In the Gemara (Berachot 35b), the following question is asked: what is the purpose of the Pasuk in Parashat Eikev that states (Devarim 11:14), “VeAsafta Deganecha,” “You shall gather your grain”? Rabi Yishma’el answers that it is there to counteract another Pasuk in Sefer Yehoshua, which states, “Lo Yamush Sefer HaTorah HaZeh MiPicha,” “This Sefer Torah should never leave your mouth” (Yehoshua 1:8). If we had only this Pasuk, one might have thought that seeking a Parnasah, a living, is prohibited, for it would detract one from occupying oneself completely with Torah. Therefore, this verse in Parashat Eikev comes to teach that making a livelihood is permitted. Rabi Shimon Bar Yochai vehemently disagrees with Rabbi Yishmael, noting that if one occupies himself with Parnasah, with the plowing, the sowing, the harvesting, etc., when will one find time to learn Torah? Rather, one must study Torah the entire day, and the gentiles of the world will do the work for us. In a time, however, when we are not fully engaged in Torah study, then our work will be done by us, and the work of the gentiles will be done by us as well.
Rav Chaim MiVolozhin elucidated this Machloket in the following way. Rabi Yishma’el clearly does not mean to say that it is permitted to avoid Torah completely in order to fully engage in earning a livelihood, as is made clear by his particular wording in the Gemara cited above: “Hanheig BaHen Minhag Derech Eretz,” “You must lead a life with the study of Torah.” Right after you stop working for a livelihood, your mind must quickly revert back to Torah study. Rav Chaim went on to note that Rabi Shimon Bar Yochai’s opinion applies only to a rich person, for the Gemara continues to say that many people followed the opinion of Rabbi Yishma’el, and life was good for them, and many followed the opinion of Rabi Shimon Bar Yochai, and life was not good for them. Rav Chaim explained that the Gemara says “many” in both cases to exclude a certain social class. The “few” who followed the opinion of Rabbi Yishma’el and led unsatisfactory lives were the rich people who could afford to learn Torah all day and not work at all – their monetary status changed drastically enough to make life harder for them. The “few” who followed the opinion of Rabi Shimon Bar Yochai whose lives were good were those who could afford to learn all day and did so.
Rav Chaim says that the Pesukim themselves allude to this concept. In the first section of Shema, the Torah states (Devarim 6:5), “VeAhavta Eit Hashem Elokecha BeChol Levavecha UVeChol Nafshecha UVeChol Me’odecha,” “You shall love Hashem, your God, with all your heart, with all your soul, and with all your possessions.” In the second section, on the other hand, the Torah states (Devarim 11:13), “ULeOvdo BeChol Levavechem UVeChol Nafshechem,” “[You are commanded] to serve Him with all you hearts and with all your souls,” but not, “UVeChol Me’odechem,” “and with all your posessions.” This is because the first section is written in Lashon Yachid, in singular, and if a single person is able to serve Hashem with all of his assets, which refers to learning all day and not worrying about work, he should do so. The second section, on the other hand, is written in Lashon Rabbim, in plural, which comes to teach that such a lifestyle is not for everyone. The Jewish people as a whole are not expected to throw down the idea of earning a livelihood for the sake of engaging in Torah all day, but an individual is permitted to do so and is even expected to do so if he is able.