Reversing orbit.

For the past few months, I’ve become increasingly iPad-centric in my use of iOS. This had been happening since iOS 9 came out, certainly, but the scales tipped inexplicably about two months ago, and the momentum was only accelerated by the adoption of the 12.9″ Pro. I now spend the majority of my time on the iPad, doing everything I had been doing and a lot more.

My iPhone 6s, meanwhile, has been relegated to a different role. I still use it quite a bit, but if we’re being honest, it’s definitely my second choice if I want to do something. Sometimes it’s the only choice, in a scenario where I don’t have the iPad, but given the choice, at this point, it’s number two.

This got me thinking. I take my iPad to the office each day, and bring it home. It’s my anchor. My iPhone is the smaller device I always have with me: my camera, my hotspot, my payment token. If I’m going to carry two devices (almost) everywhere, why not lighten the load a little bit?

Then this happened.

And I went, “wow, cool, a tiny phone with big phone guts” like a lot of other people. I’ve always liked the iPhone 5/5s style. In fact, I actually still prefer it to the iPhone 6/6s style. I like the new style, but it just never felt as natural to me. And while some folks saw the SE as a step backward in terms of looks, I agree with Apple:

we started with a beloved design…

But I held onto my 6s. Then I was pushing one of my kids in the stroller around the neighborhood while trying to text with the other hand, and it started to dawn on me: my specific use cases for my phone have changed. It used to be my do-literally-everything device, and it has become my do-a-handful-of-things-well device. Which I am absolutely fine with. As such, the thought that kept gnawing at me since then has been clear.

I think I’m going back to a(n even) smaller phone.

Right now, my phone needs to be able to do exactly four things well:

  • camera
  • communication
  • payments
  • capture small bits of information

Prior to the SE announcement, there was no way a 5s was going to close out that list. It’d get there on #2 and #4, but #1 after seeing the 6s photos? Nope. And no Apple Pay–I’d be lying if I said I don’t use it every chance I get.

The SE does those. In a tiny, powerful package. With a design I always liked, without (much) compromise.

Yes, I’ll have to live without 3D Touch. In all honesty, while I do use it, I often forget it’s there. It’s never stuck with me all that much, and I’ve really tried. I always press everything to see what happens, but it’s inconsistently applied, and in some cases, just not worth the time. Maybe someday, but not now.

Yes, there’s going to be a lot less onscreen at once. This is probably the biggest trade off I’ll need to make, and the toughest to come to terms with. It’s nice having a bit of extra room to read and interact with things. But you know what? I interacted with this smaller size for freaking years in the absence of a larger phone, and my world kept turning. I do a lot of reading on my phone, but I’m prepared to make a change in how I use it to see if the difference makes sense.

Yes, there will likely be a new phone in the fall, that does amazing things. See that list up there that I mentioned? Those four things are truly all my phone needs to do these days.

But what it does do well, is plenty. The camera and internals are 6s-quality. Apple Pay is in. Touch ID, while not as fast as the 6s, is there. The things that are integral to the “portable communicator” table stakes are there.

There’s something else though.

I’ve written about my time away from Twitter and the web at large and how it changed me. Part of that was spending less time looking at my tiny screen(s) in general. I’ve set upon an internal logic for this new thought technology:

  1. If I have the iPad, I will use the iPad, because it is better.
  2. If I don’t have the iPad, chances are I am somewhere where it is either not necessary to be looking at a screen, or not appropriate.
  3. If this is the case, the only things I probably need to do are take a photo, pay for something, or communicate quickly.

Which basically means the time I spend looking at screens is better spent, and the time when I am not looking at screens is even better spent. I will be (or at least try to be, I mean, this is an experiment, after all) more present, more attentive, and more in the moment. I feel like this is a natural extension of my thought process for the past few months, and even though there’s a part of my brain that’s like “you are seriously drunk, man”… I’m thinking it’s at least worth a try.

Worst case scenario: I freak out, return it or sell it, and go back to a bigger phone. Best case scenario: I was right, a new pattern emerges, and the things I care about come into focus a little more.

Hey, if this is my biggest challenge right now, I’m thankful as hell. In the meantime, I’m off to buy a tiny phone.

Where the action is.

I’ve been steadily moving toward an iOS-only computing shift in my personal life, aided by certain bits here and there. This past weekend, after just extolling the virtues of my Air 2 and its new keyboard companion, I buckled, took the plunge, indulged my inner child, and bought myself a 12.9″ iPad Pro and Smart Keyboard. I know I’m a few months late to this party, but just allow me to say… wow.

iOS 9 is a terrific update, especially on the iPad. Paired with a keyboard, it’s as close to the hybrid device I’ve always wanted as we’ve gotten yet (although the Surface could win on a technicality, but that’s another discussion). Sure, there are things that you still can’t do (or do well) but that gap is smaller than it’s ever been. And it’s closing. And for most normal, non-edge-case stuff people do with computers, it’s tiny.

