Rabbi Lazer Gurkow
Rabbi Lazer GurkowCourtesy

The eyes of a Jew on Rosh Hashanah—the annual day of judgment, are often filled with tears and remorse. We know we will be judged for our behavior. We also know that some of our behavior has been compulsive, some of our personality has been toxic, and some of our pettiness has been obsessive, so we beg and cry for forgiveness.

Indeed, our sages declared that “even when the gates of heaven are closed to prayer, they are never closed to tears.” When G-d sees His children cry with a bitter heart, He responds as a loving father and embraces us in forgiveness.

How does this jive with the teaching that one must never pray out of sadness? The great Kabbalist Rabbi Yitzchak Luria wrote that the only way to connect with G-d through prayer is to pray with joy. If we pray in a state of sadness, our connection with G-d is blocked.

Two Objections

The answer can be found in an interesting story about the third Lubavitcher Rebbe, Rabbi Menachem Mendel, also known as the Tzemach Tzedek. A group of non-hasidim told him that they were impressed by hasidism and wanted to join the movement, but they had two profound objections. They once saw a hasid cry on Simchat Torah, the day we celebrate the gift of the Torah, and sing on the ninth of Av, the day that the Temple was destroyed.

The Tzemach Tzedek replied. “A hasid doesn’t rejoice on the ninth of Av nor is he sad on Simchat Torah. On the ninth of Av, when he realizes that the prophecies of destruction were fulfilled, he believes that the prophecies of redemption will also be fulfilled, so he sings. Not out of joy, but out of transcendental delight. On Simchat Torah, he reflects on the revelation of the Torah, on the fact that the Torah rejoices with him, but realizes that he is distant from the Torah, so he cries. Not out of sadness, but out of bitterness.”

Sad or Bitter

Tears of bitterness are different from tears of sadness. Tears of bitterness lead to joy, tears of sadness lead to toxicity. When I think about my inappropriate behavior over the past year and become saddened, I cry over how toxic and horrible I have become. If I am such a terrible person, there is little hope for me, and therefore I cry. These are tears of sadness. They don’t lift me up and don’t lead me to light. They are dark tears that lead me to heaviness, lethargy, and darkness.

Tears of bitterness flow when I reflect on my terrible behavior and realize that they don’t represent the real me. I don’t cry over what I have become, I cry over what I have done. I cry because I have committed a terrible crime against my true self. I am really a good, kind, and generous person. I am a disciplined person with stellar integrity. I am a sweet person with an easy demeanor. I am a holy person of sacred transcendence. That is the true me.

But look at what I have done to myself. I filled myself with obsessive desires, compulsive needs, toxic perspectives, and indecent behavior. I removed myself from my rightful place and brought myself to a pervasive place of spiritual darkness and moral depravity. This is not the real me. My goodness, what have I done to the real me? How could I have plummeted so low?

Such thoughts are not sad, they are bitter. They are not dark and brooding, they are intense and demanding. They are not dead weight, they are compelling energies. Such bitter thoughts are bitter pills to swallow, but they are cathartic because they are cleansing.

That is the difference between sadness and bitterness.

Transition to Joy

When I absorb my demanding reprimand, when I internalize the truth of my own charges, and accept the demands that I make of myself, I emerge from my darkness to encounter my internal light. I transition from bitterness to joy—the tension of the pent-up bitterness releases a torrent of unbridled joy. I now feel light on my feet and a spring in my step. I am motivated to climb, to soar, to reach the greatest heights of altruism and achievement.

Just as the light of dawn follows the darkness of the night, so does soaring joy follow searing bitterness. These are the tears that we cry on Rosh Hashanah. They are not tears of sadness because sadness blocks our connection to G-d. They are tears of bitterness that lead to joy.

Tears flow when we experience more than our minds and hearts can bear. The overflow drains from us in the form of tears. This overflow can be triggered by overwhelming bitterness or by overwhelming joy. Both flow in the same direction; in the same channel. Thus, both are called tears of joy. They might be tears of bitterness today, but they will produce tears of joy tomorrow.

This is why the hasidic masters taught that the only tears allowed on Rosh Hashanah are rooted in the words, “Beshimcha yegilun kol hayom,” may we rejoice in your name all day long. The Hebrew word bechiyah, which means to cry, is an acronym for Beshimcha yegilun kol hayom.

On the surface, tears and joy are opposites. But when we cry tears of bitterness, they result in tears of joy. It is, therefore, correct to say that they are already tears of joy. It just takes some time for their true nature to emerge.

A Good Year

When we transition from bitterness to joy, we transform our sins into merits. We transition from toxic behavior to healthy behavior, from obsessive selfishness to altruistic giving, and from petty resentments to expansive tolerance. We take our obsessions, our pettiness, and the small mindedness that stymies growth, and dump them into the depths of the river alongside our sins.

In return, G-d grants us a year of blessing and plenty, goodness and happiness, health and longevity for us, our loved ones, our friends, our acquaintances, and for the entire nation, Israel.

Rabbi Eliezer (Lazer) Gurkow, currently serving as rabbi of congregation Beth Tefilah in London, Ontario, is a well-known speaker and writer on Torah issues and current affairs.