High Holiday Questions

collected and annotated by Rabbi Debra Orenstein

I welcome your feedback on these questions. Please send me some of your favorite questions, gleaned from the Jewish tradition or other holy sources. If you care to share your answers, I would be honored to read them, as well. – Rabbi Debra

What have you learned in the past year?

What new choices do you wish to make for the year ahead?

Who do you think you are?

Parents everywhere have said it, but usually rhetorically. Take some time to think and ponder what is actually a deep question. The answer may redirect you, inspire you, or get you mad enough to make a change.


What is your mission here on earth?

Go out into the world and see: which is the right path to which a person should cleave [in this world]? – Rabbi Yochanan, Pirkei Avot 2:9

Five rabbis each give a different answer to their teacher. Consult the original source and see what they say, and how their answers (and Rabbi Yochanan’s favorite among them) match with your own.


What are you made of?

Everything tends to one and the same conclusion, which is clearly enunciated in that classic Berlin phrase: "Juden Raus" (Out with the Jews)! We shall now put the Jewish Question in the briefest possible form: Are we to "get out" now and where to? Or, may we yet remain? And, how long? – Theodore Herzl,The Jewish State, 1896.

What is the place of Israel in the life of the Jewish people and in your life? How can you support Israel? How can you help peace, security, and justice to flourish there in the coming year?


Who are your heroes? How can you (better) emulate them in a way that is true to yourself?

If I am not for myself, who will be for me? If I am [only] for myself, what am I? And if not now when? – Hillel, Pirkei Avot 1:14

Do I take time to know myself and track my own development, or am I on automatic pilot? Am I a true advocate for the best that is in me? Is there something beyond myself that I am living for? What is my life devoted to? And how can I act on my true priorities now?


What would you do if you knew you could not fail?

– Rev. Robert Schuller


What talents were you endowed with and for what purpose?


What is humanity, that You, [God,] remember us? What is a human, that You consider us? – Psalms 8:5

Why does an all-good, all-powerful, all-knowing Being wish a relationship with us – and with me? Creation itself is a proof that God desires partnership. What does God’s overture and love mean to you? And what can you offer, as God’s partner?


My son, what do you seek?

– Rabbi Hillel, responding to a stranger who called him out of a bath repeatedly with a series of foolish questions. – Babylonian Talmud Shabbat 31a

Two men had a bet going, as to whether anyone could anger Hillel. After the hoax of the pointless questions was exposed, Hillel said, “Better that you lose [double the money you wagered], rather than I lose my temper.” He also advised, “Be careful of your moods.” This incident was considered proof of the statement that “one should be humble and gentle like Hillel.” How might you be more gentle and more careful of your moods in the coming year? How will you choose to answer people who want something from you?


When being led in for Judgment [after death], a person is asked:

·Did you negotiate business honestly?

·Did you set fix times for Torah?

·Did you concern yourself with “being fruitful and multiplying?”

·Did you hope for salvation?

·Did you engage in the dialectics of wisdom?

·Did you come to understand [causality and] how one thing leads to another?

–Rav, Babylonian Talmud Shabbat 31a


A human being will have to give account [in heaven] for all that his eye beheld and he did not consume. [Did you avail yourself of every permitted pleasure?] – Jerusalem Talmud Kiddushin 4:12

Life is a gift. Are you enjoying it? The Talmud does not anticipate the question, “Did you accomplish everything on your to-do list?” That is not God’s concern. Rather the question is: “Did you really see, hear, feel, smell, and taste what this amazing world has to offer?”


Why me? & Why not me?

Both are valid questions.


Where did the year go?

No, really. Imagine if you had done a minute-by-minute, hour-by-hour time log of the entire year. Where and how did you spend your time? Reflect back and consider: Are you satisfied with how you spent your one irreplaceable resource: time? Do you want to make changes?


The question is not “can I,” but “howcan I” and “what support do I need?


The first question God ever asked of a human being was: “Where are you?” – Genesis 3:9

These words were spoken after Adam was hiding in shame, following his sin of eating the fruit. Are we, because of our sins,“hiding” from God? Do we feel unworthy and distance ourselves? Part of the spiritual accounting of the High Holiday seasons is to map our progress (or regression) and to recognize where we are now. Wherever that is, we can plot a course forward. But first we must know and admit where we are.


The first question a human being ever asked was: “Am I my brother’s keeper?

The rest of the book of Genesis is a meditation on Cain’s question, with biblical brothers slowly improving their outlook and developing, by the end of Genesis, an ethic of mutual care and caring. We are still struggling with this question today. Human rights and human morality depend on the answer.


What are you doing here? – – II Kings 19:16

This is the question that God asks of Elijah when he is despairing so terribly that he wishes to die. The question is posed both before and after God creates an impressive display of power. But God was not in the wind, nor in the earthquake, nor in the fire. God was in a still, small voice. This text teaches that the answer to despair is to listen closely to the voice within and thus remember why you are here on earth. God’s exchange with Elijah is drawn on in the Unetaneh Tokef prayer, recited on High Holidays: “The great shofar is sounded; a still, small voice is heard.”


Why have you come to Earth – do you remember?

Why have you “taken” birth – why have you come?

To love, serve, and remember.

To love, serve, and remember.

– Lyrics of “Love, Serve, Remember” by John Astin


Tell me, what is it you plan to do
with your one wild and precious life?

-- Mary Oliver, “The Summer Day


Our CD's and downloadable audio teachings are edited from live High Holiday recordings and include explanations of High Holiday prayers and liturgy, inspiration on themes of the day, meditations, sermons, prayers, and stories. They also include questions from the congregation and answers from Rabbi Orenstein.

For rabbis, cantors, and laypeople alike, these are the best resources we have to offer for preparing for the High Holidays. Click here for purchasing information.

NEW - Since the last High Holidays we released a double album entitled "Gratitude." These High Holiday teachings, sermons, and stories are a great way to prepare for a truly good and happy new year.