Category Archives: Essays

Is Repentance Easy?

“Giving up smoking is the easiest thing in the world. I know because I’ve done it thousands of times.” – Mark Twain

Is it easy to change behavior? Is it easy to repent? In Parshas Nitzavim we see conflicting stances on this matter. In one verse (30:2), repentance is described in a similar way to martyrdom: “And you shall return (repent) to Hashem your God, and you shall hearken to his voice as all that I command you today, you and your sons, with all your hearts and with all your soul.” Reb Chaim Volozhiner notes the overlapping word usage with the verse in Shema, “And you shall love Hashem your God… with all your soul”, which Chazal explain to mean that we must even forfeit our lives for the love of our Creator. By utilizing the same verbiage for repentance, the verse is hinting that changing behavior and adopting a new way of life is akin to the ultimate self-sacrifice. Walking away from ingrained character and behavior demands similar courage, resolve and intestinal fortitude as allowing oneself to die for God. Apparently, repentance is pretty hard. That sentiment is likely shared by those who are intimidated by the myriad components and draconian conditions necessary for complete repentance of Rambam’s “Laws of Repentance” and Rabbeinu Yonah’s “Gates of Repentance.”   

Contrast that with a string of verses (30:11-14) later on in the chapter, describing an inordinately easy mitzvah: “This mitzvah that I command you today – it is not hidden from you, nor is it distant. It is not in the Heavens that you may say, ‘who will ascend to Heaven, and take it for us, and teach it to us, so that we may do it’. Nor is it across the sea that we may say, ‘who will cross the sea for us, and take it for us, and teach it to us, so that we may do it’. Rather, the matter is exceedingly close to you, in your mouth and in your heart to do it.” While the verses themselves do not explicitly identify which mitzvah is being referenced, the great commentaries do. Rashi explains that it refers to the mitzvah of Torah. Ramban disagrees and interprets the verse to be referring to the mitzvah of repentance. How can we understand labeling repentance as being so easy – “In your mouth and in your heart”? Also, how can it simultaneously be exceedingly difficult?

Another point to ponder is the characterization (30:6) of repentance as “circumcision of the heart.” What is intended by this odd classification?  

What is the essence of repentance? There is a misconception that repentance is exclusively sin-centric: To repent you must act in opposition to the sin. My grandfather, Rabbi Shlomo Wolbe זצוקללה”ה, explained that this was precisely the miscalculation of the maapilim (Bamidbar 14:44), the Jews that defiantly attempted to ascend to Israel after the Almighty decreed that the nation will languish in the wilderness for 40 years due to the sin of the Spies, only to be slaughtered by Amalek. Their decision was not without reason. They assessed that the core of the sin of the Spies was resistance to enter the Land of Israel and even proposing to return to Egypt (14:4), and therefore attempting to enter Israel in disregard of the entailed dangers can be the only remedy.  But they were mistaken. Repentance, Teshuva, means to return to the Almighty and to His Will. At that time His Will mandated that they remain in the wilderness for 40 years, and thus accepting that was the correct avenue to repentance. My grandfather would also invoke this notion with regard to the repentance of Rosh Hashana. The days of Rosh Hashana make up the first two of the “Ten Days of Repentance” yet unlike Yom Kippur, there is nary a mention of sin. At its root, repentance is returning to your Creator. On Rosh Hashana that is manifest by us coronating Him as King of the world, and on Yom Kippur the same objective is approached from a different angle by addressing sin.

Given that repentance is about man achieving closeness to his Creator, the process of repentance is bridging the gap between man and the Almighty, between the created and the Creator. Hence, the degree of difficulty in achieving it is contingent upon the distance between the two. In essence, the question of, “Is repentance easy or hard?” is precisely the same question as, “Is man close or distant from the Almighty?” The answer to the latter question hinges upon which of the disparate elements of man is being referenced. The “body” of man, the physicality, the ephemeral – has no commonality with the Almighty. However, our Neshama (Soul) is very similar to its Creator. In one teaching in the Talmud (Brachos 10a), five parallels between the Almighty and the Neshama of man are enumerated; another (Niddah 30b) plainly equates the purity of the two. As such, we indeed have an element of our being that is already extremely close to the Almighty and thus repentance for it is natural and seamless.

