I do not live in Israel. Why do I ask for rain on a date set for somewhere else?
In winter this blessing gets the words "dew and rain." In Israel they begin on the seventh of Cheshvan. Outside Israel they begin at the evening prayer of the sixtieth day after a date the sages fixed for the start of autumn, counting that date as day one. In our time that is the evening of December 4, or December 5 in a year just before a leap year (one with a February 29).
The Gemara quotes a teacher named Hananiah: in the Diaspora, wait sixty days. Shmuel, a leading sage of Babylonia, ruled that the law follows him. The Gemara does not spell out why, but just before, Rav, another sage of Babylonia, says Babylonia is rich because it harvests without rain. The Tur (a law code from the 1300s) says "Diaspora" here means Babylonia, and that we follow the Babylonians.
That is the problem you are pointing at. The Rambam (Maimonides, the great Jewish thinker and legal authority of the 1100s) wrote in his commentary on the Mishnah that other lands should ask when rain is good for them. In some lands it is summer in Cheshvan, and rain only does damage. Asking for it then, he says, would be false and foolish.
The Rosh (the Tur's father, a leader of Jewish law in Germany and then Spain around 1300) raised a similar objection. Our Gemara is the Babylonian one, he wrote, but why follow Babylonia in something that depends on the land? Babylonia was swampy, but every land needs water in Cheshvan. He liked the custom he heard of in Provence, where people began on the seventh of Cheshvan.
His view did not win. The Aruch HaShulchan says the Rosh himself wrote that his words were not accepted, and says it was as if a voice from heaven told everyone to follow Babylonia. The Shulchan Aruch (the main code of Jewish law) sets one date for the whole Diaspora.
If you really need rain in summer, the Shulchan Aruch says to ask for it in a different blessing, Shema Koleinu ("Hear our voice"). It says this even for a whole city or country.
Taanit 10a,Rambam, commentary on the Mishnah, Taanit 1:3,Tur, Orach Chaim 117,Aruch HaShulchan, Orach Chaim 117:4,Shulchan Aruch, Orach Chaim 117:1-2I buy food at a store. Why would I pray for crops?
The Mishnah says the request for rain goes in this blessing. The Gemara asks why. Rav Yosef, a sage in Babylonia, answers in one line: since rain is parnasah, a living, they set it in the blessing about making a living.
Rabbi Yitzchak, a sage in the Gemara, ties rain to money. On a day of rain, he says, even a small coin in your pocket is blessed. His proof is the verse that puts the two together: "to give the rain of your land in its time, and to bless all the work of your hands" (Devarim 28:12).
Abudarham (a commentary on the prayers from Spain, about 1340) reads an order in the Amidah. First come the needs of the soul: understanding, return, forgiveness, and rescue from trouble. Then the body is healed. Only then does a person ask for a living, so that body and soul can both be in the blessing of the years.
Now notice who the Gemara is worried about. It puts this blessing ninth to answer people who raise food prices. Rashi says David's prayer there was: break the arm of the wicked, and give plenty to the world. The same worry shows up in the rules for fasts. A public fast for rain may not begin on a Thursday, so as not to push prices up.
So these sources are about grain and prices, because that was the economy. A paycheck is not in them, but the Shulchan Aruch rules that a person who needs a livelihood asks for it in this blessing (see the Halacha section). What the sources here do say is that food and income share one blessing, and that the prayer is for plenty, with a warning for anyone who profits from scarcity.
Berakhot 33a,Taanit 8b,Devarim 28:12,Abudarham, Weekday Prayers, Amidah,Megillah 17b,Rashi on Megillah 17b,Taanit 10a,Shulchan Aruch, Orach Chaim 119:1What does it mean to ask for blessing on a whole year? Is that just hoping for luck?
The Gemara has a specific answer about where blessing shows up. Rabbi Yitzchak says blessing is found only in what is hidden from the eye. His proof is Devarim 28:8: "Hashem will command the blessing for you in your barns."
A teaching on the same page gives an example. A farmer about to measure his grain pile says: "May it be Your will that You send blessing in the work of our hands." Once he starts measuring, he says: "Blessed is the One who sends blessing on this pile." If he measures first and blesses afterward, the prayer is wasted. The reason: blessing is not found in what is weighed, measured, or counted. It is found in what is hidden from the eye.
One way to read our blessing with this in mind: it asks about "this year," which nobody has counted yet, and about produce that has not been gathered.
Does that mean you should not plan? In Bava Metzia 42a, right next to the same saying about hidden blessing, the same Rabbi Yitzchak says a person should divide his money in thirds: a third in land, a third in business, and a third in hand. Read together, these say: plan and count, and look for blessing in what you cannot count.
These sources do not explain how blessing works. They only say where to look for it, and where not to: not on the scale, not in the measuring cup, not in the count.
Taanit 8b,Bava Metzia 42a,Devarim 28:8