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There’s a story of two elderly men who were 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 catch each other up on their lives, getting lost in their stories and jokes as the day goes 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: “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.”  

 The shofar is Hashem’s trumpet, begging us to wake up from our slumber. When we hear it, we must remind ourselves what time it is. It’s Elul; it’s time to question, to think, 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, or 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 “mitzvah goreres mitzvah”, one mitzvah leads to another (Avos 4:2). However, this same momentum can be the cause of our undoing as well. “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, 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 towards 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? To understand this, we need to develop an important theme connected to both Parshas Re’eh and the month of Elul as a whole. 

Free Will 

Parshas Re’eh begins with the principle of choice: Hashem presents us with the choice between blessing and curse, between good and bad (Devarim 11:26). In a few parshios from now, the Torah states: “u’bacharta b’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 month of Elul is deeply tied to the theme of teshuva– usually translated as repentance. The Rambam (Hilchos Teshuva, Chapter 5) includes the concept of free will within the laws of teshuva. This seems both strange and unnecessary. The necessity and nature of free will appears more philosophical than legal, so why does the Rambam include this in his work of halachic codesAnd 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 to free 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 (Hilchos Teshuva 1:1). 

The first step of teshuva is recognizing that there is a problem to fix, 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 towards 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, 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, a new reality is created within our inner world. This requires a complete assertion of willpower, an overcoming of self, 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, Hilchos Gerushin 2:20). 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, one could never become something else, someone new, 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. 

Breaking Momentum 

We can now return to our original question regarding how to stop the downwards momentum of failure and bad decisions. The answer is simple, a single word: decide! Choice is the most powerful tool Hashem has granted us. The power of choice allows us to accomplish anything. When life begins to fall apart, and bad decisions start piling up, we must cut off the downward momentum before it grows out of control, before it destroys us. The key is making the decision, asserting your inner will, and focusing its full force towards cutting off the momentum. If you can stop the momentum of bad decisions, of a lifestyle that is draining the life out of you, you can stop it from spreading. With nowhere to spread, negativity is like a flame without oxygen- it simmers out and disappears. It all starts with a single decision to turn the tide, to begin building positive momentum, to start climbing uphill, to start heading towards your ultimate destination. If you can take that first step and push towards your greatness, you will suddenly begin riding that new wave. This is the power of choice, this is the power of positive momentum. 

The Root of Teshuva 

Free will – choice – is the root of teshuva. Teshuva is about reengineering our will, recreating our desire, rewiring our wants. It’s about the decision to be better, to be great, to become our best and truest selves. As the Ramchal explains in Mesilas Yesharim, if you change what you want (akiras ha’ratzon), you change who you are. When you make a new decision, you create a new reality for yourself. When the shofar blows this year, let us truly awaken. In some sense, we all need a shofar for the shofar, we need a wakeup call to listen to this year’s wakeup call. Many are numb to the wordless blast, deaf to its existential calling. Some have given up on change, while others are too busy with life to stop and truly consider the possibility of more, of a greater life. This year, let us embrace the shofar’s call and tap into our higher purpose. May we all be inspired to fully utilize this Elul, to embark on a journey of genuine teshuva, and continue the process 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: