Rediscovering infatuation.

Every summer, I seem to go through familiar cycles, examining how I do things, and breaking down well-worn workflows to experiment with new ones. I feel that this serves two goals: on one hand, there’s a cadence to this process, as a new iOS release looms in the near distance, but at the same time, something about this time of year leads me to question how and why I do things.

I’ll chalk it up to summer being one of my favorite times of year, where the warmth of the sun energizes me physically and mentally, and I find myself stirred into new modes of activity and thinking. Whatever it is, I’ve decided not to fight it, and I almost look forward to it each year, knowing it’s on the way, quietly wondering what I’ll decide to strip down to parts and rebuild.

Last year it was task management: the psychic overhead, the bifurcation of worlds, and the sheer tactical action required to make my world keep turning. This year, I’m focused on a vector into that and many other aspects of life. This year, I’m taking a different look at the iPad.

Background

I’ve been a fan of the iPad since day one. I got the very first model as soon as it was available and adored it from the start. I always saw potential and shades of the future in it, despite its initial limitations, its basic pedigree as an older sibling to the iPhone, and the seemingly unending stream of naysayers ready and willing to knock it down for not being all things to all people.

The core argument, of course, is that it’s not a “real computer”. It can’t do all the same things a laptop can do, so it’s not worth anything. As though every tool needs to do all the same things every other tool does.

There are two fundamental tenets to my position on this that are worth remembering:

  • computing is not a zero-sum game; there are many users, many needs, and many ways to engage with technology successfully
  • value, like beauty, is in the eye of the beholder

I’m not going to waste my time (or anyone else’s) retreading these arguments. It’s beyond uninteresting, and crosses into eye-rolling so severe that it risks permanent ocular damage. What I would like to do is explore a few things I’m truly excited about as the iPad continues its slow evolution into what I’d consider a worthy independent computing platform.

Overview

I’ve been using two iPad Pros since last fall: a 12.9″ model that I bought in the beginning of 2016, and a 9.7″ that I bought in October. I’ve explained some of the thinking behind this on our show, so I’ll cut to the chase. I decided that having a big iPad at home and a smaller one to travel with to and from the office and on trips was the right choice for me. It’s been a nice way to use the devices, and I’ve enjoyed always having the right device for the right context.

Lately I’ve been gravitating toward the 9.7 though, for a few reasons. I still like the giant iPad because it’s just so nice to have that extra room, but what I’ve been exploring lately just makes the 9.7 the better overall target for this type of use.

As such, the majority of these points I’ll make directly refer to the smaller of the two iPads. I’ll likely make reference to this in certain areas, but it’s worth keeping in mind as a frame of reference, so that you aren’t constantly wondering, or—more probably—saying “that would be ridiculous on the big iPad”. Much of this would. But hey, maybe it wouldn’t for some folks.

That’s what’s cool about everyone living their own lives. You don’t have to do what everyone else does, or listen to everyone else’s opinions as though they’re fact.

Also worth keeping in mind.

Always.

Anyway, here’s what I’ve been thinking about lately.

Topics

  • The Smart Keyboard
  • Using the iPad by itself
  • Using the Pencil, replacing paper
  • Portrait orientation
  • iOS 11 and next steps

The first four have been overlapping and working in tandem. The last one is obviously pertinent for this summer.


The Smart Keyboard

I’ve long been a fan of using keyboards with the iPad. I’m not a fan of bulky cases.

I would search to find what I considered the best option that mixed a standalone, iOS-ready (when possible) keyboard with an easy way to detach, because I always like to decouple the two and use the device on its own if I’m not doing heavy text entry. I’ve always been ok with a slightly smaller keyboard size anyway, as my hands aren’t that large and I get used to them fairly quickly.

I started this quest with the Logitech Ultrathin Keyboard cover for the original iPad Air. It was a great solution for having a decent hardware keyboard while keeping weight fairly low. When I upgraded to the Air 2, I couldn’t bring myself to buy the same exact thing again, so I switched to this Microsoft keyboard because it was small, but with very good battery life and what I consider comfortable keys. It also allowed me to keep the Smart Cover attached and sit with it easily while using the keyboard. It didn’t attach the same way that the Logitech did, but it allowed me to use the iPad by itself as well.

When I bought the 12.9, I decided to take the plunge and try the Smart Keyboard. Yes, it looks a bit odd. Yes, the keys are a little weird at first. In truth, I despised them. Tried it in the store and was physically repelled by it. After 24 hours, I was a convert.

The Smart Keyboard may not be the best keyboard, but I believe it’s the best companion to the iPad Pro.

The Smart Keyboard will have its detractors, but when you get right down to it, it is the best compact solution to minimize bulk and still provide the functionality of hard keys. If you don’t mind extra heft, or need backlight, or want additional iOS-specific function keys, then move along.

I bought the Logitech Create for the 9.7 initially. I wanted something that was more like a notebook, and since I was carrying the Pencil with that device, the built-in loop was a big benefit. I used it dutifully for about six months, when it began to feel bulky. I started to think about the Smart Keyboard, but was struck with the idea that the Pencil wouldn’t have a nice little home anymore. To this day I’m shocked that Apple itself doesn’t have a better solution for this.

And no, this is not a solution.

But what I’ve come to realize is that the Pencil, the iPad, and the Smart Keyboard don’t need to be connected to one another all the time. They simply need to be in each other’s immediate orbit in order to deliver the value they can provide. The Smart Keyboard (especially at the smaller size) makes the 9.7 highly functional and barely adds any bulk.

I’ve been enjoying it way more than I anticipated.

Using the iPad by itself

One of the defining factors of all of those keyboards I mentioned was the ease with which I could pull them off and use the iPad on its own. That’s been paramount to my use case for the device for as long as I can remember.

As the iPad got thinner and more powerful, I found myself simply marveling at the hardware and the way it felt to hold it on its own. With the 9.7 Pro, this has actually shifted from “isn’t this really something” to a sea change in how I use the device.

I was thinking one day about how I was more inclined to grab my phone to do something as opposed to the iPad. I stopped and really thought about why that was the case. Broke the action down to its most elemental level.

Pick up a device, unlock, use… right? Not that complicated.

But with the iPad, there was often a keyboard of some kind, or at least a Smart Cover attached. One extra tiny action that created imperceptible friction; that on a subconscious level resulted in me going for my phone because it would “be faster” somehow.

Then I watched my wife’s dad one weekend with his iPad. He leaves it around on the counter, ready to pick up and use, no cover, no keyboard. He has an iPhone too. He almost always goes for the iPad first, likely because it has a larger screen and is more comfortable. But then it dawned on me.

If both screens are available in the same capacity and without any extra steps, apart from an app not appearing in one place or the other, why wouldn’t I use the iPad first?

So I tried it. One day at work, I was walking around my office, Smart Keyboard on the desk, iPad and Pencil in hand. It was so light, so effortless, and so enjoyable, that it began to feel like I’d discovered something new. A way of using a device—of which I thought I knew every angle—that I’d simply never considered. Put it down, go do something else, grab it and unlock, it’s ready.

It sounds positively stupid, but this simple change has made a big difference not only in the amount of time I’m spending with the device, but also in the ways in which I’m using it.

Using the Pencil, replacing paper

One of the big benefits of the iPad Pro is of course the ability to use the Apple Pencil along with it. Unlike the Smart Keyboard, I was sold on this accessory from the instant I held it and used it. I’ve tried a ton of different stylus options, and the Pencil is the best around, full stop.

I also tried a bunch of different apps for handwriting. The one that feels the most like it matches my handwriting mechanics is Notes Plus. I’ve made a conscious shift in the way I capture and process information now on a daily basis. Revisiting handwriting as a way to gather information has forced me to slow my thinking and listen more, which has led to other creative benefits as well. With my mind engaged in this way, it is freed up to do other things as I work with colleagues, and quite honestly, I find writing by hand to be a relaxing activity.

I also frequently sketch concepts, diagrams, small bits of UI that I’m describing to others, and all manner of other things. Just having the ability to do this quickly–and then immediately follow it with a digital action (saving it, sharing it, etc.) is hugely beneficial to my workflows.

I carried paper notebooks for a long time. Getting myself into the habit of reaching for the Pencil has been a lot of fun and very cool. That’s worth calling out as well: making work fun can’t be underestimated. If I’m enjoying the tools I use, it makes whatever I’m doing more pleasurable, leading to a positive feedback loop. Increasing the utility of what I’m doing (because I’m a nerd this way) is also fun, which also funnels back into that loop.

Making the ways you do your work more enjoyable is a great way to improve your daily quality of life, trust me.

Portrait orientation

The last discovery was a complete shock to me.

From the moment I got my very first iPad, I defaulted to using it in landscape orientation. I’d watched Steve Jobs demo the device onstage, sitting in that iconic Eames chair, reading and relaxing, and I thought “well that’s nice” but it never felt right to me. I guess somewhere in my mind, I always saw screens as horizontal appliances–using it in a vertical capacity just felt odd. I’d occasionally read a magazine that way, or some other very targeted activity… but it never lasted.

That’s where this whole “isn’t it fun to try new things that I ordinarily wouldn’t” thing starts to pay off. I always use Notes Plus in portrait, because I like the layout and spacing of the page in that orientation far more than in landscape. I’m using the Pencil more and more… and I’m detaching the iPad and walking around with it. So one day I just turned it and held it in portrait while I was discussing some things with people. I was taking some notes, but I also was popping around and doing a few other things. I responded to a message and realized I could type fairly easily in portrait on the 9.7, especially with nothing else attached to it because it is so lightweight, and the balance of the device when held in this way is incredible.

The balance of the device when held in portrait, with no cover or other accoutrements, is incredible.

I literally had never considered this, ever, in all the years I’d used it. It was an epiphany. But Steve knew it. It was suddenly so obvious. The device was designed to be this way.

It can’t change computing if we’re always looking at it like it’s a computer.

All this time, and it felt like I was suddenly holding an entirely different device. Again, like the notion of using it without a cover because it’s easier to unlock, this was a moment in which I considered the fact that I was a total moron. But it was undeniable. I’d stumbled onto something a whole lot of people probably knew already, but it was brand new to me.

I’ve been carrying the iPad, bare, with the Pencil, like a single sheet of digital paper, and it’s changing the way I work, and the way I do just about everything on it.

iOS 11 and next steps

This year marks the most radical shift in the iPad’s software capabilities we’ve seen. iOS 11 is poised to enable new levels of functionality in the device, unlocking increased flexibility and moving the platform forward to a level of maturity fans have been clamoring for.

I’ve been a beta person in the past, and I’ve lived with the battery-cooking, display-busting, data-losing bugs. I threw developer beta 1 on the 12.9 when it dropped because I was really curious to see it in motion after watching the WWDC keynote. I played with it for a few days, but restored back down to iOS 10 because I’d rather be using the device in a stable capacity for the time being, and because I’ve come to realize the big release in the fall just isn’t as exciting if I’ve had it for months prior.

What I saw is a wonderful but complicated step forward. iOS 11 brings incredible new things to the platform, but it also ratchets up UX complexity in ways a lot of users may not be ready for. One thing iOS has traditionally done well is to add new features and functionality but not make it necessary to engage with it. This allows most users to keep doing things pretty much the way they always have, and gets power users happy about new stuff. iOS 11 makes some big modifications–for everyone–and it’ll be interesting to see how that affects things overall.

I’m certainly not hinting at some kind of backlash (although we all know the tech press will latch onto just about anything it can find that would indicate one). It’s just that we’re about to see a big shift in the UI that means another learning curve. Anyone who loves iOS as a productivity platform is ready and willing to accept and keep running with this change, and it’s been a long time coming. But the typical year-to-year balance afforded to mainstream users is about to change too.

Evolution is hard, and not without trade-offs. But it’s what’s necessary to keep moving forward.


Conclusion

The iPad has traveled a long, strange road to get to where it is today. I’m honestly thrilled that after all this time I can still find new things to love about it, and change how I interact with my world. This next chapter will be one of the most interesting in its lifecycle to date. I’m ready for this device to cross over into a new class of utility.

With the introduction of the 10.5 Pro, and my increasing love of the smaller of my two current sizes, I may also move to a single-iPad life again when I decide to upgrade. Won’t be any time soon because my current stuff more than meets my needs and I’ve never once felt like it’s lacking in any way, but it’s on my mind. The 10.5 looks to be a fantastic device, and a great compromise for someone like me who’s experienced both sizes and wants to simplify.

I’ve said it before, and I think it bears repeating: this is not a zero-sum game. I still love the Mac, and use it every single day. It’s the best tool for many jobs. But the gaps are shrinking–not entirely, but markedly, for many use cases–and it’s interesting to watch this process. I use the Mac because it’s a great platform that allows me to do work in the way I prefer. I love iOS because it feels like the future in a way that the Mac once did, and (let’s be honest) probably won’t again.

