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Essays on Technology and Culture

Whitney Phillips: “Everyone you encounter on the internet is a person.”

[B]efore we do or say anything online, before we retweet unconfirmed details about the latest gun-related tragedy, before we post a shrill, sensationalist article to Facebook, before we furiously peck out our own hot take, we have to ask ourselves: Does this have the potential to make someone’s day worse? Someone’s life worse? If the answer is maybe, back away from the computer. Go outside and look at a tree. And remind yourself: Everyone you encounter on the internet is a person.

— Whitney Phillips – “We’re the reason we can’t have nice things on the internet”

There’s so many great things to pull from this pice, but the above is probably the biggest one. We’re so disconnected from each other’s genuine feelings by the nature of the Internet as a medium. Taking the first step, asking the questions “Does this have the potential to make someone’s day worse? Someone’s life worse?” is a small step towards bridging the empathy gap online. We may be the reason we can’t have nice things on the Internet. We also can be the catalyst to change that, even in some small way.

Towards a Grand Personal Theory of Technology

It wasn’t that long ago, when I was bemoaning the complexity of my technology, wondering whether I should give up and strip down to a cheap computer and a cheap phone. That was about a month after an article Steven Levy on the new iMac dropped. In it, Levy explained what he called Phil Schiller’s “grand philosophical theory” of Apple products:

“Ideally, you should be using the smallest possible gadget to do as much as possible before going to the next largest gizmo in line.”

This is eminently reasonable, and I’m kicking myself for missing it the first time. It’s a philosophy I’ve chosen to (try and) take to heart in the new year for my technological life. How does this play out in practice, though? Let’s start with the smallest device: the Apple Watch.

I would love to use my Apple Watch for more, but the combination of a fiddly interface and the slow speed makes me keep reaching for my phone. As I wrote in my six month update of life with the Watch: “If there’s been a theme… it’s figuring out what I want to get out of [the Watch], and dropping what it’s bad at.”

I’m still trying to settle on a set of core functions that I can do on my Watch easier and faster than on my phone. So far, that’s fitness, (some) contextual computing, and notification triage. [1] What it’s not is communication—too many friends not in the iOS messaging ecosystem. What I might have to do to get more out of my Apple Watch is insist on keeping my iPhone out of arm’s reach unless I really need it.

As for the iPhone—it’s my primary communication device, and my portable entertainment device. A huge chunk of my music library lives on there, along with audiobooks and podcasts. The way I use my iPhone hasn’t changed a great deal since iOS 7. The extension frameworks and improvements to multitasking and sharing have made life easier, but the fundamentals remain solid, which is fine by me. I haven’t gotten much use out of the “proactive” features in iOS 9, but they look like a solid foundation for more context-based computing.

My iPad is one of those devices where I’ve struggled to fit it in with how I use technology. Growing up as a traditional PC user—craving a mouse, a keyboard, a giant display—combined with the difficulty of doing (ugh) “real work” on an iPad creates a recipe for inertia. My iPad 3—that’s the first one with Retina, for those keeping track—was long in the tooth, and an upgrade was long overdue. I got myself an iPad Air 2 for Christmas. I know there’s an iPad Air 3 in the works that’ll likely have support for Apple Pencil, but meh. In a few days with the Air 2, however, I’m already making a conscious decision to use it over my Mac for a lot of things.

The new iPad is finding its niche for me as a lightweight, fast, easy way to do reading and writing. Split view and slide over apps are so good. My previous iPad felt so limited that there was almost nothing I could do with it beyond the occasional bit of writing, reading RSS feeds and comics, and plinking around in GarageBand. I don’t know exactly what else I’ll want to do with this thing yet, but I’m willing to give anything a shot. I’m also excited to see what iOS 10 has in store for the iPad with the sheer computing power of both the Air 2 and the Pro.

Finally, there’s my Mac. The Mac is where I get all my heavy lifting done, but also where I do most of my slacking off. Games, social media, writing code, writing text, you name it, I’ve been doing it on my Mac. When I work from home for my day job, I do it on my Mac. If I’m going to be doing more on the smaller devices, the Mac has to, of course, be the device I step back from. Now, it looks like I have a setup and an ecosystem that makes overcoming the inertia of being a traditional computer user worth it. We’ll see what happens as the year progresses.


