In the wake of the sin of the Golden Calf, while lobbying on behalf the Jewish people, Moshe interjected his own personal request, "let me know Your ways, so that I may know You" (Shemos 33:13). According to the Gemara (Brochos 7a), Moshe was asking Hashem to justify and explain the suffering of the innocent and the prosperity of the wicked. Moshe followed this entreaty with a second supplication, "Show me now Your glory" (Shemos 33:18), which expressed his desire to grasp the true essence of Hashem and nature of His existence (Rambam Yesodei Hatorah 1:10). These are of course critical theological questions that are undoubtably worthy of much contemplation and curiosity, but why are they relevant to a negotiation about forgiveness? How would understanding the answers to these questions on a personal level transform Moshe into a more effective spokesperson and ambassador for a people who surely erred?
Rav Yerucham Levovitz (Daas Torah) suggests that by making these personal requests Moshe was attempting to coax Hashem into absolving the Jewish people. The Thirteen Attributes of Mercy begin "Hashem, Hashem", and the Gemara (Rosh Hashana 17b) interprets, "I am Hashem before the sin, and I am Hashem after the sin." Moshe interacted with Hashem "face to face" and was certainly well acquainted with the dimension of Hashem's mercy that exists prior to sin, but now he was asking to experience Hashem's more potent and powerful form of kindness by witnessing Hashem's forgiveness after the sin. In order to grant Moshe's personal appeal for greater spiritual understanding Hashem was obliged to reveal the depths of His mercy by forgiving the Jewish people. Moshe's strategy teaches us that sincere requests for personal spiritual growth are always granted, and ironically, the more a person struggles to understand and the more distant he feels, the more likely Hashem is to respond.
The Medrash (Shir Hashirim Rabba 5:2) states, "Hashem says to Bnei Yisrael, my son, open for me a hole the size of a needle and I will open for you an opening that wagons and chariots can pass through." This seems to underscore the importance of making the initial move in the process of teshuvah, for even small steps can unlock a disproportionate amount of Divine assistance. However, according to Rav Yerucham, the Medrash also intends to convey that just like when one pokes a hole in a vessel, it now has a void that needs to be filled, so too if we create a deficiency in our heart, if we demonstrate that we are missing something in our relationship with Hashem, that vacuum itself opens and unleashes the potential for greater closeness and dveikus. After numerous attempts, Moshe realized that the most effective way to persuade Hashem to forgive Bnei Yisrael was by focusing on his own lack of knowledge and desire for greater spiritual discovery, because Hashem is committed to fulfilling those requests.
Therefore, an essential step in curating a fertile religious mindset is digging holes and opening spaces wherein the seeds of spirituality can sprout and flourish. The stones that rested in the breastplate of the Kohen Gadol are described as "filling stones" (Shemos 25:7) because they "filled" the indented settings that were carved into the gold. However, each of these priceless gemstones had its own unique beauty and color, how then can they rightly be reduced to simple space fillers? Perhaps the Torah overlooks the value of the stones and emphasizes instead the cavities which they occupied in order to indicate that Hashem's presence can only fit into our lives if we first hollow out space for Him. If we are satisfied and content with our religious status and spiritual intensity there is no room or reason for further development. Only if we feel some sense of emptiness, only if there is a gap between our current state and our desired destination, can Hashem enter our hearts and fill our souls.
The Gemara (Yevamos 79a) establishes that "there are three marks of the Jewish people. They are merciful, they are shamefaced, and they perform acts of kindness." The Baal Shem Tov traces these defining characteristics back to the three avos. Avraham epitomized kindness (Michah 7:20), Yitzchak represents fear and shame (Breishis 31:42), and Yaakov corresponds to mercy, which sits at the intersection between kindness and fear. However, we are told that at the time of Maamad Har Sinai, Moshe said to Bnei Yisrael, "Be not afraid, for Hashem has come only ... in order that the fear of Hashem may be ever with you so that you do not go astray" (Shemos 20:17). The Gemara (Nedarim 20a) infers from this pasuk that "one who does not have the capacity to be shamefaced it is known that his forefathers did not stand at Har Sinai." This implies that the Jewish attribute of shame was not inherited from the avos but rather developed later as a product of the experience of Maamad Har Sinai.
The contradiction about the origins of Jewish shame leads Rav Yaakov of Izhbitzh (Beis Yaakov, Yisro) to distinguish between two types of shame. There is one kind of shame that exists after a sin or mistake. The avos ingrained within the Jewish psyche to instinctively be embarrassed when they commit an aveirah, even in private, while other nations tend to resist feelings of guilt until it is forced upon them. However, there is a second form of shame that isn't prompted by a specific sin or failure but rather is a function of the ongoing disappointment with the status quo. At the time of Maamad Har Sinai, when we encountered the unbridled revelation of Hashem's presence, we also accessed our own potential for holiness and transcendence. Subsequently, upon returning to regular life, we now confront an inherent sense of shame about the disparity between the normal and ideal states. However, it is precisely this frustration with our reality that opens the door for progress and change.
Similarly, Rav Yaakov of Izhbitzh (Beis Yaakov, Noach) suggests that a drunk is prohibited from davening (Brochos 31a) because intoxication relaxes inhibitions and induces serenity, as the Gemara (Yoma 75a) states, "whoever casts his eye on his cup, the whole world seems to him like level ground." Prayer demands a certain uneasiness, a healthy sense of apprehension about the status quo, because in that tension lies the impetus for all improvement and growth. When one feels completely satisfied and content, ironically, prayer has no traction. A similar notion is expressed by the Gemara (Chagigah 13a) which establishes that the secrets of Torah may only be shared with one "whose heart inside him is concerned" about his sins and desires to repent. Rav Tzadok Hakohen (Pri Tzaddik, Beshalach) explains that intimate knowledge of Hashem can only be attained by someone who first appreciates and is worried about the distance between his current state of affairs and the expectations the Ribbono Shel Olam has for him.
In his Kuntres Hahispaalus, the Mitteler Rebbe, Rabbi DovBer of Lubavitch, records that he heard from his saintly father in the name of the holy Maggid of Mezeritch, that it is impossible for a person to absorb the secrets of the Torah and grasp the true depth of the light of Hashem unless he possesses an innate tendency towards "mara shchora" - "melancholia". This statement should not be taken as a glorification or sanctification of sadness and depression, for these traits can be unhealthy and harmful and indeed, they are an impediment to becoming an effective and successful oveid Hashem.[1] Rather, the Maggid is describing a spiritual longing and aspiration for what we could have been and what we need to become. The cushy couch of confident complacency doesn't leave much room for extrospection and introspection. Only when there is some frustration with the status quo, some tension with our current reality, can the light of Hashem begin to break through.
[1]See Shaarei Kedusha 2, 4 and Likkutei Moharan 282 and Tinyana 10.