With this understanding, the conflicting messages about the difficulty of repentance can be reconciled. It is true that repentance is really difficult. By default we identify as an ephemeral body, and in that state repentance is unachievable. To repent we must shed ourselves clean of that attitude and identity. That is a painful process, akin to martyrdom. However, once we identify as our true and lasting element of self, our Neshama, we are already in close proximity to our Creator, and have achieved repentance. This process is illustrated by the circumcision of the heart. We already have everything that is needed to be close to the Almighty, it is just concealed. All we must do to reach our goal is to peel away the inhibiting factors, and reveal our true self that was all ready to go, lying dormant and awaiting liberation.  

This is a helpful and heartening thought to take with us during the season of repentance. It is very difficult to repent. But it is comforting to know that all we are really doing is clearing out the path for our true self to shine. It may be back-breaking labor to dig out buried treasure, but it’s made easier knowing that the treasure is there, and it is complete, and once it is unearthed it’s yours.

Matza: A Truly Free Man’s Food

The differences between chametz (leavened bread) that Jews are forbidden to eat on Passover and the matzah that Jews are required to eat on Passover are seemingly minute. In fact, chametz and matzah may have the exact same ingredients – flour and water – the only difference being that chametz bread was allowed to puff up and rise while the matzah is fastidiously flattened and swiftly baked to avoid any puffication. Seemingly a minor distinction indeed. Yet the prohibition of consuming chametz on Passover carries such enormous weight that a person who violates this commandment is spiritually cut off (kareis) from the Jewish people. This very strict punishment for what looks like a very small infraction begs the question: What is the meaning behind this enigmatic mitzvah and what is so fundamental about it that its transgression results in being disenfranchised from the Jewish nation? This is question number one.

We are all aware of the important role that the yetzer ra (evil inclination) plays in Jewish philosophy; namely to be the chief impediment in our paths to achieving what is required of us in our spiritual lives. The yetzer ra is the reason why we struggle to identify ourselves as spiritual beings, why mitzvahs sometimes seem to us a burden, and why we have a tendency to refrain from seeking spiritual successes and instead crave physical pleasures alone. This formidable foe is classified in the Talmud (Brachos 17a) as “the leaven in the bread.” This puzzling classification brings us to question number two: What does the force that is constantly compelling us to sin – our evil inclination – have to do with the culinary quality that makes bread rise; that transforms matzah to chametz?

Perhaps this Talmudic statement can shed some light on the root of the yetzer ra and illuminate our eyes to the path to overcome this great obstacle. The core conflict of our lives is the struggle between our bodies and souls, between the physical and spiritual. Are we going to prioritize our body, its whims and agenda, or will our soul be the sole goal of our existence, and our body merely the tool to actualize the soul’s desires? Will we view the physical as a means to accomplish our real goals which are our soulful eternal desires, or will we make the fatal error of forgetting that this world is a transient one, a mere corridor to a world where mitzvahs and spiritual accomplishments are all that matters, and get caught up with the trappings and glamour of this physical world? This equation of viewing our physical entities as a means or as an end is the challenge of existence and is symbolized by the difference between matzah and chametz. While it is true that everyone must take steps to ensure that their physical needs are met, the proper attitude must be that one can suffice with matzah, with the realization that their interactions with the physical world are only to provide fuel and energy to accomplish life’s true goals. The aim of the yetzer ra is to take the physical world and enlarge, expand, augment and aggrandize it – mirroring precisely the transformation from matzah to chametz – and attempt to deceive us into believing that this physical life is what we should strive for. On Passover when we chew on the minimalistic matzah – that unpretentious food devoid of any trappings of excess – we remind ourselves of this crucial lesson at the core of the Jewish Weltanschauung: to eschew the mistaken notion that this passing world and all of its physical distractions have any intrinsic value, rather to adopt the matzah view of life that physicality must take a back seat to the true aims of our existence: Torah, mitzvahs and other soulful activities. This is the lesson behind matzah and chametz, and this is why the Torah views this mitzvah so stringently, because it underscores the very essence of the Jewish mission.

