Spiritual Connection and Discipline in Jewish Prayer

(יג) רַבִּי שִׁמְעוֹן אוֹמֵר, הֱוֵי זָהִיר בִּקְרִיאַת שְׁמַע (וּבִתְפִלָּה). וּכְשֶׁאַתָּה מִתְפַּלֵּל, אַל תַּעַשׂ תְּפִלָּתְךָ קֶבַע, אֶלָּא רַחֲמִים וְתַחֲנוּנִים לִפְנֵי הַמָּקוֹם בָּרוּךְ הוּא, שֶׁנֶּאֱמַר (יואל ב, יב) "כִּי חַנּוּן וְרַחוּם הוּא." וְאַל תְּהִי רָשָׁע בִּפְנֵי עַצְמָךְ:

(13) Rabbi Shimon says: Be careful in the reciting of Shema and praying. When you pray, do not make your prayer routine, rather prayers for mercy and supplication before the ever-present God, as it says, "For He is gracious and merciful." And do not be wicked in your own eyes.

(א) הוי זהיר בקריאת שמע לקרותו בעונתו. וכן בתפלה, להתפלל כל תפלה ותפלה בעונתה:

(ב) קבע כאדם שיש עליו חובה דבר קבוע ואומר אימתי אפרוק מעלי חוב זה.

אי נמי, קבע, כאדם שקבוע לו לקרוא פרק אחד פרשה אחת, שאומר אותה בקריאה בעלמא, ואינו אומרה בלשון תחנונים כאדם שמבקש רחמים:

(ג) כי אל חנון ורחום הוא רוצה בתחנונים, ועל ידי התחנונים הוא מרחם מיד:

"Be careful in the reciting of Shema and praying," to recite it in its prescribed time. And so too with prayer [the Amidah], to pray each and every prayer in its prescribed time.

"Routine," like a person who has a fixed obligation and says, "When will I unload this debt from myself?"

Alternatively, like a person who routinely reads a chapter or section and says it with ordinary reading, and does not say it with a tone of supplication like a person who is requesting mercy.

"For He is gracious and merciful," God wants supplication, and through supplication He immediately has mercy.

1. What does it mean for prayer to be "routine"? Which of the Bartenura's explanations do you prefer?

2. What are the benefits of having a routine/discipline of prayer? What are the drawbacks?

3. How do you understand supplication (תחנונים)? Does it mean making specific requests of God? Could it mean something else for us?

4. What, if anything, might the last phrase from Pirke Avot have to do with routine in prayer?

5. As Jewish educators, how do we educate for both routine/discipline and spiritual connection?