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A person’s destiny in life may be to be rich and to deal with the challenges that accompany wealth. Even if one sins a lot, one may remain rich. Heavenly judgment on Rosh Ha-shana only affects the conditions of life as a wealthy person; will one enjoy the wealth, or will one be persistently worried? Will the wealth present one with difficulties, or will it help to observe mitzvot, do good deeds, and earn the World to Come?
Another person’s destiny may be to struggle with poverty. Even if one is righteous, one may remain poor. Heavenly judgment on Rosh Ha-shana only affects the conditions of the life as a poor person. Will one be a little strapped or totally destitute? Will the poverty be bearable or unbearable? Will it contribute to service of God or disrupt it? (Occasionally, a person’s destiny can be changed due to truly outstanding merits or extremely grave sins.)
Sometimes a person is not destined to be either rich or poor. Those who make good choices in financial and charitable matters, deserve wealth so they can continue to use their wealth to benefit people. However, sometimes it is clear to God that were certain people to become wealthy, they or their family members would likely become arrogant, stingy, and hedonistic. People's relationship to God is the most important thing in life, so heaven has mercy upon them and sentences them to struggle with making a living. This way they are spared a difficult challenge, able to live a meaningful life in this world, and rewarded greatly in the World to Come. Without such mercy, they would experience wealth in this world but face such serious challenges that they would likely spend time in hell.
Another consideration in Rosh Ha-shana judgment is how difficult it is for a person to choose good or avoid evil. Some people are born with a strong evil inclination, or grow up in a very difficult and toxic environment. If they manage to learn even a small amount of Torah and do a few good deeds, this is extremely impressive, and they will receive tremendous reward. As the Sages say, “In accordance with the pain is the reward” (Ethics of the Fathers 5:23). Other people are born with a strong good inclination, or grow up in a supportive environment. If they sin, they will be severely punished. (See 15:15 above for more about destiny and free choice.)
