In an ideal world, I wouldn’t have to trust my data to a third party. I could simply plug a box into my home Internet connection, and trust that my digital life would live there while being accessible on any other device I own. It would hold everything from email to personal files, from photos to music, from my health data to my identification credentials. It would be 100% reliable, secure, encrypted, and accessible only to me—and maybe my partner. And, as long as I’m living in a fantasy world, it would cost a nickel, use no power, and come with a free pony.

So, I’m stuck offloading my personal data to an assortment of companies with varying degrees of reliability and trustworthiness. The chart below helps break down where several of the services I use—or used to use—fall.

The services in the bottom left corner are ones I’ve stopped using, save for LinkedIn. Jawbone and FitBit are flaky services that silo my data. LinkedIn is just frustrating and annoying. There is only one service in the bottom left corner, which will surprise no one, because no matter how much I can trust something, I will not use it if it is unreliable. I conflate reliability and utility, mostly because three-dimensional charts are terrible, and also because unreliable services are generally useless anyway.

Reliability is a huge factor—will I open an app to find that all my pictures, files, music, what-have-you is exactly where I left it? Will the changes I made on one device propagate to all the others without errors or data loss? This is a hard problem to solve, and nobody’s gotten it completely for everything. The more complex the data set, the bigger the problem is to solve. Google seems to have a lock on this, along with Dropbox. iCloud is getting there, but has its share of weird issues that are slowly being ironed out. We’re not hurting for Internet services that fail to deliver on their promises in terms of having our data everywhere. There’s another factor we need to consider.

That factor is Trustworthiness. Trust is a question of data security–not just against malicious actors, but also how the company will be using that data. Let’s go back to Google. Though I’ve had nothing but bad luck with Google Now, I like the idea in theory. I had high hopes for the new “Proactive” features in iOS 9, but they’ve been largely a non-entity for me. If Google was just going to be using the data I feed it to better my life, I’d have put them on the other side of the chart.

Instead, Google sells my data—supposedly anonymized, chopped up, and in bulk—to advertisers. That’s a violation of trust. In all other respects, Google is a solid steward of my data. They’ve had data leaks and security breaches, but no more so than most other companies in this space. I’ve also never run into synchronization issues or data loss with Google.

iCloud loses a few points on reliability, but makes up for it immensely in trust. Apple’s commitment to privacy has me more willing to use their services for my personal data than any other, even if I’ve run into a handful of issues with synchronization. It’s a choice based on principles, and I’ll take a handful of frustrations with the knowledge that my data is safe, over knowing my data belongs to people who I didn’t explicitly authorize access to.

One day, I hope I can have all the services I choose to use in the top right corner of this chart. I want to trust that my data stays safe, stays mine, and is not sold to the highest bidder. It’s not going to be an easy battle, since it’s more lucrative for companies to sell data and keep the services free. Data is the currency of the Internet. We’ll probably never be free from trading data for services, but I can hope that one day we’ll have more options on how much of our data to spend. Until then, I’ll keep holding out hope for the free pony.

The Apple/FBI comedy of errors continues, and it’s likely to end up being argued in court. This means there is a possibility—following appeals and other legal maneuvering—that Apple will be compelled to write a tool to unlock iPhone encryption. This wouldn’t be just for one iPhone 5C, but for every iPhone.

Let’s get hypothetical for a moment. Suddenly, there is a single piece of software—a master key for nearly a billion iPhones. Can you imagine what people would pay for access to this? There would be governments and security firms swarming every iOS developer at Apple, and every digital forensics person in the FBI, with promises of untold riches—that is, if someone doesn’t leak it for free, first. There’s a non-zero chance that someone within Apple, or within the FBI, would make a copy of this software and put it on a Warez IRC channel or a torrent of it on The Pirate Bay. I wouldn’t be surprised if it happened inside of a day. And you can bet that whatever way it gets out, it will never be contained.

If you don’t believe this, know that it’s happened before. Microsoft COFEE, a forensics tool for Windows PCs, was leaked in 2009. A leaked tool called EPPB which can download a user’s complete iCloud backup was implicated in the iCloud nude photos leak. What makes anyone think an iOS master key would be any different? Apple may have the right to keep, and even destroy the software, but that isn’t a defense of it being leaked during the investigation. If someone can leak 3D models of the TSA master keys, nothing is safe.

And if it leaks, there will be teams of hackers working to reverse engineer the code. Most of them will working out of sheer curiosity, not because they want to crack into people’s iPhones. That’s just what hackers do. Some, however, will do it out of malice—or just a paycheck. Look at the iOS Jailbreak community. Every time Apple locks down iOS, Jailbreakers manage to break it open again, with all the security risks that entails. Anything Apple is forced to do by the FBI will probably be a lot easier to run, and easier to spread. What happens then? Now, there’s a cat and mouse game as Apple tries to keep iOS locked down from the US government, foreign governments, and black hat hackers with their own copy of the master key.

