There’s a story of two elderly men who were childhood friends but had not seen each other in the past 30 years. One day they run in to each other on the street and are delighted to recognize one another. One of them lives in the neighborhood and invites the other into his home. They happily begin talking and catching up, getting lost in their stories and jokes as the day goes on. The guest finally notices that it has become dark outside, and asks his friend to look at his watch and tell him the time. 

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

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

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

Puzzled, the first man asks the second man: “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 replies.

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

“I’ll show you.” The second man picks up his trumpet, opens the window, and blows a long and deafening blast. A few seconds later, his neighbor yells out: “Three o’clock in the morning and you’re playing your trumpet?!” 

The man turns to his friend and announces, “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 time to question, to think, to redirect.

Often, though, life has a way of running on autopilot, subject only to the flow of momentum. When things are going well they tend to flow forward, steadily picking up speed. When things fall apart they tend to continue downhill as well, refusing to ease up.

For example, making the healthy-eating choice can serve as inspiration to wake up early the next morning and exercise. The great feeling from making a great decision leads you to another great decision, and that 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. However, this same momentum can cause our undoing as well.

Maybe it starts with a small slip-up in our diet, when you promised yourself you would do better. Now you feel weak and foolish and begin muttering self-degrading jabs under your breath. Your confidence may take a major hit, you may think of yourself as a failure or even a loser. The next morning you might hit the snooze button, making yourself feel even worse, even weaker, even more of a failure. Next, you may sabotage your relationship, miss a meeting, or let your growth and spirituality slide. Of course this makes you feel even worse, so you break your diet again, making you 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, I’m sure 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 this week’s parshah, 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 blessings and curses, between good and bad. In a few parshios from now, the Torah states: “u’bacharta b’chaim,” you shall choose life (Devarim 30:19). This is the source used by most commentaries for the principle of free will, the power of choice.

The month of Elul is deeply tied to the theme of t’shuvah, usually translated as repentance. The Rambam (Hilchos T’shuvah, chapter 5) includes the concept of free will within the laws of t’shuvah. 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 work of halachic codes? To understand this, we must delve into the true nature of t’shuvah.

T’shuvah: Act of Return

While t’shuvah is often translated as repentance, its literal meaning is “return,” as in the word “shuv.” The goal of t’shuvah is not only to free ourselves of punishment and responsibility from our past. It’s about self-transformation, returning to a higher and better version of ourselves. We don’t only wish to escape; we wish to ascend. It is with this premise that the Rambam describes the three-step process of t’shuvah.

The first step of t’shuvah 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 always 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 t’shuvah is to regret one’s mistake. Often we know a problem exists but we don’t feel ashamed, hurt, or even bothered by it. Without internal regret or hurt we won’t be motivated enough to take the actionable steps required to make actual 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 can generate the emotional response necessary to genuinely regret any past mistakes.

Third, one must commit to an improved and ideal future, one in which this mistake will not be repeated. In other words, one must commit to strive toward a greater version of themselves, whereby if given the chance to repeat this mistake one would not give in to temptation but would overcome the challenge.

The Necessity of Free Will

There is one principle that is absolutely fundamental in order for this process of t’shuvah to exist: free will. The only way one can genuinely change, transform, and evolve is with the unique capacity to assert their inner will and create a new reality within themselves. This requires a complete recreation of self within one’s inner world. While yesterday one was the type of person who did this, today a new decision was formed, a new reality was created, a new form was conceived within their 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 you are for who you want to be, sacrificing what you think you want for what you truly want. It means overcoming the emotional and overwhelming pull of current desire and generating a new want within your very core. This is why the Rambam places his seemingly philosophical discussion of the concept of free will within the halachos of t’shuvah; it is because free will is the very root and foundation of hilchos t’shuvah. 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 expression of free will because of its objective difficulty. It is for this reason that many people don’t change; change is hard, uncomfortable, and requires sacrifice. One needs to believe so strongly in their new future in order to give up their current lifestyle. However, when one pushes with all one’s might and expresses a full force of inner will he comes in touch with the sublime, a taste of truth, an experience of destiny, and a glimpse of their true self.

Breaking Momentum

We can now return to our original question regarding how one can stop the downward momentum of failure and bad decisions. The answer is simple, self-evident, and yet the most difficult truth to swallow. It’s a single word: decide! Choice is the most powerful tool Hashem equipped us with. With the power of choice you can accomplish anything. But most important for our discussion, the power of choice is the essential tool needed to stop any downward momentum in life. When life begins to fall apart and the bad decisions start piling up, we must learn to cut it off before it expands, before it destroys us. The key is making the decision, asserting your inner will, and focusing the full force of your will toward cutting off that momentum. If you can cut off the momentum of bad decisions, of a lifestyle that is draining the life out of you, you can stop it from spreading, and the virus will wither and die. With nowhere to spread, it’s like a flame without oxygen: it extinguishes, it disappears. It all starts with a single decision to turn the tide, to begin building that positive momentum, to start climbing uphill, to start heading toward your ultimate destination, your true and higher self. If you can take that first step and push toward your greatness, your life will suddenly begin riding that new wave. That is the power of choice, that is the power of momentum.

The Power of Decision

This is the root of t’shuvah. T’shuvah is about re-engineering our will, recreating our desire, rewiring our wants. It’s about the decision to be better, to be great, to become our best and true self. As the Ramchal explains in Mesilas Yesharim, if you can change what you want (akiras ha’ratzon) you can change who you are. If you can make a new decision you can create a new reality for yourself. When the shofar blows this year, let us truly awake. May we all be inspired to fully utilize this Elul to embark on a journey of genuine t’shuvah and continue the process of becoming our true and higher selves.

 Shmuel Reichman is an inspirational speaker and has spoken internationally at shuls, conferences, and Jewish communities. You can find more inspirational shiurim, videos, and articles from Shmuel on Facebook and For all questions, thoughts, or bookings, please email This email address is being protected from spambots. You need JavaScript enabled to view it.