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There is a point of halacha that any money spent on Shabbat, Yom tov, or Torah learning is "on Hashem", and one should have complete trust that Hashem will pay it back as He guarantees it. I will find the exact source a bit later, it's in Yalkut Yosef Hilchot Yom Tov for example. It's well know.

The question is, how exactly does He pay it back?

I have a tendency to go off topic, so if a moderator tells me to delete the following I will, but I find it hard to ask the question without the following two kashes as I consider them highly relevant:

  • If one is to say that He pays it back through miraculous means, then the obvious kashe is, what counts as a "miraculous" means?
  • If one is to say that He pays it back through natural means, then how is that any different to what He does anyway, organising our financial situation through hashgacha pratit? I.e, how does this "guarantee" have any actual practical difference to anything?

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The gemara you are referring to is Beitza 15b:

אָמַר רַבִּי יוֹחָנָן מִשּׁוּם רַבִּי אֱלִיעֶזֶר בְּרַבִּי שִׁמְעוֹן: אָמַר לָהֶם הַקָּדוֹשׁ בָּרוּךְ הוּא לְיִשְׂרָאֵל: בָּנַי, לְווּ עָלַי, וְקַדְּשׁוּ קְדוּשַּׁת הַיּוֹם, וְהַאֲמִינוּ בִּי וַאֲנִי פּוֹרֵעַ.

Rabbi Yochanan said, attributed to Rabbi Eliezer beRabbi Shim'on: The Holy Blessed One said to Israel, "My children, borrow for me, and declare the sanctity of the day, and have faith in me, and I will repay [the loan].

But there is a contrasting gemara at Pesachim 112a where Rabbi Aciva is quoted as saying: "עֲשֵׂה שַׁבַּתְּךָ חוֹל וְאַל תִּצְטָרֵךְ לַבְּרִיּוֹת — Make your Shabbos [like a] secular [day], and do not become beholden to other people." (Although Rabbi Aciva does say one should borrow money to pay for four cups of wine at the seder.)

The Shulchan Arukh (OC 242:1) writes:

אפילו מי שצריך לאחרים אם יש לו מעט משלו צריך לזרז עצמו לכבד את השבת ולא אמרו עשה שבתך חול ולא תצטרך לבריות אלא למי שהשעה דחוקה לו ביותר על כן צריך לצמצם בשאר ימים כדי לכבד את השבת מתקנת עזרא שיהיו מכבסים בגדים בחמישי בשבת מפני כבוד השבת:

Even regarding someone who depends on others for his livelihood, if he has [even just] some [food] of his own, he must make an effort to honor the Shabbat. The halachic devisors [poscim] who said, "make your Shabbat as a weekday so that you do not rely on others," only said it regarding one in a time of dire need. Therefore [a person who has a bit of their own food, i.e. the initial situation discussed,] must practice restraint during the week so that he can honor the Shabbat. This is based on the decree of Ezra, that people should wash clothes on Thursday (i.e. prepare during the week) for the honor of Shabbat.

(The Rama does not address this point, so Ashkenazim are apparently on the same page.)

Rav Melemed (Peninei Halkhah 1:12.3) is the earliest halachic source I could find that quotes Rabbi Yochanan. (That's someone alive today!) And he does so in particular with regard to Yom Tov, not Shabbos. I don't know why. Anyway, he writes:

הנמצא בגרעון זמני, ראוי שיכנס למשיכת יתר בבנק או שיקח הלוואה כדי לשמוח בחג. ואל ידאג שמא תארע לו תקלה ולא יוכל להחזיר את חובו, ש"אמר הקב"ה לישראל: בָּנַי, לוו עלי וקדשו קדושת היום והאמינו בי ואני פורע" (ביצה טו:). וזאת בתנאי שלא יסמוך על הנס, אלא שיש לו עסק מסודר או משכורת קבועה, או חסכון שעליו הוא יכול להישען. שעליו אמרו חכמים שלא ידאג שמא לא יצליח להחזיר את חובו, כי אם יעבוד בחריצות ולא יבזבז את כספו על מותרות, ה' יברך את מעשה ידיו ויסייע בידו לשלם את חובו. אבל מי שאינו יודע כיצד יחזיר את חובו, לא יקח הלוואה לצורכי החג, שלא יהיה רשע שאינו משלם את חובותיו. וגם לא יפשוט ידו לקבל צדקה, אלא יאכל בחג מאכלים פשוטים, וכפי שאמר רבי עקיבא: "עשה שבתך חול ואל תצטרך לבריות" (פסחים קיב.). ובזכות שלא יזדקק לבריות – יתעשר (פאה ח:ט). אמנם עני שכבר נאלץ לפשוט ידו לקבל צדקה לצרכים שונים, ייטול צדקה כדי לשמוח בחג (משנה ברורה רמב:א).

