Hear and Now - Preferred Podcasts

Arresting Aphorisms

  • "You can't hold a man down without staying down with him." (Booker T. Washington)
  • "Mishaps are like knives, that either serve us or cut us, as we grasp them by the blade or by the handle." (James Russell Lowell)
  • "Vision is the art of seeing things invisible." (Jonathan Swift)
  • "Beauty without grace is the hook without the bait." (Emerson)
  • "What I like in a good author is not what he says, but what he whispers." (Logan Pearsall Smith)
  • "The sole substitute for an experience which we have not ourselves lived through is art and literature." (Alexander Solzhenitsyn)
  • "Genius is one percent inspiration and ninety-nine percent perspiration." (Thomas Edison)
  • "My country is the world and my religion is to do good." (Thomas Paine)
  • "Human felicity is produced not so much by great pieces of good fortune that seldom hapen, as by little advantages that occur every day." (Benjamin Franklin)
  • "The basic difference between an ordinary man and a warrior is that a warrior takes everything as a challenge while an ordinary man takes everything either as a blessing or a curse." (Carlos Castaneda)
  • "Not everything that can be counted counts, and not everything that counts can be counted." (Albert Einstein)
  • "Throw your heart over the fence and the rest will follow." (Norman Vincent Peale)
  • "The palest ink is clearer than the fondest memory." (Chinese Proverb)
  • "Think like a man of action, act like a man of thought." (Henri Bergson)
  • "History doesn't repeat itself, but sometimes it rhymes." (Mark Twain)
  • "We do not remember days; we remember moments." (Cesare Pavese)
  • "The only way to have a friend is to be one." (Emerson)
  • "The only way around is through." (Robert Frost)
  • "Mountaintops inspire leaders but valleys mature them." (Winston Churchill)
  • "Friendships are like money - easier made then kept." (Samuel Butler)
  • "Black words on a white page are the soul laid bare." (Guy de Maupassant)
  • "A man is wealthy in proportion to the things he can do without." (Epicurus)
  • "Mistakes are the portals of discovery." (James Joyce)
  • "Happiness is wanting what you have, not getting what you want." (Sheryl Crow)
  • "Experience is simply the name we give our mistakes." (Oscar Wilde)
  • "Your worst enemy cannot harm you as much as your own thoughts, unguarded. But once mastered, no one can help you as much." (Buddha)
  • "You understand life backward but you live life forward." (Soren Kierkegaard)
  • "Love decreases when it ceases to increase." (Chateaubriand)
  • "I quote others only the better to express myself." (Montaigne)
  • "Be quick .. but don't hurry." (John Wooden)
  • "Pain is just weakness leaving the body." (Nike Slogan)
  • Happiness = Performance - Expectations
  • "It is never too late to be what you might have been." (George Eliot)
  • "Always make new mistakes." (Esther Dyson)
  • "People more often need to be reminded than informed." (Samuel Butler)
  • "Old people are fond of giving good advice; it consoles them for no longer being capable of setting a bad example." (La Rochefoucauld)
  • "History doesn't repeat itself, but sometimes it rhymes." (Mark Twain)
  • "We are what we repeatedly do. Excellence, therefore, is not an act, but a habit." (Aristotle)
  • "Yesterday is history. Tomorrow is a mystery. Today is a gift." (Eleanor Roosevelt)
  • "We do not remember days ... we remember moments." (Cesare Pavese)

Books marinating in my mind ...

  • David Allen: Ready for Anything: 52 Productivity Principles for Work and Life

    David Allen: Ready for Anything: 52 Productivity Principles for Work and Life
    Allen is the productivity guru behind 'GTD' (the appropriately-named 'Getting Things Done' system). Far more than a simple recipe on how to optimize your To-Do Lists, this very readable book walks you through the philosophy behind his approach. This is a must-read for GTD devotees, but also an extremely useful primer for anyone who seeks to be more effective. His simple premise - that one's ability to be productive is directly proportional to one's ability to relax - is both elegant and powerful.

  • Maureen Dowd: Are Men Necessary?: When Sexes Collide

    Maureen Dowd: Are Men Necessary?: When Sexes Collide
    Dowd - one of the few women to have broken through the 'glass ceiling' to gain a coveted column in the New York Times - serves up her familiar fare of quick wit, rapier-sharp ripostes and cutting political commentary. While there are a number of gems here, the book disappointingly ends on a flat - instead of a high - note. Still, the tome is worth reading for her incisive insights into modern sexual politics alone.

  • Daniel Gilbert: Stumbling on Happiness

    Daniel Gilbert: Stumbling on Happiness
    This book has less to do with happiness and more to do with perception, but I won't quibble with its' ultimate value to the reader. Daniel Gilbert lays bare the fascinating process by which we perceive, recall and reflect on the events that dot our lives. In doing so, he disabuses us of some of our most cherished notions about our memories. As he pithily points out, 'perceptions are portraits, not photographs.' You won't look at how you remember quite the same again after digesting this enthralling work.

  • Jillian Straus: Unhooked Generation: The Truth About Why We're Still Single

    Jillian Straus: Unhooked Generation: The Truth About Why We're Still Single
    It's become a trite cliche today to remark that marriage has waned as the premier social institution. If people wed at all, they marry later and for shorter periods - certainly not for richer or for poorer, as in our parents' day. This book goes a long way in explaining why ours has become the 'unhooked' generation, by shedding light on contributing factors such as the collapse of courtship and the emergence of our multiple-choice society.

  • Nancy Etcoff: Survival of the Prettiest: The Science of Beauty

    Nancy Etcoff: Survival of the Prettiest: The Science of Beauty
    Ever wonder what informs our impressions of beauty? I did, until I devoured this book. It turns out that those notions are hardwired in the brain and reinforced by the forces of evolution. The author marshalls an impressive array of biological, psychological and anthropological arguments to explain that our attraction to beauty is, in the final analysis, driven by our desire to successfully pass on our genes. Beauty, therefore, is in fact much more than skin deep ...