This is the worst case scenario in the Apple vs FBI fracas: an official backdoor into iOS, precedent for the FBI, the NSA, and other governments to demand Apple—and any other technology company—decrypt their phones. On top of that, the same backdoor will have a million lock-pickers trying to turn it into a master key for close to a billion iPhones.

If Apple loses this fight, be afraid. Be very afraid.

I use iTunes a lot. I’m also one of those rare people who have very few issues with iTunes. It imports my music. It plays my music. It synchronizes my music to my iPhone. It works. Barely, sometimes, but it works. I’d love to see an update and a rethink of the UI, but whatever happens with upcoming versions of iTunes there is one thing I don’t want to see. I don’t want my music to live in the cloud.

That’s not to say I wouldn’t mind having my music be in the cloud. As long as the cloud is an accurate mirror of my locally stored music library, access to it from any device would be awesome. There’s no way to keep a local copy of all my music, anyway. Apple doesn’t make a portable device large enough, anymore. Even if they still made the iPod classic, it couldn’t hold all my music. I sync a subset of my massive library onto my phone. This means that if I want to listen to an album at work that isn’t on my phone, I’m out of luck.

Yes, I am an edge case.

So, cloud-based music locker services are pretty much made for me, right?

No.

There’s a lot of trust that a cloud-based music locker needs that I am not willing to give up yet. I need to trust that the music locker will respect my anal-retentive metadata and organization. I need to trust that the music locker will not replace my rips from vinyl or remastered CDs will be replaced by different versions. I need to trust that the music locker will not replace my live recordings—of various degrees of legality—with studio recordings. I need to trust my music will remain mine, and not used as a way to get more data to display more relevant ads. I need to trust that the software I use to access and play my music works the way I think. I need to trust that the right music will play, without issue, when I tap the play button.

Right now, none of the options out there meet that level of trust. I’m wary of using Google and Amazon’s lockers, because I don’t trust those companies with my personal data. This leaves iTunes Match and/or iCloud Music Library. Until recently, my library was too large to use either. I actually whittled my library down to make it fit, and my readers will already know how that worked out.

Even if the issues around iTunes Match and iCloud Music Library are sorted out—and I have no evidence this is the case—Apple has lost my trust in this area. It might not be a permanent loss of trust, but they’re so far behind that it will take a lot of work to do it. If iTunes, or whatever replaces it, puts the cloud first, it needs to be flawless for me, and other obsessive music nerds (like, say, Jim Dalrymple).

What does I mean by flawless?

It means that my music remains my music—that nothing is modified by Apple between my media drive, the cloud, and my iOS devices. End of story. The only way I can have this, with services I can trust, is to synchronize files to my phone. This might be going away. Rene Ritchie wrote on the possibility of iTunes moving to a cloud-first model, and the idea scares the hell out of me.

What worries me most about a cloud-first iTunes is that it means I will lose the ability to simply synchronize music files to my iPhone. Right now, iTunes has this bizarre (to me) hybrid approach where music can live in either a set of local files or in the cloud. My way of dealing with the ambiguity is to disregard every cloud element of iTunes and use it purely with local files. This is the way I’ve managed my music for over a decade. A cloud-first iTunes will, at best, leave local media as a second-class citizen.

I don’t suspect malice on Apple’s part for this, though I’m sure they would love more Apple Music subscribers. I suspect that the Music and iTunes teams at Apple feel that the cloud for media is the future: streaming first, a music locker second. They genuinely think is the best solution for everyone, and maybe it is for your average music listener. I am not the average music listener. On the day I wrote this, I dropped $75 on a two LP reissue of DEVO’s E-Z Listening Muzak collection. This is not normal—for multiple reasons. If Apple has to leave anyone behind for their ideal music listening future, it’s going to be the loonies like me.

So, if Apple leaves me behind, what do I do? There are iTunes replacement apps, but they don’t synchronize my phone. Plus, while all my digital music is DRM-free—both what I purchased in iTunes and acquired through, er, other means—I have videos that are copy protected. If I ditch iTunes, I lose access to them, unless I break the DRM. How soon before I buy a Sansa Clip, a high capacity SD card, and manually manage my music again, down to the file level, like it’s 1998 all over again?

I try not to be afraid of technological change. I try not to be cynical. As it stands right now, I see no way out. Music is a huge part of my life. I even own music on cassette tape. I don’t even have a tape player. Music moving to the cloud threatens to upend so much of how I experience something that brings me no end of joy. I can’t be the only one.

Did you hear? iPad sales have dropped again. Clearly this means that the iPad—if not the entire tablet industry as a whole—is doomed. As Jason Snell, an iPad fan, put it, “[P]erhaps I’m kidding myself, and in the end the iPad will be small niche product, an outsized iPhone accessory.” Sure, Apple’s probably not going to sunset the darn thing, but five years in, and clearly the iPad style tablet is not the future.