  1. As for notification triage, one of the few notification focused apps I use is Due. It’s a wonderful app, but something about dismissing notifications in it from the Apple Watch has been broken since iOS 9. Very frustrating.  ↩

Can Empathy Scale to the Internet?

Cynicism is easy, especially when all you can see serves as justification for it. It also blinds you to anything that might serve to contradict that same cynicism. Reading about the growing Internet counterculture of racism and misogyny that festers in the Web’s darkest corners, and see it not only refuse to be disinfected by sunlight, but encouraged—cynicism is an easy refuge.

The problem with cynicism is that it solves nothing. A cynic may be a failed idealist beneath the prickly exterior, but it’s not for want of trying. Because we cynics have tried—or tried to try—and seen our efforts go nowhere, we take our ball and go home to snark from the sidelines. Cynicism works for us because it feels good. If we can’t save the world, let’s at least enjoy watching it fall apart. Cynicism also eats away at our empathy, and empathy is what we need most now. This came into focus for me while reading a wonderful piece by Parker Molloy. Her conclusion stuck with me:

“[S]o long as we look at the world through the lens of objective good versus objective evil, we’ll never truly be able to understand why anyone does anything… The world would be a better place if we could all learn to empathize a bit more with one another… to not view people as pure evil or pure good, and to understand that we’re all in this world together so we might as well make the best of it we can, as one big happy human family thing.”

To get past the false dichotomy of “objective good versus objective evil,” we need to develop the skill of empathy—and it is a skill. Some of us have a more developed, innate sense of empathy than others, much in the same way that some of us have a more developed sense of musicality than others. That doesn’t mean whatever degree of skill we have in empathy can’t be improved through effort and practice.

The Internet and social media provide countless opportunities to practice empathy. What comes through our timelines and streams, whether we agree with it or not, comes from a real place and real emotion. This is true, whether we’re seeing anger, joy, sadness, bemusement, threats and abuse, or support and love. Even the darkest, cruelest, and most cynical attempts at humor come from a place of genuine emotion. Understanding this is the first step—and that step is the hardest of all.

Online communication remains text-based for the most part, meaning we lose much of the metadata of conversation; facial expressions, tone, and—too often—context. A Tweet in isolation offers at most 140 characters of information. It’s place in a larger conversation is lost, making it easier to decontextualize and for someone to apply their own meaning and agenda to it. There are imperfect methods—hacks, really—to bring that missing data back into our online conversations, but an Emoji or a GIF can only go so far. For minds that expect more information in a conversation than the basic content of a message, communication, and thus empathy, becomes all the more difficult.

This may explain why so many view what happens online as being less than “real.” How can it be, when all the hallmarks of human interaction are lost to the medium? That unrealness also gives us license to be someone other than ourselves—in whatever capacity we could be said to have one self—when interacting online. The normal laws of behavior and propriety are suspended, and we are free to express ideas and behaviors we never would in the “real” world. In practice, this is known as the Online Disinhibition Effect. It is beyond real, and the data speaks for itself. For example:

“A Johns Hopkins University study in 2007 found that 64 per cent of bullied children were exclusively attacked online. That is, many children who were habitual bullies on social media would completely refrain from this behaviour when meeting their victims in person.”

The above data point comes from a remarkable essay called “Possessed by a Mask” by Sandra Newman for Aeon Magazine. Newman draws parallels between the historical role of masks in human society, and the way we behave behind the mask of the Internet.

Even if we’re using our real names, we’re so disconnected as to be masked by default. When we’re masked in a room of other masked people, the rules often stop applying to us. It take a conscious act of will to see past the masks. As Newman says in her conclusion: “Above all, we should remember that, behind the masked figures that surround us, there are people as vulnerable, fallible, as real as ourselves.”

While empathy is hard before you add the Internet, that’s an explanation, not an excuse. Ideally, empathy would be baked in to every social and communication product from the beginning, but empathy, as a concept and a skill, is not valued by technology companies in their products.

There are many reasons for this, beyond the nature of the medium. One is the massive amount of privilege afforded to those who build our communication tools. If you’ve never experienced abuse, harassment, or even the inevitable painful memories that come with time, you won’t think about it. It becomes a blind spot in product development, further deprioritized in favor of juicing the numbers, monetizing the service, and generally serving “investor storytime” to keep the money rolling in.