To the point of all these personal observations, however: the fact that I can still find these small bits of discovery and everything continues to feel new to me is testament to how interesting a device this really is. We’re on the verge of some very big changes, and it’s one of those rare times in which I am unabashedly excited about what’s around the corner.

They seem to be harder to come by as I get older, so I have to revel in these moments when they show up.

Using Drafts and Workflow as a clipboard manager.

As I continue to play this little game I’ve created for myself in which I try to use and install fewer apps while discovering new ways to use the ones I love, my latest run is based on replacing a dedicated clipboard manager app. While I do really like Copied and other apps like it, the truth of the matter is that I don’t need an app solely devoted to holding and managing snippets of information like this. I do occasionally have this need, and so it’s something I like the idea of having, but it’s almost only for text/links, which I can do in a variety of ways.

The trick is storing the snippets, but also making them accessible and easily retrieved, and because of the way iOS works, we’re limited in a few ways. Any app that does this can only run in the background for so long, and even if you’re using a widget for this, there’s only so much room in the UI to account for the things you can do without launching a full app UI. But since my specific needs are limited, I’ve experimented with pairing Drafts and Workflow together: one as the snippet storage and one for the quick access to my most-used bits of text.

A quick note: I think it goes without saying that if you use an app like Copied for images and other rich media, this wouldn’t really work for you. This is really centered on text, and the impetus for this was restoring my iPhone recently and for the millionth time not having my iCloud text expansions appear. Given that my needs are fairly limited anyway, I’m giving up on that broken-ass bullshit and building a replacement with the tools that I know will work. I still don’t understand how this far along and with all it can do having iCloud remember a three-letter shortcut for my email address and making it available on new devices consistently is such a fucking Herculean task.

Anyway.

Drafts as the library

I used to use TextExpander. I also used to have a million snippets I couldn’t remember. Then I decided to simplify and keep only the stuff I could. Once I realized this was a relatively small number of items, I decided to use the native iOS keyboard expansion for shortcuts. As you can see from my above comment, when it works, this is more than adequate for my needs. However, all too often I restore a device or set one up and I never get the shortcuts. Or they show up a month later.

But Drafts is always there. Building on my thinking for how I was using filters to move tasks out of my inbox, I created a filter to separate these text snippets out too. I liked the way Copied allows you to have a title for the snippet, so I created that same structure in Drafts. I just added a tilde to the end of the title line.

Along with that, I needed an action that would copy the body text but ignore the title line. Drafts has just such an action built in; just use the clipboard replace action, and instead of the draft tag, use the body tag. This takes everything but the first line and sets the clipboard.

From here you can go wherever and slap it in. You can even search right within the filter if you have a lot of these.

Workflow for quick access

So that takes care of the storage and the occasional browse to find a thing you want. The other time I need this ability is when I’m doing something in another app, and the easiest way to do this is with a widget. I headed over to Workflow and built a very simple list of some frequent snippets that loads right in the widget body, replaces the clipboard, and can be dismissed immediately. I noticed that 15 lines is the max I can fit in one of these on my iPhone 7; any more beyond that and you won’t see everything. Again, my needs are simple, so this is fine. What I’ve done is build a multi-step action that first asks which list you want to display, and then displays the snippets in that list.

The simplest way to get started is to just do a basic text list, add the exact text you want, and have it replace the clipboard. But you could also use the text list to show a label, and then add “Replace Text” blocks for each one, and then send the replacement to the clipboard. This would work better if you had bigger blocks of stuff that you weren’t going to see anyway, or if you just like things looking tidy. (This was Tim’s idea, I like it; I like tidy things.)

What I’ve described is two separate sets of actions that manage this content. Now you can can get Workflow to talk directly to Drafts by using the “Get Contents of Draft” action. This requires you to copy the UUID of the draft you want and place it in the action. This would be true automation, and way more fun. Unfortunately, when you do this, Workflow can’t grab the content directly from Drafts without first switching to the app, so you leave the widget and do a quick round-trip, which defeats the whole purpose of having a widget action in the first place. So I chose a few of my most-used snippets for access within the widget and spent the time up front to save it later.

Now, you might be thinking: boy, that seems like a LOT of dumb work to do just to get the same functionality that a single app can provide, and you’d be totally right! It is. I will not argue this, not even a little. But, there are two reasons I like this.

  1. I always have both of these apps installed, which means they’re always on every device anyway, and it’s one less app to install/manage in addition to that.
  2. Every time I do this kind of thing, I figure out new things. In many cases, these dumb little experiments end up allowing me to refine something else I might have been doing already. This feels good.

