Transforming Your Worst Qualities Into Your Biggest Assets

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Everyone has a story that defines who they are. The question is: Is your story empowering you to maximize what G-d has given you? Or is your story causing you to fall short?

It’s easy to recognize what our talents are, and most of us enjoy thinking about them, but the value of our lives is often determined not by our strengths, but by our limitations. Think of someone you know well, and identify their core weakness. (It’s easy to do when you’re thinking about someone else….) Now imagine that the person could turn that weakness into a virtue. Their lives would rapidly change for the better.

Each of us has a core sin we need to confront. (Ask your friend. They were just thinking about yours a moment ago….) If we see our flaws honestly and find ways to use them for good, then we change the kind of person we are, and the kind of world we live in.

Yom Kippur is the day to be profoundly honest about our own shortcomings, whether they are selfishness, the desperate need for approval, hard-heartedness, or failure to fulfill a certain mitzvah.  How can we confront them each day? How do you overcome a long-standing habit or trait, and become strong in your weakest spot?

This speech provides a unique and inspiring angle on the transformation we seek on Yom Kippur. It includes many provocative insights and engaging anecdotes, including:

  • The man who gave up sinning for the wrong reason
  • Moses’ perplexing words, with which the commentaries struggle, and Chasidus’s original interpretation
  • Why is Yom Kippur called “Like Purim” and why does the Megillah trace Mordechai to an “impure one”?
  • An incredible (yet not widely known) story of Jewish ingenuity and commitment that played a major role in the Jewish victory over the Arabs in 1948
  • The boy who transformed himself and later become president (with a follow up quip about the 2016 elections...)

Tonight we turn to G-d and say, “Look, I am a complicated story. I don’t know if I can change my life, I may not be ready for a complete transformation. I don’t have the energy or even the will to surrender every bad habit and every sin, but there is one core sin that is nagging me. It is eating up my conscience. Help me, G-d, turn it around so that it may become a force for good in my life and for the people around me.”

And G-d’s response will be, as He responded long ago, “סָלַחְתִּי כִּדְבָרֶךָ”— “I will forgive you as you asked. And I will be with you and help you. I will give you the amazing ability to be somebody different next year than you were this past year. I will give you the qualities you didn’t believe you possessed, so that you can turn that core sin into a strength.”

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