A lot has changed since then. But sometimes I wonder if the computing industry — all of it, from software to hardware to web services — really has the right priorities in mind. So here’s my list of the things that I hope to hell are working flawlessly by 2018. The frustrating thing is that every single one of these things can be done with today’s technology (except possibly for #7).

1. Automatic file syncing. It’s astounding how badly computers do this. Every operating system on every computer sucks at syncing files; it’s only a matter of degree. I should be able to turn on any device I own and access any file I own, and it should all happen transparently. I don’t want to have to think about where I put a particular file, or whether I can access it from my iPhone. My calendar events should automatically sync between my Blackberry, my desktop, my Google Calendar, and my websites. Perhaps the key is to have everything save to “the cloud” and sync locally for offline access; I don’t know. I just want it to work.
2. Automatic configuration syncing. The younger, hotter sister of automatic file syncing. Now that we’re all starting to use web applications for everything instead of sending files around, these web applications all need to be able to talk to each other. My bookmarks should follow me from machine to machine, and from browser to browser. Every time I configure my Firefox or my Windows Media Player just the way I like it, I shouldn’t have to go through the same painstaking customization process on every machine I touch.
3. Automatic backups. Macs now do this as a matter of course with Time Machine software. But Windows doesn’t. Well, let me qualify that — Windows will back up important system files as a matter of course, and create confusing “shadow copies” of documents in the background that you can roll back to. But it’s confusing as hell and inefficient to boot. What’s more, I want my computer to back up to an online storage facility, not some clunky piece of crap that’s hogging space on my desk.
4. Automatic upgrades. I’m not just talking about the operating system software here — I’m talking about every piece of software and hardware should automatically check for upgrades on a regular basis from a single, unified interface. And then give me the option to install or not install. Linux does this, and Microsoft has made efforts towards this with their Windows Update facility. But right now I have separate programs on my desktop working in the background to check for updates from Java, Logitech, Apple, Adobe, ESET, Mozilla, and Dell. And that doesn’t include all of the programs that check for updates when you fire them up.
5. Integrated security. This whole system of remembering a million different passwords in a million different places is unworkable. Not only that, but it’s not secure, because everyone on Earth except for Bruce Schneier either a) has their passwords written down on a Post-It note, b) uses ridiculously insecure passwords like their dog’s name, or c) has a handful of relatively secure passwords that they use over and over again, because we can only remember so many garbled strings of letters and numbers. I’m not a security expert, but it seems to me that biometric security would be a step up from where we are today.
6. Centralized identity management. Why do I have to constantly retype the same address information, the same email address, the same websites? Why is it that when I update my official bio to reflect a new book release, I have to log in to 4000 different websites and manually change my bios one by one? I understand the need to respect privacy — but if I want to share my information with a particular website, application, or company, shouldn’t I be able to do that with a click or two? We need trusted, universal services that can verify your identity wherever you are online.
7. Useful battery life. I am sick to death of power cords. If I never saw another power cord in my life, it would be too soon. But I could deal with power cords if they only led to docking stations that charged up my appliances enough to make them usable for an entire day. But right now, my laptop barely survives three or four hours untethered; my Blackberry struggles to get through the day with the WiFi switched on all the time. Fer the love o’ Christ, people, I need at least a day’s worth of juice for every machine I own. Please.
8. Everything wireless. I’ve got connecting cables for my BlackBerry and my iPod. The printer’s wired to the desktop, as are the quad speakers and the subwoofer. The keyboard and mouse aren’t wired anymore — but the wireless transmitter for the keyboard and mouse is wired. I want, at most, one power cable snaking from the back of my computer to the wall. Apple is leading the way on this one, as usual. But with Bluetooth moving onto more and more devices, we’re getting close to achieving this one on all platforms.
9. True, modular upgrades. For years, I’ve had the dream of having a single system that could be upgraded in a modular fashion. I’ll snap in the newest processor every couple of years. I’ll beef up my sound card on alternate years. I’ll upgrade the video card as circumstances warrant. But it seems that no matter how hard I try, I have to scrap everything and start from scratch after a few seasons. Is it really that difficult to future-proof hardware so I can upgrade my systems one piece at a time?
10. True plug and play. Let’s say it together: every piece of equipment I buy should be able to interface with every other piece of equipment I own. I should never be in the position of having to struggle to get photographs from the camera to the printer, or having to figure out whether the DVDs I burned on one computer can be read on another — much less have trouble networking my Linux, Mac, and Windows boxes together.

Agree? Disagree? And what have I missed?

So we clearly haven’t yet mastered the science of user interface here in the 21st century. But what is it we’re striving towards? What’s the perfect user interface? In, say, a thousand years, when we have unlimited computing power and unlimited energy (like the characters of my novels Infoquake and MultiReal), what kinds of user interface will we be using?

Let’s take the question one necessary step further: do we really need user interface at all? Or are we evolving toward the point where intelligent tools automatically understand what we’re trying to do? In a thousand years, will the concept of giving commands be obsolete?

Software developers are taking the first tentative steps in that direction now. Apple’s Steve Jobs has always taken that “benevolent dictator” approach: we’ll decide what you, the user, need to handle, and the machine will just automatically handle the rest. Take disk defragmentation, a software task that only the wonkiest of technowonks has any interest in controlling. There isn’t any standard disk defragmenter for Macs, but that’s not because Mac hard disks never need defragmenting. OS X simply does it for you behind the scenes, as this article on the Apple website makes clear.

Microsoft is moving in this direction too. One of the advantages that Windows users have historically held over Mac users is the fact that it’s generally easier to get under the hood and tweak the gears that make the system work. But that’s going away. Not only because OS X has brought command-line tweaking to the Mac, but because Vista is taking away a lot of tweakability from Windows. Disk defragmentation under Vista is a simple on-off proposition; flip it on, and the OS will handle it as needed. Likewise, throughout the operating system, interfaces that were once cluttered with hierarchical menus and interactive dialog boxes are giving way to much smaller lists of context-sensitive tasks. (For more of my thoughts on this, see old blog posts Don’t Worry, Vista Will Handle It and Look Ma… No Program Menus!)

It’s the same long-term trajectory of user interface we’ve seen in automobiles. Look at the user interface for the Model T (pictured, below; original photo, with explanations and more detail, here). Most modern automobiles have reduced this to a standard set of four controls — the gas, the brake, the steering wheel, and the gear shift. It’s not that the car doesn’t still need all those functions, but now the car handles everything itself. It’s not exposed to the end user. If you believe the so-called experts, we’ll all be zipping around in self-driving robot cars within a generation.

Follow this trend several hundred years, and where does it lead? I talked previously about elevators that automatically know which floor you’re going to via RFID chips in your apartment keys. Why couldn’t that work elsewhere? Maybe you’ll pull into the Starbucks parking lot and find your usual soy milk decaf latte waiting when you get up to the counter. Maybe the refrigerator will automatically order more eggs from the store when you take the last two out. Maybe the polling station will know that you’re a member of the Christian Coalition and have a ballot all queued up with Mike Huckabee’s name checked when you get up to the voting booth.

There’s something very unsettling about these scenarios, and it’s not just the potential privacy hazards. Humans want to be in control of our environment; we instinctively resist environments that control us. Not only that, but we quickly grow bored with environments that coddle us. Humans are designed for dynamism, dissatisfaction, and change; despite the stereotype of modern man as couch potato, as a species we don’t handle stasis well.

So we like to be in control of our surroundings. But how much of this control is just feel-good illusion? When you order a hamburger at Burger King, sure, they’ll make it your way — as long as “your way” only involves their nine predefined toppings. And when you ask for lettuce, you can’t control how much, or whether they use shredded iceberg or delicately layered romaine, or whether it comes from West Virginia or Peru or Ecuador. Burger King’s real slogan should be “Have It Your Way, As Long As Your Way Falls Within the Narrow Parameters of Our Way.”

