On Rosh Hashanah, upon consuming the head of a fish, the custom is to recite the prayer, "may we be the head and not the tail". This noble aspiration can rightfully be understood as a fulfillment of the blessing, "Hashem will make you the head, not the tail, you will always be at the top and never at the bottom, if only you obey and faithfully observe the commandments of Hashem your God that I enjoin upon you this day" (Devarim 28:13). What is the nature of this request? Must one always be in charge in order to be satisfied? If Hashem makes everyone Rebbes who will be the Chassidim?
Moreover, it is arguably preferable to be the tail as the Mishnah (Avos 4:15) advises, "be a tail unto lions, and not a head unto foxes". This philosophy is rooted in the pasuk, "he who keeps company with the wise becomes wise, but he who consorts with dullards comes to grief" (Mishlei 13:20). In other words, it is better to be an adherent of the wise rather than a leader of the crooked because people tend to be influenced by their surroundings. Indeed, Rav Matisyahu HaYitzhari, in his commentary on the Mishnah, observes that if a fly lands on the head a lion it will bend and curve its tail towards its head in order to chase away the fly, alluding to the followers of the clever who will likely be uplifted by association. Whereas the nature of the fox is to tilt its head towards its tail in order to deal with the nuisance, symbolizing the regressive effects of commanding a bunch of buffoons. Indeed, in Paradise Lost, it is Satan who declares, "better to reign in hell than serve in heaven".
But even if all are pious and good, it is still worthwhile to mingle amongst those who are more righteous and more accomplished than oneself. Working and socializing with those who possess a greater degree of sophistication and achievement than ourselves inspires and engenders additional growth and development. Chazal reject the popular notion that it is better to be a big fish in a small pond rather than a small fish in a big pond. A gifted student might acquire greater self-confidence in an ordinary class, but he will only be pushed to maximize his potential in an environment where he is challenged by his peers. Certainly, in the religious sphere, this is true as well. An accomplished scholar is referred to as a talmid chacham - a wise student, precisely because he needs to be the perpetual student who appreciates the value of role models and possesses the humility to learn from others.
For this reason, Rav Tzadok Hakohen (cited in Mishneh Sachir, Rosh Hashanah) submits that the desire to "be the head and not the tail" is not related to our position within the organizational flow chart of the community, because it is always beneficial to strive and reach for higher ground rather than to gaze downward from an elevated perch. The prayer to "be the head and not the tail" is not a personal wish but a communal expression of hope regarding the individuals we have chosen to exalt and emulate. May they be leaders who are genuinely worthy of our allegiance and support and not tails masquerading as heads.
Alternatively, Rav Shimshon Pincus (Tiferes Shimshon) suggests that "to be the head and not the tail" refers to the capacity for independent thought. The head examines its path and after careful consideration and deliberation steers the body forward, while the tail mindlessly drags behind. Both will reach the same destination in the end but in very different ways. In order to maximize and deepen our relationship with Hashem, we should seek to keep the mitzvos and learn Torah not because of charismatic speakers, the pull of social pressure, or even the inertia of yesterday, but because we consciously and genuinely concluded to do so ourselves. It is possible for a person to arrive in the heavenly court with knowledge of all of shas and still be told that he is nothing but a tail. If his primary impetus to learn is the yeshiva schedule and the surrounding atmosphere, and not his own personal initiative, then his achievements are tainted and inferior.
It is praiseworthy to be the lion's tail, to shadow tzaddikim and gedolim and learn from their every move and manner, but at the same time a person must also utilize his own head, to think for himself, and not just blindly follow others. The Mishnah (Avos 1:1) teaches that a rebbi should "stand up many disciples". Rav Soloveitchik explains that the language of the Mishnah is precise, because a good rebbi creates talmidim who are self-sufficient, who can stand on their own two feet and use their own head, not who are clones of himself. As we embark upon the new year, we must renew and deepen our commitment to the mitzvos not only by learning from the example of our role models but also by using our heads to think for ourselves, for only in this way can we develop a personal and profound relationship with Hashem.