Finally, I figured I needed a quick way to make adding snippets easier, so I created a basic Workflow that asks for input or grabs the clipboard (assuming I’ve copied what I want), asks for a title, and uses Tim’s nifty Auto-Archive action to dump the filtered draft in the right bucket.

Needless to say, since Tim and I go back and forth on this stuff all the time, I’ll drop an idea on him, and he’ll latch onto it and improve the flows.

So he figured out how to construct the text as a dictionary, and have Workflow present the list and pull the right text that way. Which means you can build a single text file in whatever app you want containing the labels and links/snippets/etc. and then just drop it into the leading text block in the workflow. This makes things very easy and nice. Here’s the template for that.

And then sometime later I went to bed. But he didn’t.

I woke up to a long message and a few links. One to a new Drafts action and one to a Workflow that’s called by that action. Basically, since Workflow can’t get the info directly out of Drafts in the background, he thought to create a text file that Workflow could access in the background, and stuck it in its iCloud folder. Within that text file is the dictionary, containing the names of the text snippets, and the corresponding values for them. You can store these files in Drafts, and update them whenever you need to. Save the file again to that same folder in Workflow’s iCloud storage, and it’ll overwrite. The next time you run the workflow, it calls the new information from that file. It’s still not quite directly linking the two apps the way you’d think you should be able to, but it’s damned creative, and I told him so. And it’s way easier to edit the dictionary within Drafts than in a tiny box within Workflow.

As far as I’m concerned, that’s the best way to do this: maintain a text file (or a series of text files for whatever you want) in Drafts, save out changes to Workflow’s iCloud folder, and the updated versions are always available when you want them. If you want to keep this in the widget, you’re still limited to the row number, but if you don’t care, you can have a list as long as you want.

I realize it seems circuitous and somewhat silly, but the whole point of all of this is to play and learn. The game of reducing apps has a direct benefit in that every time I restore or set up a new device, it takes less time to get up and running. But these small excursions also allow me to think through problems and find new ways to solve them. Some people engage their leisure brain with crosswords or sudoku. These are the little puzzles I like to solve.

Update 2017-01-13: I realized a week too late that I was mistakenly referring to dictionaries as arrays. So I corrected this egregious mistake. Sorry about that.

Using Drafts, Reminders, and Slackbot as a task management system.

I know, this sounds like a fever dream. Stay with me. I promise it’s headed somewhere.

Over the summer, I made the decision to split my work and personal tasks between two separate systems for a lot of reasons. It’s stuck, and I’m really happy with that decision.

I also decided that in terms of thinking about personal tasks, a basic hierarchy is all I need. There are things that need to get done by a certain time, and then there’s everything else. I was using OmniFocus for this to great success.

But if I’m honest with myself, I’m still over engineering things. Work stuff, ok, there’s other people and dependencies, and lots of other things at play. But my life? At home? I essentially need lists, and that’s about it. Simple, basic lists. With the occasional nudge to do something once in a while.

I’ve also been (re)drawn to the idea of using as much of the stock OS as possible, which means I’m looking at Reminders for things. I’ve been down this road before.

Reminders is great because of what it does, which is exist on all your devices without a bunch of extra effort and mostly capture things in a reasonably expedient manner. But what it doesn’t do is allow you to make changes to those items easily and quickly. Or sometimes sync reliably (I had weird duplication of tasks, and stuff marked as done come back from the dead multiple times). All it takes is a few cracks in the facade, and I’m running. So while in principle, having all those unchanging things (bills, medication alerts, household stuff) always available on any new device via iCloud, it just didn’t feel like enough to take the throne.

iOS 10 seems to have fixed a lot of the weird behavior I noticed previously. Also, if I’m not forcing Reminders to be a system it’s not–i.e., using it for what it’s actually good at–I can actually derive an incredible amount of value from it. Here’s what it does well: it reminds you to do stuff. If an alert fires, and you don’t dismiss it or complete it, it hangs out on your lock screen until you do. Every time you look at your device, it’s there, like “hey, yeah, hi, don’t forget this thing”. Simple, quiet, persistent. I like this behavior.

