Psalm 27 and Teaching Our Children to Try, Try, and Try Again

Israel has a custom during the days of Elul and Tishrei until Shemini Atzeret to recite the psalm “For David, Hashem is My Light and My Salvation, from who shall I fear…” (pasuk 1). Of the many approaches put forth by sages as to why this psalm is appropriate to be recited, the Midrash that associates the phrase My Light to Rosh Hashanah and My Salvation to Yom Kippur is the most prominent.  

Upon a deeper look into the chapter, we find prayer to be a recurring theme, which is also a pillar in the work people do during these days. We find ourselves in the synagogues for extended periods of time. In fact, the Musaf on Rosh Hashanah is the longest prayer of the year. In the famous prayer in the Musaf, Unetane Tokef, we declare that tefilla, teshuva and tzedaka will wipe away sins. Let’s take a closer look at this connection.

The last pasuk in the psalm is, “Pray to Hashem, strength and firmness for your heart, pray to Hashem” (pasuk 14). The Gemara asks the question, from where do we know, if you pray and your prayers were not answered, you should pray again? The answer, “Pray to Hashem…pray to Hashem (pasuk 14).”

This same message is repeated a second time in chapter 27 of psalms. It’s written, “One thing I ask of the Lord, only that do I seek, to sit in the House of Hashem all the days of my life” (pasuk 4). Sages point out the inconsistency in the grammar construct of the verse. It begins in the past tense “I asked” and continues with, “I will request…” They commented that the inconsistency underscores the notion that David prayed to “sit in Hashem’s house…” from his earliest years until his last days. He prayed for the same thing his entire life, and in the end, Hashem did not let David experience the Bet HaMikdash as he desired.

Either one of these two references would send a powerful tefilla message, but its repetition makes the connection between chapter 27 of psalms and the Days of Awe ironclad. There is a midrash about Moshe which strongly reinforces the connection. Moshe in his last weeks of life shared the content of Sefer Devarim with the nation. He said, “And I prayed to Hashem at that time saying.” Moshe shared with the nation his deep desire to enter the land and the great effort he made to convince Hashem. Unfortunately, the answer remained no.

The Midrash explains why the word ואתחנן was used instead of a more common word for prayer. Our sages see from the use of the word a connection to the days of Tishrei. The numerical value of ואתחנן is 515 and the number of hours between the beginning of Rosh Hashanah and the end of Shemini Atzeret, which is the last possible day of teshuva and the last day we recite the 27th, psalm is 516. The Midrash records that Moshe prayed to enter the land of Israel every hour for 515 straight hours. Had he prayed the 516th time, Hashem would have been compelled to let him in.

The message to pray again and again for your needs is an awesome lesson. A person of faith never puts limits on his efforts in service to Hashem. It’s a lack of faith if a person pleads with Hashem two or three times and then stops, thinking Hashem won’t or G-d forbid He can’t. Moshe and David comported themselves with the greatest act of faith by willingly praying for what they truly wanted repeatedly, never tiring. We need to share with the children what Moshe and David did, explain how it is a magnanimous show of faith and they need to become enamored with such a mindset.

There is another great lesson for children both in all aspects of service to Hashem and in all aspects of life. Grit. One of the great habits of the mind that sets apart people who achieve greatly in life and those who hover around mediocrity. Grit is a character disposition that will enable a person to pursue long term goals with passion and perseverance.

This character trait matches the requirements needed for people to be successful in their Torah pursuits. All goals in Torah are ultimately long term and a love and passion in the service of Hashem are essential to extensively pursue them. Perseverance is one of the habits of the mind that helps a person to pursue a goal despite glaring obstacles. King Solomon described the behaviour with the words, שבע יפול צדיק וקם. A righteous person will try and fail time and again and will always get up and try again.

In training Jewish children to become “gritty” for their pursuit of Torah and mitzvot, both components of this disposition should be trained separately. A good place to begin in the passion-love paradigm is the educational philosophy of Rabbi Yechiel Yaakovson in his sefer, Spare the Child.