I still do some stuff on my Mac: podcasting, heavy audio recording/production tasks, certain massive file management/admin tasks. But the fact of the matter is that I don’t even open my MacBook Air most days… most weeks. Right now, it’s got a local copy of my iCloud Photo Library content, and I occasionally open up Transmit there to move giant amounts of files between destinations. But even before I got this behemoth, I was doing way more on the iPad than I ever had. Having a little more room to do it (ok, a lot more room) has been transformative.

I use a Mac every day at work. I know it inside and out. I’ve been using Macs every day since the early 90s. But that’s not where my interest is anymore. iOS is far more interesting than OS X, and that trajectory has never been clearer. The past me would have bemoaned the lack of file system access, but the me of today is grateful that security is handled by design. The lack of interoperability has been addressed, and while there’s tons of room for improvement, moving data between apps on iOS is good, and getting better. Conveniences like Touch ID and Apple Pay, solid battery life/performance, extreme portability, and fast wireless radios afford these devices a place in our lives that laptops can never take. We’ve reached a point where the thought of even carrying a second camera for most people is nonsense. Your iPhone takes incredible pictures, and things like Live Photos capture moments in ways we didn’t even realize we wanted. (Admittedly, I totally thought they were a gimmick when they were announced, and all I do now is shoot my kids for a few seconds at a time and grin like an idiot; they are absolutely one of my favorite parts of iOS.)

I have immense respect for the history of computing. I’ve grown up through what I would consider the breadth of its most important developments and most rapid advancements to date. But the thing about technology is that it never stands still, it’s always moving, evolving.

There will always be trucks, and some of us (myself included) will want and need them for certain things. But what we really all want is new bicycles. iOS and the devices that run it capture our imaginations and interest more every day. Sometimes I get anxious at the very thought of keeping up with just how quickly things are changing. But I can’t help but marvel at the incomprehensibly thin slabs of glass I carry around and smile, because we are truly living in an incredible time.

iCloud Drive, Finder, and missing folders.

09-23-2015, 1:55 PM
For about the past two months, I’ve been exploring iCloud Drive as a single destination for my working data. I’ve realized that support for it within apps is coming along quite nicely, and I’m already paying for the storage (photos) so why not give it a shot? Since paring back what I keep online in favor of storing at home on my Synology, the total set of data I’d want access to is minimal. Add in iOS 9’s iCloud Drive app and I’d probably be able to get by just fine.

Let’s get something out of the way right now. Many of you are pulling your hair out now, screaming “JUST USE DROPBOX” at your screens. I have been a paying Dropbox customer for seven years now. It’s an amazing tool and has changed the way I use computers. But for the purposes of this experiment, it was an extra point of friction. The goal was to have things be as “normal” and seamless as possible between devices, as a typical user of Apple products and services might experience. And the truth of the matter is that for weeks, it’s been a seamless, enjoyable process, to my great delight and surprise.

I was using iCloud Drive between my 2014 MacBook Pro, my iPhone 6 Plus, and my iPad Air 2. All updated to latest software releases, and all talking to one another consistently. I had built a few new workflows to account for the quirky ways iCloud Drive handles and sequesters certain files in app-based folders, and was pleased with the results.

Yesterday, I restored my former 2013 MacBook Air to a clean Yosemite install and signed in to iCloud. And some of my folders were missing in iCloud Drive. Folders that had been specifically created by apps (Drafts, Scanbot). Every other folder that I created myself and to which I uploaded files was there, and their contents accounted for. Only app-created folders were missing from this machine. So I began testing.

  • I tried restarting, to kick the iCloud Drive sync services again, multiple times. No joy.
  • I tried relaunching Finder via the Force Quit menu, multiple times. No joy.
  • I tried signing out and back into iCloud. No joy.
  • I tried adding files to those folders via my other Mac to perhaps nudge them into existence. No joy.
  • I tried adding files via the connected iOS apps, same rationale. No joy.
  • I thought that it might be that there were no OS X counterparts to those apps (Pixelmator, for example, showed up fine), but this didn’t seem reasonable, as they’re working on another Mac anyway.
  • I tried deleting the folder and the iOS app, reinstalling and recreating the folder, to see if this was tied to the actual creation event. Worked on the MBP, not on the MBA. No joy.
  • I tried creating a folder on the affected system with the same name, wondering if it might “find” the missing folder. No joy. Now I had two “Scanbot” folders.
  • I added a completely new, previously unconnected iCloud-based app (iA Writer Pro) to see if a new folder would be generated. Worked instantly on the MBP, nothing on the MBA. No joy.
  • I tried physically connecting my iPhone, thinking this might have something to do with the “Trust this computer?” dialogue. No joy.
  • I tried syncing my iPhone through iTunes. No joy.

