Apple’s historically been a company that treats the privacy of its users as a high priority—iCloud hacks not withstanding. The encryption on their proprietary iMessage platform, for example, is strong enough, and common enough to piss off the US government. And it’s not just privacy from the government that Apple’s known for: it’s protecting user data from advertisers, best expressed in Tim Cook’s angry invictive at EPIC’s Champions of Freedom event in June. It’s not a new thing for Apple, extending back to Steve Jobs’s tenure as CEO, but it’s gained new focus under Tim Cook. And I think I know why.

Tim Cook is 54 years old, born and raised in Alabama, and gay. For a gay man growing up in the Southern US in the 60s and 70s, the idea of being outed, or being out yourself, comes with huge, huge risks. In 2015, it’s a lot easier to be open about your sexuality—at least in some parts of the Western world—than it used to be. It’s still no guarantee of acceptance from your family or friends. While I’ve kept my own sexuality fairly private, I only came out publically on this site recently, and there are still people in my family who (I think) don’t know—and my family is, for the most part, open and supportive. In his excellent talk, “How Designers Destroyed the World”, Mike Monteiro tells of two gay people outed to their homophobic famlies due to Facebook privacy changes. Because of Facebook’s negligence, these two people have now lost their famlies. It’s getting better and safer to be LGBT, but the risk of losing families, friends, and jobs is still higher for LGBT people, even now.

The attitudes and priorities of the founders and CEOs of companies filter into the products they make. The risks of being outed aren’t going to be on the mind of your average straight, white, male CEO. When you don’t have to worry about what people think of you, when you carry no secrets that risk you losing your family, friends, or livelihood, it’s easy to assume the rest of the world has the same luxury. It’s not hard to see a CEO who knows what is at risk, as much in 2015 as it was in 1975, to have your secrets shared with those you need to keep them from. And if you’re going to be keeping your secrets private from them, you’ll want to keep them private from advertisers too. Nothing like an automated ad serving algorhitm to show you something that jeopardizes your secrets, without the awareness and compassion of humanity behind it.

One huge benefit of increasing diversity in the technology industry is to have more points of view into solving problems. Would Facebook have opted to reveal memberships in groups publically if one of the decision makers in the process was gay, and knew the risks? It’s hard to say for sure, but I can imagine knowing the risks would give them pause. We’ll never know for sure. Apple under Tim Cook is only one data point, and there’s other things that set it apart beyond just the CEO’s sexual orientation. They’re also not perfect, but they are taking the lead on privacy in a space where the focus is on forcing users to be more open, and algorithms to be more secret. I know which side I would prefer to be on, regardless of sexuality.

Everyone’s talking about ads, and tracking scripts, and web performance, and ads, and ads, and ads. As someone who works in media—albeit niche, specialized media—and someone whose job involves setting up lists and tracking codes for targeted advertising, it all hits home. It’s the part of my job I hate the most, even more than the gross pictures of dermatological disorders that end up in my inbox at least once a week. [1] Yet, as someone who also uses the web, who makes things for the web, who genuinely loves the web, and who wants to somehow make a living with making things for the web, I’m genuinely conflicted as hell about the whole thing.

Let’s face it, advertising is a necessary evil—only not actually evil, at least in theory. Someone has a product they need to sell. Someone has a need for a product to do something for them. Advertising is often how that gap is bridged, and there is nothing wrong with that. Yet, some people roll their eyes and view advertising as an affront to all it means to be human. Sure, many ads are bad, and advertisers in the digital age want more and more data so they can get closer and closer to the creepy world of one-to-one advertising—which both evil and unnecessary—but advertising as a general concept is not.

Speaking as both a digital media employee who has to deal with ads, and as a web user who uses an ad blocker and a tracking script blocker at home, the frustration—and the conflict—arises, when advertising becomes more important than content. We’re not going to The Verge, or iMore, or wherever to look at ads. We’re going there to read cool stuff, and the ads are getting in the damn way.

