Things would be a lot different if you had to deliver your status updates on horseback.

This summer marks the 150th anniversary of the Pony Express so I’ve been thinking about the wildly different factors that informed our communication in 1860.

Even though it holds a solid historic spot in our communal memory, the Express was only actually around for about a year. It was quickly replaced by the rise of the telegraph. During the time it was considered the new and cool way to send messages, a letter that was relayed from Missouri to Sacramento would require a new horse every 10 miles or so and a new rider every 75.

Adjusting for inflation, it would probably cost you a couple hundred dollars and require about twenty-five guys and a couple hundred horses to deliver a message. One assumes that would dramatically cut down on retweets and messages that contained only the letters LOL.

Sending messages, sharing and responding is remarkably easy today. It usually feels like there is very little at stake with each press of the publish button. No one is arguing that we’d be better off using the Pony Express – least of all the horses. But it’s interesting to look at past modes of communication and wonder if our current stream of realtime updates would be a little more interesting – or at least a lot different – if we had to work a bit harder to share an idea.

The speed record for the nearly two thousand mile Pony Express route was set at seven days, 17 hours with the delivery of Lincoln’s inaugural address. Can you imagine if the recipients of that letter opened the dust-covered envelope to find a message that only included one line: Abraham just checked-in at the U.S. Capitol.

When I first re-met my wife eight years after we graduated high school, I spent about seven hours writing her a letter. I went back through all of my old writings, pulled out the best material, pieced it all together with some pithy transitions and really poured it on. And it worked.

If I had encountered her a decade later, I’m not sure a couple of Tweets and instant messages would have been enough for me to overcome my appearance.

Would your typical piece of communication be more or less effective if the available tools required a little more time and effort? Does the speed with which we rattle off opinions, suggestions and reactions have a broader impact on the way we communicate? Will our short bursts of language ultimately make us more fluid with our use of words, or just gradually eat away at our ability to crank out quality material?

More to the point, which of your recent writings — from emails to Tweets to status updates — would really be worth the effort a horse would have to exert for its delivery?

And I’ve got to be willing to apply that same consideration to my own posts. While I think this article is pretty interesting and has a few good lines, I probably wouldn’t dedicate more than about a hundred bucks and eighteen horses to share it with you. So if you’re east of Reno, you might have to saddle up and meet me halfway.

The controversy around Facebook’s privacy policies has been growing. And now some instant messages that may have been sent by a then 19 year-old Mark Zuckerberg are fueling the fire. Here’s the conversation that’s being circulated.

Zuck: Yeah so if you ever need info about anyone at Harvard

Zuck: Just ask.

Zuck: I have over 4,000 emails, pictures, addresses…

[Redacted Friend's Name]: What? How’d you manage that one?

Zuck: People just submitted it.

Zuck: I don’t know why.

Zuck: They “trust me”

Zuck: Dumb fucks.

While I focus on these privacy issues for the purposes of this blog, I am not a particularly private person. When I was a kid, I used to print out and bind multiple copies of thirty-page rants and mail them to my friends. I was oversharing long before anyone had heard of social networks. If I thought there was a chance you’d subscribe, I’d run an RSS feed out of my unconscious.

But there are things that even I want private. For example, my wife and I have a very clear Facebook strategy. As the CEO of Splendora, she has a public persona and accepts almost everyone from her company’s extended community as a Facebook friend. On the other hand, I use Facebook very sparingly and I only friend those people who I really know. So on the rare occasions when we decide to share a couple photos of our kids, we only do so via my Facebook account.

But here’s the key. I never share anything on any site anywhere on the web regardless of any privacy settings unless I am willing to accept that the data might one day be public.

Now I am all for people fighting back against Facebook’s constantly mutating privacy policy – which is now longer than the U.S. Constitution. As this graphic so elegantly illustrates, they have been changing the rules and turning on more sharing by default. So sure, give them a hard time and maybe even take your (personal) business elsewhere. But that won’t completely solve the problem.

Does Mark Zuckerberg care that his old instant messages are being revealed? I have no idea. But you can bet that when he wrote them, he was not expecting they’d be made available for public consumption. And now they are. And that’s the point of this story.

If this Facebook privacy controversy teaches you anything, it should teach you this: The one internet privacy policy that really matters is your own. If you want it private, don’t share it. Because what’s private today might be public tomorrow. Period.

