"...I have set before you life and death, blessing and curses, choose life so that you and your children live" (Devarim 30:19).
When looking at this parsha, the exhortation to choose life seems to be just another prompt to do the right thing; instead of "to choose" I could have said "to do" with a similar meaning. It actually is the only place in the Torah where "bechirah" is used in the sense of "human free will." [We do find it in regards to Hashem's choices, and to "choose men" which really means "to examine and decide who is fit".]
Moreover, it does not seem to be the precise term. When someone is confronted with a choice between two positive values, then the exhortation "to choose" is in place. Thus, if a person is struggling between two honorable professions, I may tell him, "you must choose between profession A or B." But if someone is lazing off, and I reprimand him and tell him, "you must choose between an honorable profession or a life in the gutters", I am not really referring to "making a choice." What I mean to say is "It is obvious that you want a normal life. You must do better to get there." Isn't that in effect what the Torah is telling us? After clarifying that a Torah life is "life" and "blessing", while the opposite is "death" and a "curse", is it choosing that is necessary, or action?
There is another important reference that seems to reinforce the problem. Rabbeinu Yonah (Shaarei Teshuva 3:17) talks about the importance of doing positive mitzvos (mitzvos aseh). He says that all of the positive virtues of Torah are to be found in the positive miztvos, such as talmud Torah, fear of Hashem, love of Hashem, etc. He also includes "and you shall choose life" in the same category! This is strange. How does it become a specific commandment, on par with love and fear of Hashem?
It seems that Rebbeinu Yonah understands the injunction of "and you shall choose life" not as a generic exhortation to do what's right, but rather a specific commandment to do it not out of habit, nor because of the flow of society, but rather because of choice. This means that a person ponders what is the meaning and purpose of life, what is the good that is the essence of life, and accomplish it out of recognition and cognizance, rather than our of rote and habit.
This understanding gives us insight into the flow of Yamim Noraim. We are focused on Yom Kippur and Aseres Yemei Teshuva. The teshuva process makes sense to us. We have done wrong, and we need to rectify what we're doing wrong. But Rosh Hashana somehow is hard to reconcile with this. There is no mention of sin, nor really of teshuva, except in an incidental way.
Perhaps Rosh Hashana is the day for "choosing life". It is a day that focuses on Hashem as Creator, man as his primary creation, and the expectations of man as the focus of all of creation. It sets the basis for our fulfillment of mitzvos, and the wrong done by not sufficiently accomplishing what is incumbent upon us. If we choose life, then im yirtzeh Hashem we will be zocheh that Hakadosh Baruch Hu endows life upon us.
More divrei Torah from Rabbi Lopiansky