Avot 2:18 Rabbi Shimon says: (a) Be meticulous in reading the Shema
and in prayer; (b) when you pray, do not make your prayer a
set routine but rather [beg for] compassion and supplication
before the Omnipresent, as it is said, ‘For He is gracious and
compassionate, slow to anger, abounding in kindness, and
relenting of punishment’ (Joel 2:13); and (c) do not judge
yourself to be a wicked person.
Rabbi Shimon says: (a) Be meticulous in reading the Shema and in prayer…
The Shema is the one unifying prayer of all Israel; the first taught to young Jewish children and the last uttered before death. “Hear O Israel! Shema Yisrael! The Lord is our God, the Lord is One. Adonai,YHWH/ Eloheinu. Adonai/YHWH, Echad.”
The Midrash offers the interesting comment that initially this proclamation was made by Jacob’s sons at his deathbed. By this time they had lived in Egypt for many years and were influenced by that culture, even if superficially. They enjoyed a comfortable life and Jacob-Israel’s deep concern was that his sons and their families might gradually become assimilated and turn to the pagan gods of Egypt. To reassure him of their faithfulness to the God of their forefathers they proclaim, in effect: “Hear us, O Israel our father, we believe with perfect faith that the Lord, YHWH, is our God and that He is the One true God.” In great relief Jacob whispers the blessing that forms the second verse of the Shema: “Baruch Shem kavod malkhuto, le’olam va’ed! Blessed be His Name whose glorious kingdom is forever and ever!”
In the biblical narrative, these resounding words first were proclaimed by Moses to the people of Israel, the family of Abraham, Isaac and Jacob, after their deliverance from Egypt and the Revelation of God at Mount Sinai. Before they could go forward as His holy nation and the subjects of His Kingdom to face the hostile pagan nations, the Israelites needed this one foundational truth – the knowledge of the One, the true God – to permeate their very beings. Only when one knows Him, and understands who we are in relationship to Him as His people in the world, can one proceed to the next verse of the prayer, “And you shall love the Lord your God with all your heart, with all your mind and with all your strength” (Deut. 6:5).
Moses then continues with an exhortation that emphasizes the importance of the Ten Words spoken by God, together with the Torah and teachings he is now passing on to them. “These words, which I am ordering you today, are to be on your hearts and you are to teach them carefully to your children. You are to talk of them when you sit at home, when you are traveling on the road, when you lie down and when you get up. Tie them on your hand as a sign, put them at the front of a headband on your forehead, and write them on the doorposts of your home and on your gates” (Deut. 6:6-9).
Two further sections were added by the Sages before the Shema was set as a daily prayer in the Siddur (The Jewish Prayer Book), and it was recommended that it should be recited morning and evening. First, Deuteronomy 11:13-21 was added, which describes God’s promises of rain and good harvest when His people love and serve Him and of His wrath when they turn from Him to idolatry. Then Numbers 15:37-41 was included, which outlines God’s instructions regarding the making of tzitzit, fringes worn on the corners of garments, that would be a visual reminder to be holy in obedience to His mitzvot, commandments.
(b) When you pray, do not make your prayer a set routine but rather [beg for] compassion and supplication before the Omnipresent, as it is said, ‘For He is gracious and compassionate, slow to anger, abounding in kindness, and relenting of punishment’ (Joel 2:13)
The Siddur contains beautiful set prayers and Orthodox Jewish males are expected to pray the three daily prayers of Shacharit (morning), Mincha (afternoon) and Ma’ariv (evening). Rabbi Shimon here cautions, however, that a person’s prayers should not become a matter of habit and rote. Prayer, tefillah, is communication with God and, in Judaism, both the fixed times of prayer, prayed by men  with a minimum quorum of ten – a minyan, and also personal, unprescribed prayer from the heart, hitbodedut, are of vital importance in one’s relationship with Him. God is Omnipresent and, while it is good to have a particular place to pray, one also can turn to Him in prayer at any time and in any place.
There is power in corporate prayer; it strengthens and unifies those who pray together. However, it can become a duty to be accomplished as quickly as possible in order to get on with other important matters and the benefit is lost. Hence Rabbi Shimon’s advice to carefully prepare one’s heart before prayer and to focus on the meaning of the words with kavvanah – deep heartfelt concentration. One should always remember with Whom one is communicating and that He is kind and compassionate, and quick to extend His love, forgiveness and grace when we call to Him. Then, whenever we turn to Him in prayer, praise or petition, it will be with all our hearts, mind and strength and at no time could it become a meaningless, “set routine.”
(c) …and do not judge yourself to be a wicked person.
This appears to be a moral warning to not see oneself as hopelessly sinful – born in sin, a slave to sin – and so to give up on improving one’s character by standing against any temptation or weakness. We always should see ourselves as the redeemed of God in Yeshua, who paid the ultimate price and overcame sin and death. Every person is a beloved child of the Father with a free will and the power to choose good over evil, life over death.
Rabbi S.R. Hirsch translates this phrase as, “…and do not consider yourself as wicked when left to depend on your own efforts.” Sometimes one may physically find oneself facing life’s challenges alone and isolated from a like-minded community. The biblical ideal always is to live in community, to participate with others in study, prayer, work and play; to be in a place where people can support and encourage one another and share both joys and sorrows. There are times, however, when support and encouragement may not be there and one may be inclined to consider, “What good can I do on my own?” Our weaknesses can loom as large obstacles causing us to become disheartened and to see everything in a negative light, including ourselves.
Rabbi Hirsch points out that prayer is a gift given by a redeeming God who longs to communicate in love with His people, and he exhorts, “Prayer uttered in the proper spirit will be the source from which you derive the strength and Divine aid that you need in all your efforts.”  We do indeed find guidance and support when we pray and find the comfort of Divine aid in our great High Priest, Yeshua, who constantly is interceding on our behalf before the Throne of Grace  and who assures us that we are never alone. “Behold, I am with you always, even to the end of the age” (Matt. 28:20)
1. Deut. 6:4
2. Women are not obligated to these time-bound prayers, as with other time related commandments, although they are free to do so if and when they can.
3. Rabbi S.R. Hirsch, Chapters of the Fathers; 37
4. Romans 8:34