Musar for Ketubot 99:2
א"ר אילעא באושא התקינו המבזבז אל יבזבז יותר מחומש תניא נמי הכי המבזבז אל יבזבז יותר מחומש שמא יצטרך לבריות ומעשה באחד שבקש לבזבז [יותר מחומש] ולא הניח לו חבירו ומנו רבי ישבב ואמרי לה רבי ישבב ולא הניחו חבירו ומנו רבי עקיבא
R. Elai stated: It was enacted at Usha that if a man wishes to spend liberally he should not spend more than a fifth. It was also taught: If a man desires to spend liberally he should not spend more than a fifth, lest he come to need the help of people. And it once happened that a man wished to spend more than a fifth but his friend did not allow him. Who was it? R. Yeshevav. Others say [that the man who wished to spend was] R. Yeshevav, but his friend did not allow him. And who was it? R. Akiva.
Shenei Luchot HaBerit
Perhaps the answer is similar to the statement by our sages in Ketuvot 67 that if someone wishes to be generous in his charitable gifts, He should not give away more than 20% of his wealth so as not to risk becoming poor and dependent on others. Wealthy people are able to donate 20% of their wealth. What they are left with will still be ample. When one has limited means, however, giving away 20% of those means may represent a great hardship. When Rashi speaks about something being beyond a person's ability he refers to something beyond a person's ability to part with without suffering hardship as a result.
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