If we’re not willing to manage our own privacy, then maybe the 19 year-old Zuckerberg’s description of us was right on the mark.

A few weeks ago my attention was grabbed when a good friend and fellow parent forwarded an email to me. The email warned of a potential threat to kids at a playground a few miles from my house. I could tell from the variety of introductory statements and subject lines that the email had been forwarded several times before it reached my inbox.

The original subject line read: Bad Man Lurking in Mountain Lake Park. The email featured a photo of an ominous looking guy near a play structure and included the following message. I made some slight edits for purposes of clarity.

Hi Parents…Please help spread the word to people you know in this neighborhood. I have seen this man 2 times at the lower playground at Mountain Lake Park. He does NOT have children and pretends like he does and is there to do pull ups. He takes pictures of the kids with his phone … He looks for kids that don’t have caregivers near by … I personally believe that given the chance he might engage the kids and who knows what could happen…

My initial reaction to any mass-forwarded email is to assume it contains some misinformation or that it’s an outright hoax. But this was different. It had to do with kids in my general neighborhood. And social media makes the sharing of information so effortless that — in the moment — it’s often easier to share than to deliberate.

So I forwarded the message to another parent who lives a couple blocks from the park. He already had a few copies in his inbox. My wife told me she had received several as well.

For days, this forwarded email became the talk of the extended neighborhood. Every parent I spoke to had received at least one copy. There was certainly a sense of concern among these recipients. But there was also a lot of confusion about the original source of the email and skepticism about what to believe. The real world concern over anything that could threaten kids had run headfirst into the varied levels of trust each parent felt towards social media.

About a week after I received my first copy of the email, an administrator at my son’s school sent out a link to a story in the San Francisco Examiner. The police had been notified of about the email going around and had visited the alleged lurker. They determined that the guy posed no threat.

Police identified the man last week and visited his home Monday, according to a police update. He was “cooperative,” “unguarded,” and “surprised at being the subject of a police investigation,” according to a report from Richmond Police Station Capt. Richard Corriea.

“He allowed officers to examine his cell phone and his laptop computer,” the report said. “He stated that he hadn’t taken any photographs. He explained that he was looking at his phone’s screen while using the telephone’s stopwatch feature as part of his workout.”

What percentage of the parents who were warned about the “bad man” also received a link to the story in the Examiner?

I’m not sure.

Am I less concerned about a potential threat now that I’ve read the newspaper account of the police reaction?

No, I’m not.

If you take everything into a account from the safety of the children to the potential destruction of an innocent person’s character, did the forwarded email ultimately do more harm or good?

I don’t know.

After this experience, will I forward similar emails in the future?

I’m really not sure whether we were deputized or just weaponized, but yeah, I think I will.

This is a tale of the intersection of social media and journalism at a playground in Mountain Lake Park. I’ve talked to parents who are glad the community had their backs. I’ve also heard from those who think contacting law enforcement would’ve been a better first step than sending emails. Some think the guy at the park presents a danger, others believe he was wrongfully defamed. By the end, I was armed with a tremendous amount of data from parents, police and journalists and yet I was left not quite knowing what to believe.

So is this story a celebration or a condemnation of social media?

That’s a really good question.

What can I say? Forward it if you want to.

Twitter CEO Evan Williams recently tweeted, “The future of book reading is clearly collaborative.”

I’d have to agree that the future of reading should be collaborative. But only if you are under four years old. From then on, reading should be done alone.

Evan was reacting to the news that Kindle will now let you see if others have highlighted the same passage in a book and then aggregate those saved passages into a list of what they’re calling, Recently Heavily Highlighted Passages. Matthew Ingram provides an good overview of the new service along with this quote from Amazon.

We combine the highlights of all Kindle customers and identify the passages with the most highlights. The resulting Popular Highlights help readers to focus on passages that are meaningful to the greatest number of people. We show only passages where the highlights of at least three distinct customers overlap, and we do not show which customers made those highlights.

Wait, we’re all going to start reading together?

Don’t get me wrong. I’m happy to discuss a novel with a book club or listen to a critic give his take on NPR. But I don’t want that external information delivered at the time of my reading. That’s one of the few things I still do alone. Reading a book provides a unique, important (and yes, private) interaction between author and reader, between you and the art. I don’t want to go to bed and curl up with a good book only to find that I am being spooned by a few million folks I’ve never met.