If one finds himself with a temporary shortfall before a festival, it is appropriate for him to go into overdraft at the bank or to take out a loan, in order to enjoy the festival. He should not worry that something might go wrong and prevent him from repaying his debt. After all, God assured the Jews: “My children, borrow money on My behalf and sanctify the day; and believe in Me and I will repay” (Beitza 16b). This is on condition that one does not rely on a miracle, but rather has a stable business, regular income, or savings upon which he can draw. It is in such cases that the Sages say that one should not worry lest he be unable to repay the loan. As long as he works diligently and does not waste his money on luxuries, God will bless his efforts and help him pay off his debt. In contrast, one who does not know how he will repay a loan should not take one out to cover festival expenses, as people who borrow money and do not repay it are deemed wicked. He should not ask for charity either. Rather, he should eat simple foods on the festival, following R. Akiva’s dictum: “Turn Shabbat into a weekday rather than accepting charity” (Pesaḥim 112a). As a reward for not taking charity, he will become wealthy (Mishnah Pei’ah 8:9). In contrast, if one is already poor and must accept charity in any case, he should accept charity to cover festival expenses as well (MB 242:1).

It would seem that in practice, we basically follow Rabbi Aciva. Rabbi Yochanan's words are limited to people who have every natural reason to believe they will get ahold of the money. You still have to make room in your weekly budget for Shabbos. Just don't be more thrifty, or even as thrifty about Shabbos expenses than when we want to treat ourselves in other ways.

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  • It seems difficult. If you know you will have no issue paying those debts back, then why would you need any encouragement from Hashem to do so? The phrasing should therefore be "if you don't feel like borrowing for Yom Tov expenses, do so anyway". The whole inyan of "I'll pay it back" isn't a chiddush, especially in light of the qualification that we shouldn't do so if we don't see any natural means of this happening. I appreciate the answer and will ponder it further. I still want to know how exactly Hashem "pays back" in light of the above kashes
    – Rabbi Kaii
    Jan 3, 2023 at 12:50
  • By the way, Yalkut Yosef brings it 529:3 but doesn't go into as much practical detail as the Peninei Halkhah you brought, so much appreciated
    – Rabbi Kaii
    Jan 3, 2023 at 12:51
  • @RabbiKaii, knowing you have a realistic expectation of getting the money back isn't a sure thing. Many people on principle don't buy luxuries with borrowed money for this reason. (What would Polonius say?) Jan 3, 2023 at 22:12
  • @RabbiKaii, the quoted SA is arguably more restrictive, saying like R Aciva - don't borrow money, save up the week before! Jan 3, 2023 at 22:14
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I don't have a written source for you, just a maaseh that I personally somehow merited experiencing.

The first few years I started doing teshuva, I was living in a remote location in a third world country with a very small Jewish population. If I wanted kosher wine, I had to order it by the case from an importer in the country's capital, and it would take about a week to arrive.

One Sunday I noticed that I was down to my last bottle of wine. This was particularly problematic because due to the business I was running, I had accounts recieveable due in 30 days, but just enough to make payroll in the bank, and the wine had to be paid for in cash.

I read that passuk somewhere in my limmud that week (by "coincidence" of course), and decided to put HKBH to the test (remember, this and maaser are the two ways we are permitted to test Him). I borrowed the amount needed (it came to something like US$ 186 at the then-current exchange rate) and ordered the wine.

Two days later a client called me up and needed a small job done, and wouldn't you know that when we calculated how much it would cost, it came to....that exact same amount, $186. He then proposed to settle up right away. בה, message recieved!

This differs from the standard h.p. concerning our parnassah in that, as the gemarrah explains (I don't remember where), our income for the year is determined during the Yomim Noraim, but our spending for Shabbat and Yom Tov is outside of that. Meaning, if I was "supposed" to make $100,000 that year, the $186 I spent on wine was additional to that, pushing me up to $100,186.

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    This is an amazing story and does indeed practically illustrate an answer to the question. I will ponder it thank you
    – Rabbi Kaii
    Jan 3, 2023 at 13:54

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