Or, you know, maybe the doomsayers are overreacting. Here’s an interesting measure. In 2014, the iPad accounted for 70% of all tablet web traffic, at least in North America. I can’t find statistics for 2015, but I see no reason to assume that number has changed much. People have iPads, and they use their iPads. It might not translate to upgrade sales, at least not yet, but any product with that much of a share in its market can’t be a complete failure, let alone doomed.

Back in November, I suggest that the iPad of 2015 was the Mac of 1990. It’s not a perfect metaphor, but let me expand on it a bit. The original Macintosh was a brand new idea of what a computer could be [1], and formed the foundation of modern computing. It was revolutionary, it had passionate users who stuck with the platform during Apple’s mid–90s doldrums, but PC users until the mid–2000s considered it a toy that couldn’t be used for real work. (I should know. I was one of ’em.)

In the same way, the iPad is a brand new idea of what a computer could be. It has its passionate users who are sticking with the platform during the sales doldrums, but hardcore traditional computers users often think of it as a toy for writing iPad reviews. Episode 154 of the Accidental Tech Podcast lays out the counter case against the iPad as a device for real work. Sure, people like Marco, Casey, and John can’t do their programming jobs on an iPad. That doesn’t mean you never will be able to. I’m certain in the next couple years, we’ll see some sort of iOS development environment on iOS, if only because I suspect Apple’s on iOS app developers would love to write iOS apps on iOS.

But as long as Apple continues to develop it, the iPad should become a powerful enough computing platform to replace the Mac for most people.

Ask yourself if you can do all your work on a Macintosh II, or even a Mac 512k. The answer is probably going to be no, but that’s fine—they don’t make those anymore. Now ask yourself if you think you’ll be able to do all your work on the iPad of 2025. The answer to that is almost certainly yes. We just have to wait until then.

To go back to the Mac for some historical parallels—Apple sold the Apple II along the Macintosh for almost a decade. It took until the early 1990s for Macintoshes to outsell Apple IIs, and the product line was finally discontinued in 1993. I don’t think we can expect to see the Mac discontinued that soon, but history does serve as a guide here.

I’d love to have some Macintosh sales numbers to use for illustrative purposes here, but I can’t find them. Either way, maybe we should look past the numbers for now. I don’t think it’s unreasonable to just ask people for a little patience as the iPad develops into a fuller-featured platform. And when it does, maybe the sales will finally start going up again. Was there this much doom and gloom about the Macintosh in the late 80s?

Like many nerds with blogs, I have a very large Instapaper queue. It got to the point where, at the start of the new year, I gave up, declared bankruptcy, and deleted anything older than a week. This included, of course, an article on “How to Rebuild an Attention Span” that sat, partially read, for a good three months. You can write your own joke.

Then, I came across M.G. Siegler’s piece on using text-to-speech to get through his reading backlog. There was some initial skepticism on my part. Sure, I listen to a lot of podcasts, and I try to listen to audiobooks, but text-to-speech to get through my Instapaper backlog? Surely this is madness. But, dang it, M.G. was convincing enough that I had to give it a try. So, one ride home on the subway, I kept my headphones in, and had Instapaper read back a couple of articles to me.

Well, it’s been two weeks, and right now the oldest item in my Instapaper queue is… three weeks old. But that’s a video, and I should probably turn it into a podcast instead. Aside from that, and an article on a new way to do responsive HTML email that isn’t really suited to audio, I’ve maintained a steady turnover of Instapaper articles. But text-to-speech on the iPhone isn’t just limited to read-later apps. M.G. shows how to turn on speech as an accessibility option, so your phone can read anything to you.

I’ve taken to having Alex, an optional text-to-speech voice, read my email newsletters on the ride into work in the morning. I love reading Dan Lewis’s Now I Know, and I love having it read to me even more. The text-to-speech feature isn’t dependent on an Internet connection, so I can listen underground with no cell service, leaving me free to keep my phone in my pocket, or more often, play a few rounds of Threes. There’s probably more I could do with text-to-speech—I haven’t used it with the Kindle app or iBooks, but some testing as I write this shows that it does work, at least with some books. I’m sure it would be useful in plenty of other apps too.

Oh, sure, it’s not as good as an actual recording with a human narrator. Alex—and the default Siri and Samantha voices—often stumble on names and get confused by homophones. Their cadence is a little stilted and weird, and the simulated breaths Alex makes before starting a new sentence are a bit of an uncanny valley like audio skeuomorph that I’m still not used to. On the usability side, the two-finger swipe to start speaking often takes a couple tries to get right. Also, Instapaper’s speech playlist feature doesn’t play well with its Apple Watch app, which is probably among the most First World of First World Problems.

Quibbles aside, it’s been a great way to keep my queue of web reading manageable. If you’re suffering from the dreaded Instapaper Overload Syndrome, consider giving text-to-speech a try for powering through it. Honestly, I’m amazed the idea never came up sooner. To M.G. Siegler, I give my thanks, and to Alex, this could be the start of a beautiful friendship. Well, maybe not a friendship, but a beautiful reader-audience relationship. I hope he figures out homophones better in iOS 10, though.