You don’t have much control over Google search results either. Try searching for “Bob Dylan.” You can choose to click on any one of the 25 million results pages you want — but Google determines the order in which they appear, which is tantamount to choosing your search results. (Try selecting the 4,523rd result sometime.) You can select “Advanced Search” and filter those 25 million results a number of ways, but you can’t choose the algorithm that Google uses to determine search results. Nor would you want to, because you’re not a computer scientist specializing in advanced information processing. If Google allowed you complete and utter granular control over every aspect of your search query, you’d either go insane or you’d never get anything done.

So is the Burger King experience a premonition of our future? Do we need to just trust the benevolent dictatorships of Google, Microsoft, and Apple (not to mention Burger King)? Is the future of user interface just a big pie of machine control with a thin crust of user choice on top?

As frightening as that scenario is, the opposite extreme is equally worrisome. It’s the future of total individual control. And boy, would that future suck.

We’re all familiar with the totalitarian sci-fi future where Big Brother boxes you in to a world of limited choices. 1984, Brave New World, Logan’s Run, etc. But what about the world of ultimate choice, where you have to control everything? The world has gotten smaller, our capabilities have grown larger, and the number of choices we have to make is bewildering. Once upon a time, you could choose to be a blacksmith, a farmer, or a priest. Now your career choices expand into the hundreds of thousands. Your parents went to the store and bought apples. Just apples. We go to the store and have to choose between Granny Smith, Macintosh, Fuji, Braeburn, Pink Lady, Red Delicious, Gala, Pippin, and Rome Beauty.

Big deal, you think. So I have to choose between a dozen brands of apples. How’s that a bad thing? It’s not. But what happens in thirty years when you’re expected to specify the size, tartness, color, firmness, ripeness, and pesticide of every piece of fruit you buy? What happens in 150 years when you can bioengineer your own hybrid apple/pear/mangoes right in the store while you wait?

If you want to see the beginnings of the future of total individual control, look at Linux. The Wikipedia list of Linux distributions catalogs around 200 different flavors of Linux. DistroWatch has much more. And these are just the prepackaged bundles of Linux. The hood’s wide open and the tools are sitting right there on the dash, giving you complete and total freedom to replace anything you like.

But who can deal with that kind of freedom? Unless you’re the kind of guy who likes to write display drivers in your spare time, you probably don’t have the time, the resources, or the expertise to make informed decisions about all of that. Perhaps one day we’ll all have neural implants to help us cope with all that cognitive processing. But until then, even the Linux geeks rely on consortiums of developers to make those decisions for them.

My point is not to bash Linux or to get into the whole open-source-versus-proprietary discussion — please, God, I don’t want to get into that right now. Rather, I’m pointing out that whether you use a MacBook Pro, a Dell Inspiron with Windows Vista, or a custom box with Kubuntu Linux, you end up relinquishing control. There’s only so much time you want to spend fine-tuning your computer, so instead of letting Microsoft make your decisions for you, you let a worldwide network of open source developers make them. We can argue about whether that makes a better operating system some other time; the point is that the practical effect of too much control on user interface is… giving up control.

So we’ve got the two extremes of User Interface Hell: the world of the benevolent dictator, where your control over your environment is deceptively limited; and the world of ultimate freedom, where you’ve got so much control that your ability to get anything accomplish is equally limited. Both of those extremes are equally unlivable; and you’ll notice that what those futures share in common is a lack of common-sense user interface.

Obviously we need happy mediums. We need to reconcile these two extremes, and simply, reductive user interface is the key.

The machinery that runs your information technology grows more intricate by the day, as does the machinery that powers your car. (Hamburgers, thankfully, seem to have reached an evolutionary plateau.) Despite what some Slashdot readers may fervently wish, I don’t think we’re headed for a future where everyone tweaks their own Linux distribution. If the freedoms we gain from our technology is the time and luxury of tweaking our technology, then we’ve gained nothing.

What often gets overlooked is that user interface isn’t a technological issue; it’s a sociological issue. Bad user interface limits freedom, it limits capability, it disempowers minorities. Think of how much difficulty your grandma has using the ATM. Technology has become too integrated into our society for us to leave people behind through insufficient user interface.