This a different kind of privacy invasion. I really don’t care if the world knows which paragraphs I’m highlighting. I just don’t want to give up the privacy of being able to read a book without knowing what passages other people found worthy. I want to be alone with the author and I don’t want to turn the page and find you there. Isn’t it odd that the merit of that goal is even up for debate?

I’m also worried about this trend from the author’s perspective. Take it from a longtime website creator. It’s not always so pleasant to know which pieces of your content are attracting the most views and clicks from visitors. Authors get to blissfully exist in a world where they can assume all their readers are geniuses and are focused on the right parts of the work. Do writers really want the truth? Do they really want to be called into an editor’s office to find out their novel needs a few photos of cute cats doing funny things?

You can be certain that non-fiction publishers will scan those heavily highlighted passages and realize that we love lists. And fiction editors will realize, that, yes, Dan Brown’s use of all-caps led to more readers highlighting a particular section. Get ready for books that are entirely made of up of lists written in all-caps

If both you and the authors already know all most heavily highlighted passages, we ultimately run the risk of the twitterization of the book. Just show me the good stuff. I’ll take the Cliffs Notes version, but I want it even Cliffier than before.

Ultimately, this move towards collaborative reading is a bad direction for Amazon – and yes, they’ve added Twitter and Facebook integration as well. The Kindle is currently positioned as the purist’s choice when it comes to e-reading, while the iPad is a multi-purpose device – loaded with distractions – that happens to have a book application. Does Amazon really want to compete on bells and whistles with all-in-one Steve and his magical marching band?

Maybe I’m being a little ornery about this topic. Well, that’s my goal. I’m worried that if I’m too pleasant, you all may want to collaboratively read with me. For now, that role is being exclusively filled by my toddlers.

Although it’s a slight misquote, the most lasting Oscar acceptance line of all time is Sally Field’s 1984 exclamation: “You like me, you really like me.”

That was back when it really meant something to like.

Between the spread of the Facebook “like” buttons and the seemingly ubiquitous opportunities to retweet, I wonder whether the whole meaning of liking or linking to something has been devalued.

You perform a single click on a big button to share your interest and affection. But what does it mean? Do you like my blog like you like the combined efforts of DaVinci and Einstein, or do you like it like you like the picture of that cat in the ski cap?

Maybe it’s just too easy to like something these days. I’ve had people with Twitter followers in the millions kindly link to my blog and the result has been anywhere from a handful to a several hundred new visitors. That’s a pretty small click-through rate. In the past, people who wanted to share content usually did so on a blog. They had to create a blog, build a following, and maybe learn a little html. It took some commitment and effort to share. It was an active choice as opposed to a knee-jerk reaction. And from that time until now, I find that the number of visits from even a lightly trafficked blog is markedly higher than many Facebook likes and Twitter retweets combined.

The musician and renowned over-sharer John Mayer addressed a related point when he announced his TMI migration from Twitter to the Tumblr blogging platform.

This is where Tumblr comes in. It’s the future of social networking if your image of the future features intelligent discourse. I love reading other Tumblr users replies, because they’re thoughtful by virtue of the fact that if they’re not, they’ll bring the intellectual property value of their own blog down, and that’s a commodity on Tumblr.

Sharing on a blog isn’t hard, but it puts a little more of your personal brand on the line and it leaves more time for potential reflection than just applying some pressure with your index finger or performing today’s version of long form work: the rattling off of a hundred forty characters and a cloud of dust.

The user interface of the web’s like buttons is so efficient and its output so transitory that together we’re all liking millions of things a day. That certainly provides a goldmine of data to marketers, and it also creates some great aggregate content for regular web civilians who want to browse the most popular news, videos and photos on the web.

But this trend towards such prolific and easy liking ultimately depreciates the value of each individual like. I am interested in something because you like it. Too much liking destroys the value of that personal recommendation.

