The rich, the poor, and the wicked (lustful) will all come to judgement. To the poor man they will ask, "Why did you not busy yourself with Torah study?" If he will answer, "I was destitute and was preoccupied with my livelihood..." he will be admonished, "Were you any more destitute than Hillel?"
The gemara goes on to relate that Hillel used to work everyday until he earned a half dinar. From this half dinar, he used half to support himself and his family and the other half to pay the entrance fee to the yeshiva. One day, he was not able to earn the money and could not pay the entrance fee. As he was denied entrance, he climbed to the roof of the study hall and sat near a skylight to hear the session. He remained there oblivious to a heavy snowfall until he lost consciousness. Eventually, he was discovered, rescued, and revived.
I have always had difficulty with this story. The brevity of this story leaves many details undisclosed. One question is: Does "half" mean literally half? Was the cost of admission equal to the minimal amount of a day's living expenses for a family?
I guess tuition was as expensive then as it is now.
A more likely approach is that the word "half" does not mean a literal 50% but means "a portion". In many places in the Talmud, any amount less than a whole (100%) is called "a half" such as the shitta: חצי שיעור אסור מן התורה .
Be that as it may, there were other more substantial questions. One of the main ones is:
If he could earn enough to cover his most basic needs in a few hours a day, why is that called being poor? Okay, so he had no extravagances - but he didn't need any. He could meet his daily basic needs in a few hours a day. A poor person is one who cannot meet his minimal needs. It doesn't seem like he was in debt. Yet, so many of us that work all day long are in debt. Aren't we poorer than Hillel?
What were his working hours? What did he do? Did he go to college and have a degree in accounting or engineering and work part time in an office?
I don't get that impression. It seems to me that he did not have any formal vocational training and hired himself to do odd jobs like shlepping or handywork. But, does this mean that although he was an unskilled laborer, he could nevertheless meet his minimal needs in a few hours? Did he pay any taxes on the money? Bituach L'umi and Mas Briut?
Who is included in the term "anshei beito" - his family members? Is that just his wife, or does it include his children? How many children did he have at that time and how old were they? Did poor people support their children then? Did he have to pay tuition for his children? Did he have to buy diapers? Did they wear costly glasses that break and get lost? Did they get cavities in their teeth or need braces?
Where did he live? Did he rent or own? Did he have a mortgage? Did he have to pay arnona and mandatory insurance? If somebody trips over their own feet in his house, could they sue him? How much did he pay for Gema"ch? (גמ"ח = גז - מים - חשמל ) Did he have a washer, dryer, and refrigerator that soak up electricity?
Was he not able to get along without these things and still meet the typical living standards of lower income people of his time and place?
If anybody knows Hillel's secret* about how to "work for a living" and meet all of our most basic needs and yet be able to spend most of our time in the bais midrash like it says in Rambam, Talmud Torah 3:7 and Shulchan Aruch Yorah Deah 246:21 (also Orach Chaim 156:1; see Mishna Berura s.k. 2 and Biur Halacha) - please tell it to us.
Is Hillel here? Is Hillel here? (Shabbos 31a)
*I highly doubt that he practiced birth control.