So what form will these perfect user interfaces take? To be continued…

Or at least, so says Starbucks founder Howard Schultz in a memo that circulated on the Internet recently. The chain went from 1,000 to 13,000 locations in a decade. As a result, Starbucks has gone from the epitome of cool — which it really was, back when grunge was the hip thing — to, well, Starbucks. I think I literally pass about 15 Starbucks on my way to work in the morning, and those are just the ones that are within half a mile of the highway.

And yet, it’s easy to forget that Starbucks practically invented the modern coffeehouse. When I was in high school, there were no hip coffeehouses to hang out in. If you wanted to hang out and gab with your friends in a public place, you went to the mall. If you wanted to drink coffee, there was the Folger’s brand dreck you buy at the supermarket, or there were fancy-schmancy imported European brands. The first Starbucks were a revelation. Great coffee, great eye for design, quirky attitude, and socially responsible too! (Or so we believed then.)

Daniel Gross wrote a fascinating piece in the L.A. Times this weekend about companies, like Starbucks, that expand too quickly and sacrifice their brand magic. Other case studies of the trend, according to the article, include Krispy Kreme, Restoration Hardware, Snapple, and California Pizza Kitchen. All once exclusive — nay, magical — consumer experiences, all blanded down by Wall Street’s push for ever-expanding profits. Remember the first time you walked into Restoration Hardware? It was awesome. Now? Not so much. I might add to this list The Sharper Image, Tower Records, Boston Market, the Olive Garden, TGI Friday’s, and IKEA.

Extend the concept to television, and you’ve got Seinfeld, Who Wants to Be a Millionaire, and Star Trek. Film franchises? All I have to say is that Lethal Weapon was considered edgy on its release in 1987. The Batman and Superman series fell into self-parody and both needed expensive reboots. (Star Trek is supposedly next in line for a reboot, with Matt Damon, Adrien Brody, and Gary Sinise reportedly in line to play the young Kirk, Spock, and Bones. I kid you not.) Books? I would argue that Orson Scott Card has screwed the pooch on the marvelous Ender series with his increasingly wretched (and seemingly endless) series of Bean books and tie-in stories. (I could even go so far as to suggest the United States is subject to this phenomenon as well, but I don’t feel like getting political today.)

I wrote about this phenomenon in Infoquake. In fact, this arc of rise, bloat, and fall is one of the principle themes of the Jump 225 Trilogy. It seems to me that this is simply the way the world works. Brands, like people, like companies, like everything, are only allotted so much time on this Earth. Marketplace pressures demand that they expand quickly, and then the same marketplace pressures will pull them back down again. Nobody has yet found the magical formula to extend a company indefinitely, just like nobody has yet found the magical formula to extend people indefinitely.

Think of the brands that have stood the test of time. Coke, Sears, J.C. Penney, Ford, KMart. The only reason Coke continues its market domination, I’m convinced, is because of the virtual monopoly on the soda industry it shares with Pepsi, and that mostly has to do with distribution. There’s not a major stadium or movie theater chain or fast food franchise in America that doesn’t carry either Coke or Pepsi products. Give consumers a real choice and I’m betting that many of them would opt for R.C. or Virgin. Sears and Penney’s will soon go the way of Montgomery Ward, and Ford’s and KMart’s futures aren’t exactly looking promising.

Other companies survive for a while by remaining boutique brands — the L.A. Times article mentions In-N-Out Burger and Trader Joe’s, two companies that have resisted the impulse to line their stores along every freeway offramp in America. But it seems to me that this strategy only has so much currency too. Keep your company small, and you remain more vulnerable to economic shifts and shareholder revolts. Keep your company family owned, and eventually the family dies off. Small missteps (which are inevitable) can have drastic consequences.

