Holistic Repentance: Life as a Story

The Seven Ages of Man by William Mulready
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Natan Oliff


How great is repentance?! God created repentance prior to creating the world (see Midrash Tehillim 90). It hastens the redemption, brings healing to the world, and lengthens one’s days (see Yoma 86a-b). Even immediately preceding one’s death, one may repent and acquire the world to come.[1] These descriptions provide a romantic aura to repentance along with the possibility to achieve great feats. Yet one cannot read these statements without thinking them to be hyperbole, exaggerations meant to highlight the importance of repentance. Has anyone ever repented and brought healing to the world? Surely not. However, at least two of Hazal’s statements regarding repentance may be understood literally, providing greater power to repentance and humanity. First, Rabbi Avahu proclaims, “In the place where penitents stand, even the full-fledged righteous do not stand” (Berakhot 34b). R. Avahu implies that not only do past transgressions not inhibit the penitent’s standing, but repentance raises the penitent to heights beyond the completely righteous. Second, according to Reish Lakish (Yoma 86b), repentance alters the past. Repentance motivated by fear transforms intentional sins into unintentional transgressions, and repentance performed out of love transforms intentional sins into merits. While Reish Lakish and Rabbi Avahu grant repentance incredible power, they fail to explain how repentance achieves these results.

The trouble with understanding these statements stems from a larger problem concerning repentance. Hazal were privy to this problem and expressed it eloquently in Yerushalmi Makkot (2:6):

It was inquired of Wisdom, “What is the punishment of a sinner?” Wisdom said “Evil pursues the wicked.” It was asked of Prophecy, “What is the punishment of a sinner?” Prophecy said to them, “The sinful soul shall perish.” It was asked of the Holy One, “What is the punishment of a sinner?” and He said “Let him repent and he will be forgiven.”[2]

Repentance makes no logical sense. The institution of Wisdom, and even the divinely inspired Prophecy, cannot comprehend repentance. Just as the physicist claims that “for every action, there is an equal and opposite reaction,” so too, the Jew must proclaim, “God rewards those who obey the commands of the Torah and punishes those who violate its prohibitions” (Rambam on Mishnah Sanhedrin 10:1). Only the Holy One―Blessed be He―in His omnipotence may validate repentance.

Human experience further supports these qualms with repentance. As Rabbi Joseph B. Soloveitchik explains:

Just as God remembers the beings of ancient times, so does man remember and revisit the past which is preserved in his memory… What will happen when he [the sinner attempting to repent] looks back and recalls all those years of violating the Sabbath, of exploitation and thievery?[3]

A person must face the humbling reality that the rushing current of time flows in only one direction. Any act remains ingrained forever in the past. The soul aches and groans when it casts a backwards glance and beholds the mistakes of the past self. The thin and clear yet impenetrable wall of time separates the soul from its past, quashing any hope for respite.

R. Soloveitchik reconciles these statements about repentance with logic and religious experience. Instead of downplaying the frustration that plagues the soul reflecting on sin, he views it as the key to repentance:

It is the memory of sin that releases that power within the inner depths of the soul of the penitent to do greater things than ever before… In repentance of love, love rises with the flames of repentance and burns brightly in the flames fanned by sin; the bonds of love pull man up to great and exalted heights.[4]

The penitent may harness the memory of sin to reach greater heights, as sin possesses a power that merit lacks:

Hate is more emotional and more volatile than love. The destructive forces are stronger than the constructive forces. A thoroughly righteous man is not given to feelings of hatred or jealousy; he is distinguished by natural feelings of love and mercy and kindness.[5]

This insight of R. Soloveitchik explains both statements I cited earlier about repentance. According to R. Avahu, the completely righteous person lacks sin and its reservoir of energy, which the penitent―on the other hand―may channel to reach greater heights. For Reish Lakish, properly utilizing sin changes its meaning. Harnessing the sin’s energy produces positive effects that outweigh any previous negatives. Therefore, the sin creates a net positive outcome and transforms into a merit.