When the companies that define our online communication start to take the abuse of their platforms seriously, we’ll finally hit the turning point on the technical problems of harassment and abuse. It’s largely been lip service until now. We’ve seen it on Twitter through GamerGate, with Reddit, and even at South By Southwest. But we can no more place the blame for tech companies failures of empathy on the Internet entirely at the feet of Venture Capitalists any more than we can place it at the feet of the companies they fund, the engineering teams building the products, or entirely at the feet of the users.

We’re all to blame at some level, and we’re all responsible for finding a solution. It is possible to build systems on a technical level that—if not ones that strengthen empathy, at least making it prohibitive to be cruel and abusive before the fact. Makerbase is a great example, and Anil Dash’s “8 Steps” are a good start for anyone entering the social space. It starts with a willingness to think about these problems before they occur. And, as long as we’re sticking to the VC model, it takes a willingness for VCs to reward companies that think about these problems.

As for us, the end users who have to live with these flawed channels of communication? Thank goodness for the work of people at Crash Override Network and The Online Abuse Prevention Initiative for building strategies and tools to protect us from bad actors of all stripes. More can be done, but we’ve started having the conversation, and it’s slowly starting to pay off. But, any solution must have empathy at its core, for all users.

Here is where I need to make it clear that I am not equivocating. The behavior of certain groups, such the deliberately offensive “Chanterculture,” is often indefensible. There is no excuse, no defense for the harassment, abuse, threats, and violence their victims have experienced. We need to develop empathy for the abusers who lack empathy, as well as their victims. As I said before, even the abuse comes from a place of genuine emotion. There’s more to the callous cruelty than its visible manifestations. Understanding it will go a long way to helping the perpetrators of online abuse mend their ways and finding peace for all involved.

Empathy has to work both ways for it to be effective. The challenge in scaling empathy is the struggle of developing empathy for those we would prefer to have nothing to do with. Empathy doesn’t mean agreeing with their viewpoint, merely trying to understand where they come from. It doesn’t mean freeing abusers from the consequences of their actions, but those consequences must draw from empathy. No obstacle—a mask, a lack of information, a lack of the metadata of communication—should stand in the way. Surmounting these obstacles takes substantial effort, but it’s within our reach. It just requires us to care—and to drop our cynicism.

Internet and social media companies need to develop empathy for their users. Users need to develop empathy for other users. Top-down technological solutions can get us part of the way there, but we can try in our own digital lives to be more empathetic on a daily basis. I find myself going back to Jess Zimmerman’s excellent piece: “Can the internet actually be an empathy boot camp?” Many of the points she makes I have echoed above. I’ll echo another: we’re all going to screw this up, and often.

“It’s harder now to be convincing, and easier to put your foot in your mouth; you’re virtually guaranteed to accidentally hurt someone and have to apologize… But this lack of control over your audience forces you to consider more people’s needs more deeply, to become and remain more aware of the variety of human traumas, motives, histories and concerns.”

Each of our mistakes, our failures of empathy, are a chance to learn and strengthen our skills. It feels, however, that we often don’t bother to notice those failures for all the reasons outlined above. If our empathy is going to reach Internet scale, we have to start building it here and now. Let’s, all of us, work towards a more empathetic Internet, beginning with us. Stop, slow down, and think before you post another snarky comment. Try to understand the motivations of others, and try to get less outraged over outrage. Practice, practice, practice empathy in our lives, whether we’re an end-user, an engineer, or a product manager. This applies to the Internet and the “real” world, but the former is where the bigger challenge lies.

My Top Five (or so) Albums of 2015

This year has been a remarkable one in terms of new music. I didn’t pick up nearly as many new albums this year as I have in previous years, but of the ones I did, I had a way higher hit-to-miss ratio than usual. I also had the pleasure of seeing some incredible live music this year, including seeing a handful of bands I thought I would never get to see. Of course, you don’t want the setup, you want the best ofs, so let’s just get to it.

Top Five Albums of 2015

Honorable Mentions

Like I said, 2015 had an insane hit-to-miss ratio of the music I checked out, and I need to single out the releases by Belle & Sebastian, Erase Errata, Hot Chip, New Order, Rocket From the Tombs, They Might Be Giants, Zhala, and !!! for some of the best music of 2015 for me. But, there can be only five top five.

Except this year, when there’s six, because there’s a tie for 5th. If we can do it in Competitive Air Guitar, I can do it in my best of list.

