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20 Questions for the New Year

20 Questions for the New Year

Effective ways for moving your life forward.


One effective way to move your life forward is to ask yourself existential life questions. The traditional time to do this is around the time of Rosh Hashana.

Don't try to answer all the questions at once. Take some time and meditate on each question for at least five minutes.

When you feel satisfied that you have a concrete, workable answer, move onto the next question. You will want to spread this out over a number of sessions.

Later, go back and refine your answers. Then, work out an action plan for achieving your goals. has a series of articles on the mechanics of a “Spiritual Accounting.”

You may want to have this list with you at the shofar blowing, a time of special inspiration and insight.

(1) When do I most feel that my life is meaningful?

(2) What would bring me more happiness than anything else in the world?

(3) What are my three most significant achievements in the past year?

(4) What are my biggest mistakes in the past year?

(5) What project or goal, if left undone, will I most regret a year from now?

(6) If I knew I couldn’t fail, what would I undertake to accomplish in life?

(7) What are my three major goals in life? What practical steps can I take in the next two months toward these goals?

(8) What is the most important decision I need to make this year?

(9) What important decision did I avoid making last year?

(10) What endeavor gives me the strongest feeling of self-respect?

(11) What kind of person do I want to be one year from now?

(12) What kind of person do I want to be five years from now?

(13) Over the last year, did my most important relationships become closer and deeper, or was there a sense of stagnation and drifting?

(14) What can I do to nurture those relationships this year?

(15) In what areas of my life am I hiding from God?

(16) What is one step I can commit to that will bring me closer to God?

(17) If I could change only one thing about myself, what would it be?

(18) Are there any ideals I would be willing to die for?

(19) If I could live my life over, what would I change?

(20) What do I want written on my tombstone? And how do I begin living that way now?

Adapted from "Rosh Hashana/Yom Kippur Survival Kit" by Rabbi Shimon Apisdorf

September 5, 2011

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Visitor Comments: 7

(7) ROZANNE, September 23, 2012 11:29 PM



(6) Tanya Strusberg, October 4, 2011 7:25 AM

These questions added a really special dimension to RH

I decided to print off these questions and then cut them into individual strips and put them in a bowl. As we enjoyed our dessert on Erev Rosh Hashanah, we each took turns and took out a question to read out loud and then say whatever came to mind. It turned out to be a really beautiful and very meaningful exercise for all of us and everybody really enjoyed it. I think it perfectly captured the essence of Rosh Hashanah and I have a feeling it will become an annual tradition in our family! Thank you for posting such thoughtful questions!

(5) Joey, September 28, 2011 7:48 PM

Thank you for these thought-provoking questions. God bless and shana tova!

(4) Elisse, September 27, 2011 7:30 PM

Great questions- todah raba!

Truly great questions- at least some of which I can answer! Thank you...

(3) Bob, September 23, 2011 8:55 PM

good questions . . .

Some of these are good questions to ask the person you're on a date with. (Not the first date.) I'd think the worst answers would be the pat, expected answers from elementary school mussar shmooze. That would mean the person is not willing to disclose their true self to you.

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