That might not be too important as it relates to the sharing of funny cat videos or favorite Lady Gaga songs. But I worry that this pervasive and seamless socialization can ooze into our personal relationships and potentially dilute the value of friendship as well. If I order two copies of photos of my kids so I can send some to you, that is one manifestation of my affection; I “like” you. If I email you those same photos, it’s less effort for me, but the meaning is similar. But what if I share those same photos on a public blog or with a few hundred folks on Facebook? Hasn’t that very personal connection between you and me been watered down?

In the past few paragraphs, I’ve argued that blogs are thoughtful and I’ve quoted John Mayer. This is either a groundbreaking post or a desperate cry to be – in the words of my three year-old – really, really super liked.

Maybe we just need to come up with a different word for like when it comes to real life.

I suppose Sean Penn was prophetic about the evolution of the word “like” when he paraphrased Sally Field in his 1996 Independent Spirit Award acceptance speech:

“You tolerate me, you really tolerate me.”

On my first day as a high school teacher in Brooklyn, I passed through the front door metal detectors and climbed the crowded stairwells to the fifth floor. I was to report to room 526 where I would be substituting for a Physics teacher who, the day before, had asked a student to put away his Walkman. The student responded by stabbing the teacher in the hand with a pencil.

I was handed a Physics book and I began my slow, nervous walk down the paint-peeled fifth floor hall. As my mind filled with visions of a No. 2 Dixon Ticonderoga being jammed into my person, I realized I had already adopted my first teaching-relating philosophy: I was strongly against gadgets in school. But, at least on that first day in room 526, I had no intention of being part of the enforcement process.

Back then, cassette players were the only gadgets teachers really had to worry about. Today, students walk onto campus equipped with an arsenal of connected devices from iPhones to laptops. According to the latest numbers from Pew, three quarters of all teens own a cell phone, and almost all of them regularly exchange text messages with friends. While many adults complain they can’t get anything more out of their teen than the occasional eye-rolling shoulder shrug, active teen texters are rattling off a cool 1500 text messages a month.

Most schools have rules against texting in class while others have adopted school-wide cell phone bans. But even when bans are in place, more than half of the teens surveyed said they manage to send off an occasional text message from a classroom. And if you’re wowed by the today’s teens and the way they fire their machine gun thumbs at tiny keyboards, just wait. Their younger siblings are already training to smash the current texting pace. Twenty percent of kids between the ages of 6 and 11 have their own cell phones.

From my perspective as a former Brooklyn high school teacher, I can see how hard it would be to compete for classroom attention when the students have a pocketful of friends, music, videos, games and incoming text messages.

From my perspective as a parent, the issue is not quite so simple. While I am hesitant to willingly enable my children to follow too closely in my iPhone-zombie footsteps, I am attracted by the prospect of always keeping them within seven digits in case of emergency.

This always-on connection between parent and child can put a parent’s mind at ease, but I’m not certain it’s beneficial to the development of the child. Digital devices tend to blur the important line that separates parents from kids during the school day. At my son’s preschool, the teachers regularly take digital photos and then share them with parents. I used to sit on the couch and watch those online slide shows with my son. It was almost like I was there. And that’s the problem. My son’s awareness that I could see him in this environment infringed on the fundamental purpose of his preschool experience — to be in a place that was completely separate from his mom and me.

For a preschooler, the digital camera makes it seem like I’m almost there at school. For a teenager, the smart phone will do the same. Add that to the phone-based social and media distractions that will be a constant source of temptation, and I could easily make the argument against giving my son a cell phone for as long possible. But I’m not going to kid myself. The trend towards younger kids owning cell phones will only accelerate and that social reality along with my (real or perceived) need to be connected to my son will likely overpower any philosophical concerns I may have.

But I do hope that I can convince my then teenage son to break from his dad’s addicted ways and occasionally experience the glory of a disconnected life. I figure by that time, the worst thing that could happen is my avatar getting stabbed in the virtual hand with a pencil shaped cursor.

It was the best of times, it was the worst of times, it was the age of wisdom, it was the age of foolishness …

Dickens’ opening line in a Tale of Two Cities aptly describes the way I feel about the spread of Facebook. Moments after the announcement of the new social platform, I was already seeing what articles had been read by friends when I was at the CNN site, and what movies were liked by my social circle on IMDB. Every founder of every startup with even a hint of social ambition has imagined his product spread across the web like Facebook is today. This is the race to create the broadest sharing platform and unlock the social web’s holy grail.

