One of my favorite sefarim at this time of year is “Return and Renewal” by Rav Aharon Lichtenstein. The essays are rigorous, brilliant, and inspiring. This year I learned just one chapter, but it gave me more than enough food for thought. The essay is titled “La-kol Zeman: Teshuva Within Four Time Frames of Our Lives” (pp. 139-161), and I wanted to share three insights which I found most powerful.
(I would recommend reading the original, for two reasons. The first is that I am just presenting my very basic understanding of these three ideas, and I’m sure the reader will find more depth in Rav Lichtenstein’s penetrating words. And second is that there are other wonderful ideas contained within this same chapter. This is not a comprehensive summary- just a few personal highlights.)
Teshuva for Old Sins
There seems to be a machlokes tannaim (Yoma 86b) about repeating confession for sins that were already confessed in previous years. (And the Rishonim dispute how to pasken.) But Rav Aharon writes that this whole conversation is puzzling. Each of us is on a lifelong journey. Our current state is a result of all of our experiences leading up to this moment. Therefore, can we really say that an old sin has no relevance to our present moment, even though we said viduy for that particular sin way back when? Rather it’s clear that one should remember these sins, and take them into account when making a chesbon hanefesh.
I found this very moving, for a number of reasons. The first is that we rarely take the time and think of our life as one long story. Even though our minds are preoccupied with the hustle bustle of daily life, we shouldn’t lose track of the bigger picture. Being aware of our spiritual history helps us examine our lifelong trajectory as avdei Hashem.
The second thing that struck me about this idea is that certain challenges can reappear at different points of life. I am now at an age where I have seen certain issues take a seat on the bench, leave me alone for a few years, only to hop back into action. Maybe what I thought at one point was sufficient teshuva, is actually still lacking. Additionally, certain sins that at first glance seem disconnected, may actually be tied together on a deeper level. Taking the broader outlook on our entire lives helps put this into context, and allows us to dig deep inside ourselves and experience real growth.
(For a deeper explanation of the machlokes in Yoma, as well as a fascinating proof from Rabbeinu Yonah, see the essay itself.)
Laundry Lists
On a recent episode of Shtark Tank, Simon Baum spoke about a crisis he faced following a massive deal which he had just closed. He surprised me when he seemingly minimized the role of making a cheshbon hanefesh. I pushed back on this, saying that if God Writes down all of our actions, shouldn’t we also keep track of our faults and areas for growth? Simon answered that we need to mainly focus on our relationship with God. And no married couple ever achieved love and connection by keeping a list of every sock left on the floor and garbage bag that wasn’t taken out.
Rav Lichtenestein raises this issue in the essay, and he really struggles with it. (While Rav Lichtenstein uses different terminology, I believe he’s addressing the same core issue.) On the one hand, an unexamined life is not worth living; on the other, a life of constant examination leaves no space to truly live. Therefore, a balance must be struck. Rav Aharon doesn’t give a clear formula, but he does emphasize the need to exercise constant vigilance. We believe in the existence of the yetzer hara, and this obligates us to always be on our toes. We can’t afford to simply say, ‘It’s all good — just live your life and hope for the best.
Confusion
During the viduy on Yom Kippur we confess for sins committed through timhon levav, often translated as inner confusion or bewilderment. Rav Lichtenstein writes that confusion is the enemy of passion. Rav Lichtenstein suggests that this uncertainty often arises among Torah Jews who strive to integrate holiness into all areas of life — not only in the beit midrash, but also in the workplace, family, and broader society.
This idea is very relevant for Bnei Torah in the workforce, like myself. One of the most common themes of the Shtark Tank podcast is how to balance a plethora of good values? How do we manage our time and allocate it amongst many different good things? How do we create an outlook that incorporates all of these things, but also has the proper emphasis and priorities?
This does not mean that any sense of confusion is bad. And this doesn’t mean that we should exchange our outlook for something simpler. But we must remain aware of this dynamic and seek out the clarity and conviction that enable passionate Avodas Hashem.
Summary and Conclusion
Teshuva means looking back at old sins as part of our lifelong story, recognizing how they continue to shape who we are today. It also requires balancing vigilance and reflection with the ability to live fully, without turning our avodah into a tally sheet. And finally, it calls us to push through confusion, finding clarity and conviction so that our many commitments can flow into passionate service of Hashem. May we all be zoche to a wonderful new year.