Hazal implicitly express this relationship between sin, repentance, and greatness: “Four people died due to Adam’s sin with the serpent, in the wake of which death was decreed upon all of mankind, although they themselves were free of sin. And they are: Benjamin, son of Jacob; Amram, father of Moses; Yishai, father of David; and Kilab, son of David” (Shabbat 55b). The four characters who never sinned―Benjamin, Amram, Yishai, and Kilab―are minor Biblical characters, while their listed relations―Jacob, Moses, and David―are major characters. Despite being sinless, the minor characters never achieved the greatness that their relations achieved. It is noteworthy that David appears as a relation twice. David sinned gravely by committing adultery with Batsheva and effectively murdering her husband Uriah by sending him to the frontlines of the war (II Samuel 11).[6] Yet, upon rebuke, David immediately admits to his sins and repents. In fact, Hazal describe David as the paradigmatic penitent, as the man “who raised and lightened the yoke of repentance” (Avodah Zarah 5a). A strong correlation exists between sin and greatness. Thus, Hazal implicitly affirm R. Soloveitchik’s claim that sin lifts penitents to greater heights than the completely righteous.

Former professional basketball player Antoine Walker exemplifies the phenomenon that failure, loss, or sin often motivate people to create positive change. Throughout his successful career in the National Basketball Association (NBA), Walker made multiple all-star teams, won a championship, and amassed over 108 million dollars in salary. However, Walker went bankrupt less than two years after retirement due to overindulging on luxury goods, providing unaccounted loans to relatives, and bad luck with real estate investments. Walker eventually recovered from his financial woes and decided to harness his experience to create positive change.[7] Walker’s case is not unique. According to Sports Illustrated, 60% of NBA athletes go broke within five years of retirement.[8] Additionally, over three quarters of professional football players go broke or are under financial stress within two years of retirement. To fight these trends, Walker created a documentary about his story and works with Morgan Stanley to educate professional athletes about financial literacy. Walker’s story illustrates how past woes motivate people to create positive change.

Yet the idea of harnessing sin’s power does not truly explain Reish Lakish’s statement. While repenting creates a net positive outcome, it does not erase the sin, which continues to exist in the past. While the meaning of the past changes, its essence remains unaffected. Truly understanding Reish Lakish’s statement requires an understanding of the self and identity, which appears in the research of Israeli psychologist and Noble Prize winner Daniel Kahneman. Kahneman asserts that the self comprises two modes: experience and memory.[9] Experience refers to the pleasure and pain of each independent moment. It only knows the present moment. Memory, on the other hand, assesses the past, downplaying the duration of experiences while overrating important moments and endings. For example, the self experiences a long distance run mainly as painful moments interspersed with short moments of elation and a feeling of accomplishment upon finishing. However, the self remembers the run by overlooking the quantity of painful moments, instead focusing on the important moments of elation and how it ended with a feeling of accomplishment. In other words, the memory of the run is more positive than the experience of the run.

Kahneman observes that remembering parallels storytelling. Like memories, stories derive meaning from key moments and endings. To his surprise, Kahneman discovered that the self prioritizes memory over experience when making decisions. Kahneman bemoans this finding, noting that memories skew objective experience. People will choose suboptimal experiences if they create optimal memories. The dominance of memory reveals a deep insight into the human psyche: humans make decisions to create the best life story. People view their life as a coherent story rather than a collection of disjoint experiences.

R. Soloveitchik also discusses the relationship between experience, memory, and the self:

The problem of repentance is intertwined with an apprehension of the concept of time and how it relates to the human experience. Rabbi Jedaiah Ha-Pnini was the one who coined the phrase: “the past is nothing, the future is not yet, and the present [passes] like the blink of an eye.” According to this conception, man’s life is meaningless; he has no hold in time whatsoever. But the truth is that man does exist within two distinct dimensions of time: (1) in memory, and (2) in expectation for the future. . .  Memory replies to the question: “Who am I?” I am he who remembers these feelings and those experiences, these moments of happiness and those moments of sorrow.[10]