  • Robert Baer: Blow the House Down: A Novel

    Robert Baer: Blow the House Down: A Novel
    Baer's book of fiction blows the doors off the CIA and lets the reader inside the rarified air of intelligence analysts, spy tradescraft and convoluted geopolitical intrigue. The author writes with an arresting authencity, gained as much from his prose as his past as a twenty veteran of the CIA's Directorate of Operations. Many an armchair secret agent will devour this novel in one sitting ~

  • Thomas Friedman: The World is Flat

    Thomas Friedman: The World is Flat
    Friedman's central thesis - that globalization creates a flat playing field where your competitor can be next door or on the next continent - is more of an evolutionary than revolutionary insight. However, he is a master at making complex matters appear simple, and this book's powerful conclusions will scare you as much as educate you.

  • William Gibson: Pattern Recognition

    William Gibson: Pattern Recognition
    My introduction to the man who invented 'The Matrix' was this book, his first foray into contemporary (as opposed to science) fiction. Gibson proves to be as shrewd an observer of today's technological dystopia as he was a prognosticator of tomorrow in 'Neuromancer.'

  • David Brooks: On Paradise Drive: How We Live Now (And Always Have) in the Future Tense

    David Brooks: On Paradise Drive: How We Live Now (And Always Have) in the Future Tense
    Brooks understands and deconstructs modern Middle America better than any writer today. This book peels back the layers to reveal the lives and longings of minivan-driving, church-going, cul-de-sac living suburbanites in all their glory.

  • Barry Schwartz: The Paradox of Choice: Why More Is Less (P.S.)

    Barry Schwartz: The Paradox of Choice: Why More Is Less (P.S.)
    This book will change your life - if you let it. It should be on the core curriculum for everyone living in our 21st Century world of the Long Tail and limitless choice.

  • Richard Linklater: Before Sunrise and Before Sunset

    Richard Linklater: Before Sunrise and Before Sunset
    I love reading screenplays from dialogue-driven movies. This anthology of the scripts from the two 'Before' films will not disappoint, with many a profound observation on life, love and longing proferred here by Linklater's two protagonists.

  • Thomas de Zengotita: Mediated

    Thomas de Zengotita: Mediated
    'Mediated' will help you make sense of the MySpace Generation. De Zengotita explains how so much of our existence is intermediated by representations of reality, and the consequences this holds for both our society and our self-conscious. This books offers up fascinating insights into our mediated age, and you won't walk through life quite the same way again after reading it.

  • Daniel H. Pink: A Whole New Mind

    Daniel H. Pink: A Whole New Mind
    This books is the perfect follow-up to reading The World is Flat. Friedman's opus frightens you into thinking that your job can and will be outsourced in a 'flat' world. Pink issues a persuasive manifesto for avoiding that fate, imploring one to develop the "right-brain" qualities of inventiveness, empathy, joyfulness and meaning to complement the "left brain" capabilities that powered the Information Age. Read this book to enhance the skills that can't be so easily replicated and outsourced ...

  • Chuck Klosterman: Sex, Drugs and Cocoa Puffs

    Chuck Klosterman: Sex, Drugs and Cocoa Puffs
    Klosterman wields one of the truly most unique voices in social commentary today. Only he can establish the thread leading from Puck on MTV's 'The Real World' to Zack on 'Saved by the Bell'. Klosterman comes off as a pop culture polymath in this sweeping trip across the mass media landscape.

  • James Geary: The World in a Phrase

    James Geary: The World in a Phrase
    This compact little book charts the history of the aphorism, perhaps the perfect philosophical medium for the MySpace Generation. Along the way, Geary enlightens us with his lifetime's worth of collecting the pithiest turns of phrase. You will no doubt marvel, as I did, at how aphorists succeed in suffusing one small sentence with so much meaning ...

  • Chris Anderson: The Long Tail

    Chris Anderson: The Long Tail
    It's a good measure of this book's influence that Anderson's central metaphor has already penetrated into society's common lexicon of tech-savvy terms. This book does more than just popularize a phrase, however; it persuasively and painstakingly postulates the end of the mass market and the rise of selling, as the author puts it, "less to more people." One must read this book to understand the Internet's impact on the future of commerce itself, let alone what it might do to your business.

  • Frans Johansson: The Medici Effect

    Frans Johansson: The Medici Effect
    This books provides both epiphany and exasperation in almost equal measure. On the one hand, Johansson piques our interest with the catchy central insight that combining fields and concepts leads to a boost in creativity. Sadly, this point is made over and over again, rendering his book somewhat of an intellectual run-on-sentence. This would have made an absolutely brilliant essay if he had distilled his message rather than doubled-down on it.

Pop Philosophy Preferred

  • Tim Ferriss
    I love Tim's concepts of 'lifestyle design' and 'going on a media diet'. His advice and hacks on how to simplify your life are a welcome respite to our hyper-mediated world.
  • Thomas Friedman
    The Walter Lippmann of this generation. Whether you agree with his views or not, he is the most influential pundit today on the two issues that matters most in the modern world: globalization and the Middle East.
  • SHardy, Creative Generalist
    A genuinely inter-disciplinary intellectual - in the most positive sense of the term.
  • Merlin Mann
    One of the first - and best - Life Hackers out there.
  • Mark Cuban
    This Internet business pioneer and owner of the Dallas Mavericks also happens to be one of the most original - and outspoken - thinkers in media and technology today.
  • Malcolm Gladwell
    Gladwell practically invented the entire category of books that I devour with his seminal work, The Tipping Point.
  • Jon Kay
    He will come to be known someday as Canada's George Will. In the meantime, he influences friends and foes alike from his perch as Comments Editor at The National Post.
  • Fareed Zakaria
    Anyone who has watched 'This Week with George Stephanopoulos' (c'mon, you know you want to admit it!) has seen Zakaria consistently demonstrate his lucidity, eloquence and coherent world view. Not many people can go toe-to-toe with George Will and emerge unscathed, but he does it every week. Oh, in his spare time he is the Editor of Newsweek International, too ...
  • David Brooks
    Today's most trenchant social and political analyst.

