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Essays on Technology and Culture

Pizza Valley

All across the Valley, the majority of big start-ups are actually glorified distribution companies that are trying, in some sense, to copy what Domino’s Pizza mastered in the 1980s when it delivered a hot pie to your door in 30 minutes or less. Uber, Lyft, Sidecar, Luxe, Amazon Fresh, Google Express, TaskRabbit, Postmates, Instacart, SpoonRocket, Caviar, DoorDash, Munchery, Sprig, Washio, and Shyp, among others, are really just using algorithms to deliver things, or services, to places as quickly as possible. Or maybe it’s simpler than that. As one technologist overheard and posted on Twitter, “SF tech culture is focused on solving one problem: What is my mother no longer doing for me?”

— Is Silicon Valley in Another Tech Bubble? | Vanity Fair

Nick Bilton nails the problems in the Valley, and this is just one of a whole holy host of quotable sections. That said, Dave Pell is on to something too, if you need a TL;DR version.

Pen Support Won’t Save the iPad, But It Needs It Anyway

As we approach Apple’s Fall Announcement season, rumors are swirling up once more about the “iPad Pro” and its purported stylus. Will pen support be the magic bullet that saves the iPad? Absolutely not. For the most part, pre-iPad tablets had styluses to make up for technical limitations of touchscreen accuracy and the need to hit tiny, fiddly buttons on desktop UIs. We’ve come a long way since then, unless you’re Microsoft. And we know how we’ll the Surface Pro’s been doing these days. Besides, styluses suck. They’re expensive, and easily lost—and the more expensive and fancy they are, the more likely you are to lose them. Considering Apple’s predilection for smaller, thinner devices with fewer ports, do you think Apple’s going sell a device with a slot to tote a stylus in?

That’s not to say that pen support won’t come to the iPad. It has to. Pen support is, to borrow a phrase from John Siracusa, necessary, but not sufficient for the tablet to replace the PC as the dominant form of computing. I doubt Apple will make their own stylus, and if they do, it certainly won’t be a “smart” stylus. Apple’s methodology with iOS devices is to add capabilities and sensors to the device itself, not to add hooks for outside hardware. A stylus runs counter to this approach. All Apple needs to do to bring pen support to the iPad is something they’re clearly planning to do anyway: add Force Touch.

When the new MacBook launched, with the Force Touch trackpad, a few people noticed that in the Force Touch section of the design page, it mentions “pressure-sensitive drawing” as a feature. Within a week, it was forgotten, mostly because everyone freaked out about the new keyboard. Force Touch trackpads have enough pressure sensitivity that one could use it to sign something, even without a stylus, but it works with one, too. An iPad with Force Touch sensors in the display will suddenly make every stylus on the market be pressure sensitive. The only reason Apple would need to make their own stylus is to snag a couple extra bucks of profit from accessory purchases.

Screen Shot 2015-08-29 at 9.57.27 PM

On top of all that, baked into MacOS X is Inkwell, a handwriting recognition technology first created for the Newton (replacing the licensed technology that gave us “Eat Up Martha”). iOS is built on the same core technologies as OS X, and so, if Inkwell isn’t already baked in to iOS, it probably wouldn’t be difficult to port it. All you need to do is look at the new Notes app in iOS 9 to see where Newton-style handwriting recognition could be used on a first-party basis. And if Inkwell can be turned into an API, all kinds of crazy apps could tap into it, creating myriad new uses for pen computing.

Reading the tea leaves, it’s pretty clear how Apple will bring pen support to the iPad, and to other iOS devices: a Force Touch display, Inkwell handwriting technology (or a successor), and leveraging the huge array of pre-existing styluses to match everyone’s preference. Boom. We’ll find out in October if I’m even close to right on this, but for anyone hoping for a first-party stylus, don’t hold your breath. I’m not a betting man, but I’d bet on that.

For the iPad, and tablets in general, to supplant traditional PCs, there’s more that needs to be done: longer battery life, more CPU power, better input, and—most importantly—faster inter-device wireless connectivity. Pen support certainly goes a long way towards solving the input problem, but that alone won’t save flagging iPad sales. It’s a very good first step, though.

“Means Well” Technology

“Ultimately, the technology shows you a problem, but not how to deal with it afterwards, or prepare you for it. It attempts to nudge you into behaviors without know what behaviors it is nudging you out of. As designers, we know how we’d like our designed object to work, that you, or your user, are saved in the nick of time, or that you can have a good laugh about the STI that has been revealed afterwards, but we know that just isn’t the case.”

— “Means Well” Technology and the Internet of Good Intentions — Thingclash

Food for thought on the disconnect between the technology world and the real world.

Empathy Boot Camp

“When you learn to write you are taught that a deep understanding of your audience is essential to effective communication. On the internet, though, you are often shouting to your intended listeners as they stand in a thick, noisy crowd. You may be appealing directly to their interests and ambitions, but if their neighbor disagrees, you could still face pushback, complaints or even abuse. The potential for criticism from unexpected parties is, on the whole, positive – a boot camp in radical empathy, one that makes it ever more difficult to hide behind provincialism as an excuse for insensitivity. But for many, it’s disorienting.”

— Can the internet actually be an empathy boot camp? – Jess Zimmerman

The first step towards empathy is to slow down and think before you hit post. We’re all still figuring out how to live in a world where everyone has megaphones, but Jess is pointing towards a good way to manage it.