Lulav: The Spirit of Jewish Unity and Continuity

Few Torah commandments have the same double-take effect as the mitzvah of shaking the lulav and etrog. On all the seven days of Sukkot, save Shabbos, we hold one citron (etrog) fruit in our left hand and combination of a single lulav (branch of a date palm), two aravas (willow branches) and three hadasim (myrtle branches) in our right; we bring our two hands together; make a blessing and shake the coalition of all four species in six directions – straight ahead, to the right, left, behind us, up and down. Seems bizarre indeed. Uninitiated onlookers will certainly do a double-take.

The Torah does not ask for our complete attention needlessly. When it gives us a double-take mitzvah, it’s clearly trying to convey an important message. What lesson can possibly be taken from this perplexing commandment?

As you might expect, our Sages present us with multiple explanations for this ritual. According to the Midrash, the four species are representative of the four kinds of Jews, and the uniting of the four is indicative of the imperative of Jewish harmony, unity and peace. The etrog has both a pleasant smell and taste, and symbolizes Jews who are both Torah scholars and people of impeccable character. The inedible and fragrance-free aravah represents Jews who have neither quality – are ignorant in matters of wisdom and display unremarkable character. The lulav branch of a date tree and the myrtle hadas branch each have one of the qualities and not the other, and they represent Jews who demonstrate either great scholarship or great character, but not the entire package. These four species corresponding to four very different Jews are united as one in the lulav shaking ceremony.

This imparts a critical lesson. We do not live in a world where all Jews maintain the same level of observance or dedication to Jewish living and learning. Irrespective of practice, we are, regrettably, not even united on philosophical or ideological principles. The unfortunate reality is that there have been major schisms that fractured the Jewish people. The mitzvah of lulav reminds us that despite the bitter infighting, partisanship and disunity that plague our people, we are still a single indivisible unit. Shaking one of the species without the others is meaningless. For better or for worse, the Jewish people are viewed as a single entity. The lulav procedure is thus a sign of Jewish unity.

Alternatively, lulav can viewed as a symbol of the miracle of Jewish continuity. Statistically, we should have disappeared a long time ago. A small itinerant nation bereft of a homeland and not bound by common language or culture should never have survived 2000 years of relentless economic, physical and spiritual marginalization. We should have retired to the annals of history like the many great civilization of the past. The fact that we are still here is nothing short of a miracle.

In Jewish philosophy, we attribute our survival to the annual personal and communal atonement we undergo on Yom Kippur. Every year we are granted a total spiritual cleansing and our sins are forgiven and never accumulate enough in quantity or severity to justify our extinction. During the holiday of Sukkot, on the heels of Yom Kippur, we shake the lulav high, like a victorious warrior returning from battle triumphantly brandishing his sword. We have, once again, survived Judgment unscathed. Accordingly, the lulav ceremony is demonstrative of Jewish continuity.

Perhaps it is no coincidence that the ritual of lulav and etrog can be linked to both Jewish unity and Jewish survival. Perhaps we can also learn a synthesis of these two ideas: Jewish survival hinges on Jewish unity. The survival and success of the Jewish national mission depends on us being able to unite as one man with one purpose. If history is of any indication, our greatest national contributions occurred when we were united, mobilized as one to achieve our destiny; and our collective failures and downfalls are conversely marked by internal conflict and strife. If we truly want to fulfill our national destiny of tikkun olam – of being the world’s spiritual guides and moral guardians – we must rid ourselves of any traces of sectarianism, factionalism, division or discord.

This Sukkot, when we do our lulav double-take, let’s remember and internalize the messages of the four species. Contemplate the importance of Jewish unity and the miracle of Jewish survival, and remember that they are interlocked: We will survive and thrive if we are united.

Don’t languish in Shawshank: A Yom Kippur lesson

The feeling of loneliness experienced when someone you love is distant from you occurs in two varieties. The person you love can be materially distant from you; on a remote island off the coast of Timbuktu without Wi-Fi, running water, or access to modern forms of communication, or better yet, on a rocket ship hurling through the Milky Way an unfathomable, steadily increasing, distance from Earth and a sad, hollow void fills your heart. A nearly identical feeling can be experienced when the person you love is ten feet away; a barrier of reinforced steel or the Berlin Wall separating you two.