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December 10, 2007

The Importance of Planning Exits rather than Entrances: Ending with the Beginning in Mind

I came across a thought-provoking Moet & Chandon advertisement recently (shocking, I know) where two impossibly glamourous young model-types are pictured leaving a limousine with a magnum of the eponymous champagne. The tag line reads:

Turn an Exit into an Entrance. Be Fabulous.*

It was the first time that I came across a perfect summation of the counter-intuitive philosophy that I've proselytized for years, namely that exits are often more important than entrances.

Let me explain. People frequently go to great lengths to plan their entrances, but they almost never give thought to their exits. Perhaps this is driven by the belief that you never get a second chance to make a first impression, as the saying goes. But what we often forget is that you never get a second chance to make a final impression, either. What makes the latter in some ways more critical than the former is that we are usually given opportunities, over time, to reinforce or - if need be - reverse the impact of an entrance. We are not afforded that luxury with our exits, however. Our last act is, in fact, the last word.

I've been thinking a lot lately about endings. Perhaps it's because I experienced the passing of a loved one recently, and the reality of her being gone is still being absorbed. As someone put it well, I will never get over her departure, but I will start to get used to it. While she didn't get to completely stage manage her exit, she clearly had put a great deal of thought into the way she wanted to leave, as well as what she left behind. She understood that those final acts would serve as her adieu, and that those statements, both verbal and symbolic, would echo beyond her earthly lifetime.

Unfortunately, many of us fail to have that foresight. Most of us forget the importance of the final frame. We focus almost exclusively on the opening credits in the scenes of life.

The primacy of entrances over exits is a long-standing component of conventional wisdom, even if it is fundamentally ill-conceived. Nearly every aspect of public and private life, both past and present, reinforces this notion.

In the political square, for example, elected officials have 'advance' people who arrive well before they do to map out, in meticulous detail, every aspect of their entrances. Presidents give Inaugural addresses every four years but rarely, if ever, make as much-ballyhooed farewell speeches. In the run-up to next year's presidential elections, we've been treated to a meticulously staged-managed declaration of candidacy by Barack Obama, but I doubt that we'll see a similar spectacle if he drops out of contention.

History offers many of the same examples of this error. General Dwight David Eisenhower spent almost 3 years devising the amphibious D-Day invasion in Normandy - the opening of the Western front in World War II - but it fell to General George Marshall to cobble together his plan for the reconstruction of Europe in a few short months. Closer to today, US military commanders carefully choreographed the commencement of combat operations (the 'Shock and Awe' phase) in the recent Iraq war but failed to formulate so much as an outline of a strategy for the occupation afterwards.

On a more personal level, people succumb to this same strategic misstep frequently as well. We fret over first dates but end entire relationships with something as desultory as a text message. We prepare fastidiously for an interview and dress to impress on our first day at a new office, but we quit jobs on a whim and slink out of a company, hoping not to have to honor our two weeks' notice. In an unintended irony, we labor over and spend lavishly on weddings, our introductions to married life, but leave both the details and the debt of our funerals largely unarticulated and unaccounted for.

Indeed, there is an instinctive and, some might say, intellectual bias towards beginnings. Even the great Aristotle wrote over two Millennia ago that "well begun is half done." At the same time, however, we all probably intuitively suspect how important exits are to forming that last - and lasting - impression. But do we realize just how much weight those final moments carry? Probably not.

Cognitive psychology is crystal clear on the subject, however. One of the most influential books I ever read, The Paradox of Choice by Barry Schwartz, makes a powerful and impassioned argument about the 'tyranny' of too much choice. In building his very persuasive case, Dr. Schwartz introduces us to a psychological Power Law called the Peak | End Rule. First discovered by Nobel-prize winning psychologist Daniel Kahneman, the principle states that "what we remember about the pleasurable quality of our past experiences is almost entirely determined by two things: how the experiences felt when they were at their peak (best or worst), and how they felt when they ended. This 'peak-end' rule is what we use to summarize the experience, and then we rely on that summary later to remind ourselves of how the experience felt." Simply put, our entire recollection of an event, a period of time, a relationship or even a person can come down, in large measure, to how we felt at the zenith or nadir of the experience and especially at its' conclusion.

Would it were that this was the only psychological force at play in making endings matter. The more we learn about how we think, the more it becomes apparent that perception and memory are fickle and partially false constructs. "Memories - especially memories of experiences - are notoriously unreliable. Perceptions are portraits, not photographs,", as Daniel Gilbert put it in his recent best-seller, Stumbling on Happiness.

In some ways, this should not surprise us. The faithful representation of all that we've seen and felt would take up terabytes of a 'human hard drive'. How, as Gilbert asks, "do we cram that vast universe into the relatively small storage compartment between our ears?" The answer is that "the elaborate tapestry of our experience is not stored in memory - at least not in its entirety. Rather, it is compressed for storage by first being reduced to a few critical threads ... or a small set of of key features. Later, when we want to remember our experience, our brains quick reweave the tapestry by fabricating - not by actually retrieving - the bulk of the information that we experience as a memory."

What this means is that those 'snapshots' in our mind, the seemingly oh-so-vivid memories, should be more properly viewed as impressionist paintings rather than high-resolution photographs. What's more, as we have learned through the Peak | End Rule, exits shape and 'paint' those perceptions, and in turn they inform the interpretations that we mistake for memories. We "misremember the past", in effect, and exits have a direct influence on that process.

Clearly, our emphasis on entrances is not serving our best interests. What can and should we do? Simple - we ought to put as much time and thought into our exits as we do our introductions. We should end with the beginning in mind.