Saving the Web We Have

There’s been a few interesting pieces circulating around about the “web of relationships” and “the web of links” vis-a-vis the blogging environment of the early to mid 2000s, before Twitter and Facebook mucked it all up, siloing our content, locking in our friends, and limiting our interactions. I have a lot of respect for the revolutionary bloggers of the Arab Spring. They did a great service to their countries, got screwed over for it, and are continuing to be screwed over for it. They have every right to miss that world where a good blog post can be shared and responded to at length, rather than through a 140-character—or likely less—Tweet, or an easily missed Facebook post.

Part of why these pieces have been circulating around, though, is a sense of nostalgia among people like me for the old ways of doing things online. We miss the mythical golden age of the web, where it was wild, weird, and wooly. We miss the days of blogrings, of links pages, of early blogs and building up a readership that you could share with. In the mid–2000s was a sense that blogs could change the world, and they did, at least in a small part of the world where the stars all aligned.

Once, there was a dream where everyone would have their own domain, their own presence online that they could own and control at their will. It’s a dream that never happened. Instead, everything got bought up by Google, or everyone jumped ship to Twitter and Facebook. Now everything is siloed off and locked down. Links mean nothing, and if you’re not writing for one of the big media sites, are lucky enough to go viral on Medium, or managed to get an audience large enough to support your work before everything blew up, you’re screwed. Now, a blog link is just another piece of disembodied content in the stream. As Hossain Derakhshan puts it:

Nearly every social network now treats a link as just the same as it treats any other object — the same as a photo, or a piece of text — instead of seeing it as a way to make that text richer. You’re encouraged to post one single hyperlink and expose it to a quasi-democratic process of liking and plussing and hearting: Adding several links to a piece of text is usually not allowed. Hyperlinks are objectivized, isolated, stripped of their powers.


In 2002, I set up my first blog right at this domain. I begged my parents to spring for a year of web hosting and a domain name as my high school graduation present. I set up GreyMatter, built a template, and started blogging. Over the intervening years, I switched to MovableType, then to WordPress. I changed hosts, built new templates and themes, and tried to find the right voice, and the right subject matter. I didn’t change the world, or pick up Daring Fireball-level readership, but I’m still here, typing away.

What we so easily forget is that, in the early 2000s, it was a huge pain in the ass to get anything up online. There were two options. The expensive, hard, but more respectable way, was to do it yourself—either by setting up your own web server, or paying for hosting. Either way, then you had to set up blogging software, which was also a pain in the ass. FTPing to a server to upload the files, SSHing into the server to set the permissions using the arcane incantations of the UNIX command line. Finally, running the configuration software on the server in your browser, crossing your fingers, waving a dead chicken, and hoping very hard that you didn’t mess anything up. (This is how I did it. Even that process is easier now.)

The cheap and easy way was to sign up for Blogspot or LiveJournal. Even a paid account on LiveJournal, and the cost of a domain was less than paying for web hosting. You had less control, and you could be linked to by the outside world, but let’s not kid ourselves. Among the tech-elite, having a Blogspot or LiveJournal account was usually a sign that you couldn’t be taken seriously, unless you were Jamie Zawinski. Thank goodness for those free services though, because if you told an ordinary person in 2003 that they needed to learn how to use FTP and UNIX just to put words online, most would check out. Tumblr is the closest thing we have to a 2015 version of LiveJournal and Blogspot, and while a few tech elites use it, most just eye it warily. At least you can link to Tumblr posts.


While I’m no fan of Facebook or Twitter these days, I have to admit that they do something well that a lot of people want. They let people put out their words, pictures, and ideas in front of an audience without requiring too much effort or financial outlay. Could DeRay McKesson have the reach and importance he has now if he were a self-hosted blogger, instead of leveraging the low overhead of posting to Twitter? You can still tweet via text message from a flip phone, if it really comes to it. As long as you are connected and have an account, you can put your words out there.

Centralized publishing platforms carry the risk of censorship, of course, but this isn’t new. Even in the days of Blogspot and LiveJournal, there was the risk that some regime change at the publisher could come down on something they don’t like. Even my web host, if I should do something on here that violates their Terms of Service, and they learn about it, cancel my hosting account. But that’s direct, human action. The new worry is the risk of algorithmic censorship. This is something not enough people are talking about. At least Zeynep Tufekci brings it up:

Facebook engineers will swear up and down that they are serving people “what they want” but that glosses over the key question that if the main way to tell Facebook “what we want” is to “like” something. How do we signal that we want to see more of important, but unlikable, updates on Facebook? We can’t, it turns out.

Of course, this isn’t a zero-sum game. The existence of social media, of Twitter, Facebook, Snapchat Stories, Apple News, et. al. doesn’t mean that blogging and linking is going away forever. If you’re looking at this in a web browser, that’s proof enough. If you’re looking at this in an RSS reader or a Read Later service, that’s also proof. We can save the web of links, of people, and of connections without dismantling the new social media infrastructure. We need tools that make it easy for people to have a space of their own on the web that isn’t necessarily part of some giant network like Twitter, or locked into a service like Facebook.

How do we maintain the balance of making it easy and accessible for people to use their voices online, without getting them bogged down in the technical details? I don’t have an answer to that question. I just know it doesn’t have to be an all-or-nothing world. It’s going to take an act of will, and some new tools that balance ease, cost, and flexibility for a world where people’s primary way of access isn’t necessarily a traditional computer. There’s bound to be some push-and-pull along the way between the extremes of the social media silos and the full control of independent spaces. Nothing is set in stone yet, and we can still figure this out. Let’s take the good parts of the web we have to save, and merge it with the ubiquity and easy of the web we have now. The rest are implementation details.