The brand that I find most fascinating to watch today is Apple. Somehow, they’ve gone from being the coolest thing on Earth (the original Mac) to a lame also-ran (during the Sculley/Amelio days) to the coolest thing on Earth again (iMac, iPod, MacBook, etc.). There’s no doubt in my mind that Apple will one day fall — and it’s probably going to be in our lifetimes. In the past decade, Steve Jobs has wisely steered the company towards a more exclusive brand strategy that seems to be working pretty damn well. Keep the prices high. Don’t quite fulfill all the demand. Emphasize the coolness factor. Keep your audience relatively small. Why else would Apple enter the cell phone market with a $500 base model that only the Cool People will be able to afford?

But what happens when Steve Jobs retires or goes to that big Trash Bin in the sky? What happens the next time he makes an expensive blunder and the suits push him out to make way for some bland, faceless middle manager?

For now, don’t let the rhetoric fool you: Apple is very happy where they are. People watch the series of “I’m a Mac, I’m a PC” ads bashing Windows Vista and think that Apple’s really going to steal a lot of market share from Microsoft now. But that would be Steve Jobs’ worst nightmare. He doesn’t want 85% of the desktop market, or even 60%; once Apple is no longer the cool, hip alternative, they become — well, Microsoft.

They become Starbucks.

It’s almost impossible to come up with a single answer, or even a single set of answers. What do Google, Microsoft, YouTube, MySpace, Digg, Mozilla, Adobe, Dell, and Apple have in common? I came up with a number of factors off the top of my head — empowering users, keeping a steady pace of innovation, good PR, making easy-to-use products — but none of them seemed to be the end-all, be-all of high-tech success.

So I decided to look at the question from the opposite angle. What makes a technology company fail? Here are a handful of companies from the past twenty years that strike me as prime examples of organizations who lost a commanding lead and/or market dominance in a particular field due to their own idiocy or incompetence.

1. Atari. The mass market videogame console was more or less invented by Atari in the late ’70s. Their only real competitor for years was Mattel’s Intellivision, which may have had vast technical superiority but had inept marketing. (George Plimpton? You’ve got to be kidding me.) But instead of innovating, Atari took the road of suing anyone and everyone who touched its much-beloved system. (Activision, Coleco, Starpath, Odyssey, Nintendo, Phillips, and Epyx all suffered Atari’s litigious wrath.) There was also a precipitous drop-off in videogame quality, as anyone who remembers notoriously bad media tie-ins like E.T. The original company was sold off many times and finally diluted to nothingness in the ’90s. The name still had such cachet, however, that Infogrames later licensed it for themselves.

2. Netscape. Netscape partisans and Microsoft haters have long promoted the urban legend that Microsoft drove this company into obscurity. And while Bill Gates & Co.’s anti-competitive practices certainly helped, ultimately the blame lies with the company itself. Netscape was running neck-and-neck with Microsoft in the browser wars for several years until its hideous Navigator 4 browser (which earned the company the Nutscrape label, among many other less complimentary names). Undeterred by their slipping fortunes, the company followed Navigator 4 with… nothing. For years. They pursued a ruinous portal strategy instead and sold out to AOL, who let the company completely die on the vine. Now Netscape is stuck with a dying portal website and an also-ran browser that piggybacks on both Internet Explorer and Firefox.

3. Palm. The early PalmPilots finally found the magic formula that had eluded so many other companies for so long. They were easy to use, integrated tolerably well with your PC, and were extremely reliable machines. No wonder the company built up such a network of software developers. And then a long series of ownership switches threw the platform’s future in the toilet. The result? Microsoft’s Pocket PC platform (now Windows Mobile) overtook the Palm on basic, must-have features (like oh, say, enabling a contact to have both a home and business address, which the Palm still can’t do). I read recently that the Palm OS actually still funnels everything through emulation software for its ancient Dragonball processor, which is a good indicator of how far behind the innovation curve these folks have gotten.