An exit is a passage, after all, from one state to another. We need to start by recognizing that every ending is actually an opening of sorts - the start of the period of time where memory and revisionism 'reweaves' the tapestry of events that just happened. Seen in this light, the end is really prologue to a perpetual epilogue, whereby the 'ending' we thought that we experienced is actually constantly being rewritten and reviewed.

So how does one put this 'Exit-tential' philosophy into practice? First, you should focus on how you want the encounter you're ending to be remembered. I call this legacy thinking, and it should - to a greater or lesser extent - suffuse many aspects of your previously entrance-centered existence. When you prepare for your life's set pieces, ponder on how you can better dictate their perceived denouement. Approach each concluding stage - no matter how anodyne or seemingly small - the way presidents attack their final terms in office, obsessed with what historians will write of them.

This probably all sounds highfalutin and hard to accomplish, but it's actually easier than you think. The next time you move on from a job, take the time to tie up all the loose ends and exit on a high note. When you terminate a relationship with a girlfriend, find the feelings to do it properly, respectfully and sensitively. As you leave a party, set aside a moment to say goodbye to everyone to whom you talked (and especially the hosts).

To some, this might seem to be common decency and | or common sense. No argument from me there. However, these simple gestures are sadly infrequent in our increasingly ill-mannered world. Moreover, they represent small but significant steps towards a new level of thinking that factors in the epilogues to one's entrances.

This approach can be applied at a very granular level. When you are leaving a place where you've just visited friends, give them a goodbye call from the airport before your flight boards and let them know how much you appreciated the time that you spent together. Try to close out cafe conversations with confidantes as you would write a conclusion to an essay, capturing key ideas and charting the date for the next chat.

A lot of this must appear absurd, and on some level I can see why. However, we all recognize that when an event or experience is well-ended we appreciate the difference. When rock god Bono departs the stage after a live concert, he and U2 have fine-tuned their finales so well that they simultaneously satisfy their audience with at least one encore, while still leaving them wanting more. When Jerry Seinfeld concludes a comedy set, he does so as the words - and the raucous laughter - of his last great joke linger in the air.

Jacqueline Kennedy understood this reality, even in her moment of maximum grief. She carefully choreographed her husband and assassinated president John F. Kennedy's state funeral, down to the last decisive detail of having the coffin, draped with the Stars and Stripes, laying on a gun carriage drawn by six grey horses while a black riderless horse pranced along behind. That iconic image, along with that of the slain leader's casket lying in state in the Capitol Rotunda, simultaneously served to give the country ceremonial closure while cementing JFK's Camelot legacy. Of course, Mrs. Kennedy was simply taking a page from ancient history and the Egyptians in particular, who perfected the glorious goodbye with their elaborate tombs and pyramids to honor their fallen pharaohs.

These, then, are examples of graceful and well-considered exits. There are others. Some industries and disciplines incorporate this thinking into their orthodoxy. Entrepreneurs and venture capitalists talk about having 'exit strategies' for their companies and investments. The language of theatre, too, has included the idea of 'exit, stage right' in its vernacular. Presidents, as well, are preoccupied by perpetuity and often engage in a flurry of activity towards the ends of their tenures in order to shape their legacies.

As mere mortals, maybe we don't need to ponder our place in history. But we ought to turn a wider-angle lens on life, look beyond our natural bias towards beginnings and plan the postscripts to our experiences. We need to stumble through fewer emergency exits, and compose more carefully crafted epilogues.

What makes an excellent exit, in my opinion? First, one must wrap up loose ends, putting a period at the end of the metaphorical sentence. Second, one should leave a lasting and positive impression, so that their lingering thought of you is ultimately a flattering but not fleeting one. Finally, a perfect postscript brings with it classy closure.

Endings matter, and the sooner we realize this and respond accordingly the better off we'll be. Even ostensibly 'final' exits aren't really final, though (Funerals aren't the last time you find yourself thinking of someone, for instance). They are more properly viewed as transitions rather than finales. In some ways, every end is a beginning. It's the start of the period that follows the one you just concluded. Endings always seem to be followed by epilogues, which then serve as prologues themselves. Today, more than ever, everything seems to be cyclical, if not circular. This philosophical fatalism should not numb one to the importance of leaving a mark when you leave, though. Instead, it should embolden you to compose every conclusion with a coda, so that you don't leave up to chance the legacy you're about to create.

If Stephen Covey made famous the mantra to "begin with the end in mind" as one of his sacrosanct Seven Habits of Highly Effective People, I'd like to add (and perhaps memorialize) an eighth:"end with the beginning in mind". Keep an eye on your personal postscript. Practice legacy thinking, but start today. Don't just leave - depart. Don't just end - climax. Don't just stop - culminate. Conclude with a crescendo, not with a clunk. Take time to formulate your final impression.

I'll leave you to ponder these provocative words from Mary, Queen of Scots, perhaps the original 'Exit Strategist', as they sum up rather succinctly my sentiments and put an elegant, if figurative, period on this peroration:

"In my end is my beginning."

The End. (or is it?)

May 30, 2007

The Magnificent Mistake

When I was doing my MBA a number of years ago, much of the curriculum centered around the infamous case study. In preparation for our career as management professionals, we studied essentially two types of stories: those of how small companies became big, and how big companies acted small in somehow nimbly sidestepping strategic pitfalls.

I recall a few quite vividly. The Southwest Airlines success story was particularly memorable, as I was struck by certain anecdotes that reverberate in my mind to this day. CEO Herb Kelleher had seen the future of airline travel and zigged when everyone else zagged, it seemed. While large airlines were arrayed around hub and spoke routing systems, he flew point to point. While the flag carriers amassed impressive fleets filled with all types of aircraft, he flew only one. As the rest of the industry competed on perks and in-flight goodies, he stripped those out and focused like a laser on rapid turnaround and on-time departures for his flights (without food to clean up, it took less time to prepare the cabin for departure again). He even borrowed the operations expertise of Formula One pit crews to streamline his processes and shave critical minutes off the down-time planes spent on the ground.