At this point, having read plenty of discussion threads and FAQs on Apple’s site, I’m giving up. The files appear correctly on iOS (iCloud Drive app), on the web at iCloud.com, and on my MacBook Pro, as it’s the computer I’ve been using. These app-based folders remain missing on the MacBook Air. The problem isn’t iCloud Drive – it’s doing exactly what I expect it to (surprisingly well and quickly, I might add). The problem is with the Finder integration… on certain Macs.

I noticed the same issue on my Mac mini, which made me wonder if this could be related to older hardware. This seemed unlikely to me, but it’s the only thing I can think of that would set these machines apart. The only difference I can see across these three computers is their age.

So what about them is causing them to not be able to see these folders? I’m at a loss, and in the process of moving some files back to Dropbox because I need access on OS X and can’t seem to get it. I would genuinely appreciate any assistance, tips, or otherwise constructive ideas. iCloud, for all its improvements, remains a black box. My experience with it has been better than most, and I’ve truly enjoyed its ubiquity the past few weeks. But I need it to work everywhere for it to work at all, so I’m stuck.

09-23-2015, 2:43 PM
I shit you not, the Drafts folder just appeared. Scanbot is MIA.

09-23-2015, 3:00 PM
Scanbot is back.

I don’t know how to feel about this. iCloud is like a variation on ‘the Aristocrats’.

09-26-2015, 8:21 AM
So I’m pretty sure that the missing folders issue is a byproduct of massive network activity during background processes related to iCloud Photo Library. This was suggested to me by my friend Sam as he mentioned noticing some similar weirdness. I was monitoring iCloud Photo Library activity as it was ongoing, but there are perhaps some processes that (like everything else with iCloud) are fairly obfuscated to the user, sucking up network connections and saturating them even after things seem complete.

It makes sense, but it’s still kind of weird to me that file operations wouldn’t be prioritized over photo operations. Some of them seemed to be, since 95% of my iCloud Drive content showed up quickly, but something held up those iOS-related folders for some reason. I guess the takeaway from this exercise is to ensure all your iCloud Drive content shows up first, and then enable iCloud Photo Library if you’re using it. Next time I set up a Mac, I’ll be sure to do it in this order, and hopefully the arcane incantations I performed this past week will be a distant memory.

The whole purpose of going all-in on Apple apps and services is because I’m trying to use these devices as a normal user would, deriving the integration benefits and ease of use Apple offers. But being the kind of person I am, it’s tough to shake the need to debug a problem like this. Had I just waited, evidently everything would have sorted itself out. Perhaps there’s a lesson in here for me somewhere beyond the setup order I’ll use in the future.

Collateral damage.

Generally, by the time iOS beta 3 or 4 rolls out, I can’t help myself and throw it on my carry phone. But I haven’t had time to play this summer. It’s been a particularly busy few months and I needed to make sure my primary phone was as stable as it could be. As such, I’ve been pining away to play with the new Notes app that Apple debuted at WWDC this June. It looks like a tremendous update to one of the built-in apps that could actually change the way I currently use my devices. I’m not alone in these sentiments; I know many other folks in the tech space who are begrudgingly admitting that it’s pretty cool.

Since I’ve been keeping my devices as standard as possible too, I’ve been using Notes between OS X and iOS, even in its current form. I’ve found it to be a useful scratch pad and short-term landing area for little bits of text that don’t even merit creating a new .txt and saving somewhere. And they do sync between devices pretty well (for the most part).

On Wednesday, I’m excited to finally update my devices to iOS 9 and get all the cool stuff I’ve been hearing about, like any other normal user. But something occurred to me yesterday.

When I update my mobile devices, El Capitan is still two weeks away from shipping. Which means that my workflow breaks. If I didn’t have the foresight to think about the disparity in ship dates and extrapolate that one extra step, I’d have been caught scratching my head on Wednesday afternoon as I update and keep working through my day. Like any other normal user.

This isn’t good. For me, or for anyone. But sadly it’s become the norm. Marketing pressure and ship dates trump user experience more and more. Working in software, I understand a great deal more than the average person about how this process takes place and how you don’t always get to make the decisions you want to about the fate of your users when external pressures start exerting force on the business. I know that releasing both mobile and desktop OS updates in the same day is insanity, and I wouldn’t expect that. I know that two dedicated groups of people, working hard to ensure they hit their dates have made every effort they possibly can to make my experience a good one. I know that with the advancements in both operating systems, no decision–no matter how small–is a simple one.

