We need to end the kesef equals kavod equation (admittedly easier said than done). Honor should be bestowed on people who exemplify good values, not those who merely possess large portfolios.
Additionally, the undue emphasis on results and status rather than process unwittingly (or wittingly?) leads some teenagers to conclude that their parents would rather have them cheat their way into the Ivy League than succeed on their own in some lesser academic clime. Parents should impart to children that virtue matters more to them than scholastic or material success.
On the other side of the spectrum, parents who do not provide their children with the education or skills needed to support themselves have failed in one of the most essential aspects of parenting. Worse, they fulfill the Talmudic injunction “Whoever does not teach his child a profession (or trade) teaches him thievery” (Masechet Kiddushin 29a).
Modernity has also presented an especially critical dilemma that undoubtedly plays a significant role in much of the low-level deception that occurs in Jewish life. Cheating on taxes is rampant in America in all sectors of society, attributable to simple greed, discontent with government, and even occasionally the arcana or unfairness of the tax laws. The acquisition of money as a desideratum in its own right, together with the power and prestige that riches often bring to the holder, leads even extraordinarily wealthy people to connive for more.
But in our world, the cost of living a Jewish life is obscenely expensive and also plays a role in inducing moral mischief. We are simply living beyond our means and beyond normalcy. There are families with children in yeshiva elementary and high schools that are paying over six figures in tuition. Few can sustain that.
Conversely, those elements of our lives that are perceived as “necessities” (clearly, some are but many aren’t) – yeshiva tuition, summer camp, Pesach in a hotel, Yom Tov expenses, clothing, vacations, residence in communities with a crushing real property tax burden, the need to maintain appearances among one’s friends, neighbors and peers, etc. – all place tremendous pressure on the breadwinner. In fact, to maintain our lifestyle, being a breadwinner is not enough; one has to own a successful chain of bakeries.
That pressure often eventuates in the corner-cutting that usually heralds some ethical lapse. And so we need to reduce our material footprint in the world. The Kli Yakar (Devarim 2:3) famously lambasted his contemporaries (in 16th-17th century Prague) for their materialistic excesses that contributed nothing to their spiritual lives and aroused the jealousy of the non-Jewish world.
“Vihamaskilim yavinu likach mussar – and the intelligent will draw the appropriate lessons from it.” Much unethical conduct is prompted by the need to sustain fancy houses, cars, clothing, and vacations – and the image that is engendered by them – with a percentage sliced off for tzedakah as a salve for the conscience and to further bolster that image.
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Finally, I have heard occasionally from people that “we are entitled” because of the historical injustices inflicted on the Jewish people. The entitlement mentality currently entices most Americans but has an especially pernicious manifestation for Jews.
The thought process goes something like this: “They murdered us and plundered our assets during the Holocaust; the Communists cheated, robbed, persecuted, and enslaved us. We are entitled. It’s payback time.”
In other words – if I understand the argument correctly – the historical injustice of the maltreatment of innocent European Jews by Christians, Nazis, and Communists can be (partially) rectified by the deceptions practiced on innocent Americans by American Jews.