He didn't do this all just to be different. These moves were designed to strip away cost and increase efficiency. Point to point travel eliminated the problem of missed connections and the need to re-route passengers. Maintaining a fleet of the same aircraft meant that he only needed to train and equip his repair crews for one model of plane and keep an inventory of fewer parts (since they were interchangeable on every one of his planes). Finally, by adopting F1 efficiencies his airline achieved the shortest turnaround speed in the business, reducing lost time on the ground and increasing the amount of (revenue-generating) flights possible. Within a few years, Kelleher flipped the airline model on its' head and built the regional, low-cost flight category that is the most profitable segment of the market today. To wit, last year the market capitalization of a low-cost European carrier, Ryanair, was at one point higher than that of venerable British Airways.

I remember thinking at the time that Southwest was a logical success to study, if not emulate, as many low-cost airlines have come to since (Ryanair, Easyjet and JetBlue, to name but three). I laughed privately at the idea of an analysis of TransWorld Airlines, the old TWA of our parents' generation. Wouldn't it have been fun to read instead about how that airline figuratively crashed and burned in the space of a few short years? But business school case studies are all about successes and what they can teach us, I quickly realized. Putative MBAs spend much of their first year reverse-engineering growth stories in the belief that they can identify the strategic tipping points for that particular corporation. In essence, we were taught to plumb those companies' trajectories in order to discover the power laws of superior business performance.

It made sense at the time. Knowing what I know now, however, I've come to wish that we had analyzed the likes of TWA instead. We should have focused on failures rather than studied successes.

I'm sure that this sounds a bit counter-intuitive, if not heretical, but hear me out. We have far more to learn from failure than we can glean from success.

For one, successes are often either spontaneous or serendipitous. In contrast, failures are frequently systematic. How many times have you committed the same mistake? It's a particularly cruel tenet of the human condition that we tend to make the same errors over and over. Whether it's something as innocuous as that persistent penchant for going to the net in tennis behind a weak serve, or more ominous activities such as sabotaging your career with antagonistic behaviour at the office, most of us are guilty of repeating both big and small miscues. Those who don't learn from history, they say, are condemned to repeat it; the same can be said of mistakes. To avoid the Sissyphean fate of constantly rolling our personal boulder up a hill only to have it fall down the other side, we owe it to ourselves to identify and ultimately excise that error-prone behaviour. It's more important to analyze and deconstruct errors (in order to avoid them) than try to replicate 'random' successes. As Esther Dyson pithily puts it, "always make new mistakes."

Another reason to focus on failure is that, in some senses, it's easier. It's very hard, if not impossible, to actually 'reverse-engineer' and reproduce winning performances, much as we'd like to. Failures, on the other hand, are simpler to understand.

Finally, it's almost fatally limiting. Focusing solely on successes while ignoring failures is a bit like trying to be profitable while only looking at the revenue side of the balance sheet and ignoring costs; one is, in essence, only attacking half of the problem.

My Dad and I have discussed this issue for many years. As he is in some ways the proto-Pop Philosopher (pun intended), it should come as no surprise that he actually devised a theory and taxonomy of errors (he also, apparently, has lots of time on his hands). His Grand Theory of Errors - to which I've come to subscribe - posits that people make bad decisions most of the time, and that by virtue of this error rate alone we should act vigilantly to avoid miscues. Moreover, he believes, as I do, that most of these mistakes are systematic, not spontaneous, and that there are essentially 4 broad types of errors: diagnostic (for example, a doctor diagnosing the wrong disease from a particular set of symptoms), prognostic (predicting the wrong outcome from an event), strategic (identifying the wrong course of action for a given problem), and executional (not implementing the right course of action).

This analytical approach to errors is actually borne out by a more intuitive understanding of everyday life. It's clear that people make mistakes all of the time. Psychologist Daniel Gilbert, author of Stumbling on Happiness, points out in his book that "the average American moves more than six times, changes jobs more than ten times, and marries more than once, which suggests that most of us are making more than a few poor choices."

We don't really need an author to tell us this is the case; all we have to do is look around our own private worlds to see the evidence. At home and at work, aren't we more commonly surrounded (and suffocated) by failure than inspired by success? Most marriages, sadly, end today in divorce. Over my professional career, I've learned as much, if not more, of what NOT to do than by witnessing positive role models of behaviour and excellence. Isn't that true of most of us? True greatness - in the corporate world as in life - is hard to come by, while mediocrity is rampant. Sadly, I've come into contact with many more execrable managers than excellent ones. As a result, I've tried to tap that far richer vein of flawed executives and the object counter-examples they provide. In life, many of the best lessons come not so much by emulating the rare air of excellence as by avoiding the regular, repeated and routine pattern of other people's errors.

The concept of what I have come to call the Magnificent Mistake is neither new nor original. The Romans understood it when they wrote about a Felix Culpa, which in Latin means a happy error. Millennia later, the expression 'sometimes you win by losing' comes to mind as another plank in the philosophical view that miscues have a sometimes hidden worth. Even more recently, Harvard Business Review posted a podcast extolling the virtues of the 'deliberate mistake' (HBR IdeaCast 4, June 7 2006). Just a short while ago, the venerable New York Times ran an op-ed entitled "The Power of Negative Thinking". In it, guest columnist Atul Gawande extols the virtue of "looking for, and sometimes expecting, failure." He recounts how surgeons at the much-maligned Walter Reed Army Medical Center were able to lower the death rate for wounded soldiers from 25% in the first Persian Gulf War to less than 10% today. How did they accomplish that feat? Not by studying 'successful' trauma centers abroad and transplanting or reverse-engineering their processes. Instead, they "actively looked for failures and how to overcome them." As the author concludes, "negative thinking is unquestionably painful. It involves finding and exposing your inadequacies. That's an unhealthy way to be in large parts of your life; but in running schools or business, in planning war ... negative thinking may be exactly what we need."