5. (TIE) – Eskimeaux – O.K. / CHVRCHES – Every Open Eye

I first heard Eskimeaux in a very different incarnation three years ago, and was blown away by the sparse, haunting beautiful of their music. It even made my Top 10 Albums of 2012 list, which is no small achievement. O.K. fills out the Eskimeaux sound, and brightens the palette, while keeping the emotion and the haunting beauty. “Broken Necks” is a brilliant piece of alt-pop, and a perfect gateway into Gabrielle Smith’s world.

Buy Eskimeaux – O.K. on iTunes

CHVRCHES might not need an introduction. Their breakthrough “The Mother We Share” was everywhere in 2013. Every Open Eye, their sophomore album, doesn’t quite hit the highs of their debut, but it also doesn’t hit the lows. Opting for a refinement of their sound, Every Open Eye is uplifting, danceable, feminist synth pop for the ages. I have to single out the song “Keep You On My Side” which is a dance floor rager, if there ever was one. I know I was moving constantly when they played it live in Central Park this year.

Buy CHVRCHES – Every Open Eye on iTunes

4. Princess Chelsea – The Great Cybernetic Depression

I’ve been waiting for a follow-up to Princess Chelsea’s debut album, Lil’ Golden Book for four years. It did not disappoint. Where Golden Book was a slice of childhood morality play in shades of grey, The Great Cybernetic Depression steps boldly into the modern era, with spacey synth-laden songs of digital social isolation. It works quite well, and the surprisingly blistering guitar solos from collaborator Jonathan Bree add just the right tones to ground everything. Guaranteed, you don’t have another album like this in your collection.

Buy Princess Chelsea – The Great Cybernetic Depression on iTunes

3. FFS – FFS

The team-up between Glasgow dance-punks Franz Ferdinand and Art Rock geniuses Sparks might have tied with Grimes for my most anticipated release of 2015. As soon as the debut single, “Piss Off” dropped, it was in near-constant rotation. Then came “Johnny Delusional”, and so much more. FFS manages to combine the urgency of Franz Ferdinand’s sound with the lyrical wit and musical cleverness of Sparks into something entirely unique. If you’re a fan of either band, you need this album in your life. If your just like amazing rock music with incredible lyrics, you need this in your life too.

Buy FFS – FFS on iTunes

2. Holly Herndon – Platform

Holly Herndon broke my mind into a million pieces when I saw her open for St. Vincent back in February of 2014. Not long after that show, the powerful video for her NSA breakup song, “Home” landed, and I was hooked. Imagine, if you will, Laurie Anderson coming up in the Berlin club scene, and you might have a halfway decent frame of reference for Herndon’s sound. Platform is a powerful statement of intent. Music for the Internet age, that somehow manages to maintain a pure listenability while communicating a powerful technological optimism.

Buy Holly Herndon – Platform on iTunes

1. Grimes – Art Angels

I still remember my initial suspicion of Grimes, the same suspicion that I have of anything and anyone that gets a lot of hype. Thank goodness I got over it. “Oblivion” was one of my songs of the year in 2013. I was hooked, and after picking up Visions, and her first two albums, I devoured what little she released in the interim, from the R&B-influenced “Go”, to the demo of “REALiTi” and enjoyed it all.

Then I woke up to the first taste of Art Angels, the music video for “Flesh Without Blood” and “Life in the Vivid Dream”. It was everything I hoped for from Grimes’s return to music. Everything I read about the album made me want to hear it more, and when I found out she was doing a song with Janelle Monaé, I went from hyped, to beyond hyped. This level of anticipation is almost bound to end in disappointment. Art Angels does not disappoint. Fifty minutes of pure electronic pop genius. The future of electronic pop is Grimes. It’s not too late to get on board.

Buy Grimes – Art Angels on iTunes

Song of the Year: Grimes – Kill V. Maim

This year has had some of the best single songs, and it’s hard to just pick one. I singled out some of them from the top five albums this year, but from the first notes of “Kill V. Maim”, I knew the competition was over. Not only is it an wild dance-floor rager, the backstory is just as wild. Grimes was inspired to take on the character of a mobster modeled after Al Pacino in The Godfather, Part II., only “he’s a vampire who can switch gender and travel through space.” Sure enough, the song is pure swagger, and gender bending vocal fluidics. When I had the pleasure of seeing Grimes in concert—even sick with the flu, she’s an incredible live performer—“Kill V. Maim” was the encore. Exactly where it should be. It left the entire audience breathless.