The Torahs depiction of the relationship between man and God is complex and confusing. The concept of an invisible, omnipotent God, not bound to time or space nor defined by any physical relatable qualities is very distant from our conscious, yet we see indications that we are extremely close, perhaps even similar to God. For one, the Torah[1] describes man as being created in the image of God. Additionally, we are taught[2] that the etymology of the Hebrew word for man – אדם – is a play on the word –אדמה לעליון – similar to God. Furthermore, the Talmud[3] delineates three entities that are “pure”: God, His angels, and the soul of man. The Zohar[4] proclaims with finality: Nothing and no one is closer to God than the heart of man. In some dimension, man is really close to God. How is it that we feel so distant, so removed from Him?

The answer lies in the physiological development of the body and soul. The Talmud[5] describes a child in utero as having an unsullied soul that “gazes from one end of the world to the other end;” a soul innately knowledgeable of the entire Torah[6]; a soul not under the influence of, and untethered, immune and inaccessible to the three headed[7] monster of evil, the yetzer ra (evil inclination), the satan (prosecuting angel) and the malach hamaves (angel of death). Man’s unadulterated soul is extremely pure; to some degree similar to God. That is the soul of man in its original state. As a child is being born, the three sister forces of evil are draped over him and this reality is totally changed. Henceforth, the power of the soul is muffled by the physical body and the powers of the yetzer ra. A seemingly impenetrable barrier has been erected between man and God; between man and his roots. God is not far away in the cosmos; God is really close, but a massive barrier separates us from Him, and our life-responsibility is to puncture holes and eventually breach that fence.

On Yom Kippur, something magical happens. “For on [Yom Kippur] He will atone you to purify you from all your sins, close to God become pure[8].” The verse indicates that aside from atonement, Yom Kippur is a day where we are close to God. This sentiment is echoed elsewhere[9] when is said in reference to the High Holidays: “Call out to Him when he is close.” The structure of this phenomenon is somewhat unclear. What happens on Yom Kippur that changes the status quo and creates a situation where God is close to us?

To unravel this mystery we must examine another confounding statement in the Talmud[10]: “The gematria[11] of השטן (the satan) is 364, for he has power on 364 days a year; on Yom Kippur he has no power”. On Yom Kippur we are uninfluenced by the three headed monster that created the blockade between us and God. For one day a year the barrier is lifted. We are returned de facto to our original state of being close to God. Yom Kippur is a magical day, indeed.

Our closeness to God on this day is reflected by many of its practices and laws. Unlike other Jewish fast days, fasting on Yom Kippur is not a form of mourning or sadness, rather an expression of our state of angel-like closeness to God. Angels do not need to eat, and neither do we on Yom Kippur. We also pray like angels[12] and dress in white as a testament of our state of purity.

This reality presents us with the tremendous opportunity called teshuva, loosely translated as “repentance”, more correctly as returning. Repentance entails returning. Returning to your roots; returning to God. The rest of the year one can and must seek to return to God, but he must encounter the tremendous obstacle that stands before him. Repentance during the year is akin to Andy Dufresne chipping laboriously at the seemingly impregnable wall; On Yom Kippur the doors of the prison are temporarily opened. The path to God is clear. A small effort is all that is needed on Yom Kippur.

Personal growth has been compared to climbing a ladder; you may only ascend one rung at a time. Chipping away, slowly, methodically, at the imposing barrier. On Yom Kippur those rules are scrapped. On this day we are close to God. The doors are wide open. Do not be the only inmate who stays in his cell.



[1] Genesis 1, 27

[2] See Alei Shur vol. II pg. 27

[3] Niddah 30b

[4] I do not learn Zohar, but I heard this from my Grandfather זצוק”ל.

[5] Niddah 30b and Sanhedrin 91b

[6] Ibid. See Maharal in Niddah

[7] See Bava Basra 15a

[8] Leviticus 16, 30

[9] Isaiah 55, 6

[10] Yoma 20a

[11] Every letter in Hebrew is assigned a numerical value, with א equaling 1, and ב equaling 2, each successive letter increasing by an integer. After 10 we increase by measure of 10, and after 100 by measures of 100.

[12] Declaring the sentence of ברוך שם כבוד  after the shema out loud.

