Lordy Lordy.

I am 40 years old today.

When I was growing up, 40 was the official over-the-hill birthday. A 40th birthday party involved novelty canes, ear trumpets, black armbands, walkers and other unfunny, made-to-be-thrown-away crap that occupied a dedicated shelf at Spencer’s Gifts. It still does, somewhat, but as I’ve aged I’ve noticed that culturally, we have tacitly agreed to move back the point beyond which “it’s all downhill from here.” As more Baby Boomers edge closer to the abyss, we have grown less willing to draw the line at which we must admit to ourselves that we are, finally, old.

I am a bit unsure of what to make of it all. Statistically, the odds are that my life is more than half over. When I think of all the things I would like to have done by this age – mostly involving writing and traveling, neither of which I’ve done to anything like the extent I once hoped – I am torn between two competing realizations: that youthful dreams rarely come true and mostly aren’t even meant to, and that I have squandered too much of the only existence I will ever have.

How badly should I feel that I have never lived abroad (well, apart from that semester in college), written a novel or been to Italy? That I work in the corporate world and have often substituted workplace ambition for personal or artistic goals? Is there any point in regretting the many mistakes I’ve made — situations where I sacrificed my happiness for someone else, gave into fear and laziness or knowingly made a bad decision to spare someone’s feelings?

I tell myself that any mistake is worth making as long as I learn from it. I tell myself that it is never too late to do the things that matter to me: to live in a place I don’t know, to use my talents for my own ambitions rather than for my bosses’, to live a life I will be grateful for once it’s over. I think these are valid views — but I would, wouldn’t I?

Shortly before he died, Christopher Hitchens said, “You have to choose your future regrets.” We can never fulfill all our dreams — not if our dreams are worth the name. I haven’t fulfilled all that many of mine. But I do have a beautiful, intelligent and fantastically talented woman to share my life with; reasonably good health; and that persistent, nagging urge to do something more than show up to a job every day — to make something lasting that reflects who I am.

Yes, I wish I had more time ahead of me. But do I wish I were younger? Not a chance. What wisdom I have has been very dearly bought. I wouldn’t rather be anywhere else than where I am today.

Happy birthday? Why, yes it is, thank you.

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Walter Isaacson, Steve Jobs and the Wrong Question

You have no fucking idea what it’s like to be me.
— Steve Jobs

While I have deliberately avoided reading most of the critical reaction to Walter Isaacson’s biography of Steve Jobs, the broad consensus seems to be that Isaacson had the biographer’s opportunity of a lifetime, and blew it. Despite having unprecedented access to one of the most relentlessly private of public figures, Isaacson’s is a book without insight: his Steve Jobs is the same collection of contradictory impulses he has always been, a self-centered, unlikeable man who somehow created products that people adored, changing whole industries in his wake. In a world full of assholes, critics complain, what set Jobs apart? What made it possible for him to do the extraordinary things he did?

Let me say first that I agree in principle with the critics: Steve Jobs is a lousy book. I believe I arrived at the conclusion via a different route from a lot of other people, and I’ll get into that soon. First, let’s consider the argument, articulated well by Thomas Q. Brady, quoted on Daring Fireball:

I know lots of people that could be described [as “self-absorbed, immature, emotionally unstable control-freaks”], and none of them started a company in their garage that became one of the most valued corporations in the world. What made Jobs different? This isn’t really answered.

Actually it is, at least to a point. There is the asshole half of the Jobs equation, and then there is the other half, which Isaacson documents and which everyone already knows about: his fanatical obsession with spare, minimalist design; his belief that he was destined for greatness and his determination to achieve it; his tremendous persuasiveness; and his knack for infusing technology products with an underlying human friendliness. Unlike Jobs’s more unsavory characteristics, these are not common traits. Combine them with the ones above, and the story of Steve Jobs begins to seem, if not inevitable, then at least somewhat plausible.

Our civilization has spent centuries debating the origins of genius — even the definition of genius — and yet with each new transformational figure that comes along, we start the debate all over again. The truth is that genius has no formula. It cannot be predicted, reconstructed, feigned (for very long) or dissected, at least not in any way that is remotely edifying. You can quantify the factors that make it possible for people to be successful; for instance, Jobs acknowledged how lucky he was to grow up in Silicon Valley, surrounded by people who could nurture his talents and fire his ambitions. Had his parents opted to raise him in the suburbs of Wisconsin, we’d likely never have heard of Steve Jobs. But creativity — or inventiveness if you prefer, since we don’t tend to associate creativity with non-artistic pursuits — is a process that ultimately operates beneath the threshold of awareness. Indeed, it can operate in no other way; inspiration is not an algorithm.

Many people seem to have expected Isaacson’s book to provide the missing piece of the puzzle — the key that would finally unlock the secret of his genius and forever solve the enigma of Steve Jobs. They were never going to get what they wanted, because it didn’t exist. There was no “one more thing.” The enigma is its own solution.

I don’t want to give the impression that any inquiry into the inner workings of a genius is futile, or that Isaacson should be let off the hook for writing a superficial book about a man who was anything but. I merely suspect that no one could have written an entirely satisfying book on Steve Jobs, because the things people want to understand about him aren’t really explicable. What made Jobs different? How did he look at a Rio MP3 player and conceive what would become the iPod, where everyone else just saw a clunky, half-assed music player? You can posit various intermediary reasons — because he was driven to achieve perfection, because poor design caused in him something akin to physical pain — but what do those explain? What are the reasons for the reasons? The truth is that Steve Jobs did what he did because his unique blend of innate qualities, combined with the people and places that helped to shape his worldview, allowed him to. His career was the result of a confluence of circumstances so unlikely as to appear impossible. “What made Steve Jobs different?” is more a rhetorical question than an actual one. It is a way for our mathematically hampered brains to acknowledge the  baffling unlikelihood of his achievement — the incredible fact that in this world, a man like him could exist at all.

So having put that issue in perspective, what is my primary objection to the book? I will put it in straightforwardly Jobsian terms:

The writing sucks.

This is a dull book, and I don’t mean that in a small way — I mean that in a big way. Isaacson’s prose is as flat and limp as a boned fish. Writing about the most fascinating inventor and visionary of our time brought out no poetry in him, no spark, no consciousness that a man of Jobs’s caliber merited an uncompromising effort. Steve Jobs is a Bill Gates kind of biography: unflavored, drily factual (which is not to say it is accurate), pedantic and, despite the occasional adverbial interjections the author makes to demonstrate he hasn’t been completely taken in by his subject’s point of view, cringingly deferential.

The purpose of a biography — of any kind of writing — is to make its subject come alive for the reader. Empathy and imagination are two of the writer’s most powerful gifts, and to the biographer they are essential tools to bridge the gap between the subject’s consciousness and the reader’s. On my bookshelf near my desk is a copy of Schulz and Peanuts by David Michaelis (the dust jacket of which features a laudatory blurb by Walter Isaacson). I opened it, flipped around for a few moments and came upon this passage, describing the young Charles M. Schulz making his first drawings:

Having dutifully put away the table arrangements, he would bend over the paper, tense, almost sick with excitement, as his pen followed the arched back of the panther threatening Tim Tyler last Sunday. Sometimes he drifted just far enough outside the forms of the cartoonist he was imitating to find himself watching in surprise as his pen point twisted a mouth or curved an eyebrow in a way that seemed somehow distinctively his. But design, proportions, pacing still belonged to the masters, and his drawings still lacked the professionalism that he was ever more aware of pursuing.

Michaelis gives himself license to depict Schulz’s artistic process from the artist’s own point of view; reading this passage, you feel one with Schulz, sharing his struggle and triumph as he experiences them. Note the forceful, dramatic verbs: “his pen point twisted a mouth or curved an eyebrow.” Even the picture Schulz draws adds drama and tension to the scene. The arched back of the threatening panther reinforces how much is at stake here: for Charles Schulz, getting this right is everything, and his best efforts still land him short of where he knows he needs to be. A driven, almost monomaniacal artist is born virtually before our eyes.

There is nothing in Steve Jobs that comes within a hundred miles of this. Despite (or even because of) the 40 interviews Isaacson conducted with his subject, which are reproduced on the page in great undigested gobs, we never feel close to Jobs or get swept up into his story. This I think is the real reason so many have found the book unsatisfying. It’s not because Isaacson didn’t tell us “what made Steve Jobs different” — he explained that as much as it probably can be. It’s because we never get a sense of what it was like to be Steve Jobs, and thus never understand how truly different he was, or wasn’t, from everyone else.