And right now, Facebook is winning the race. Hundreds of millions of users are sharing where they go, who they know and what they like. This newly distributed social playground and marketing goldmine is big, powerful and possibly the most significant product to hit the internet since a few engineers thought to themselves, “Browsing is pretty cool, but wouldn’t search be even better?”

That’s my take as an internet investor and entrepreneur. My take as an internet civilian is a little different. In some cases, I find the data about what my friends have shared useful. I can see the benefit of knowing that on Yelp, my friend David “liked” the restaurant Papalote in San Francisco. There’s also probably some value in being forewarned that on IMDB he also “liked” the 1987 flick Spaceballs.

So yes, I do care what my friend David likes. In the last decade, I haven’t made a major consumer electronics purchase without checking with him first. And in general, my love for him is completely unconditional.

That said, I’m not sure I want to open up my morning newspaper and find him inside. Sometimes I really want to know what David likes. Sometimes I really like to spend time away from David and the rest of my extended social network. I am amazed that Facebook is powerful enough to tell me that David read a certain article in the Washington Post this morning. But in the moment, I am distracted by that information. I still want to be able to curl up with my virtual newspaper and read it by myself, and maybe even serendipitously stumble across an article now and then.

Facebook CEO Mark Zuckerberg described his growing suite of tools by explaining: “We are building a Web where the default is social.” That makes total sense. The web should default to social. It’s a network after all. The problem is that the web is everywhere. And I don’t want every aspect of my life to be social. How can I have a moment to quietly think when I’m in a room filled with my four hundred million closest friends?

I know the sharing stuff is easy enough to turn on and off. But I am convinced that it will be increasingly difficult to shut out the noise. That’s certainly been the case with every other piece of technology – from email to texting to Twitter – that’s entered our lives in recent years.

I am in awe of the social graph and the power of sharing. But I am worried about group think and a growing inability to be alone. I worry that someday my entire world will be shared, annotated and generally infringed upon by everyone I’ve ever met (and maybe a few hundred million folks I haven’t).

I started this confession with a famous first line from a novel. I’ll end it with a look at how the experience of some other famous first lines may be altered for future readers if the trend towards being always-on and always-sharing and always-Facebooked continues.

Love in the Time of Cholera
It was inevitable: the scent of bitter almonds always reminded him of the fate of unrequited love.
371 people like almonds

Moby Dick
Call me Ishmael.
Herman has changed his username to Ishmael

The Stranger
Mother died today.
42 people like this

Wide Sargasso Sea
They say when trouble comes close ranks, and so the white people did.
Edward, Annette and 1.3 billion others  joined  group “White People”

Pride and Prejudice
It is a truth universally acknowledged, that a single man in possession of a good fortune, must be in want of a wife.
Bingley changed his Relationship Status to Single

The Old Man and the Sea
He was an old man who fished alone in a skiff in the Gulf Stream and he had gone eighty-four days now without taking a fish.
Block Santiago or the Fishville application

Invisible Man
I am an invisible man.
Ralph Ellison just quit Facebook

Everything I know about internet privacy I learned from Curb Your Enthusiasm.

A season one episode of that show begins with Larry David’s best friend Jeff lying in a hospital bed just prior to going under for some serious surgery. He calls Larry to his bedside, hands him a key to his house and tells him where to find his porn collection. In a closet next to the TV there is a linen closet where eight adult tapes and some magazines are hidden behind a sliding wooden door. Jeff tells Larry that he wants him to retrieve this collection while he is in surgery just in case something goes wrong and he doesn’t make it. His wife, he explains, “is not a big fan of the porn.”

In the same episode, Larry uses a landline telephone, takes notes with a pencil and paper and asks someone to fax him directions. Times have changed. But Jeff’s concern for privacy might be more applicable than ever.

If Jeff was lying in a hospital bed today and had some things to hide, would he even know where to begin? More and more often, our worldly or private possessions – from porn, to passwords, to bank accounts, to photos, to blog posts and status updates – are not hidden in secret compartments or under our mattresses. They’re in the cloud. And if Jeff is anything like the rest of us, he probably hasn’t given a whole lot of thought to the legal or privacy related issues connected to moving his life online.