But I’m the end user. It shouldn’t have to matter to me, and it’s not my problem. However, it’s become my problem. What if I don’t want to upgrade to 10.11? What if I can’t? What if my laptop is company-issued and there are no immediate plans to upgrade the OS? My stuff is broken, and I get a big shrug from the company to which I trusted my data. (Which of course, is a much more nuanced and complicated discussion for another time.)

This isn’t the first time this has happened. Apple did this last year with the transition to iCloud Drive. It caused more than a little confusion for both users and developers. But this isn’t just an Apple thing either. Many companies are breaking implicit promises with their users to further push their products into the future, and leaving confusion and doubt in place of a feeling of consistency as people use these products. Apple, of course, has the momentum to carry it forward, and we’ll all forget about this, the way we mostly did when Yosemite shipped and the iCloud Drive transition wasn’t such a big deal anymore. And I fully realize that writing this much because my notes stop syncing (temporarily) seems like absolute overkill. But I spend a lot of my time trying to come up with creative solutions for users so people enjoy the software we produce. I try to solve problems so they don’t have to. It’s the right thing to do. Tim Cook from WWDC 2014:

Apple engineers platforms, devices, and services together. We do this so that we can create a seamless experience for our users that is unparalleled in the industry. This is something only Apple can do.

Software updates have always been risky. I’ve been using computers since I was about five years old, and I know this. I understand it at a level most people don’t. But at this point, with the way software has reshaped our lives, I shouldn’t have to. It’s disappointing that even a company like Apple, so proud of its experiences across hardware and software and delivering the best to its users still falters on these kinds of things. This’ll all blow over. I know that. But it’s a troubling trend, and I don’t have to like it.


PS: It was pointed out to me that iCloud.com will sync/display Notes after the iOS 9 transition. Given the state of the site as an afterthought in almost everything Apple does, I’m not surprised it didn’t occur to me. This will certainly suffice in the time between upgrades, but I wouldn’t have immediately thought about it if someone didn’t point it out. And considering any regular user of iOS probably doesn’t even know that iCloud.com exists as a destination, neither will they.

Person-based OmniFocus context triggers with Launch Center Pro.

During a discussion with some fellow OmniFocus friends in a Slack channel, we talked about how great it would be if contexts that we assigned to people could trigger when we’re with them automatically. While there isn’t a good way to do this yet, I thought about it a bit and made what I would call a halfway decent substitute, all things considered. It combines connecting some hidden OF features on the Mac with Launch Center Pro and OF on iOS. And while it isn’t quite automatic, it’s pretty close, as long as you build a habit around it.

I remembered seeing a post about using OF’s URL scheme support to trigger actions a while back. Some of OF’s features have obvious URL scheme support, but some are a little more hidden. In order to get an actionable URL for a context, you need to have the Mac app open and right-click on the context you want to use. An option called ‘Copy As Link’ will appear. That’s what you want. Unfortunately, there’s no way to do this on iOS, so unless you’re using OF on all platforms, you may be out of luck. But if you’re like me, and you have that beautiful purple icon everywhere, proceed to step two.

With that URL on the clipboard, get it over to your iOS device any way you want. I used Notes.app, because it’s probably the easiest way to do this, as it syncs fairly quickly. With the URL on the iOS clipboard, go ahead and open up Launch Center Pro.

Now you can drop this URL in as a single action, sure, but if you want to really light your world on fire, collect URLs for all the contexts you have that pertain to people. For me, it was about a half-dozen, mostly folks at work, but I also have one for my wife, and one for my parents when I see them. Use LCP’s list format option for your action, adding a label and the appropriate URL for each new item.

When you’re all done, save the action, add an icon, and place it somewhere. You now have a single button that brings up a list of names. If you’re talking to someone for whom you have a context, fire this action off and tap his/her name. OF will open directly to the context and display all the actions associated with that person. Of course, you need to remember to do it. (You could set a notification directly from LCP to fire if you definitely know you’re seeing someone in advance, e.g. for a meeting, to even better safeguard against forgetting to do this.)

Short of having your device know who you’re talking to, as long as you have the sense to pull out your phone and tap that action in the course of the conversation, you’re all set. I have a feeling this is going to help me immensely, especially with people who have very little time and are tough to pin down. Getting all your questions answered or discussion items covered at once is invaluable if time is short. And even if it’s not, you’ve got a nice, quick way to jump to a person’s associated items the next time you sit down together.