Is this merely a matter of Isaacson not knowing what questions to ask, as some critics have said? No, because interviews are only one of the biographer’s tools, and not necessarily even the primary one. Better interviews would have resulted in a better book than we have now, but I doubt even then that it would have made a great biography. If anything, his easy access to Jobs actually undermined the finished work. Isaacson seems to have believed that simply quoting his subject at length would, ipso facto, provide the definitive word, with a contrasting recollection by a former associate thrown in for balance. This is the stuff of magazine profiles, not biographies. A great biography of Jobs would have required an author willing to get inside his subject’s head by whatever means necessary, a writer with the determination to make his subject his own and the writing chops to convincingly show us the world as he saw it.

Maybe someone someday could still write that book using Isaacson’s materials, should he be generous enough to make them available. In the meantime, we’re stuck with the longest commemorative issue of Time magazine ever written.

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And My Dream of a Better iPod Takes Another Blow

Good news, everyone! Oh wait — not so good news:

If you want to buy an iPod shuffle or iPod classic from Apple, you should do it sooner rather than later. We’ve heard those two iPods are getting the axe this year. (Courtesy TUAW)

Assuming this is true, is it likely that Apple is going to release a 128-gigabyte iPod touch this Christmas, so that die-hard music lovers might find something in their stockings that comes close to suiting their needs? I’m guessing not. The mp3 player market is dead. They are to this young decade what digital watches were in the ’80s: formerly sleek emblems of progress reduced in price and stature until they ended up being sold out of gumball machines.

Time was that Apple needed to offer a high-capacity iPod model to stand out from the competition. Now that race is run, and music playing is just one more function on a smart phone, or a handheld gaming and Internet device (to describe the iPod touch accurately). If the rumor is true and the shuffle is in line for the axe along with the classic, that means that the iPod nano will be the only remaining device Apple makes whose primary function is to store and play music — and i think it’s reasonable to assume that the nano will itself continue to exist only until Apple can price an iPod touch below $199. (Side bet: if the above rumor comes to pass, watch the nano drop to $99.)

So why is this a big enough deal that I keep harping on it? Because there is no smartphone or iPod touch that can do what an iPod classic does: hold a library of songs numbering in the tens of thousands, all stored locally and accessible without a network connection. And it does not offer a hardware interface optimized for playing music.

Don’t mistake this for sentimentality or Ludditism. (Ludditery?) I recently started using Rdio and was sufficiently taken with it that I thought it might obviate the need for my iPod classic. It offers a sizable library to choose from, the mobile app is pretty slick and it has some nice music discovery tools. But it doesn’t offer the granularity of iTunes: the ability to rate songs, tag songs, construct dynamic playlists or change metadata. In short, it doesn’t afford the kind of advantages that come from owning and curating your own music files. So Rdio on my iPhone is like having two different, mutually incompatible music libraries, one of which has everything by the Beatles (in mono, even) and not much else, the other of which is so ungainly it has 12 different songs called “Learning to Fly,” just because I wanted to see how many there are. (There are more than 12, but it was starting to get ridiculous.) And if I want to, say, make a playlist with “Flying” and Kate Earl’s “Learning to Fly”? Well, that ain’t happening. I can put Kate Earl on my iPod, but I can’t put the Beatles on Rdio.

If the classic is going away, then I and thousands of others like me are marooned. Our choices are to either keep our devices operating until Apple offers a new product that can serve our needs (mine is already three years old and on its second battery), or jump ship for something else. Such a change, for all I know, may not be possible, or if it’s possible, it may not be worth the trouble. Leaving the iPod will also mean leaving iTunes, and the information that app has stored about my music — my ratings, my playlists, which songs I’ve played or skipped in a given time — is, given the nerd-tastic way I listen to music, almost as valuable as the music itself.

So while I am chagrined to arrive at the end of the road with my iPod, I am hopeful that some competitor out there will finally seize the opportunity to build a music player that offers us what Apple will not. People are still buying vinyl records, for god’s sake. You mean to tell me there is really no return on catering to rabid music listeners — people who have already demonstrated their willingness to devote a lot more of their income to music than the average person?

Anyone want to sell me an mp3 player?

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