From a legal perspective, Jeff’s privacy was lot more secure in the back of his linen closet. The data you store on servers hosted by Google, Microsoft and others is subject to the Electronic Communications Privacy Act, which hasn’t been updated since 1986. Law enforcement officials merely need a subpoena (as opposed to a warrant) to get one of the online giants to give up your personal data. Google and Microsoft know this is a problem which is why they’ve teamed with other corporations and advocacy groups to urge lawmakers to get with the times.

“The U.S. Constitution protects data in your home and on your PC very strongly,” said Mike Hintze, an associate general counsel at Microsoft.

“We don’t believe that the balance between privacy and law enforcement should be fundamentally turned on its head,” Mr. Hintze added, simply because people now choose to store documents online rather than in their homes.

Our laws are lagging behind technology. And our personal concern for these issues could be lagging behind both.

Here are just a few items for you and Jeff to consider as anything – from the most private data to a drunken tweet – is pushed into the cloud.

- It’s highly unlikely Jeff has ever read the privacy policies or terms of service agreements on any of the sites he visits. For example, fewer than one out of thousand people even glance at the terms of use on an ecommerce site.

- Jeff likely shares small details about himself across several sites. He should note that: “Computer scientists and policy experts say that such seemingly innocuous bits of self-revelation can increasingly be collected and reassembled by computers to help create a picture of a person’s identity, sometimes down to the Social Security number.” Something as seemingly harmless as Jeff’s birthday can ultimately become part of a marketing profile, or one element of a puzzle being pieced together by identity thieves.

- If Jeff has ever used an online coupon, he’d likely be pretty surprised by how much his favorite retailer knows about him.

- While some big companies are concerned about your legal rights when it comes to privacy, it’s important to be aware that many social networking executives think of privacy as something antiquated. And of course, those companies are better off when more of your data is made public to search engines and marketers. That’s why in Confession #16, I wrote that I Never Tell Zuckerberg Anything.

- Jeff might think he’s now surrounded by millions of oversharing kids who don’t care about the sanctity of his porn collection or anything else. Well, recent studies indicate that young people say they are as concerned as the rest of us about privacy. The question is whether our concerns ever have an impact on our behaviors. We’re all sliding head first down the black diamond slope that is realtime, social web. Who has time to think?

- Both Facebook and Twitter are looking to extend Jeff’s sharing and liking to websites across the internet. It could make these sites more social and more personalized. It also means that more site owners and marketers will know about Jeff’s browsing history, what he likes, who he knows, etc.

- Even if he’s not quite ready to worry about web profiling or identity theft, Jeff will likely want to watch his words when he shares messages via Twitter or Facebook. Last week, the Library of Congress anounced they will maintain an archive of every Tweet ever posted. This content will be made searchable by Google. We all might have a lot of explaining to do someday.

- If he wants to give a little more thought to privacy in the age of social networking, Jeff should read Making Sense of Privacy and Publicity, a recent lecture presented by Danah Boyd at SxSW.

These are complicated issues and I offer this handful of links merely as a launching point to start thinking about what we share and where we share it. In the meantime, it might be a good idea to follow Jeff’s lead and keep the really good stuff behind a secret door in your linen closet.

The web has spoiled the plots of hundreds of TV shows on my DVR. And now it has spoiled the novelty of the next iPhone. An Apple employee left a next generation iPhone in a bar, someone found it and sold it Gizmodo. Gizmodo published photos and videos of the upcoming gadget and the details of how the the guy named Gray Powell lost it. And the internet did what the internet does. A blog post and an article here, some status updates and a few hundred thousand Tweets there, and before you know it we’ve all got a series of published opinions on a something we’ve known about for approximately twenty seconds.

We find ourselves in an age of write, don’t think — look, annotate, regurgitate, repeat. Yet we’ve all boarded this realtime, social roller coaster without taking much time to consider the ramifications of our actions. Our behavior is somewhere way out ahead of our consideration of that behavior. In honor of Gray Powell, the man whose lost iPhone set off this firestorm, I’ll call this the internet’s Gray Area where there is seemingly nothing that can come between a man and his publish button. And in this case, any takes, positive or negative, attacking or supportive, merely add to the pile of noise beneath which Gray Powell is now buried.

And where did this perfect storm of oversharing lead us? To the relentless humiliation of one poor dude and the spoiling of an upcoming surprise.