Unwittingly, I have come to embrace the mantra of negative thinking. One of the axioms that I live by is the following: learn from your mistakes, then forget about them. Like a Quarterback who just threw an interception, you need to realize why you made the miscue but not obsess over it on the next series of downs. In order to extract excellence out of an error in such a way, however, you need to study it first. Don't shrink away from facing your failures; instead, embrace them as the incredibly valuable learning experiences that they are. Turn those miscues into magnificent mistakes.

The next time you hear a success story, ignore it. Chances are that 'success' was more about chance than conscious choice; moreover, you are unlikely to be able to repeat the combination of moves that led to that fortuitous outcome. Rather, search out examples of massive, abject failures - either in real life or in your life - and try to deconstruct what went wrong and why. By uncovering the root causes of your errors, you can ensure that they won't likely be repeated. As you wean yourself off wrong decisions, you will actually edge ever closer to success - in a way that is more organic (as opposed to reverse-engineered), systematic (as opposed to spontaneous) and sustainable (as opposed to serendipitous).

The perfect definition of the cynical German concept of Schadenfreude comes from de la Rochefoucauld: "it's not enough that I succeed; my friends must also fail." Let me take poetic license and paraphrase it to capture my overarching view on mistakes: it's not necessary for us to succeed, so much as it is critical to avoid failure. Maneuvering through life without making mistakes may actually lead to extraordinary success, and steering clear of errors - especially systematic, repeated and avoidable ones - seems to constitute more than half the battle towards that goal. At the very least, we all ought to aim to break the cycle of recidivism and never make the same mistake. If we can stand to look at our failings coldly and analytically in the face, though, we can only benefit from the opportunity to exorcise the one demon we actually have control over - our own errors. So forget success, and focus on failure; you'll ultimately be glad - and better off - that you did.

February 28, 2007

The 7 Milestones of Maturity

When did all my friends become adults?

The question came to me the other day for no particular reason. Perhaps it was prompted by yet another (happy) announcement of a friend's new addition to the family, or the steak dinner with a mate in Manhattan two weeks ago where the conversation centered - as it mostly does these days - on couples, kids, and careers. Was it that long ago that our lives were consumed by markedly more adolescent activities, I wondered? Don't get me wrong. I don't miss the days when hooking up was more on our minds than, say, buckling up the kids in the back seat or optioning up our stake in the company. But when - exactly - did this cataclysmic change occur, and why didn't we throw a party to celebrate the momentous occasion?

Perhaps because it didn't happen so much as it's still happening, one stage at a time. Adulthood, I've come to believe, is - like life - a journey not a destination.

I used to think that the transition from adolescence to adulthood was accomplished through one seminal event - not unlike a metaphysical border crossing where one moment you're in one state and suddenly you're in the next. As I got older (notice that I didn't say 'old'), I came to realize that adulthood and adolescence are as much states of mind as they are concrete life stages. In both instances, the graduation from one to the other is more likely achieved in steps - milestones, if you will - that mark our development and maturation as individuals.

Defining 'adulthood' is difficult, not to mention subjective. I'm reminded of the parable of a judge who, when asked to define 'evil', responded: "I don't know what it is, but I recognize it when I see it." Adulthood is not like evil, but it is equally mercurial to define yet intrinsically familiar to all. We won't necessarily all agree about what constitutes being an adult, but perhaps we can find consensus about what it takes to get there. In pondering this question (I may have too much time on my hands, I know), I humbly propose the following 7 Milestones of Maturity.

(Why seven, you ask? Good question. For one, it felt right. For another, it sounded nice. Since Stephen Covey's Seven Habits of Highly Effectively People, 7 has been the ultimate lucky number for lists, so who am I to mess with success? Seriously, I came up with seven because these seven spoke to me ... )


1) Monogamy

The decision to be exclusive to a partner - especially for a male - is possibly the first concrete step an adolescent takes towards adulthood. For one, monogamy implies restriction and limitation of choice; the act of closing off possibilities is in and of itself a milestone of maturity. Selecting one person over another introduces you to the idea of opportunity costs - that every decision brings with it the realization that you have to give up something to have another. This is a hard but important lesson to children, heretofore accustomed to having their cake and eating it, too. What's more, monogamy also serves to reveal the significance of sacrifice - of postponing short-term pleasure today for greater benefits tomorrow. Finally, fidelity forces you to make a commitment to your partner, which is also a novel experience for most young people. Dedicating yourself to someone for an unspecified amount of time is, for many, their first exercise in trust, faith and future. In illustrating the concepts - and costs - of choice, sacrifice, and commitment, monogamy is a critical first gate to adult experiences.


2) Mortgage

If monogamy is about making a choice and committing to it, assuming a mortgage is all about taking on responsibility. Whether we fully realize it or not at the time, buying a property, and going into managed debt to do so, brings with it real world consequences. No longer are our lives - or more precisely, livelihoods - entirely our own. A bank owns a majority of our home, and holds a lean against all of our future earnings until we repay it back fully. Accepting and embracing this reality requires a measure of fiscal sanity and sobriety that is inconsistent with adolescence, where money conceivably grows on trees - or at least out of our parents' pockets. Moreover, a mortgage is a personal (as opposed to communal) commitment; this is not a burden one can share, absent a spouse. The responsibility of a mortgage serves to restrict - for many of us for the first time - the range of our possibilities. Life suddenly has limits, and a commitment made in such a way is not easily nor painlessly broken. While monogamy may have acquainted us with the concept of choices, mortgages present us with its' corollary - consequences. It is realizing the ramifications of our decisions that we add an important measure of maturity, and take another step towards 'seniority'.


