….The word for repentance in Judaism, teshuvah, translates literally as “return.” A secular Jew who becomes observant is deemed a ba’al teshuvah, literally a “master of return.” Or, in modern Israeli parlance, a chozer be-teshuvah, which we might translate as a “returner to returning.” (His Christian equivalent is described as undergoing conversion or, in certain circles, as being “born again”—both of which are more radical than returning.) The word teshuvah implies that no great break is needed on the way to spiritual renewal. Rather, moving forward is a process of getting back in touch with what was, in some sense, there all along, though what you return to might be neither the religion of your great-great-grandfather in the Pale of Settlement nor that of an affable Chabad outreach rabbi half your age. Return need not be to any discernible prior place at all. The Talmud writes that God created the possibility for teshuvah before creating the world (Nedarim 39b). Return is a state of mind….
In the discussion of Yom Kippur that appears in The Human and the Infinite, a compendium of translated essays by the late Rav Shagar (Rabbi Shimon Gershon Rosenberg z”l), Rav Shagar describes the difficulty of truly feeling awe during the Days of Awe. A serious attempt to grasp the Absolute during this time-period will, according to Rav Shagar, invariably lead to a kind of anxiety. This anxiety, which may at times be confused with piety, is not actually religiously productive. It can even cause deep despair: “there is an essential paradox in the attempt to understand the Holy with the limited faculties at our command – words, deeds, etc… This paradox, then, fuels despair in the believer.”
The solution to this despair, for Rav Shagar, is a healthy dose of irony. Irony, he reminds us, should not be confused with cynicism: “Cynicism ridicules its subject, presenting it as pathetic. Irony, on the other hand, is a delicate instrument able to grasp two different sides of an issue at once. It can understand the true gravity of a subject, while at the same time showing up its limitations.” Rav Shagar explains that “[i]rony emphasizes new and different possibilities – even for those subjects that are seemingly absolute. The reflectivity of irony can breathe a new spiritual life into the stolid…. The ironic stance adds a lighter side to the religious act and so enlivens it. The religious can no longer stay fixed and see itself, as it were, as its own absolute. The ironic allows the religious to become what it should be.”