Navigating the Paradoxes of Teshuva

In this article, we will delve into two different instances of seemingly paradoxical elements within the concept of teshuva, as explained by Rav Steinsaltz. We will discover that teshuva involves balancing different elements, where these contrasting aspects work together to create a complete and cohesive process.

Teshuva: Embracing the Challenge, Igniting the Change

Rav Steinsaltz explains that teshuva embodies two distinct yet interconnected aspects that highlight the complexity of personal growth and change, raising the question: is teshuvah an easy thing to do or a hard thing to do? He writes as follows:

It is, on the one hand, an exceedingly lengthy path with no clear end… On the other hand, teshuva can be seen as a flash of regret and resolution, a sudden insight that change and improvement are needed. These two aspects of teshuvah are not contradictory but complementary. When teshuva is seen as a process of complete self-transformation, nothing could be more difficult; yet nothing could be easier than the momentary resolve that sets the process going.¹

Teshuva can be viewed as a long, ongoing journey of self-improvement and transformation. This aspect emphasizes the gradual, often challenging work required to truly change one’s behavior, attitudes, and patterns. In line with this, the Rambam opens chapter seven of Hilchot Teshuva (7:1) by stating:

Since free choice is granted to all men as explained, a person should always try to do Teshuva and to confess verbally for his sins, striving to cleanse his hands from sin in order that he may die as a Baal Teshuva and merit the life of the world to come.

Rav Lichtenstein picks up on this unusual phrasing – “The Rambam’s formulation – “he should try” is uncharacteristic. Does Hilchot Shofar stipulate that a person should “try” to hear the shofar? One is obligated and there is nothing more to say.”² He explains that the Rambam phrases the halacha in such a way because teshuva for character traits is a life-long mission – this type of teshuva is not just a response to particular sins but a lifelong commitment to personal growth and self-improvement. It is not merely a reactive response to past transgressions; instead, it is a proactive and forward-focused journey throughout one’s life. 

Teshuva can be viewed as a long, ongoing journey of self-improvement and transformation. This aspect emphasizes the gradual, often challenging work required to truly change one’s behavior, attitudes, and patterns.

In contrast, teshuvah can also be experienced as a moment of clarity or realization—a flash of regret that prompts a desire for change. This insight can strike suddenly, often triggered by an event, a conversation, or a moment of reflection. It represents the initial spark that motivates a person to consider the need for change and improvement in their life. This aspect of teshuva is about recognizing the possibility of transformation and feeling a deep sense of urgency to act. Unlike the lengthy path, this moment can be quick and straightforward, requiring a simple decision to commit to change. We see this in the Gemara (Avoda Zara 17a), which recounts the story of Elazar ben Dordaya, who lived a life of indulgence and sin, engaging in immoral behaviors without regard for their consequences. Upon realizing the error of his ways, he turned to the natural elements, asking them to pray for mercy on his behalf. When they replied that they could not help him:

Elazar ben Durdayya said: Clearly the matter depends on nothing other than myself. He placed his head between his knees and cried loudly until his soul left his body. A Divine Voice emerged and said: Rabbi Elazar ben Durdayya is destined for life in the World-to-Come.

These two dimensions of teshuva— the arduous journey and the immediate insight—are not in conflict; instead, they complement each other. The sudden realization that change is necessary can serve as the catalyst that begins the longer process of self-transformation. While the path of teshuva may be difficult and require sustained effort, that initial flash of regret can simplify the decision to start.

Teshuva: The Tension Between Breaking Free and Embracing the Past

Another seemingly paradoxical aspect of teshuva involves its relationship with the past:

On the one hand, teshuva entails a break with the past, fixing a cut-off point that divides one’s life into a “before” and an “after.” Indeed, the ability to atone for and rectify one’s mistakes rests on the assumption that such a break is possible, that teshuva results in the creation of a completely new being. The past is severed from the present; one’s former self becomes a stranger or ceases to exist…

… On the other hand, it is the past that motives teshuva and gives it its specific character…

…In teshuva, these two apparently contradictory moments – the break with the past and the thrust provided by it – must both be given expression.³

On one hand, teshuva signifies a definitive break from one’s previous life. This break creates a clear division between a person’s life before and after the act of repentance. It is rooted in the belief that genuine atonement can lead to a radical transformation, allowing an individual to become a completely new person. This perspective suggests that the past can be severed from the present, enabling one to move forward without being shackled by previous mistakes. In this sense, the former self is viewed as almost foreign—an entity that no longer defines who the person is now.

On the other hand, the very desire to engage in teshuvah is motivated by the past itself. The memories of previous actions, along with their consequences, provide the impetus for change. It is the recognition of one’s mistakes and the pain associated with them that drives a person to seek redemption. Even after completing the process of teshuvah, we should continue to reflect on our past. This ongoing reflection helps us identify any actions we may have overlooked and areas where we still need to seek kappara.

These two elements—the break from the past and the motivation drawn from it—may seem contradictory, but they are actually complementary. For true teshuva to occur, one must acknowledge and confront their past while simultaneously striving to move beyond it.

This Elul, and these Yamim Noraim, let us embrace the important idea that teshuva involves balancing paradoxical elements. As we reflect on our lives, we recognize that the journey of repentance is not straightforward; it’s a dynamic interplay between moments of ease and difficulty, as well as moving on from the past while using it to propel us forward.

1. Adin Steinsaltz, Teshuvah – A Guide for the Newly Observant Jew (Maggid, 2010) 7 ↩︎
2. Aharon Lichtenstein, By His Light (Maggid, 2017) 184 ↩︎
3. Adin Steinsaltz, Teshuvah – A Guide for the Newly Observant Jew (Maggid, 2010) 14 ↩︎