3) Marriage

The act of getting married is, for many, the ultimate rite of passage. Perhaps more than any other milestone on this list, it is almost universally recognized as the moment when a father's daughter leaves the nest for good, and a mother's son takes on the responsibility of matrimony and, ostensibly, lifelong commitment to another. If the long, steady road to adulthood is characterized by conscious acts that limit choice and increase responsibility (such as monogamy and mortgages), the selection of a life partner is certainly the most ominous instance when we are faced with the proposition: "choose one item from this list, and one item only, forever".

One's selection of husband or wife is the single biggest decision one ever gets to make. Other determinations in life - such as choosing a certain college, or accepting a particular job - may in fact turn out to be the more influential inflection point in retrospect, after all is said and done. Our trajectories may be forever altered by a fateful decision to move to London on a whim, for example, as that choice may have the knock-on effect of placing you there when you meet your future wife, settle in that city for 30 years and raise your kids as Chelsea football fans. All of us can point to moments of extreme influence to our life's course that we didn't know at the time would be so dispositive; marriage, however, is not one of them. We know - or presume, at least - at the very outset that this will likely turn out to be the most critical choice we ever make. Marriage is pregnant with possibility and portent, yet paradoxically is the ultimate point of no return as well.

For that very reason marriage is a momentous milestone of maturity. The acts of choosing one person for life, consecrating that selection in ceremony in front of families and friends, and symbolically shedding the individualism inherent in singledom, all contribute to mark, in some senses, the end of the beginning. Marriage accelerates the onset of adulthood like no other event, and it should. This is not to suggest that one cannot be an adult without getting married, of course. Being a husband or wife to someone is neither a necessary nor sufficient condition to adulthood, unfortunately. Moreover, a church or civil ceremony is not needed, either, to confirm a commitment between two people. What remains true, however, is that marriage - in its literal or more allegorical sense - is for many the watershed moment between adolescence and adulthood.


4) Munchkins

I'm never been married, nor do I have any children. But those of my friends who have done one, then the other (the traditional but increasingly less fashionable sequence) describe each stage quite differently. Marriage, they say, is largely an evolution on coupled life. Having kids, in contrast, is a revolution.

It's easy to understand their point of view. Many of us have experienced living with a girlfriend, if not leading what essentially constitutes 'married life' with someone. Setting aside the sacrament of the wedding day, a young married couple's quotidian life is largely the same after the big day as before it. Sure, the stakes are higher and the stationary may have changed, but the fundamental dynamic of interaction has probably not altered one iota from pre to post matrimony. Not so when the munchkin arrives ...

It's a cliche, but children change everything. The entire family unit shifts from being about your own wants and needs to the child's. The two individuals who previously made up the couple now fuse into a 'family', with its seemingly sole and central task to protect, provide for and promote the well-being of their son or daughter. Jon and Jen fade from view, replaced by the more functional titles of Daddy and Mommy; Exit personal time and parties, enter parenthood.

Bringing another life into the world is probably the biggest responsibility one can ever assume. Monogamy was the first step on that road, but it can be undone without much consequence. Mortgages hold repercussions, but they threaten credit ratings, not defenseless kids. Marriage is a major statement of faith made to friends, family and especially the female with whom you're wedding, but alas we all know this doesn't make it impervious to the desire for do-overs. Marriage mulligans happen all the time. Munchkins, on the other hand, offer no such flexibility. Once you have a child, he or she is yours for life. In some ways, it's the ultimate caveat emptor.

It is in that irreversibility that becoming a parent accelerates our inexorable movement to maturity. For the first time in your life, you really can't change your mind. There is no option (pace adoption or abandonment) but to fulfill the implicit promise you've made to your offspring to raise them to the best of your ability. It will mean DVD nights instead of decadent and debaucherous soirees, red eyes instead of rest, sacrifice instead of self-orientation. Doing so will require, as my cousin Marcus once eloquently put it, turning 'me' into 'we'.


5) Monotony

The responsibilities of parenthood are huge, but the rewards seem to be greater still. When one graduates to the rank of parent, we undertake the biggest role of our lifetime - in deeds if not in significance. You can't help but be matured by the experience, but also mellowed by your new lifestyle. Part of the challenge in adapting to parenthood, it seems to me, is accepting, even embracing, the simpler pleasures that parent life brings. My friends now find joy in pushing their daughters on the swing, when they used to thrive on putting the moves on someone else's daughter. Saturday mornings in the park now rightfully take precedence over Saturday nights at the pub.

Moreover, my friends who have made this switch are genuinely happy. Sure, some grumble from time to time about missing some aspect of their formerly childless life, but all of them speak glowingly, evocatively and poignantly of the pleasure of coming home to their kids at the end of a long day. Play time to bath time, then bed time, is the new triple crown of contentment, even if these moments are largely routine and repetitive to the outside eye.

Let's be honest: parent life is monotonous. But it's a marvelous monotony. Bringing your kids up is a blur of boring but beautiful moments: reading them stories, putting their snow pants on, carrying them to bed. Those early memories are joined by equally mundane, but no less meaningful, events: their first words, their first day at school, their first date. In the proverbial blink of an eye, twenty years of tiny steps forward - tender and wonderful for you, tedious and without significance for others - have come and gone. In this life-stage, time simultaneously slows down and speeds up. You experience seminal, singular and signature events much less frequently (that crazy weekend in St. Tropez!), and the sheer pace of change of your life comes to a crawl. On the flip side, the regular - and regulated - rhythm of parenthood paradoxically makes the years fly by.

One has to mature before making monotony your friend. Much like quicksand, If you struggle against it you will suffocate; however, if you accept it warmly, you will be enveloped by its embrace. Maturity allows you to make this counter-intuitive leap of faith.


6) Midlife

At a certain point in time, you realize that you have more yesterdays than tomorrows. For some, that epiphany comes crashing through on a significant birthday - say when a man hits the big 4-oh. For others, it occurs at one of life's more natural inflection points, such as when your daughter gets married or your son gives you grandchildren. Whatever the trigger, some form of trauma will follow. Why? Because the idea that one has reached the turn in our life journey is among the most sobering thoughts that can cross the transom of our mind. Accepting that fact forces us to acknowledge that we've begun the home stretch of our existence. It means coming to grips with the concomitant decline in our capacities. It requires us to shelve some of our grander misconceptions about ourselves and what we would accomplish. In essence, midlife confronts us with the chilling calculus that we've reached the beginning of the end.

