Recently Yishama asked me about the sequence of putting on Tefillin. The box for the arm is fastened first, we get up to the hand, then we break to put on the head Tefillin, and then we finish putting on the hand section of the Tefillin. It would seem to me that the tefillin should be placed on the head first. Why is this the case?

The verses describing the commandment of wearing tefillin give us clues about how to put on and remove the tefillin :

And you shall bind them for a sign upon your hand, and they shall be for ornaments between your eyes.(Deuteronomy 6:8)

The Talmud explains:

When you put them on, you put one on your arm first and then one on your head. When you take them off, first remove the box on the head and then the one on the arm. This is understood from the order of the verse which states, “And you shall bind them for a sign upon your hand,” and then, “and they shall be for ornaments between your eyes.”

Rabbah says that Rav Hunnah explains it this way:

The verse says, “They shall be for ornaments between your eyes.” When should you be wearing the head tefillin? Only when “they” are both being worn (i.e., the hand tefillin should always be on when the head tefillin is on). (Menachot 36.)

But maybe that is just part of the story. I was thinking about this question as we prepare for Shavuot, the holiday we commemorate the receiving of the Torah. Regarding the story of Revelation and the faith of the Israelites we say:

And he [Moshe] took the book of the covenant, and read in the hearing of the people; and they said: ‘All that the Eternal has spoken na’aseh v’nishmah- we will we do, and understand.’ (Exodus 24:7)

What does na’aseh v’nishmah actually mean? While in general would want to understand something before you commit to it, in the case of the receiving of the Torah we committed to doing it first. And in the doing we understood we would come to understand. Maybe this itself is echoed in how we put on Tefillin.

First we put on the arm Tefillin, the symbol of our doing-na’aseh, and then we put on the head Tefillin, the symbol of our understanding- nishmah. Before we understand the commandment we are doing it.

In Perkei Avot Rabbi Yehoshua Ben Levi says:

Every day a heavenly voice goes forth from Mount Horeb and makes proclamation ( Avot 6:2)

Maybe there is also something to learn from how we put on Tefillin to also impacts our daily practice of connecting to Revelation. Yes we do the arm doing-na’aseh first and then we do the head understanding- nishmah. But, after the head we go back and finish with the hand. We should do first. In the doing we will come to understand. And after that we are not done. In the understanding we will come to refine our doing. In our lives we should strive to live lives of Na’aseh V’Nishmah V’Na’aseh. We are always in a process of doing, knowing, and growing.