What are we actually meant to be doing on Rosh Hashanah?

What are the goals of the day? What does an ideal Rosh Hashanah look like? What should be going through your mind when you are sitting in shul?

The answer to these questions can completely change your experience of Rosh Hashanah this year, and, even, transform your entire life.

Every Jewish festival has a clear objective. On Yom Kippur we repent and confess. On Pesach we remember the Exodus. On Sukkot we remember how God protected us in the desert. Each one takes a theme that matters all year round and gives it a specific time of complete focus.

Rosh Hashanah looks like the exception. We never mention sin. There is no explicit reference to repentance. We call it the Day of Judgment, but what does that ask of you when you are sitting in shul with the machzor open in front of you?

The key lies in one line of the Mishnah, which departs from its usual legal language and turns poetic. On Rosh Hashanah, all who pass through this world come before God one by one, in single file. Not as a congregation. Not as a family. Alone.

Drawing on Pirkei Avot, the Rambam, Rabbeinu Yonah and the Rema, Chief Rabbi Goldstein explores the mitzvah that lies at the heart of Rosh Hashanah and gives meaning to its judgment, its prayers, the shofar and the kingship of God.

We call these days the Yamim Noraim. Many people hear that as the days of dread. But the phrase is better understood as the Awesome Days. Understanding why can transform not only our experience of Rosh Hashanah, but the way we live throughout the year.

• Every other festival tells us exactly what to do. What is Rosh Hashanah actually asking of us?

• What does it mean to be judged on a day when we never once mention sin?

• We spend Rosh Hashanah surrounded by family and community. Why does the Mishnah describe us coming before God one by one?

• What does it really mean to call Rosh Hashanah one of the Yamim Noraim, the Days of Awe?

• Can two days of the year really change how a person lives the other 363 days?

Inner strength is needed to succeed in everything in life.

But how do we build the strength we need?

Avot gives us high-impact tactics for this. And more than that, it offers a profound understanding of the nature of life itself that can give us the strength we need to overcome all the obstacles in our path.

Courage is usually defined against fear. In the parsha of Vayelech it is defined against weakness, which makes courage a matter of strength. And that turns an abstract virtue into a practical problem. Where does a person actually get strength?

The parsha sits at a moment of handover. The forty years in the desert are ending, and Moshe is giving way to Yehoshua. A people who have had everything provided for them are about to enter a land they will have to fight for and then run themselves. Two words carry the whole transition, stated three times here and repeated another four more at the opening of the book of Joshua. Chazak ve'ematz.

In our lives, the stakes are more ordinary rather than epic. We set out to build families, earn a living, become the people we want to be, and we meet resistance we did not expect. Resistance from other people, from circumstances, and from our own character.

Drawing on Pirkei Avot, the Malbim, Rashi and the Maharal, Chief Rabbi Warren Goldstein works through the practical answers to dealing with fear and anxiety, and then deeper to what the Mishnah says about the nature of this world.

• If courage is the opposite of weakness rather than the opposite of fear, what have we been calling courage all this time?

• We are told to be strong. What use is that instruction to someone who does not feel strong?

• Which is harder to stand against, the people in your way or the parts of yourself that are?

• The soul, before it enters this world, meets no obstacles and no friction at all. Why is that not the better arrangement?

• What would change if the resistance in your life turned out to be the point of it?

Understanding that feelings of guilt come from the depth of the soul, can empower us to transform the discomfort they bring into a catalyst for personal change and new beginnings.

This understanding comes from understanding the deeper meaning of teshuva, which is often mistranslated as repentance. Repentance comes from the Latin for penitence, meaning remorse and regret. The same root gives us penitentiary. A prison. Time served for what you have done.

That is not what teshuva means. Teshuva means return. During Elul, the month of teshuva, we are then faced with a difficult question: if teshuva is return, what is it we are returning to?

The distinction is not just semantic. It changes what a person is actually being asked to do at this time of year, and what they are being asked to believe about themselves.

The parsha of Nitzavim is read every year in the days before Rosh Hashanah. Drawing on this parsha, Pirkei Avot, the Ramban, the Rambam and others, Chief Rabbi Warren Goldstein follows that question from guilt through to redemption, and asks what the discomfort has been trying to tell us all along.

• Guilt tells us something is wrong. Why can't it tell us what is right?

• Is the wrong a person has done evidence of who they are, or evidence of the distance they have travelled from it?

• If our deepest nature is already good, why would we need commandments at all?

• If the mitzvot express who we already are, why do they so often feel like rules imposed from outside?

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?

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?

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?

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?

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 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?

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?