When Moshe Rabbeinu recounts his prayers and pleas to merit entering the land of Yisrael, he offers us a profound lesson about the correct approach to prayer.
According to Chazal (דברים רבה יא יא), Moshe Rabbeinu prayed an astonishing five hundred and fifteen times for permission to enter Eretz Yisrael. Despite the repetition - which would have continued unless Hashem ordered him to stop - his prayers remained heartfelt and sincere, never becoming a mere routine. Moshe's pleading with Hashem was characterized by genuine supplication, not just a simple request.
This approach should be adopted by all of us, as the Mishnah states (אבות ב יג), "And when you pray, do not make your prayer a rote thing, but a plea for compassion before Hashem, for it is said: 'for He is gracious and compassionate, slow to anger, abounding in kindness, and renouncing punishment' (יואל ב יג)." The Mishnah underlines the essence of prayer, stressing the need for sincere, heartfelt supplication, rather than just a mechanical recitation of words.
The Core of Tefillah
The Abudarham emphasizes the importance of תַּחֲנוּנִים in prayer, and he says that whoever wants his prayers to be heard in Heaven should put their focus on pleading with the Creator. The numerical equivalence between the term וָאֶתְחַנַּן and תְּפִלָּה reveals to us that supplication is the main component of prayer, illustrating that genuine prayer is inseparable from sincere supplication.