Rosh Hashana: A Vocal Cry for Personal Reinvention

If you are like most people, you hate the sound of your own voice. Most people would rather listen to fingernails scratching chalkboards than to a recording of a voice mail they left. Some attribute false and overly negative characterizations to the sound of their voice. Personally, I was assured many times that I was mistaken and my voice does not sound nasally and squeaky. Anecdotal research has demonstrated that many people have similarly poor self-voice-esteem. This ubiquitous phenomenon is uniquely perplexing. A person’s own voice is a sound s/he should be very familiar and comfortable with. With the possible exception of one’s spouse, there is no voice that a person hears more than his/her own. Furthermore, not a single decibel that one emits is not the product of his/her own utterance. Why is it so unsettling to hear yourself talk? What is so cringe worthy about the sound of our own voice?

The answer to this puzzling question is the same answer as to why we have trouble finding meaning on Rosh Hashana. When you hear yourself talk you are striking a chord that both unnerves and disorients: you are thinking about yourself. Your thoughts are directed inwardly; a most terrifying experiment indeed. There is no one scarier to meet than oneself. The mere sound of one’s own voice is often too frightening to bear.

Directing your thoughts inwardly is the point of departure for making Rosh Hashana meaningful. Rosh Hashana is the birthday of mankind, and therefore the day best suited for personal re-creation. It is a time when man can fundamentally refocus and reprioritize his life and experience a paradigm shift that will forever accompany him. Rosh Hashana is the most auspicious time to cast away the petty small mindedness that plagues our life, and begin living a life of purpose and meaning. It is a day when we are capable of total personal reinvention.

However, there is only one way to maximize the incredible opportunity of Rosh Hashana and that is to do what we dread most: true honest personal introspection. If we desire to utilize Rosh Hashana as a tool to propel spiritual growth it is imperative that we overcome our fears and assess, analyze and critically evaluate ourselves.

We have to look back and reflect on the year past and all the opportunities squandered. When doing so we cannot lose sight of all the isolated personal failings; every individual misdeed and mistake needs to be addressed, yet it is far more important to get a general overall accounting of who we are as a person, what are our goals in life; asking: what am I living for? In our hearts we all know that we have nearly limitless, largely unused, potential. We are all intimately aware of the fact that nothing stops us from achieving a goal that we set our minds to accomplish. The realization that we are wastefully misappropriating our talent, abilities and time is specifically what scares and depresses us. To mitigate the pain we do what humans are wired to do – avoid pain; and therefore refrain from thinking about ourselves. This tendency to avoid thinking inwardly greatly jeopardizes our ability to tap into the awesome powers of Rosh Hashana.

Rosh Hashana is the day where we can experience a personal renaissance, provided that we undergo a rigorous, likely uncomfortable, self-examination. On the Day of Judgment we have to judge ourselves as well. We have to ask ourselves and dwell upon questions like these:

  • What am I living for?
  • What are the obstacles blocking my path to greatness and how can I overcome them?
  • What difference does it make if I live or die?
  • What am I willing to die for?
  • How should I live my life so that I have no regrets on my deathbed?

These last few questions that make us ponder our death are particularly valuable because thoughts of our own demise assist our efforts of deep and genuine personal introspection. It is no coincidence that our Sages incorporated liturgical emphasis on death on Rosh Hashana. When we think about our own death we view our life differently. If the thought of one’s own death hangs over him, his outlook on life is entirely different. Thinking about our own death galvanizes us to reexamine, reframe and renew our life and priorities, and therefore it is an appropriate emotion to capture on Rosh Hashana.

The hallowed sounds of the Shofar are likewise designed to wake us up from our slumber and begin asking ourselves these life changing questions. Rosh Hashana is too vital an opportunity to sleep through.

It is ironic – or perhaps by design – that the most valuable of pursuits  – contemplating one’s character, actions and life-direction – is the one we fear most. If only we can take the time to dwell on these thoughts and questions, there is no telling of the dramatic self re-creation that we can achieve.

Friends, on this Rosh Hashana let’s overcome this great fear that we all share, and truly evaluate and assess ourselves. There are no limits on what we can accomplish on Rosh Hashana if we engage in real self introspection. We can emerge a different person. Who knows, perhaps the new you will love the sound of your voice as well.