In contrast to Kahneman, who explains the drawbacks of the memory, R. Soloveitchik details the downside of possessing experience without memory. Without memories and expectations, a person loses their sense of self. Identity comes from memories and the narrative that ties them together. Psychiatrist Oliver Sacks provides real life examples of this phenomenon when discussing two patients who possess Korsakoff’s Syndrome, a long-lasting amnesic syndrome.[11] Every few moments, Jimmie’s memory would reset to his experiences until 1945. This peculiar condition led Sacks to remark―in the same vein as R. Soloveitchik―that: “He is man without a past (or future), stuck in a constantly changing, meaningless moment.”[12] Eventually, Sacks discovered that Jimmie occasionally achieved meaning through religious worship. Yet his lack of memory severely diminished his ability to form identity and meaning. Similarly, Mr. Thompson also experienced Koraskoff’s Syndrome. However, unlike Jimmie, Mr. Thompson had recently developed the syndrome upon meeting Sacks. Sacks quickly noticed that Mr. Thompson obsessively created stories, continuously reinventing himself and the world around him. Sacks attributed this tendency to Mr. Thompson’s lack of memory and thus lack of identity. Without memories to create a narrative, Mr. Thompson resorted to storytelling.

Communities and nations also rely on memory to form identity. Yosef Yerushalmi notes that, for most of exile, Jews relied mainly on the Bible to interpret events instead of producing new historiography.[13] The Akeidah, for example, served as the framework to interpret and understand The Crusades. Jews viewed Christianity as the modern-day Esau and Islam as the modern-day Ishmael. The Bible sufficed to form the robust, complete identity of the Jewish people. Thus, Yerushalmi notes that non-Biblical Jewish historiography mainly began in the early 19th century concurrent with the rise of new movements such as Zionism and the Enlightenment. These novel movements and ideologies turned to the past to acquire a sense of identity and legitimacy.

As mentioned earlier, Kahneman identifies memories and self-narratives as a distortion of reality. By creating memories, the self imposes meaning on the past. Nevertheless, the self only ever experiences independent moments, and so objectively the past is a chronological chain of these moments. However, Dr. Samuel Lebens offers an alternative theory, suggesting that reality is God’s story.[14] This “storied reality” exists in a two-tiered system alongside objective reality.[15] This two tiered system allows for a duality of truths. For example, in the storied reality, humans possess significance and free will while lacking these attributes in objective reality. Lebens argues that this duality does not detract from human purpose or freedom. The lack of human purpose and freedom in objective reality is only relevant in a technical metaphysical sense. Pragmatically, however, humans only care about truth in their reality―a storied reality―and the practically relevant truth of a storied reality is that humans possess significance and free will. Furthermore, a storied reality possesses additional practical implications for human identity and meaning. Unlike Kahneman’s empirical reality, a storied reality behaves according to the characteristics of literature and stories. First, in stories, the value of an action partially depends upon its role in the entire story. In other words, actions possess “relational value.” Second, stories require conflict and resolution. Third, stories increase the importance of their characters’ actions. Fourth, stories immortalize their characters. Relational value is the key to understanding Reish Lakish’s statement about repentance.

In a story, individual actions cannot be evaluated independently in a vacuum, but rather by their role in the story. Rabbi Abraham Kook describes this phenomenon by comparing reality to painting.[16] A painting comprises many paint brush strokes. However, during the painting process, one disparate stroke may seem meaningless or confusing. Only the completion of the painting bestows context and meaning to each stroke. Similarly, individual actions or events may produce fear or confusion. However, as life progresses and the person’s “painting” edges closer to completion, the purpose of each event becomes clear. The true meaning of a moment can only be comprehended―with the complete context of an entire life―by how it relates to other moments.

The concept of relational value also appears in modern psychological research. Harvard psychologist Daniel Gilbert coined the term “psychological immune system” to describe the process by which people adapt and achieve happiness regardless of external circumstances.[17] Gilbert describes relational value as the driving force behind the psychological immune system. Events, objects, or situations possess objective value. For example, apples possess an objective chemical makeup and ratio of nutrients. However, buying a specific apple activates the psychological immune system, which searches for subjective reasons to prefer that specific apple. Thus, the apple’s value partially derives from being bought and owned, from its relationship with the buyer.

