Photo Credit: Jewish Press

There’s a story of two elderly men who had been childhood friends but had not seen each other in many years. One day, they ran into each other on the street, and were delighted to recognize one another. One of them lived in the area, so he invited the other into his home. They happily caught each other up on their lives, getting lost in their stories and jokes as the day went on. The guest finally noticed that it had become dark outside, so he asked his friend if he had the time.

“I don’t have a watch,” his friend replied.


“So, look at the clock and tell me what time it is.”

“I don’t have a clock either,” his friend replied.

Puzzled, the first man asked his friend: “If you don’t have a watch, and you don’t have a clock, how do you tell the time?”

“I use my trumpet!” the second man proudly replied.

“A trumpet? How can you tell time with a trumpet?”

“I’ll show you.” He picked up his trumpet, opened the window, and blew a long, deafening blast. A few seconds later, a window opened below and his neighbor shouted: “It’s three o’clock in the morning, and you’re playing your trumpet?!”

The man turned to his friend and proclaimed, “It’s three o’clock in the morning.”

Sometimes, Hashem will send us a wake-up call, begging us to wake up from our slumber. When we hear it, we must remind ourselves what time it is. It’s time to question, to think, and to redirect. Often, though, life has a way of running on autopilot, controlled only by the flow of momentum. When things are going well, they flow forward, steadily picking up speed. When things fall apart, they tumble downhill, refusing to ease up.

Making a healthy eating choice can serve as inspiration to wake up early the next morning and exercise. The feeling of making a great decision leads you to another great decision, and the cycle continues. The energy and confidence from this positive momentum leads to an increased surge of confidence, leading to another great decision – perhaps a push forward in your career, a positive development in your relationships, or a focus on the next step of your spiritual growth. This is the beauty of momentum. This is also the psychological and practical root of the concept of “Mitzvah goreres mitzvah – One mitzvah leads to another” (Avos 4:2).

However, this same momentum can be the cause of our undoing as well, as “Aveirah goreres aveirah – One misstep leads to another.” Maybe it starts with a small slip-up in our diet, when we promised ourselves we would do better. Now, we feel weak and foolish, and begin muttering degrading insults to ourselves. Our confidence takes a major hit, and we begin to see ourselves as a failure. The next morning, we hit snooze, making ourselves feel even worse, even weaker, and even more of a failure. Next, we sabotage our relationship, miss a meeting, or let our growth and spirituality slide. Of course, this makes us feel even worse, so we break our diet again, making us feel even worse, yet again. This is the deadly cycle of momentum. One thing leads to another, creating a cataclysmic landslide toward complete and utter breakdown.

While this picture is extreme, we can all relate. Sometimes things seem to fall apart in our lives, and we struggle to pick up the pieces. When we start that downhill slide, how do we stop the momentum? How do we pick ourselves up?


Free Will

Hashem presents us with the choice between blessing and curse, between good and bad (Devarim 11:26). The Torah states: “U’vacharta ba’chaim – You shall choose life” (Devarim 30:19). This is cited by most commentators as the source for the principle of free will, the power of choice.

The Rambam includes the concept of free will within the laws of teshuva, which seems both strange and unnecessary (Mishneh Torah, Teshuva, chap. 5). The necessity and nature of free will appears more philosophical than legal, so why does the Rambam include this in his work of halachic codes? And more specifically, why include this in the context of teshuva? To understand this, we must delve into the true nature of teshuva.


Teshuva: Act of Return

While teshuva is often translated as repentance, its literal meaning is “return,” as in the word “shuv.” The goal of teshuva is not only freeing ourselves of punishment and responsibility for our past. Teshuva is about self-transformation, returning to a higher, better version of ourselves. We don’t only wish to escape; we wish to ascend. It is on this premise that the Rambam describes the three-step process of teshuva (Mishneh Torah, Teshuva 1:1).

The first step of teshuva is recognizing that there is a problem to fix and that a mistake has occurred. It is impossible to solve a problem without first admitting that the problem exists. It is all too easy to simply push forward in life, ignoring our inner and outer struggles. But that results in the downward cascade described above. Only by acknowledging the problem can we stop the downward momentum and actually solve it.

The second step of teshuva is to regret one’s mistake. Often, we know that a problem exists, but we don’t feel ashamed, hurt, or even bothered by it. Without internal regret or hurt, we will not be motivated enough to take the actionable steps required to make change. When we yearn for the truth and allow ourselves to powerfully feel the inner contradiction between how we could be living and how we currently are living, we generate the emotional response necessary to genuinely regret our past mistakes.

Third, one must commit to an improved future, one in which this mistake will not be repeated. We must commit to strive toward a greater version of ourselves, whereby if given the chance to repeat this mistake, we would not give in to temptation but would overcome the challenge instead.


The Necessity of Free Will

In order for the process of teshuva to exist, there is one essential element: free will. The only way we can genuinely change, transform, and evolve is if we have the capacity to assert our inner will and to create a new reality within ourselves. This requires a complete re-creation of self within our consciousness – a remolding of our inner world. While yesterday we were the type of person who did one thing, today a new decision is formed and a new reality is created within our inner world. This requires a complete assertion of willpower, an overcoming of self, and a breakdown and reformation of inner drive and character. This means giving up who we are for who we want to be; sacrificing what we think we want for what we truly want. (See Rambam, Mishneh Torah, Gerushin 2:20, where he discusses the relationship between our true ratzon [“rotzeh ani”] and our lower self.) It means overcoming the emotional and overwhelming pull of current desire and generating a new “want” within our very core. This is why the Rambam places his seemingly philosophical discussion of the concept of free will amongst the halachos of teshuva; free will is the very root and foundation of Hilchos Teshuva. Without free will, one could never change and one could never become something else, someone new, and someone better.

Strikingly, Rav Eliyahu Dessler explains that many people never experience a true assertion of their free will due to its immense difficulty. This is why many people do not change. Change is hard, uncomfortable, and often requires sacrifice. One must fully and wholeheartedly believe in their new future in order to give up their current lifestyle. However, when we push with all our might, expressing a full force of our inner will, we get a taste of truth, an experience of destiny, and a glimpse of our true self.

However, this understanding of teshuva, namely, that of return, has an even deeper layer to it. After all, if teshuva is an act of return, what or whom are we returning to? In our next article, we will delve deeper into this fascinating topic and try to answer this question. In the meantime, may we all be inspired to continue to embark on the journey of becoming our ultimate selves!

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Rabbi Shmuel Reichman is the author of the bestselling book, “The Journey to Your Ultimate Self,” which serves as an inspiring gateway into deeper Jewish thought. He is an educator and speaker who has lectured internationally on topics of Torah thought, Jewish medical ethics, psychology, and leadership. He is also the founder and CEO of Self-Mastery Academy, the transformative online self-development course based on the principles of high-performance psychology and Torah. After obtaining his BA from Yeshiva University, he received Semicha from Yeshiva University’s RIETS, a master’s degree in education from Azrieli Graduate School, and a master’s degree in Jewish Thought from Bernard Revel Graduate School. He then spent a year studying at Harvard as an Ivy Plus Scholar. He currently lives in Chicago with his wife and son where he is pursuing a PhD at the University of Chicago. To invite Rabbi Reichman to speak in your community or to enjoy more of his deep and inspiring content, visit his website: