Last month, I wrote about why Second Life failed so I didn’t have to write about why Second Life failed. I mean, that post wasn’t about reasons for failure, it was about the fact of failure. My thought was that there are many people who simply assume Second Life failed, and they’re wrong, and there are many who will passionately argue that Second Life has succeeded … and they’re wrong too. Failure can only be judged by the ones who were trying to succeed.

It would be safer for me to say that failure is a matter of perspective, for surely failure passes through the same lens as beauty in the eye of the beholder. I do understand that many SL Residents were on their own journeys, and so of course they are their own best judges of the success of those journeys. But it would be an artful evasion to claim that any of those journeys, or even all of them together, constitute the sum total equation for the success of Second Life. We were trying to do something more – or at least, something else – and we failed. (Of course, I’m talking about the team and the company that I knew, years ago. The team there today is on their own journey, which I know next to nothing about.)

So if I’m willing to be this myopic and insular about judging failure, you can bet I’d be just as parochial in reviewing the reasons. I’ve seen and heard a lot of speculation that I don’t agree with: poor strategy, worse execution; lack of focus, misplaced focus; poor technology, doomed architecture; dumb marketing, uncontrollable PR; niche market, bizarre customers; crazy culture, undisciplined development; bad hiring, bad management; feckless board, dominating board, ignorant board. I’ve heard it all, and while there may be a grain of something like truth here and there, none of these things holds real explanatory power as a reason for why Second Life failed.

We failed as people. We failed as a team. Our failure was intensely personal, particular to each person involved, and ruinous to the overall team.

I’m going to switch now from “we” to “I” but I want to be really clear about why. We Lindens were all in it together, and there is a broad sense in which all credit and blame goes to all of us … but not in this post. Here, I’m talking about maybe half a dozen people, and so it would be too much of a personal attack for me to try to describe the failures of anyone other than myself. I’m willing to attack myself in this forum, but not my former colleagues, all of whom I still respect and a few of whom I love like my own family. But I want you to remember the “we” because otherwise the rest of this post is going to seem incredibly egocentric: there’s a certain kind of self-blame that’s really self-aggrandizement, and though I regard my own failures as critical, even the most deluded version of the story couldn’t claim it was all about me.

So. I failed as a person. I failed the team. I was responsible for many elements of our strategy, execution, culture and management, and those decisions aren’t the ones I regret. What I regret, to the extent that I’m capable of regretting such a rich learning experience for me, is giving up. I don’t mean at the end, when I was tired and disillusioned and looking around at a company I didn’t recognize and a future I didn’t want to live. A lot earlier than that, I gave up on people that we needed, people who were flawed and fragile but necessary. I let people fail, I let people go, I let people hide in their illusions and fears, I let them give up because I’d already given up.

The irony was, when I joined the company, I was supposed to be an experienced hand that would bring some sanity to a crazy world. But I indulged my own worst instincts - throughout the craziest times, when I could’ve done the most good, I just brought more crazy. I was having fun, but I chose my own twisted growth over a higher goal, and at times I was just plain mean or selfish or drunk. I really wasn’t ready for the opportunity that Linden Lab presented to me. I really wasn’t the guy I should’ve been when I got there; I didn’t know what I needed to know until I left.

Too many of the key leaders at the Lab were working through similarly damaging personal limitations. You might ask whether this really points to a failure in culture or hiring or leadership, and that would be a fair question. It’s true that Linden had a way of hiring certain kinds of people and forcing them to confront their own deepest flaws – but I think that’s beautiful, a feature not a bug. What we needed was one or more or all of us to conquer our flaws, to enable the entire team to rise above the limitations of each of us. But none of us defeated our own demons, and so all of us perished.

I’ve been gone from Linden Lab for over two and a half years, and still my failure haunts me. The last day of the year is always a good moment to come to terms with the passage of time, and this New Year’s Eve I’ve decided I should finally accept the fact that I’m never going to let it go. I’ll try to reach peace through the zen realization that peace is unattainable.

Praise follows death like the glowing debris that trails a comet, and the writing in the sky says that Jobs was the greatest CEO ever. A few muted voices remember that he was famously harsh to work with, but this is universally regarded as an entirely justified mania for perfection. Considering his accomplishments, it seems almost irrelevant that he denied the obligations of paternity for one child, and consciously decided that his children should know him through biography rather than time spent with him, even – or especially – in the final stretch towards death, when the remaining time must be remorselessly allotted like oxygen in a sealed room.

This isn’t criticism of a great man. It’s a reminder that many of us would willingly make the same choices, were such greatness within our reach.

We say it’s not so, and try to believe it. We encourage each other to remember family, remember health, remember that a life of striving includes the quest to achieve a full and humane life through our work. But the life of Jobs is the story of his jobs, of his one true job: making a dent in the universe through the creation of products that become a part of our lives. For his success in that, we forgive and excuse his personality defects. We cannot blame a man for failing to uphold principles that we would throw aside ourselves if only we could be assured that the universe was malleable to our touch.

Saying that “you are not your job“ is a comfort; it alleviates the cognitive dissonance between your self-image and the productive economic output you contribute to the world. The lessons of Steve Jobs deny that comfort; his strongest exhortations insist that you are all about the things you make for the world – not for yourself, not for your hobbies or leisure, not even for your family and certainly not your friends if you have any. You have to do great work, never settle, remember that each day could be your last, don’t waste time living someone else’s life.

There is no obligation to community, family or friendship in these words – though strangely, there is an overwhelming commitment to society in the desire to dent the universe, for this is not a universe of cold cosmological phenomena, it’s a universe of people, and his ambition is all about changing how people live. For Jobs, if this ambition involved sacrifices of a more universal personal nature, there is no question that it was worth it. It was worth it for him, and his efforts were certainly worth it for us.

It’s touching to see the determination with which Jobs’ sayings are repeated in the wake of his death. But the message of his most appealing words isn’t quite the message of his life. He told us to follow our hearts, to trust our intuitions, to ask ourselves if our plan for this day is how we’d want to spend our last. But those are not goals, they are only beautiful means to an uncompromising end. The goal of Jobs was to be insanely great in a world-changing way. That’s the hard part of the message to understand. All of us can hope to understand what is in our own hearts, and can hope to have the courage to follow it. Almost no one alive has a realistic ambition to change the world – what many of us think of as world changing is merely interesting, hopefully entertaining, and possibly enriching.

My wife was screaming about something on TV, but I couldn’t get out of bed. My head was heavy with flu, the sounds couldn’t penetrate the haze of mucus and sick. We had moved to San Francisco from New York two and a half years ago. I still missed The City, still missed the feeling of living in the giant beating heart of the world, a heart that pounded with the rhythm of my own. I grew up in a Jersey suburb 45 minutes from the Holland Tunnel. One of the few reliable moments of magic in my youth was the anticipation of a trip to NYC, which peaked the moment the towers came into view around a bend in the turnpike. The towers were monumental, elemental, permanent – I could no more imagine the city without them than the sky without the sun.

But a plane had just crashed into one of them. Surely an accident, I’ll read about it tomorrow when I’m over this flu. My wife is still yelling, and I bury my head deeper into the pillow and ignore the looming reality. And then the second plane into the second tower. Now even my virus-addled mind has enough strength to put together the picture, or maybe, isn’t strong enough to construct an alternate interpretation. It’s not an accident. The towers are coming down, the world is ending. I finally roll out of bed with just enough momentum to come to rest in front of the TV, where I sit slackjawed for the next two days, watching the grim images pile up, the towers falling, bodies falling, people running, debris and dust and ineffable dismay, the pictures and posters of the lost.

A call from the office asks when I’m coming in, gentle but insistent. I don’t know, it doesn’t matter, I’d already decided I couldn’t do this work anymore, before that day. And now, these people, they couldn’t understand, with their happy California sunshine and bleeding optimism. They couldn’t understand what it meant to turn a corner of anticipation and be greeted only by empty sky. I wanted nothing of them. I wanted to go back, back home, back East. Now that trip could seem like a run to a ravaged home rather than a run from a broken promise.

But that was a problem; the excuse was too easy and at the same time, insurmountable. I could tell myself that I was going home to help, but no one could look at that smouldering hole in the earth and believe in selfish lies. I wasn’t running to help, I was running away, away from expectations, dissatisfactions, disappointments. The loss of September 11 deserved better than to serve as easy explanation.

Four months later, I had quit the firm but hadn’t left the Bay Area. My life had become unmoored from a certain stable career path, into a meandering decade of exploration and discovery, of triumph and loss and the subtle closeness of the two, of searching for monuments to fill the hole in the sky.

I’m not too flexible about the term, unlike those who believe in four types of entrepreneurs. I think an entrepreneur makes a for-profit business that didn’t exist before, without the benefit of existing infrastructure. That rules out what some call social entrepreneurship, because working for nonprofit good is too different than pursuit of viable commercial enterprise. And it rules out corporate entrepreneurship, because starting a new division or business line for an existing company is very different from starting a company from a cocktail napkin.

I said different – I didn’t say harder or more admirable. The numbers probably say that social and corporate efforts are harder, as there seem to be more new companies than there are new social efforts or successful businesses started within large companies.

I’ll differentiate some more: Although I’d include both the fruit stand owner and the tech company titan within my view of entrepreneurs, I don’t think they’re the same in most ways, even at their respective starts. Fruit stands aim for some daily living, selling a well-understood product, within a social infrastructure that understands and supports the concept of buying and eating fruit. The most extreme tech founder dreams of all the money imaginable, with a product that initially seems bizarre, with no apparent revenue model, distribution channel, or plausible customer interest. Although these two kinds of people have something in common, they have a lot more differences. So “entrepreneur” isn’t a binary label – it’s possible for one entrepreneur to be more entrepreneurial than another. Labels are most useful when we use them to distinguish and measure concepts. I don’t like seeing a meaningful word diluted to appease egos or ease conversation.

Because the company I work for now is fairly well known, I should doubly-triply-quadruply emphasize that this is all my opinion, and moreover it’s my opinion about me. I can believe that for many entrepreneurs, coming to Google doesn’t mean that your days as an entrepreneur are over – those entrepreneurs are more entrepreneurial than I ever was, which I’ve admitted isn’t a high bar.

And although I’m still a startup guy at heart, I can believe that Google can in important ways return to its startup roots, even though I’m naturally inclined to disbelieve that a large company can have the “energy, pace and soul of a startup.” But I’d say that you have to measure the energy and pace in the context of the scale of the ambition. People who think that Google is slow or that the competition is anything other than the unknown future are probably underestimating the enormous opportunity remaining in the information economy.

Ah, but that last bit, the “soul” of a startup … what does that even mean? That’s tricky, and probably the topic of another post.

To be fair, 7 out of the 9 jobs were really a single job to me:  learning how to be an entrepreneur in Silicon Valley.  I’ve learned some good lessons, and although I didn’t achieve the outcomes I aimed for, I’m not sad about the experiences of the last dozen years.  How can I be sad?  After all, everything I’ve learned only gives me fodder for another book . . .

I’m going to title this book The Age of Illusions.  If I can do this properly, I’ll be working on three intertwining themes:

Illusions of youth.  In your 20s and 30s, you’re at the peak of your powers, or at least in the prime of your unrestrained ambitions.  You’re out of childhood, with the energy of youth and none of the detritus of age. Maybe I’m taking turning 40 too seriously, but I mean this as a celebration, not as resignation:  If you haven’t crashed into a wall by the time you’re 40, you’re doing it wrong.  If you haven’t learned your limitations the hard way, you wasted the resilience of youth.

Illusions of enterprise.  My core work experience of the last decade was at a startup that could be considered the most successful failure of the Internet age.  Changing the world is hard, and most of the people who say they’re doing it aren’t even really trying.  At Linden Lab, we weren’t just trying to change the world, we were trying to recreate it in a better image.  We didn’t get where we wanted to be.  Some say that failure is a badge of honor, but I can only agree with that sentiment where the goal was so great that even trying is reasonably regarded as lunacy.

Illusions of empire.  The first decade of this millenium was a rollicking cascade of unreal events.  The background of all of our tales of this decade may be the end of the American empire.  It’s a story too large for me to tell with my limited skills, but somehow I have to acknowledge that I’m fingerpainting on the canvas of epochal history.

Folks, don’t hold your breath:  I estimate that it’ll take me almost six years to write this book.  I think I’ll only average around a page per week, and I’m aiming for at least 300 pages.  Ah well – it’s nice to have a slot filled for those annual resolutions all the way through 2016.

Happy New Year!

The first hundred times or so I heard “You gotta love yourself,” I thought:  ”No I don’t.  You don’t tell me what I gotta do.”  Then I began to ask “Why?” and I finally heard a reason that made some sense to me.

Loving yourself requires accepting your faults, and accepting your faults gives you more options for how to react in any situation. That’s a quantifiable rationale, testable both in theory and in practice – and as a bonus the measurement also gives guidance on whether you’ve taken self-love too far.  Here’s a simplified example:

Let’s say you receive a bad outcome that is at least partially based on something you did.  Here is a count of your options for how to react -

• Self-hate: Since you will blame yourself to the exclusion of other factors, you only have two choices: (1) rigorously apply yourself to skills improvement, even though it’s likely that no amount of improvement would have given a different result, or (2) drink enough to obliterate your self-hating identity.
• Self-love, of the over-indulgent kind: Certainly the outcome wasn’t your fault, so your choices are (1) smugly wait for the next chance for the world the properly join you in your love of you, or (1) ignore any possible evidence that your actions contributed to failure.  Yes, those are numbered the same because they are the same.
• Goldilocks self-love, the kind where you love yourself just right: You can be clear-eyed about what really happened.  You can apply yourself to change, you can recognize the factors that were out of your control, you can put the outcome out of your mind in good humor and good health.  You can do all of these things and you probably will.

Basically, loving yourself just right gives you all of the options of the other two conditions, with the additional optionality that comes from not being ideologically compelled to react in a way that is harmful or indulgent.  You gotta love yourself just right, because the alternatives are suboptimal.  Sure, that’s a particularly dry and uninspiring way to put it, but what can I tell ya, I love this way because it’s mine.

So when I tell you that “We are all authors of our own lives” – I don’t mean to trumpet the primacy of your own role in shaping your destiny, even though that’s a useful bit of affirmation.  I mean for you to think about the process of authorship, the task of writing a story from both facts and fantasy over many years.

Whether you realize it or not, you carry around a story in your head about who you are.  You draft, write and rewrite your internal explanation of the kind of person you are, the character you have, the things you will and will not do.  This work of self-conception is the greatest novel ever written, or at least it should be for you.

Early on, very little of your story is constrained by actual events, since you’re too young to have been in all of the situations you anticipate that you’ll experience.  You have the freedom of your imagination, and you write your story based on what you’ve seen in your family, friends and others in life and fiction.  You’ll imagine, for example, that you’re just like your dad, or not at all like your mom, or a bit like Al Pacino in Scarface, or a lot like Lindsey Lohan on Twitter.  Then as you grow older, your story becomes a lot more personalized to you, based more on your experiences and less on your aspirations.

You have years, maybe decades, to write your beautiful story of who you are, and then something happens. It may be one traumatic event, or a series of little events that are only clearly related in retrospect – but it’s something that happens that doesn’t fit into the story you’ve been spending your whole life on to that point. You thought you were a good guy, but then you did something that was undeniably bad.  You thought you were an honest woman, but you then you’re confronted with your repeated pattern of little lies.

You race back to your story, flipping madly through the pages of the Book of You.  Who is this person in this story?  Who is this stranger living this life, holding this tattered book in shaky hands?  Can these possibly be the same person?  Faced with this disconnect between your life’s work as an author, and the actual facts of your life, you have two choices:  You can rewrite your story to fit the facts, or you can rewrite the facts to fit your story.

Perhaps this is the point where I’m supposed to say that the facts are sacrosanct, and your job as an author is to fit the story to the facts.  But no:  I said you were an author, I didn’t say you were a journalist, and I can’t presume to tell you what kind of story you’re writing. You have to make the choice that satisfies your art as the author of your own life.

Maybe you’ll just choose straightforward reporting, because you do want to match the story exactly to the facts.  Or you might be like Mark Twain, writing fiction truer than fact; or Jack Kerouac, making facts into truthful fiction.  I wouldn’t advise going full-on into fantasy, with complete disregard for any events from reality.  Not because it’s wrong, but because all of the best fantasies are rooted in something real.  As an author, you’re an artist, and art without truth is trivial, and you don’t want your life to be trivial.

Finally, be aware that we are all engaged in these acts of authorship.  You can get very far in understanding other people if you think about the story they’ve written in their own heads, and observe what they do with facts that don’t match the story.

• To each his own.
• One man’s trash is another man’s treasure.
• It’s apples and oranges.
• It’s all good.

But I don’t like these easy sayings, because it’s not all good – what I’m trying to get across is hard to understand and hard to live, and has little relation to the soft-headed permissiveness implied in those easy clichés.

This happens to be the only life lesson that I actually learned in a classroom as the direct subject of a lecture, and this lecture justified a year of college tuition all on its own.  ”Incommensurability” is a simple enough concept – it just means that there are things that do not share a common standard of measurement, like the proverbial apples and oranges.

Apples aren’t oranges, could anything be simpler?  But it struck me as a thunderbolt to understand how this affects the search for the good life.  I’d always thought that the task of living a good life was largely about understanding the difference between good and bad.  Maybe I’ve got a moral compass that doesn’t have a reliable fix on true north, but that difference hasn’t always been obvious to me.

As life goes on, it has become easier to tell the difference between good and bad – or rather, it’s become harder to delude myself into believing that that there isn’t a difference or that I can’t see it.  Now I can see that choosing between good and bad was simply the entry-level exam for the good life.  The hard task of living a good life is to choose among things that are good that can’t be compared with one another.

Choosing among incommensurable goods is sad because you are by definition choosing not to do things that are good.  You know that the choices you make will sacrifice things that you would also like to have.  The good things you choose may be vastly outnumbered by the good things that you gave up.  And yet, your choices are a triumph that isn’t second-best to any other set of choices.

One of the great things about understanding this is that you won’t be limited, as many people are, to only having friends who have generally made the same moral choices that you have.  You’ll be able to see that others chose among the same set of incommensurable goods that you did, and even if they made different choices, they are still people who share a common sense of good with you.

Just to make sure that this isn’t interpreted with a mushy morality that I actually despise:  This doesn’t mean that everything and everyone is all good, it doesn’t mean that any set of choices is as good as any other, it doesn’t mean that you can be friends with anyone, it doesn’t mean that there’s no difference between good and bad.  It just means that many goods are incommensurable, and you should think carefully about what that means as you make your choices for a good life.

Now, maybe you’ve never had that superpower smartness – that’s also a good thing.  Because that means you may have had a chance to observe really smart people at the height of their powers, glorying in their intelligence and in love with their knowledge of the world.  And you may have achieved a striking insight that is beyond the understanding of many smart people, a special insight that seems to routinely escape the most massive intellect.  This insight is painfully obvious to everyone else:  Smart people suck.

Intelligence is a largely genetic trait that is also substantially influenced by environment and circumstance.  In this way, it’s a lot like height.  So before we talk more about smart people, let’s talk about tall people for a bit.  Tall people get some pretty nice prizes from winning the genetic lottery.  Tall people make more money and find more attractive mates.  Height provides some advantage in many sports, and is a virtual requirement for success in some.  So being tall is overall a good thing.

And here’s the point:  Tall people know they’re lucky.  They know that they have an advantage in life that others don’t have, and they know that they did very little to secure this advantage.  They also know that to maximize their advantage, they have to add their own efforts – if they want to make the team, get the job, get the girl or guy – they have to eat right, work out, study hard, take care of their skin, hair and personality.

Not so with smart people.  Even though smart people are generally aware of the genetic, environmental and circumstantial contributions to their intelligence, they rarely think of these as luck.  Instead, smart people tend to think they’re better than other people because they’re smart, not because they’re lucky.  And smart people often think that the world owes them something merely for being smart, as opposed to being diligent, sincere or personable.  Smart people think that being smart should be enough, where tall people know that being tall is just a start.

The problem with intelligence is that it does, to some extent, make up for the absence of other admirable qualities.  Smart people can get the same or better results as others even when they work less, care less and cooperate less.  Intelligence is a crutch. And a smart person who leans on that crutch to the detriment of other important traits can become a monstrously malformed person.  Intelligence is used worst when it’s used as a crutch to escape the hard work of being human.

People who give advice usually believe that some particular experience has given them an authority that others might want to regard seriously.  That isn’t the case with me:  although I’ve had many instructive experiences, I don’t think my historical record is what makes me qualified to give advice, and I don’t think everyone should take my advice seriously.  Instead, what makes me qualified to give advice is that I am spectacularly bad at taking it.

I’ve had the great good fortune of having many wise people tell me many wise things, and my usual practice is to squander that good fortune by refusing to take even the best advice at face value.  Instead, I question, I doubt, I criticize, I experiment, I delve down dark alleyways of impulse and instinct – and in the end I painfully find that I should have listened to the wisdom of my betters.

The problem with wise advice is that you have to have wisdom to appreciate it beforehand.  And if you had the requisite wisdom in the first place, you wouldn’t need the advice so badly.  I never understand good advice until I’ve had the opportunity to fail to follow it.  Only by living the bad consequences first-hand can I understand the underpinning that upholds solid wisdom.

Let’s hope that my misfortune is your bounty in these next four posts.

1. Intelligence is a crutch.
2. Many goods are incommensurable.
3. We are all authors of our own lives.
4. You gotta love yourself.

Of course, none of this stops me from spouting on and on about how to manage your early career.  One set piece I often relate is that there are only four personal characteristics that can advance your success: Intelligence, Diligence, Personality and Mentality.  Many people get very far early on with just one of these characteristics, and so they begin to believe that this characteristic is the most important or even the only important one.  When they begin to fail, they double down on the characteristic that they believe in, which only deepens their failure.

To understand why this is true, consider the other side of this same advice, which applies to people just learning how to manage teams.  There are few things as destructive to a team as the person who has one of the characteristics in spades, but lacks any useful amount of the others.  The brilliant genius who can’t get along with others, the guy who works terribly hard but always on the wrong things, the “people person” who plays politics rather than solves problems, the hard charger who plays to win at any cost – these are all different forms of the same cancer, and they must be excised from the team as soon as they are identified.

So development of the four characteristics rules both sides of the management divide.  And on either side, you have to have great strength in more than one of these characteristics, and you have to understand how all of them contribute to success.

The first volley in the debate may have encapsulated the entirety of its substance.  Doris Lessing, in accepting the 2007 Nobel Prize in Literature, asked:

How will our lives, our way of thinking, be changed by this Internet, which has seduced a whole generation with its inanities so that even quite reasonable people will confess that once they are hooked, it is hard to cut free . . .

As the vanguard and finest defender of the cutting edge, TechCrunch boiled down Lessing’s careful rumination into “the Internet makes us dumb,” and crafted the exquisitely reasoned rejoinder:  ”Meh.“

The following year, Nicholas Carr kicked the debate into high gear by asking, “Is Google Making Us Stupid?”  Carr noticed that after years of using the Internet as his main source of information, he’d become less able to apply sustained concentration to reading lengthy articles and books.  He found anecdotes and early research that suggested that the constant browsing and skimming of information so typical of Internet reading exercised the brain in a different (arguably more shallow) way than the “deep” reading of books.

Carr himself noted people often feared that new technologies would limit human progress, without being able to imagine the ways those technologies would expand our knowledge and further progress:  Socrates complained that writing allowed people to cease exercising their memories; the Gutenberg press was once decried as a tool of intellectual laziness.

Nevertheless, now two years later, Carr has more firmly concluded that the Internet has rewired our brains to crave new and trivial information, at the expense of deep analysis and critical thinking.  From Carr’s original article through the recent publication of his book The Shallows, the question has become a matter of popular, academic and public concern. TechCrunch continued its proud tradition in this debate, dismissing Carr’s question as merely his “axe to grind.”

This is the kind of debate that can go on for a very long time, because the titular question is ironically stupid, though in a clever, link-baiting, book-selling way.  Knowing what “stupid” is requires defining “intelligence,” which is a concept so malleable that anyone who isn’t stupid (and many who are) can argue without end that the other side is being stupid (or at least, isn’t being smart about what stupid is).  Carr is not actually stupid, and I think his question isn’t designed to be answered.

However, there is one way that the Internet has broken a chain that began thousands of years ago:  for the first time since the invention of writing, good writing is no longer crucial to the transmission of knowledge.

When information is available everywhere from anyone at little cost, the power of good writing is diminished as a vehicle for knowledge.  Think of it this way:  Was Plato the smartest of Socrates’ students, or was he merely the best writer?  If all of the philosophers of Ancient Greece had blogs and Twitter, would we even know who Plato was?  Would we hold any single one of them in such high regard?  I think not.  And yet, I think we would still have the full breadth and depth of Greek philosophy in our human knowledge base.

The constraints of physical media, from stone tablets to wood pulp, meant that only the best writing could survive the culling of editors, libraries, wars and time.  So only good writers could pass their knowledge through the generations.  Now that anyone can publish and everything is stored forever and can be found easily, anyone can transmit knowledge so long as it is relevant, and regardless of whether it is the best-written statement of the concept.  If that were the case in Socrates’ time, we might have heard about the Cave from any one of his students – or maybe a dozen of them would have tweeted about it simultaneously.  So we would know the allegory of the cave without knowing or caring who the author was.

This thought must torture good writers everywhere, including Nick Carr, so maybe that’s what his question is really about.  The Internet isn’t making us stupid, and to be precise, it isn’t really making us bad writers.  But it does make good writing matter less.  Oh sure, you can argue that there’s an art to a good blog post or tweet or status update.  But this isn’t like defining “stupid” – there really is a meaningful standard of good writing that people of taste and discernment agree upon, and people who argue otherwise are stupid, for lack of a better word.

The highest challenge in writing – as an act and art separate from the communication of information – is a lengthy work that commands sustained interest and concentration from a reader who enters the writer’s world, rather than the other way around.  The Internet is a reader’s world, and that probably does make readers smarter.  But it makes good writing for writing’s sake matter less, so people who otherwise would have had to be good writers to communicate their ideas can now just get their ideas out in 140 characters.  Is that a bad thing?

I’ve been in this cave my whole life, but now I’m free. OMG, everything I thought was real was only shadows on the wall!! via @Socrates

Privileged access is a weighty philosophical matter that is popularly stated as a question of whether a person has special access to his or her own thoughts that other people do not have.  An intuitive answer is, “Of course I know my own thoughts better than anyone else does!”  But this isn’t simply a question of what you are thinking at any given moment; it’s about whether what you think about yourself is more accurate than what any other people think about you.

Here’s a thought experiment:  Do you know what you would do if you found a paper bag containing $10,000?  What amounts would lead to a different decision, and why?

I think I would keep it. I would rationalize this action (which is probably illegal) by noting that there is almost never a legitimate reason to carry around that much in cash in a paper bag – this is almost certainly drug dealer money, and why should I give drug dealers a chance to recover it?

I would definitely keep, say, five dollars – maybe I would give it to a panhandler, maybe I would buy a sandwich, but I wouldn’t leave it on the ground.  Unless someone nearby might have dropped it, I wouldn’t consider trying to find the owner, or turning the money in to the police – no one will ever come to claim $5.  In contrast, if I found $100,000, I would definitely turn it in.  When that much money gets lost, someone will look for it hard enough to make me uncomfortable – I don’t want to end up in jail, or worse, facing the guys who stole this money before I did (these guys would give up on $10K, but they would seek $100K with violent diligence).  Even more complicated, I think that I would turn in $5000.  There are plenty of legitimate reasons that a law-abiding person could be carrying that amount around, and I would want that person to have every opportunity to recover that money.

So in short, I think I would make a risk and fairness assessment, and act with a mixture of pragmatism and greed.  (Don’t get me wrong – none of this is what I want to do.  I want to believe that I would ignore any amount too small to turn in, and turn in any amount too large to ignore.  But I’m not so self-deluded to think that I always live up to my ideal self-image.)

This thought experiment has one more part:  If you polled a dozen people who know you best on the same questions, what would they say you would do?  Who is likelier to be right, them or you?

I think the majority of this group would say I would turn in the $10K.  In fact, I would guess that a plurality of people would say I would keep or ignore any amount under $100 and turn in any amount over $1000 – their assessment would be closer to my own ideal self, which I feel quite certain is not accurate.  Their reasons for my choices would vary broadly, much more broadly than the pragmatic greed I expressed, and would include reasons that I would not expect.

Is this group likelier to be right about me than I am myself?  I can’t answer that with an intuitive “I know my thoughts – I know myself – better than anyone else.”  There have been too many times when I have been surprised to discover that someone was a better predictor of my actions than I was.

Now, I don’t think that I have particularly poor self-knowledge.  In fact, as this post perhaps deplorably illustrates, I can examine my own navel to exacting excess.  But where does that leave me if the fact that I know myself particularly well only means that I am especially aware that I don’t know myself any better than other people do?  Makes my head hurt.

At the risk of Streisanding the hell out a minor comment, I’ll talk about something I’d rather censor.  Noting the rather dated news of my departure from my prior company, an anonymous commenter to an anonymous and erroneous blog post recently said:

Thank goodness they finally got rid of this guy. He was the worst hire the company ever made.

Here’s what I have to say about that:  I like to think it could very well be true.

I like the idea that there are some people who took a good hard look at the history and said, ‘Yep, this guy was terrible, he almost destroyed the place, good bye and good riddance!’ Because that would mean that I was in a position to make some important decisions, and that I made decisions at the risk of being unpopular – that I did much more with the opportunity than just quietly collect a paycheck.

Now, please don’t misunderstand this:  I’m not saying that the critics are wrong, that they don’t understand, that I was both righteous and right.  Even my own review of my Linden tenure welcomes ambiguous judgment.  Obviously, I think and I hope that I did good things, but I could certainly be wrong, I could certainly be delusional.

But the one thing I don’t want to be is simply in the middle.  I don’t want anyone’s assessment to be, ‘Well, he was neither among the worst nor among the best, he was just there and he didn’t do a damn thing.’ To me, that’s a lot worse than being the worst.

So, if you had any opportunity to think about my work, and you thought I was the worst, then I thank you.  Let me give you my special gift in return:

Simple enough, yes?  Forget Streisand, I call this the Safety Dance.

And you can act real rude and totally removed
And I can act like an imbecile

In the very first minute of the decade, we found out that the looming Y2K disaster wasn’t real.  Then the dot-com bubble burst, proving that vast paper fortunes weren’t real.  Most of us voted against GWB for president in 2000, but he took office anyway, showing that popular democracy isn’t real.  The September 11 attacks seemed too horrible to be true, and we began a War on Terrorism with no real evidence that our target was involved in the attacks.  But the real illusion turned out to be the hope that “nothing will ever be the same again” – we quickly returned to ironic humor and emotional distance.

The Web 2.0 bubble came and went without a meaningful public company being created.  Massive investments in complex financial instruments that ultimately had no real basis for valuation led to a worldwide financial crisis.  A nation that stands as the apotheosis of capitalism turned to massive government bailouts, ultimately saving at least one sector of the economy:  big banking, whose leaders rewarded themselves handsomely for work they didn’t do.

Yep, the Age of Illusions it is.  Naughty Aughties, don’t let the door hit you on the way out.

I joined Craig’s firm in Menlo Park a few years after beginning my career in New York.  In the large Manhattan firms, the partners have big offices with spectacular views of the city.  Craig opened Venture Law Group in a modest suburban office park, and he liked to change his own office location from time to time, to dispel the office politics around a physical locus of power.  At one point soon after I joined, he occupied the small office right next to mine, making me a very lucky neophyte to Silicon Valley.  He was always kind and generous with his time and advice.  There are two bits of his wisdom that I particularly remember:

Timing and sequence are as critical as any other factors in building a successful venture. People tend to obsess over having the right idea, and building the right pieces to pursue those ideas.  And undoubtedly, it matters greatly that you pursue the right idea, building the right pieces, with the right people.  But all of those things can be right, and you can still fail if you start at the wrong time.  And more subtly, even being in the right time is not enough – you have to do things in the right order.  Attention to timing and sequence requires extraordinary strategic focus and discipline.

You are an undiversifiable piece of human capital.  This advice grows out of the notion that we are all investors in our own careers.  And one of the first principles of good investment management is portfolio diversification – by distributing your investment across asset classes with varying risk profiles, you can maximize your return while minimizing overall risk.  But as a human being with one life, you have a limited number of opportunities to diversify your career portfolio.  Life is about risk in a deeper way than rational investments.

Craig inspired us with his humility and gentle wisdom.  He carried his great experience lightly, with a twinkle in his eye at the chance to share a new thought with you.  Most of all, I’ll remember the boyish enthusiasm he always had for helping new ideas become realities.  Rest in peace, Craig Johnson.

So here is the rule of the Iron Quadrangle:

Friends, family, work and health are the four most meaningful areas of pursuit in life.  The very best that most people can achieve is to be outstanding in two areas, mediocre in one, and barely tolerable in the last.

Be wary of any advice that rigidly proclaims to know which combination is best for everyone.  For example, a lot of well-meaning homilies put family and health above all other values.  But the Iron Quadrangle means that all four values are connected; activity in any one informs all of the others.

Keep in mind that health includes physical and mental health; and that work includes all vocation, whether in pursuit of profit or pursuit of a cause.  Meaningful and lasting friendships are a critical contributor to lifelong health.  Pursuit of your true calling in work should be both emotionally enriching and intellectually revitalizing.

So maximizing your pursuit of family and health, to the exclusion of full effort with friends and work, can limit your achievement in the areas you would want to advance the most.  Would you have given all that you could to your life partner and your children if you never tested your mettle with the greatest challenges at work, or failed to develop rich friendships outside of your family?

Some will try to argue for picking work and family, or friends and family, or health and friends.  Some would claim that the limitation to two outstanding areas is false.  But in my experience and observation, the Iron Quadrangle is pitiless and brooks very few exceptions – and what exceptions I have seen are more a result of extremely fortuitous circumstances than the result of thought and effort.

This isn’t a pessimistic message, but rather a reflection on avoiding regret.  Many high-achieving people in every area look upon their accomplishments with regret for the areas in which they did not excel.  I think regret is only appropriate where people made choices while lying to themselves about the consequences for the other areas.

Faith and reason, properly understood, are intertwined sources of truth. The encyclical Fides et Ratio states this more elegantly:

Faith and reason are like two wings on which the human spirit rises to the contemplation of truth

In this light, I contemplated Fred Wilson’s note about investing on faith. The implication for some may be that this is investing without reason. However, Wilson’s leap of faith is no less legitimate than “pure” reason. Unlike religion, truth for startups has an ultimate arbiter in this plane of existence: return on investment. There are legions of startups that had all the reasons in the world to succeed – great idea, huge market, killer team – and yet they failed nonetheless. I’d bet that experienced startup investors have succeeded as many times on what Wilson calls faith as they have by stacking up reasons.

Coincidentally, the next day, Steve Blank posted on the startup transition from faith to facts. It might seem hard to argue with his view that startups begin on faith and must quickly move to facts to succeed. Again, I wouldn’t draw the divide that sharply. I’d say faith is a requirement throughout the journey, and so are facts. From day one, you must believe in what you’re doing, have faith informed by reason. And also from day one, you must engage with the facts; endlessly and relentlessly collect, examine and act on available facts with all your reason supported by your faith.

To the untrained eye, this may seem somewhat insane – that’s ridiculous, it’s completely insane.

Updated 29 Apr 2010: Finally decided what I wanted to do since Facebook acquired FriendFeed.  Going to hook up blog, Flickr and Twitter directly to Facebook, disconnect FriendFeed app from Facebook.  This means that the things that I previously shared to siloed audiences, I now share to all audiences, and I share them through Facebook as a central sharing point.  Which of course, is exactly what Facebook wanted from the FriendFeed acquisition.

Blogging’s dead, isn’t it?  Calcanis quit, hating the haters.  Arrington was pushed out by unreasonable expectations and expectoration.  The 250 have moved on to Twitter, where they are all already plotting to move off to the next big thing that you don’t know about.

So there’s no glory to gain here.  In fact, for me there’s only downside to exposure.  I’ve got a prominent role at a company that’s still climbing out of its hype cycle.  I’ll have to avoid some of the topics that I’m most familiar with, since I’m not going to say too much about my work.  And it’s not like I have a whole lot of interesting hobbies to fill the gap, notwithstanding a minor OCD compulsion to pick sentences out of The Great Gatsby.  This is just asking for ridicule.  So again:  Why bother?

The best answer I can give has to do with how I used to pick bars in New York.  This was more than a decade ago, but it’s probably still the same today:  When a hot new nightspot opens up in NYC, you can’t get in.  They put up the velvet ropes, celebs on the A-list get ushered past the line, the bouncers don’t let anyone in, so everyone else can only read the gossip rags about just how cool the place is.

But in less than a year or so, the hot new place isn’t so new or so hot anymore.  The A-list has moved on to the next place.  Now you can get in, but you probably don’t want to.  The place is stuffed with bridge-and-tunnel dorks, assorted Eurotrash, and other doofi who are overjoyed to stand where their favorite star stood just months ago, thrilled to wait in line to fight the crowd to catch the bartender to overpay for watery drinks.

I developed this fine theory Temple Bar, at Lafayette and Houston in NYC.

Ah but then, but then . . . in another year or so, the doofi have moved on.  And the place has some good bones:  the owners invested some coin in this place, and it shows.  Good location, swank interior, broad top-shelf selection, attractive service.  They’ve fired the bouncers, mothballed the velvet ropes, and lowered their prices.  The status-seekers and tourists wouldn’t be caught dead in this place.  The locals are starting to check the place out, some are becoming regulars, and they’re a friendly, interesting group.  Now it’s a good time to go.

And that’s how I think of blogging now.  Well past its coolest days, but man it’s easy to get to, everything’s clean and works well, and you sure can’t complain about the price.