I’ve taken to unblocking the ads on sites that use ads in a respectful, polite manner. Stuff like The Loop, Six Colors, Daring Fireball, Metafilter, etc. Usually these are places that use ad networks like Fusion and The Deck, who also don’t target and track users. These ad networks, however, don’t work at the scale needed to support a site like iMore, or The Verge. So, they’ve gotta go for the more gross, and intrusive ads.

But what’s the alternative? The content model on the web is broken. Nobody wants to pay for anything—who do you know who has a digital subscription to the New York Times, anyway? The only way to make money at media scale with ads is more intrusive, obnoxious ads, and it’s clear audiences are fed the fuck up. It’s unlikely that online audiences are going to start coughing up money for commoditized content. With Apple, Facebook, and other tech companies creating content platforms that free readers from the burden of obnoxious ads, content is only going to be more commoditized, and harder to make money from.

I don’t have a solution, but I can’t help but think people would be less inclined to block ads if the ads weren’t so obnoxious. We’re a long way from the days of egregious pop-up ads that spawn more pop-up ads, flashing neon-colored “YOU ARE OUR 100,000th VISITOR” banners, and “Punch the Monkey” garbage that could crash your entire machine… but that’s a small blessing. There’s going to have to be a reckoning and a pushback against the current ad model, and it won’t be pretty when it happens. I just hope I’m in a place far from ground zero when it blows up.

[H]ow many of us are asked to design things that have the potential of causing harm to the people who come into contact with our work? How many of us will work on privacy settings for large social networks at some point? Will we think of how those settings affect those who interact with them? How many of us will design user interfaces for drop cams? Will we think of the privacy violations they might cause? How many of us will design products that put people in strangers’ cars? Will we consider those passengers’ safety as we design our solution? And will we see it as our responsibility to make sure these products are as safe as possible?

And if we come to the conclusion that these products cannot be made safe, how many of us will see it as our responsibility to raise our hands and say “I’m not making this.”

— In Praise of the AK-47 — Dear Design Student — Medium

All of us who make things, words, websites, products, we’re responsible for what we make and the effects they have—intended and unintended. The sooner we learn this, the sooner we focus on the people who use what we make over the profit we can make, the better the world will be.

There’s been a lot of complaints about Apple Music from the technorati: a confusing UI, flaky search, unreliability, and general confusion abound. Plus the actual bugs. Though, none has been quite as damning and harsh as Jim Dalrymple’s recent, rage-filled, piece on The Loop

As if all of that wasn’t enough, Apple Music gave me one more kick in the head. Over the weekend, I turned off Apple Music and it took large chunks of my purchased music with it. Sadly, many of the songs were added from CDs years ago that I no longer have access to. Looking at my old iTunes Match library, before Apple Music, I’m missing about 4,700 songs. At this point, I just don’t care anymore, I just want Apple Music off my devices.

Wow.

Normally, I try not to join a dogpile when it’s going around the tech blogs. I figure I have bigger issues to focus on. This is an exception.

I’ve been using Apple Music since day one, and I’ve largely adapted to its UI quirks. As a streaming service—and only as a streaming service—it’s quite good. The human curated playlists are great, Beats 1… well, it has a show with St. Vincent making mixtapes for fans, so that’s cool. I’ve used it with some regularity to change up my listening habits. But the streaming service alone isn’t worth $9.99 a month to me. What is worth it is having my entire music library, both the stuff I bought on iTunes, the stuff I bought on CD and vinyl, and stuff that, er, fell off the back of a truck, everywhere. Apple Music promised me that with iCloud Music Library. And iCloud Music Library is a turd.

I actually can’t use iCloud Music Library with my iTunes library. I have 31,815 songs in iTunes right now, the end result of spending more than half my life acquiring music. The limit, at least for now, is 25,000 songs. So, in a fit of exuberance, I took a knife to my iTunes library, excising almost 7,000 songs so I could try iCloud Music Library. The result was a car crash, with mis-matched songs, screwed up metadata and album artwork, and several days of frustration as I restored 200GB of music from backups. All I can say is that Serenity Caldwell is my hero for posting how to reset one’s iCloud Music Library.

