of given every year for over two decades.

The laws of communal mourning work backwards from the laws of personal mourning. Grief for a relative starts intense and eases with time. Grief for the Beit Hamikdash starts light and intensifies toward Tisha B'Av, because, as Rav Soloveitchik points out, the feeling isn't naturally there. We have to be walked into it.

Drawing on the Ramban's philosophy of mitzvot, the Chief Rabbi argues that this manufactured grief was never meant to be the goal. Misery isn't a mitzvah. The mourning exists to sensitize us to a loss most of us have never named correctly. Not bricks or sacrifices, but the diminished honor of Hashem's name in the world. And the Gemara's answer for what restores it starts somewhere surprisingly close to home.

It's the same place the Chofetz Chaim started when he built an entire program around the laws of lashon hora: how we speak to, and about, one another.

Key Questions

• If grief for the Beit Hamikdash doesn't come naturally, why does Jewish law go out of its way to manufacture it?

• What did we actually lose when the Temple was destroyed, and why isn't it the building itself?

• Why is fasting on Tisha B'Av not, technically, an act of mourning at all?

• What does the way we speak about other people have to do with the dignity of Hashem's name in the world?

• Why does Chillul Hashem stand apart from every other sin in Jewish law?

Personal mourning fades with time. Our national mourning, the Three Weeks leading into Tisha B'Av, on the other hand, move in the opposite direction. It grows more intense until a day described as "sitting shiva for the world itself."

Why would we deliberately awaken grief for a loss most of us have never personally experienced?

Drawing from Rabbi Yosef Dov Soloveitchik, Rabbeinuyu Bechaye, Pirkei Avot and the wisdom of our Sages, The Chief Rabbi explores why Tisha B'Av is not only about mourning the destruction of the Temple, but about learning to see the brokenness of the world itself. And why that grief was never meant to end in sadness. It was meant to become the beginning of hope, action, and redemption.

Key Questions

• Why would grief for a loss most people have never personally felt need to intensify as the day approaches, rather than ease?

• What does the Chief mean when he calls Tisha B'Av "sitting shiva for the world"?

• Why is fasting on Tisha B'Av treated as an act of repentance rather than an act of mourning?

• What actually changes at midday of Tisha B'Av, and why does the day work in two such different registers?

• If grief is only the doorway, what is it a doorway to?

Why has the Jewish people always stood alone?

Recorded on the night of Tisha B'Av, this shiur begins with a simpler question: what does it actually mean to mourn? The grief turns out to be only the surface of it. Underneath sits something else, the very aloneness the day is built to make you feel. It's there in the halachot that shape Tisha B'Av, in the law that forbids a mezumen at the seudah hamafseket even though mourners, in every other context, are permitted one. And it's there from the very opening line of Eicha: eicha yashva badad, how she sits alone.

Drawing on Rav Soloveitchik's reading of that halacha, and on the prophecy given to Bilaam that Israel would be 'a nation that dwells alone,' the Chief traces two entirely different kinds of aloneness: one born of desolation, one born of a mission nothing else can replace. He follows the thread into the present moment, into the three years since October 7th and the resurgence of antisemitism worldwide, and into where Theodor Herzl's founding assumption about Jewish history went wrong.

What would it take to move from one kind of alone to the other? And on a day built entirely around loneliness, what would it mean to choose it, rather than simply endure it?

Key Questions

• What is actually happening, beneath the grief, when a person mourns?

• Why does Jewish law forbid mourners from comforting each other on the one day mourning is most intense?

• What is the difference between a nation that dwells alone because it has been broken, and one that dwells alone because of what it carries?

• Where did Herzl's founding theory of antisemitism go wrong, and what does Tisha B'Av say instead?

• What would it mean to choose the very aloneness we've spent three years trying to escape?

In this episode the journey we have been on together over this series takes an unexpected twist. It turns out that Avot is not only about who we become.

It is also about leadership. And it changes what that means for each of us in a way that makes it relevant for how we live every day.

One of the most famous lines in Pirkei Avot is Hillel's question: if I am only for myself, what am I? Many of us think of who we are as something fixed. A fixed size, a fixed list of people who count as ours. Hillel's question doesn't accept that. It asks how far the boundary of "I" can actually move.

Drawing on the Rambam, Rav Shimon Shkop, and the opening chapters of Pirkei Avot, we begin to uncover a new concept, and it is one that changes the meaning of personal development itself.

Perhaps becoming the person you're meant to be was never an inward journey alone.

KEY QUESTIONS

· When you say "I," who are you actually talking about? Your body? Your family? Your people? Something wider still?

· If you are only for yourself, what are you?

· Is your sense of identity fixed, or is it something that can actually grow?

· Can personal growth ever be complete?

· What does it mean if the highest form of Kiddush Hashem required no words at all?

Over the course of this journey through Pirkei Avot, we have been piecing together its vision of the human being: how we think, the character we develop, the choices we make, and the responsibility we take for the world around us.

In Part 6, those pieces come together around one of life's most fundamental questions:

What does it actually mean to succeed?

We naturally measure a life by what someone accomplished. And as Jews, we might assume the answer is even clearer: learn Torah, fulfil the mitzvot, live according to halacha.

But Pirkei Avot makes a startling claim. All of that is indispensable — and yet it is possible to do everything required of us and still miss something essential.

Drawing on the Rambam, Ramban, Maharal, Netziv and the great commentators on Avot, I explore what the Rambam calls hatzlacha amitit — true success — and why the ultimate measure of a life may lie somewhere deeper than a checklist of what we have done.

Because at the end of the journey stands another question entirely:

Who did we become?

KEY QUESTIONS

• What does it actually mean to live a successful life?

• Can a person fulfil all 613 mitzvot and still somehow miss the purpose?

• Why are Torah and mitzvot necessary, but not the final measure of who we become?

• What does Pirkei Avot mean by shleimut — the completeness of the human being?

• At the end of a life, should success be measured by what we did or by who we became?

What does it mean to be spiritually healthy?

The Rambam was a physician as well as one of our greatest sages. In his introduction to Pirkei Avot, he draws a remarkable parallel between the health of the body and the health of the soul, describing the sages themselves as "doctors of the soul."

But spiritual illness presents a unique problem. When something distorts our character or the way we see the world, it can also distort our ability to recognise that anything is wrong.

In this next part of our journey through Pirkei Avot, The Chief explores what it means for the soul to function as it was created to function, why we may need help seeing what we cannot see for ourselves, and how Avot offers us a path back to spiritual health.

Drawing on the Rambam and the great commentators on Avot, we discover a vision of spiritual health that reaches from our character and the way we see the world, to the very heights of what a human being can become.

KEY QUESTIONS

• If spiritual illness can distort our ability to recognise it, how do we know when something is wrong?

• We accept that the body sometimes needs a doctor. Why do we assume the soul does not?

• Anger, arrogance and envy are usually treated as faults. What changes if we understand them as symptoms?

• Is there a connection between becoming a better person and becoming a calmer one?

• The Mishnah says that the human being is created in God's image. The Sforno reads that not simply as a description, but as an instruction. What is it asking of us?