The concept of relational value explains Reish Lakish’s statement about repentance. During a person’s life, God (as it were) labels actions with a pencil, as the meaning of an action may change. Its value partially depends on a future yet to occur. If a person repents and harnesses the energy of a “sin” to produce greater good, then God relabels that “sin” as a “merit.” In an empirical reality, the past motivates the penitent to create a greater future good. However, in a storied reality, the penitent’s future actions rewrite the meaning of the past. This creates a symbiotic relationship where the past motivates a greater future good, which in turn rewrites the past. The past never holds sway over the living. The gates of repentance offer the eternal possibility to rescue and redeem the past.

Stories revolve around the struggle that besets and plagues their characters. In fact, characters often represent the struggles they endure. As writer Milan Kundera remarks about his character Tereza: “Tereza was therefore born of a situation which brutally reveals the irreconcilable duality of body and soul, that fundamental human experience” and later about literary characters in general: “As I have pointed out before, characters are not born like people, of woman; they are born of a situation, a sentence, a metaphor containing in a nutshell a basic human possibility . . .”[18] Completely sinless and harmonious characters ruin the very point of literature. Aiming to avoid sin misconstrues the goal. As Hazal implicitly suggest, the greatest Biblical characters sinned and lived tumultuous lives. Literary critics evaluate characters by their ability to handle and overcome failure and conflict. Thus, characters cannot be evaluated during the story, but only after their journey and struggle ends. In a storied reality as well, God judges humans not by their ability to avoid conflict or sin, but by their ability to handle and overcome their struggles.

The following midrash implies another implication of a storied reality:

When one performs a mitzvah he should perform it with joy. For had Reuven known that the Torah would record that he tried to save Yosef from the brothers, he would have put him on his shoulders and run home to his father. And if Aharon had known that the Torah would record that when he saw Moshe Rabeinu the first time and he heard that he was chosen to be the Redeemer of Israel (and not Aharon) . . . Had Aharon known, he would have come (to him) with drums and cymbals. And had Boaz known that the Megillah would record his giving Ruth some parched wheat to eat, he would have offered her a huge banquet like those of King Shlomo (Vayikrah Rabbah 34:8).

Stories often transcend people and time, surviving through either oral or written transmission. If the characters of the Bible understood the eternality of their actions, they would have approached life with urgency and vigor. Even though the character may perish, their actions remain forever. Their reputation and legacy stand for the remainder of history. In a storied reality, where God remembers every action, each choice becomes infinitely more important and meaningful.

Stories immortalize their characters, keeping them alive beyond their years. Author Tim O’Brien beautifully captures this idea by discussing his childhood crush Linda.[19] When Linda passes away from a brain tumor, young O’Brien continues to visit her in his dreams. Dream Linda insists that she is not dead, or at least, that her death does not matter. Eventually, with persistence, he convinces Linda to describe death:

I guess it’s like being inside a book that nobody’s reading . . . An old one. It’s up on a library shelf, so you’re safe and everything, but the book hasn’t been checked out for a long, long time. All you can do is wait. Just hope somebody’ll pick it up and start reading. (O’Brien, 232)

Linda captures the essence of O’Brien’s message. Like shelved books, the dead idly sit by, waiting to be noticed. By telling stories, O’Brien “picks” them up off the shelf and brings them to life. Stories carry on the lives of the dead. In a storied reality, God―the ultimate Author―grants immortality to God’s characters: “I will give them, in My house and within My walls, a monument and a name better than sons or daughters. I will give them an everlasting name which shall not perish” (Isaiah 56:5).

Two anxieties plague the human psyche: abandonment and meaning. Man fears that he may be irredeemable, that he will reach a point of no return, that he will commit a sin so grave that no one or nothing can redeem him. He fears he will be like the wayward and rebellious son whose gluttonous actions verify his future: to commit crimes liable for the death penalty. To prevent this ending, the community puts him to death (Rashi on Deuteronomy 21:18). Apparently, the wayward and rebellious son is beyond repair. His future is predictable with complete certainty. But what about free will? What about repentance? Rabbi Shimon refuses to accept such a possibility, claiming that the wayward and rebellious son never happened and never will. Rather, the wayward and rebellious son is a theoretical scenario created for studying and subsequent merit (Sanhedrin 71a). Rabbi Shimon implicitly affirms an important position: no person is beyond repair. The literal reading of Reish Lakish’s statement substantiates this position. People can always redeem their past and themselves. In fact, through repentance, they can harness their sins to reach greater heights.