There seems to be a common theme among the iCloud Music Library horror stories: people with large collections of music, with meticulous tagging that doesn’t conform to the iTunes Store, and a lot of live recordings, remastered versions, remixes, or duplicate song titles in their library. I am very meticulous about my metadata in iTunes, and meticulous in a way that Apple themselves are not. I hate having crap like “(Deluxe Edition)” on my albums, unless I’ve kept the non-Deluxe edition around for some reason. If I have a live album, I don’t need “(Live)” appended to every song title. I know it’s live—it usually says so in the album title!

Whatever Apple is using to identify the songs that exist in their library to match, it’s naïve as hell, and will match whatever is the first likely thing. If your song is on a greatest hits album, it’ll match the greatest hits track. Got a live recording that’s missing “(Live)” in the song title? Here’s a studio version for you. Hell, my friend Andrew Marvin from Crush On Radio reported that iCloud Music Library replaced some of his studio Primus songs with live versions! How does that happen?

It’s possible that Jim, Andrew, and myself are just edge cases. We’re crazy music fans with gigantic libraries, custom metadata, live recordings, and other stuff in our library that throws the matching algorithm for a loop. The problem is, the crazy music fans are the ones who are most likely to throw a shit-fit when something goes wrong. And here we are. Something’s gotta happen, even if it’s just a way to tell Apple “HEY! YOU MATCHED THE WRONG SONG. UPLOAD THIS, INSTEAD.”

At the start of the new year, I resolved to reduce the points of failure in my technological life, and iTunes came up:

[T]he reality of iTunes Match in execution, at least from what I’ve heard from people who try to use, leaves me quite content with having to plug in my iPhone, and manually manage the music I carry with me. There’s less chance of failure with locally stored music, instead of relying on the cloud. I don’t have to worry about having Wi-Fi, or a cell signal, or if the servers are behaving. The minor inconvenience of plugging into my computer is more than made up in reliable access to music.

So, I’ve divorced myself from iCloud Music Library, and unless this crap gets resolved by the time iOS 9 drops, I’m not likely to pony up $9.99 a month for the privilege of human-curated playlists and a streaming radio station I don’t care about. What sucks so much is that iCloud Music Library should be the feature that sets Apple Music apart from all the other streaming options. Until they fix it, Apple Music might be doomed to be an also-ran in the streaming space. Considering how skeptical I’ve been of paying for music you can’t keep, I think I’m going to be just fine when my trial ends. And that’s only a problem for Apple.

Ben Hammersley has some thoughts on how we interact with our personal AIs:

“It’s a little wrinkle in what is really a miraculous device, but it’s a serious thing: The Amazon Echo differs from Siri in that it’s a communally available service. Interactions with Alexa are available to, and obvious to, everyone in the house, and my inability to be polite with her has a knock-on effect. My daughter is too young to speak yet, but she does see and hear all of our interactions with Alexa. I worry what sort of precedent we are setting for her, in terms of her own future interactions with bots and AIs as well as with people, if she hears me being forced into impolite conversations because of the limitations of her household AI’s interface. It’s the computing equivilent of being rude to waitresses. We shouldn’t allow it, and certainly not by lack of design. Worries about toddler screen time are nothing, compared to future worries about not inadvertently teaching your child to be rude to robots.”

— The Miscellaneous Tumbling of Mr Ben Hammersley – Possible Problems of Persona Politeness

I’ve not tried Alexa—the idea of having Amazon potentially listening in on everything in my apartment kinda freaks me out—but I use Siri. Now that I have an Apple Watch, I want to use it more. It’s telling that there’s still, four years on, people talking up Siri’s “Easter eggs” when you speak to it, and nobody’s said a thing about Alexa’s personality, or lack thereof, and what it could mean, until now.