I’m not pointing fingers here. To paraphrase the late Michael Jackson (who knew a thing or two about public ridicule), I’m starting with the man whose reflection I see in my own iPhone. I’m with the masses. Whether I think the guy who found the phone should have given it back to Apple (I do) or whether I think Gizmodo should have published the details about the upcoming phone or how it came into their possession (I don’t) is not really the point. What I’m getting at here is the urgency with which I needed to look at the iPhone prototype and then to share my one hundred forty character take on the matter.

And what was my take? I have no idea, that was hours ago.

As the news spread around the web, some complained about the coverage of Gray Powell. The folks at Gizmodo paused to respond with a Tweet: “thx for the feedback on the How Apple Lost the iPhone piece. edited to show we aren’t picking on the guy, just telling of his honest mistake.” So I guess they edited out the part that included the guy’s name and the part about him losing the iPhone and the part about them publishing a series of stories about the iPhone prototype and the guy who lost it?

On the other hand, Grey Powell now has millions of people visiting his blog and social network pages. Sure, we’re all focused on him because he made a big mistake. But we’re all focused. There are millions of habitual oversharers who would gladly trade a little humiliation to join Gray Powell in the place where so many strive to be; at the fat end of the internet’s spotlight. He’s made it to that rarified zone occupied by the likes of Tila Tequila and the woozy kid who was filmed by his dad on the way home from the dentist.

Gray Powell: Humiliated victim or the latest internet superstar? Maybe that’s the defining principle of life in the Gray Area. There’s often no difference between the two.

In the end, Apple will get the phone back with more buzz than ever and the guy who lost it will probably end up with a guest spot on a late night talk show. And the rest of us can move on to the next realtime story of the moment. By now, we probably already have.

In 1989 I used a payphone next to Madonna. I had just finished college and moved across the country to New York. The city was in the middle of a protracted phone strike. There were no new lines going in, so if I wanted to talk to anyone back home in the Bay Area, I had walk to a corner near Spring and Sixth and drop a handful quarters into the public phone — my ear nearly sprouts fungus at the thought of it now. After spending several weeks in a new city, Madonna’s was the first familiar face I had seen.

I didn’t know anyone. I was a long way from home and I rarely contacted anyone because of the phone strike. It was one of those unique moments in my life when I had the feeling that I could reinvent myself and become anyone.

Over the months, I spent many days and nights just walking the city. New York itself became my best friend. For awhile I was alone and lonely, but eventually I started to establish my new identity, the east coast me — standing clear of subway doors, teaching high school in Crown Heights, scoring a quart of sour pickles at Guss’ on Essex below Delancey. I still remember the first time I walked across the Brooklyn Bridge. I started from the top of the six train steps and ended up three thousand miles from my childhood house, yet as at home as I could be.

This was an era before the internet became an umbilical cord.

If I were a couple decades younger, I’m not sure I could still experience the sense of solitude and liberation I had from the moment I hailed my first cab at JFK. Although I’d still be walking new streets in a different city, I wouldn’t be nearly as alone. I’d be connected to my friends and family. At least in some way, the realtime, social web would anchor me in the same stream of constant status updates and shared photos that enveloped me when I was back home. I’d still have one foot (or at least a couple thumbs) back in the comfort of my digital cocoon.

Two decades after I landed in New York, my nephew is in the throws of making a final choice on which college he will attend. One question he faces is whether he wants to attend school across the country or within an hour of his house. That’s a big question. But I’m not sure it’s nearly as big as it would have been several years ago when there was some truth to the Bruce Springsteen lyric: “When you’re alone you ain’t nothing but alone.”

A question for this era: Is it too much for my nephew to want a few minutes alone with Madonna?

Of course, it’s not just about the big moments that present the potential for self reinvention. It’s about all the gradual erosion of moments once set aside for personal introspection — previously solo-drives in your car that are now interrupted by bluetooth conference calls, or waits in bank lines that are consumed by the latest Tweets, or Facebook updates and podcasts joining you at what used to be a lunch table for one.

In the next year or so, I plan to take my family back to New York. The moment I’m most looking forward to is introducing my young son to the New York me as we get off the six train and walk hand in hand across the Brooklyn Bridge. I just hope that someday he has the opportunity to really let go and walk alone across his own bridge.