It is becoming more and more common to speak of one's investment style, which is reflective of one's personality as much as it is of one's financial sophistication. There are those who seek low risk opportunities and others who prefer the thrill of risky ventures with the lure of high returns. However when it comes to Torah observance and the investment of efforts into our relationship with Hashem, Rashi in this week's parsha warns against selecting mitzvos based on an investment- return approach.
It seems to me that this is the point of the Medrash Tanchuma quoted by the opening Rashi in Parshas Eikev. The promise of abundant prosperity described in the parsha is conditional, as explained in the first pasuk, on our Torah observance. " It will be because - eikev - you will listen to these mishpatim [laws] and observe them, that Hashem will keep the bris with you that he swore to your fathers." We have come to expect this type of conditional phrase to read, "it will be if - im - you will listen" and apparently that is why Rashi reminds us that "eikev" can in the noun form refer to the heel. The medrash thus freely renders the pasuk to say "If you will listen to the mitzvos of your heel", making the promised plenty of the parsha conditional on the careful observance of that which we often step over, or summarily dismiss because they are so easy. Almost all of the commentaries on Rashi struggle with Rashi's apparent question. After all, this usage of "eikev " is consistent with other places in chumash such as Breishis 26:5 or Bamidbar 14:24.
Yet the substance of the medrash needs to be studied. The Torah is concerned with the Jew who ignores the easy mitzvos that are not particularly challenging to one's passions or lifestyle and prefers the hard mitzvos that do bring difficulty or discomfort. Obviously we should not be choosing amongst Hashem's mitzvos for that questions Hashem's authority and shows a lack of commitment to the wholesomeness of the system. That notwithstanding, why is the nisayon-seeker singled out for censure and the one enjoying the easy road designated for grace and blessings? Are we not taught at the beginning of Mesilas Yesharim that life is a series of nisyonos / challenges, that test character and raise it at every successfully negotiated hurdle? The ongoing test of wills to refrain from loshon horo and anger, to rise up early for minyan or a seder, or to restrict what one watches and be out of the loop as a result - is that not where genuine spiritual growth is found? Affixing a mezuzah to one's home, wearing tzitzis in the winter or eating seudah shlishis in the summer - can those easy mitzvos really bring one closer to Hashem?
Perhaps the point of the medrash is to remind us that we grow intellectually and spiritually in different ways. True, we improve through confrontation and distillation. However, we also mature through steady and gradual osmosis, naturally absorbing from our environs, and harmoniously incorporating life's lessons into the way we live. Hashem in His kindness does not insist that we only raise ourselves through stubborn contrariness. Rather by surrounding ourselves with easy mitzvos, making us continuously aware of Hashem's presence through asher yotzor and tzitzis, serving Him becomes natural. This is the pleasant way of Torah referred to by Dovid Hamelech - derocheho darchei noam - and one who comes to realize it gives expression to the love Hashem has for His children and the beauty of His Torah. Surely the kidush Hashem that this lifestyle brings to life should earn the promise of prosperity that is described in the parsha.