Our morally ambiguous times

Years ago in a philosophy class I posed the question of whether it was more virtuous to have never sinned or to have sinned and then reformed. The evidence suggests the latter, as redemption and America’s culture of authenticity have become increasingly intertwined. ‘Authenticity culture’ celebrates individualism, particularity intellectual endeavors (such as stock trading or winning math Olympiads). This is the opposite of politics, which is collectivist, dumbed-down, and elevates the ‘everyday man’.

It’s not uncommon for reformed prisoners to give motivational talks to Silicon Valley entrepreneurs, who socioeconomically tend to be the complete opposite of the typical maximum-security prisoner, yet modern wisdom is that these two diametrically opposed groups can somehow mutually benefit from each other’s rapport. Other times the roles are reversed, with the entrepreneurs working directly with the prisoners:

Enter Defy. Defy’s mission is simple: “to transform the lives of business leaders and people with criminal histories through their collaboration along the entrepreneurial journey.” I received an invitation from Brad Feld and Mark Suster to join a group they were assembling for Defy; we were part of a group of CEOs, founders, and VCs who traveled to the prison to serve as judges for the pitch competition taking place that day.

Part of the appeal of ‘reform’ is how post-2008 American economy and society prizes quantifiable results (the ‘ends’) over the means (‘ethics’). The value or intrinsic worth of a person is measured by their intellectual, social, or financial status, with things like ‘morals’ and ‘ethics’, neither of which are as easy to quantify, pushed to the periphery. For example, financiers Michael Milken and Ivan Boesky, for which jail was a pit stop on the road to success, given their philanthropy are now forgiven and celebrated. Redemption becomes just another just another way to ‘cash out’ after the dubious venture has run its course.

Rather than going down the boring path of ‘strait and narrow’, many desire to to emulate those who became wealthy by taking shortcuts at the possible cost of ethics. And who can blame them: millions of people who ‘did the right thing’ only find themselves with poor job prospects, unpaid bills, and piles of student loan debt to show for it, and to add insult to injury, are snubbed or looked down upon by a culture and economy that sees these people are either invisible or victims of bad personal choices, not forces outside of their control.

In the past, America looked up to those of upstanding moral character but otherwise were kinda dull or were part of a group or team. Although the rugged individualistic characters portrayed by John Wayne and Clint Eastwood may be exception to this, such characters weren’t intellectual, relying on physical prowess more so intellectualism. America’s brand of individualism has a strong intellectual bent to it – think Edward Snowden or Julian Assange, in which the the ‘ends’ (liberating information) justified the ‘means’ (breaking the law). Rather than the ‘justice league’, it’s the rogue programmer who seeks justice. Or like Michael Burry, as documented in The Big Short, a smart person (a Randian hero of sorts) who in 2007 bet against the housing market (and the prevailing economic consensus) and became wealthy (combining wealth, intellectualism, and individualism…see it all ties together).

Marxist philosopher Slavoj Žižek situates the Randian hero in Rand’s fiction in the “standard masculine narrative” of the conflict between the exceptional, creative individual (the Master) and the undifferentiated conformist crowd…

Author Stephen Newman compares the Randian hero to the concept of the Übermensch created by philosopher Friedrich Nietzsche, saying that “the Randian hero is really Nietzsche’s superman in the guise of the entrepreneur”.[13]

In Less Than Zero, a 1985 novel by Bret Easton Ellis, disaffected, rich teenagers of Los Angeles drive around, do drugs, and party – except now it’s older people who are doing this, minus the drug and partying, permanently delaying adulthood to live lives of introspective excess.

A recent article about how smart people prefer to be alone, went viral and is relevant to America’s culture of individualism and the rise of ‘introversion culture’.

Smarter people can more easily adapt to their surroundings in the modern world, so they don’t need close relationships to help them with food and shelter, like our ancestors did. Or, in the modern equivalent, the Wi-Fi password and a spare phone charger.

From memes on Instagram that celebrate solitude and ‘being alone’ over socializing, to people choosing ‘hustling’ instead of the ’9-5′, it seems everyone is like this. For example, memes about choosing money over friends and socializing, frequently go viral:

One can argue we’re in an era of moral ambiguity…no one really knows what is right or wrong. Major pop culture productions like the hit HBO show Breaking Bad and The Sopranos, that blur the lines between criminality and everyday life, are a contributing factor or a symptom of this confusion. There is the contradiction between how culture promotes extreme sanctimoniousness, but also condones amorality, if not outright criminality, on the other.

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