The broad principles of judgment are straightforward. One who walks in God’s ways is blessed in both this world and the next, while one who is wicked is punished in both this world and the next. However, the specifics of judgment are immeasurably deep and complex. Therefore, there are instances of the righteous suffering poverty, disease, and untimely death, while sometimes the wicked prosper and endure. There are many possible reasons for this, as we will explain below, all of which are meant to improve the world.
First of all, one must know a fundamental principle: To perfect the world, people must have free choice. As long as the world has not been perfected, it runs according to the laws of nature and fate that God determined, so it is not possible for all the righteous to thrive and all the wicked to suffer. Therefore, judgment, as it applies to individuals, is incredibly complex and involves myriad details. There are always righteous people suffering and wicked people appearing to enjoy the pleasures of this world. Thus, free choice is unimpaired, and one who chooses good improves himself and the entire world.
Nevertheless, over the long term, for example, when it comes to families and true happiness in life, we find that in this world, too, usually the righteous experience blessing while the wicked suffer. The crux of our challenge is to disregard our evil inclination, which urges us to take a superficial, myopic view of the world, and instead to follow our good inclination, which encourages us to look further and more deeply. Thus, even though in this world, too, the righteous, over the long term, attain benefit and the wicked suffer, free choice remains intact, because this truth is not discernible over the short term.
Let us begin to explain some specifics. One person may be destined to be wealthy and face the challenges that accompany wealth. Even if he sins greatly, he will remain rich. His judgment on Rosh Ha-shana is about the circumstances of his life as a wealthy person. Will he find joy in his wealth, or will it cause him endless worry? With respect to the next world, will his wealth help him to withstand trials, be they minor or major? Might it even help him in serving God? Another person may be destined for poverty. Even if he is righteous, he will remain poor. The question is simply whether his poverty will be bearable or unbearable. With respect to the next world, will his impoverishment help or hinder his service of God? In rare cases, a person can change his destiny through outstanding merits or grave sins.
Sometimes a person’s destiny is not absolute, but only determines a direction that allows for change. In such cases, the judgment of Rosh Ha-shana can determine whether someone destined to have money will be comfortable, rich, or fabulously wealthy, or whether someone destined to be needy will be needy, poor, or destitute.
It is important to note that only individuals are subject to mazal, not the collective. The reward and punishment discussed in the Torah are collective (Responsa Rashba 1:148). However, individuals, with great spiritual effort, can ascend to the level of the collective, beyond the reach of mazal. It should be further noted that the Torah’s this-worldly rewards and punishments are primarily promised to Israel as a people, to be delivered naturally. Thus, free will is not compromised, since individuals are still subject to fate. (See section 8 below.)