Tech’s December Doldrums and The Bigger Picture

December is the hardest time to be on the technology beat. It’s the slowest month of the year, which is why most technology journalism bends towards the best deals on potential holiday gifts, best-of lists, or best-of lists of potential holiday gifts. If you’re wondering why so many people are writing hot take thinkpieces on Apple’s new battery case, now you know. There is nothing else to talk about.

My own writing has often tapered off near the end of the year—often there’s just nothing to write about. Combine that with the general madness of the holiday season, and it’s a recipe for doing anything but making the clackity noise. This year has been especially maddening, when you factor in recent events in the Apple blogging community. I don’t even consider myself an Apple blogger, though I certainly have a toe in that pool. For my own role in the Bielefeld saga, I apologize. I’ll probably be on Marco Arment’s Twitter blocklist for eternity, which is my punishment for being suckered, I suppose.

But it also leaves me thinking about the nature of technology writing, my writing, and a feeling of dissatisfaction with the general beat. There’s the endless cyclical arguments about App Store pricing models, about whether an iPad can replace a Mac, about thinness versus battery life, about the Android approach versus Apple. The more we go around and around in the circular arguments, the less I care. I’m a user of consumer technology: personal computers, tablets, smartphones, smartwatches—but I’m not captivated by the devices themselves. They are tools, nothing more.

And I certainly don’t care about the stock prices and earnings reports about these companies. As long as the companies that make the tools I use stay in business, that’s all I need.

I care about what we can do with these tools. I care about what these tools are doing to us. I care about the people—not just coders, hackers, and designers, artists, citizens, and the global community. It’s a sentiment I’ve stated here before, after the wonderful Facets Conference, back in May

I’m sick, tired, and just plain bored of breathless excitement over the latest and greatest consumer gadget. I’m also sick, tired, and just plain bored of breathless anger over the latest and greatest consumer gadget. It gets us nowhere, and I’m as guilty of this as anyone else… I’m not saying there’s anything wrong with occasionally looking at the tech world from that level, but right now I feel like it’s missing the forest for the fourth leaf on the middle-bottom right branch of the thirty-seventh tree to the east-southeast.

But there’s a problem. When I try to think about these things, when I step out of the comfort zone of writing about consumer technology and try to write about bigger topics, I get lost. I’m not a programmer, I’m not a hacker, I’m not a technology academic. I’m a gadget nerd who failed a Computer Science program and went back to school for a Liberal Arts degree. [1] I want to learn more, I need to learn more, and I don’t know where to start. And, why lie, the numbers on the posts where I do write about these things aren’t nearly as good as the ones about Apple and gadgets.

I’ve struggled to find people writing and talking about technology and society on the regular to learn from. I’ve read some amazing books like Ursula Franklin’s The Real World of Technology lectures, and Evgeny Morozov’s To Save Everything Click Here. I’ve found a handful of podcasts: Spark, from CBC Radio and Note to Self from WNYC, but that’s about it. (There’s also Mindful Cyborgs, which could be great if they would just bring someone on to edit the audio properly.) I’ve not found anyone writing about this on a regular basis, just the occasional diamond among the dross.

This isn’t to put down the work of the people who write about gadgets, about Apple’s finances, about battery cases, and keep up with the day-to-day minutia of happenings in tech. They do work that is valuable to someone—often work that is valuable to myself, too. Keeping up with what’s happening in this space, even if it’s just new products, is important. I just don’t feel the need to read fifty stories rehashing the same press release, and listen to six podcasts rehashing the fifty stories—but you do you, you crazy gadget lovers and Apple followers.

Moving into 2016, I hope to move further away from writing about gadgets and Apple stuff, and more into writing about the bigger issues and topics that technology touches. I also plan to write more about music, since that’s a passion of mine. (Keep your eyes out for my best music of 2015 post, coming before year’s end.) If nobody is going to write the blog I want to read, it comes down to me. It’s going to be a struggle and a journey of discovery. I’m hoping there’s a few other seekers along the path who will join me. There’s more to talk about that’s happening beyond the latest smartphone accessories. Let’s find it.


  1. I am working on a programming project that I will talk about another time. But, being able to write code is not the same thing as being able to think and write about technology on the level I aspire to.  ↩