Of course, one can choose to look at the glass half-full, and regard half-time with hope as much as apprehension. I commend the people who choose the optimist's path, and plan to be among them when I hear that whistle myself. Even if you do manage to summon that measure of sagacity however, the act can't help but age you. Either the thought of fewer tomorrows terrifies you, in which case one frantically fumbles for one last gasp of the future. Alternatively, one can serenely succumb to seniority, and accept that one's time is coming closer to the end. Regardless of the approach, midlife matures you in a subtle but unmistakable manner. It also foreshadows the penultimate phase of our life.


7) Mortality

I believe that we experience two deaths in life. The first comes with the final call on our 'childhood', when our last surviving parent passes. In that moment, we become parentless, and while it's ridiculous to compare the tragedy of a forty year-old orphan to that of a four year-old, the effect is doubtlessly still seismic on the psyche. At our core, we are all still someone's kids - even if we have some of our own. My aunt Rhea, a mother and grandmother, still calls her younger brother - my 65 year old Dad - 'le petit', and frets about how he's not 'used' to drinking wine. My Mom's eyes still well up when she thinks of her father, gone almost two decades now, and will sometimes refer to him in recollected conversations as Daddy. This is normal, and natural. In some important ways, one doesn't stop being a child; the heart is hardwired from birth to harken back to that parental bond with fondness. Losing that connection is like losing a limb: the pain may fade, but one's spirit is forever amputated by the loss.

The death of our parents, taken by itself, would mark anyone's life as a milestone. However, the onset of their mortality also serves to presage our own. The passing of the past generation pushes us to death's front of the line. We suddenly become the elder statesmen of the family, the torch of leadership being thrown to us to hold high. This new role imbues us with responsibility, and forces us to look at life from a different perspective. One can't take health, and life, for granted from that point onwards. The future is irrevocably fraught with preoccupations about our 'second' death, the one that will inevitably come to visit us personally.

Facing our ultimate end must be the most maturing moment of one's life, and it's fitting that the most significant step towards adulthood comes - literally and figuratively - last. But I imagine that for those days, months or years when we are keenly aware of our mortality but not yet upon it, life is sweeter, richer and more rewarding than at another point in time. That lesson - that life is fragile, fleeting and fabulous all at once - is the most important one of all; what a shame that too many of us realize it far too late.


Maturity is an elusive concept. For some it's relative, for others an absolute. For me, it represents the crossing of certain milestones which I've laid out above. Monogamy, Mortgage, Marriage, Munchkins, Monotony, Midlife and Mortality are the 7 gates towards that higher consciousness, the major signposts on our road to adulthood. With the passage of each one, we add a layer of self-awareness, another ring to our personal tree of knowledge.

While I generally regard these events to occur in this chronological order, they need not necessarily. Sadly, all too often marriage precedes monogamy and not vice-versa; munchkins can happily come before matrimony with great benefit to all involved. Others might suggest more appropriate - or indeed more personal - milestones that marked them profoundly. My list is not intended to be either definitive or exhaustive. Rather, it represents my first cut at cracking the code of adulthood, at charting the moments when we stopped being kids and started our path to personal responsibility, parenthood and perishability. In the final analysis, we're all entitled to our own view of what shapes or shaped our development from adolescence to adulthood. The actual stages matter less than the lessons learned, and the wisdom, perspective and self-knowledge gained from those experiences.

When did my friends all become adults? I'm not certain that they have, but I'm sure they're on their way.

October 25, 2006

Thinking seriously about not-so-serious things

Socrates may have invented philosophy when he famously declared that "the unexamined life is not worth living."

I'm not a philosopher, nor do I really aspire to be one - at least not in the classic sense of the term. The ancient Philosophers addressed such weighty matters as the existence of God, the meaning of Truth and the nature of Ethics. People still debate those fundamental issues today, and they should. On some level, however, those questions have been 'asked and answered' many times over, as the legal expression goes.

Ludwig Wittengenstein - who was a real Philosopher - perhaps described his profession best when he remarked that "Philosophy is not a theory but an activity". Pop culture commentator Chuck Klosterman, who is not a real philosopher, could have been describing what I see as the purview of this place when he wrote in his inimicably irreverent way about "philosophy for shallow people." Pop Philosophy, for me, lies somewhere in between these two propositions.

The salons of Classical Philosophy tackled the profound and the past. Pop Philosophy will be a forum to discuss the prosaic and the present.

I want to turn the pop philosopher's lens less on the issues that matter, and more on the subjects than matter most - for good or for ill - in many people's minds. Socrates' dictum still holds true, but isn't there a virtue in examining some of the more mundane aspects of life as well as its great, central questions?

I believe there is. Contemporary society contains innumerable topics which beg for considered discussion, from the changing nature of relationships in a post-modern age to the impact of technology on the minds and manners of teenagers today. These matters deserve to be dissected and debated, if only because they preoccupy people today more than the great imponderable ones do. I'm fascinated by issues arising from media, politics, modernity, men and women, psychology, sociology and society, to name but a few. I hope to use this space to modestly propose my commentaries and middlebrow musings on those topics - the prosaic preoccupations of this pop philosopher.

Philosophy, in this sense, is certainly more an avocation than a vocation for me. I like to examine life, propose theories, engage and joust in vigorous, thought-provoking conversation. Sometimes I turn my curiosity on serious issues. More often, I think perhaps a little too deeply on slightly more frivolous questions. Perhaps there are some of you out there a bit like me. I suspect there are.

This, then, is a place for 'philosophy' for the rest of us. Join me in thinking seriously about not-so-serious things ...