Additionally, man fears that his life is meaningless, that his existence is a string of independent, fleeting hedonistic experiences. From this fear arises the tendency of storytelling, of creating a narrative that ties together experiences under a meaningful goal. Thus emerges the importance of a storied reality. God, the ultimate Author, authenticates this human tendency, moving it from a naive human construct to an act of imitatio dei: “just as God tells stories, so, too should you tell stories.”[20] The stories that humanity coauthors with God give meaning to struggle, eternal importance to actions, life to the dead, and―most importantly―validity to a repentance that rewrites the past and saves humanity.

[1] See the story of Rabbi Elazar ben Durdiya in Avodah Zarah 17a.

[2] Translation from Pinchas H. Peli, On Repentance: The Thought and Oral Discourses of Rabbi Joseph Dov Soloveitchik (Lanham, MD: Rowman & Littlefield Publishers, Inc., 1996), 238.

[3] Peli, 249.

[4] Peli, 249.

[5] Peli, 262.

[6] The gemara (Shabbat 56a) suggests that David did not sin. This opinion is hard to understand at face value. The prophet Natan comes and rebukes David for his actions, to which David himself admits that he sinned. Furthermore, there are multiple statements of Hazal that imply that David did sin. He is called “the man who raised and lightened the yoke of repentance” (Avodah Zarah 5a). People can learn from David about how to repent (Avodah Zarah 4b). It seems like the plain understanding of the text and the opinion of most commentators is that David sinned. One explanation of the gemara in Shabbat 56a is offered by R. Yaakov Meidan. R. Meidan notes that the rationale used to acquit David is technical and halakhic. Technically, Batsheva was single because all soldiers who went to war during the Davidic dynasty gave their wives divorce bills. Also, technically, Uriah fell under the category of rebelling against the king because his language implied that he was loyal to Yoav, David’s commander. R. Meidan suggests that the point of these legalistic acrobatics is to show the danger of being overly focused on Halakhah. Despite being technically allowed under Halakhah, David’s actions were morally corrupt. See Yaakov Meidan, David vi-Batsheva: ha-Het, ha-Onesh, vi-Hatikun, (Herzog Press, 2010).

[7] See Matt Egan, “Ex-NBA Star Went from $108 Million to Bankruptcy,” CNNMoney, July 24, 2015,

[8] See Pablo S Torres, “How (and Why) Athletes Go Broke―Sports Illustrated Vault,” Sports Illustrated, March 23, 2009,

[9] See Daniel Kahneman, “Two Selves,” in Thinking, Fast and Slow (New York: Farrar, Straus and Giroux, 2015).

[10] Peli, 249.

[11] Oliver Sacks, The Man Who Mistook His Wife for a Hat and Other Clinical Tales (New York: Simon & Schuster Inc., 1999).

[12] Sacks, 29.

[13] Yosef Hayim Yerushalmi, Zakhor: Jewish History and Jewish Memory (Seattle: University of Washington Press, 2002).

[14] Lebens bases his interpretation of reality on the commentary of Rabbi Mordechai Leiner of Izbica, the Ishbitzer, who asserts that the world is God’s lucid dream. See Mei HaShiloah on Parshat Miketz s.v. tishma halom li-pator oto.

[15] See Samuel Lebens, “God and His Imaginary Friends: A Hassidic Metaphysics, Religious Studies 51, no. 2 (2015): 183-204.

[16] Middot Ha-Ra’ayah: Pahdanut.

[17] Daniel T. Gilbert and Jane E. J. Ebert, “Decisions and Revisions: The Affective Forecasting of Changeable Outcomes, Journal of Personality and Social Psychology 82, no. 4 (2002): 503.

[18] Milan Kundera and Richmond Hoxie, The Unbearable Lightness of Being (London: Faber & Faber, 1984). I want to thank Sam Lebens for bringing these quotes to my attention in a lecture he gave at Yeshivat Orayta.

[19] Tim O’Brien, The Things They Carried (New York: Houghton Mifflin, 1990).

[20] See Sotah 14a.

Natan Oliff ( is a software development engineer at Amazon.