4. America Online. In order to get on the Internet in the mid-’90s, the average household could go one of two routes. They could download a program called Trumpet Winsock and configure connection strings until they tore out their hair, then FTP down a series of Internet apps of varying quality. Or they could install America Online off a single floppy disk and be up and running in minutes. AOL was on top of the world at the turn of the millennium with their buyouts of Time Warner and Netscape. What happened? They turned out to be, well, a bunch of cowards. AOL so feared getting shut out of the Windows 95 desktop and losing new customers to Microsoft’s new MSN service that they bowed to Redmond’s wishes. They continued licensing Microsoft’s Internet Explorer browser and simply let the Netscape browser die a slow death. And then, in one of the most astoundingly stupid business moves ever, they utterly failed to come up with a broadband strategy until — well, they still don’t have one. I thought one of the main reasons they bought Time/Warner in the first place was to get a hold of its cable networks. Wha’ happened?

5. Apple. Steve Jobs brought the modern window-based GUI to the masses via Apple’s revolutionary Macintosh computer. His reward? Getting booted out of the company by a corporate board too concerned about Steve’s titanic ego and famous inability to play nice with others. Baaaaad mistake. The corporate stiffs (Amelio, Sculley) who followed Jobs utterly failed to grasp what made Apple so unique, and pursued a course towards unexciting, run-of-the-mill products. The company was headed for the permanent dustbin of history by the early ’90s when it had lost every market except that of the graphic design world. (Meanwhile, Steve Jobs was off creating his own horribly inept company, NeXT.) But this story had a happy ending. Apple brought Jobs back aboard, the iMac and iPod were born, and the rest is history.

6. Sony. The company’s name has been practically synonymous with quality consumer electronics for a generation. But that reputation is starting to tarnish, and Samsung is now just as much of a quality brand as Sony ever was. The company has stubbornly bet the farm on its Blu-Ray high-definition videodisc, earning the ire of consumers and unnecessarily delaying the release of its Playstation 3. (Didn’t they learn anything from their own disastrous Betamax experiment?) The Playstation 3 might turn out to be the company’s redemption — or it could be the point when the company’s videogame consoles permanently ceded ground to Microsoft’s XBox.

7. Gateway. Dell, Compaq, and Gateway were once fierce competitors for the crown of the PC industry, which boggles the mind. (Who remembers that Big Country was once just as popular and revolutionary a band as U2?) The quality of Gateway’s equipment dropped off precipitously in the late ’90s, with a number of high-profile hardware recalls. And then the company spent way too much money pursuing a boutique retail presence while Dell was busy staying as far away from retail as possible. Lately Gateway has made something of a comeback, but they’ve got a long way to go to catch up to Dell.

8. Compaq. Owning an “ultra-portable” Compaq laptop was a status symbol in the ’80s. Then the company spent several years creating their own proprietary drivers and components in an attempt to make their machines premium products. Instead they pissed everyone off. For several years, at least, Compaq machines were every computer tech’s worst nightmare (although the laptop I used from 2000 to 2003 was a pretty reliable machine). The company’s purchase by a troubled Hewlett-Packard has relegated its products to also-rans in the marketplace.

9. Intuit. What happened to Quicken? Quicken was personal finance software for more than a decade. Then the company hung around waiting for Microsoft to acquire them — which Bill Gates & Co. did indeed try to do, only to be stymied by anti-trust regulators. Quicken is still the market leading personal financial product, but it’s fighting a neck-and-neck battle with Microsoft Money. Quicken differentiates itself these days by tying in to the company’s irritating and ad-strewn websites, which doesn’t strike me as a recipe for success. The company now stakes out the niches of home tax preparation software (TurboTax) and small business finance (QuickBooks), where their products succeed because nobody’s made a serious effort lately at unseating them.

10. RealNetworks. Once upon a time, RealAudio was the coolest thing on the planet. I’m not sure when the company began its slide into irrelevance — when was the last time you watched anything in RealVideo? — but the ad-laden disaster RealOne Player surely was a major turning point. It took the much-loved and highly functional Real Jukebox and hobbled many of its features or made them premium add-ons. Like Netscape before them, it seems the company largely got spooked by the dominance of Microsoft and tripped over their own feet.

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So there we have it: ten tech companies, ten high-profile failures. The main causes? Seems to me they are failure of nerve, failure to innovate, excessive greed, excessive litigiousness, and overwhelming fear of Microsoft. Am I missing anything?