David Brooks' Philosophy of Stumbling

A friend recently shared with me the latest David Brooks column in the NYTimes. The full article, The Moral Bucket List focuses on a lot of new-age career anxieties that I hear (and to be honest, talk about myself) often. I found three bits particularly resonant:

1) Resume Virtues vs Eulogy Virtues
As Brooks defines them, "resume virtues are the skills you bring to the marketplace. Eulogy virtues are the ones that are talked about at your funeral - whether you were kind, brave, honest, or faithful."

2) The Gap Between the Actual Self and the Desired Self
"But if you live for external achievement, years pass and the deepest parts of you go unexplored and unstructured. You lack a moral vocabulary. It is easy to slip into a self-satisfied moral mediocrity. You grade yourself on a forgiving curve. You figure as long as you are not obviously hurting anybody and people seem to like you, you must be O.K. But you live with an unconscious boredom, separated from the deepest meaning of life and the highest moral joys. Gradually, a humiliating gap opens between your actual self and your desired self, between you and those incandescent souls you sometimes meet."

As far as I can tell, this gap has always existed for the overwhelming majority of the population. The desire and strive to close that gap is more indicative of a rich depth of character than actually having that gap closed. I believe Brooks gets to this when he discusses the philosophy of stumbling in his conclusion. 

3) The Philosophy of Stumbling
"The stumbler doesn’t build her life by being better than others, but by being better than she used to be. Unexpectedly, there are transcendent moments of deep tranquillity. For most of their lives their inner and outer ambitions are strong and in balance. But eventually, at moments of rare joy, career ambitions pause, the ego rests, the stumbler looks out at a picnic or dinner or a valley and is overwhelmed by a feeling of limitless gratitude, and an acceptance of the fact that life has treated her much better than she deserves."

This is easier said than done, especially in a place like New York City (or San Francisco, or Los Angeles, or Chicago, or Boston, or any other bustling metropolitan area bursting with professional ambition). But at the core of the Philosophy of Stumbling, what I enjoy most is the re-definition of ‘better’ as something that is derived from a carefully constructed set of individual values. Socially deconstructed and from within.

Random Sidenote: once a month seems like a considerably high frequency to be running into people radiating ‘inner light’, but major kudos to whatever you're doing with your daily commute, Mr. Brooks.

Thanks for sending along, Anand. 

The effective business personality?

My friend and I have been having a conversation lately around business philosophies. What gets work done? What kind of business personality drives results? 

Empirically, Jobs, Zuckerberg, Dorsey, Bezos, and most recently, Uber's Travis Kalanick would prove that a balls-to-the-wall, sharp-elbowed salesmanship style is what brings successful entrepreneurs out from the crowd. Nearly all the business and start-up self-help literature I've read places value on bringing an aggressive approach to a company. Can't say I've seen the ill-fated Jobs movie, but nearly everyone knows about Steve Job's almost sociopathic disregard for how his actions had an impact on other people. 

This personality goes against the values most kids are taught growing up. Share your toys. Be fair. And yet, now that Uber is gaining immense popularity at a current valuation of $3.4 billion, plenty of coverage is being spun out around Travis Kalanick's bull-headed work style:

"There is absolutely no way this business would have gotten where it is without Travis and his arrogance,"

says an acquaintance of Kalanick's. "Not without him being like, 'I'm going to take over the world.' He has the Steve Jobs mentality that 'It's my way or the highway.'"

Here are a few more examples of Kalanick's stubborn, nearly tyrannical methods:

1) On convincing New York Taxi and Limousine Deputy Commissioner Ashwini Chhabra to let Uber taxis give rides in New York and compete with yellow cabs: 

That said, the deputy commissioner admits the hard-knuckled tactics can be effective. "That approach actually works if you want to come in and you're challenging an orthodoxy," he says, noting he personally has no hard feelings toward Kalanick or criticisms of his business style. "He's a good and tough negotiator, and when you're negotiating, sometimes there is some posturing on everyone's part, whether it's as the regulator or disruptor."

2) On responding to public criticism from frustrated Uber customers:
Later, when Uber was criticized for charging fares eight times higher than usual during a snowstorm, Kalanick posted an email from a concerned user to his Facebook page.

"Get some popcorn and scroll down," he wrote.

3) At Failcon, an annual conference for startup founders to study their own and other's failures:
"VCs ain't shit but hoes and tricks." 

In short, and as summarized in Business Insider's feature, "Kalanick's form of hustling also means doing things most people wouldn't: picking fights, bending laws, challenging governments, and throwing tantrums." 

And so it seems that out-of-ordinary success necessitates out-of-ordinary drive and duplicitous personality. Plenty of successful CEOs exude this philosophy. 

What my friend and I are focusing on, instead of blindly adopting a Kalanick-like business philosophy, is finding counterexamples. Is there a way to become a selfless leader and thrive with equal success as Kalanick? 

Right now I'm looking into the following books and resources to build up a library of examples of the patient, kind, giving, and human leader:

• Susan Cain's Quiet
• Adam Grant's Give and Take
• Conan O'Brien's goodbye speech at the Tonight Show

If you have any, please share!