The Torah in Parashat Shoftim describes the procedure that would be followed when Benei Yisrael went out to war, specifically, the address given by an especially appointed kohen (the “kohen mashuach milchama”) before battle. In this address, the kohen announced several exemptions, including an exemption for those who felt frightened (20:8). The Mishna in Masekhet Sota (44a) cites different views among the Tanna’im as to the nature of the “fear” that exempted a soldier from war. According to one view, this refers to the fear of “aveirot she-be’yado” – sins that one has committed. Meaning, a soldier who knows that he has committed certain violations would not take part in the battle. The Gemara later (44b) cites an opinion that this applies even to one who made the mistake of speaking after placing his tefillin shel yad and before placing his tefillin shel rosh. Halakha forbids making any sort of interruption in between placing the tefillin shel yad and the tefillin shel rosh, and according to this opinion, even violating this law qualifies as a “sin” for which a soldier is sent home before battle.
Numerous writers proposed that this halakha was chosen not merely as a random example of a relatively minor ritualistic detail, but rather as symbolic expression of a fundamental aspect of Jewish life. Specifically, many have suggested that juxtaposing the placing of the tefillin shel yad and tefillin shel rosh represents the need for consistency between the heart – near which the tefllin shel yad is worn – and the mind – above which the tefillin shel rosh is worn. The Torah demands that we strive to align our emotions and desires with what we rationally know to be correct, proper and just, that there is no “disruption” between our hearts and minds.
Developing this symbolic approach a bit further, Rav Avraham Dov of Avritch, in his Bat Ayin (Parashat Tzav), sees the two tefillin as representing the balance that needs to be maintained between the conflicting emotions of brokenness and confidence. The tefillin shel yad, worn near the heart, represents our anxieties, fears, insecurities and apprehensions which are borne out of our faults and failures, and which we all keep within our hearts. By contrast, the tefillin she rosh, which rests proudly on top of the head, represents the confidence, courage, boldness and self-esteem that we need in order to aspire to and pursue ambitious goals. Rav Avraham Dov of Avritch writes that Halakha requires placing the tefillin shel rosh immediately after placing the tefillin shel yad because we must be able to regain our feelings of confidence and self-worth immediately after experiencing failure. We often feel broken, humiliated and ashamed, but we must have the strength to quickly rise from these emotions to the “tefillin shel rosh” – to a feeling of confidence and belief in ourselves. We must never allow failure to paralyze us, to keep us down, to prevent us from moving forward. We must instead have the strength and courage to proceed immediately from the “tefillin shel yad” to the “tefillin shel rosh,” to raise ourselves from disappointment and discouragement to confidence and ambition, so that we can continue growing, achieving and accomplishing all that we are capable of accomplishing during our brief sojourn on earth.