So anything with a date/time/location goes in Reminders. Easy enough. But what about this part:

what it doesn’t do is allow you to make changes to those items easily and quickly

Well. I had a good think about this, and realized that if I’m using this tool correctly, chances are I’m not making changes, but I do still need a little flexibility in assigning those dates and times. So as always, I turned to Workflow. In minutes, I had built an “add reminder” action that I can trigger anywhere from the widget that asks for input and either presents a list of my most common times for an alert or one of three most-used locations (home, office, pharmacy).

I can add a new reminder, with the right alert, in about half the time. It’s freaking great.

That brings me to all the stuff that doesn’t need an alert, but has to get done at some point, or at least should. From that same post:

More disappointingly, even though I adore Drafts more than life itself, it really isn’t the place for me to house my tasks and take action on them. The idea of a single Markdown list of the things I want to do was intoxicating, but it didn’t fit with my mental model of how I manage things I actually need to do.

Once again, I was trying to make a tool do something it shouldn’t. So I changed the way I thought about these lists. I need to keep these lists handy, and they don’t always require action but I need to remember to check them (in GTD, this is a “review”) occasionally. I’m in Drafts all day long, for a million reasons. I’d never tried filters before, so I decided to give this a whirl.

Not one list, but a few key ones. See, if these things are always accessible, in a tool I’m already using all day, I think I’m more likely to idly scroll through and do several quick reviews, and potentially cross some things off. This is definitely the big variable in this new system, and I’m waiting to see how it feels. So far, so good.

Drafts doesn’t have line spacing controls, and one of the other things I wanted was a little more padding in the list views for ease of reading while I scan quickly. So I added a very basic Unicode character that creates a little bit of space between lines, allowing for a nicer view. I added that to an action key, and made an action list to send the draft to the right list.1 This is also good because I can filter against that same Unicode character, and keep things where they belong, keeping my inbox cleaner and actionable.

Within the lists themselves, I can use the native link mode and line re-ordering functionality Drafts has to move items around (or delete them when complete) or view a URL I add to a task. Works pretty well.

But what happens if I have an item in this list that I decide I need a nudge for? I took that same Workflow action I’d built, and modified it slightly to take a selected line of text from Drafts and send it through the same flow. It kicks it over and runs the same super fast steps and dumps it into Reminders for me, to ping me at some future point.

So I’ve covered basic lists and the escalation point where I need an alert to move something along. I also mentioned Slackbot. My love for Slack is well-documented at this point. I’m always looking for different ways to use it. I decided to try using Slackbot for a certain class of nudge that is absolutely not mission-critical—one that I didn’t feel like seeing in a list every time I opened Reminders—as a test. So I have a handful of recurring reminders I’ve asked Slackbot to yell back to me every now and then.

I have a “home” list of stuff we need to do around our house. Totally not urgent, has no time sensitivity. Every Saturday at 9am, Slackbot goes “hey check your home list and see if you can do anything today”. I don’t need to mark anything as done, and if I want to hear about it again, I can defer the reminder for later or the next day. This is only for stuff I kinda don’t really care about, but still want a poke for occasionally. So far, so good. And you can review what you’ve told Slackbot to track with a simple /remind list slash command. I’m still exploring this one, but it’s been fun so far. I’m currently trying to think of other little nudges that I don’t necessarily need to take action on, but that I’d like to see now and again.

That’s pretty much it for now. For… now. Every time I change this system up, I feel like I’m losing my mind a little more, but I also feel like in restructuring everything, I keep learning about what’s important to me at different times in my life. And I’ve decided that this is my hobby. I really do like playing with these things. I have almost no free time, and a busy work and family life, and this stupid crap actually makes me happy. It’s not getting in the way of doing stuff, and that’s the important thing.

So yeah, that’s this month’s experiment. I’ll let you know how it goes.


  1. And naturally, Tim improved it by combining everything into one action, so if you want to play with this stuff, just use his instead. It’s tight. 

An update on how I’m using my private Slack team.

Almost a year ago, I began using Slack by myself, having created a private team with a bunch of purpose-based channels. If you want to know more about how that experiment started, check out that post.

People ask me from time to time if I’m still using it, and the answer is a resounding “yes”. In fact, Slack continues to improve and offer great integrations with lots of other services, and it’s even easier than before to send information into a Slack channel from almost anywhere. It’s blossomed into an indispensable organizational tool that I spend a great deal of my day in, browsing, working, and pushing information into and out of the team.

The addition of Safari View Controller to the app has made a lot of these things I’m pulling in faster to access, and provided a more centered experience. I’ve refined my channels a little bit since I started, and added some new ones, centered around other topics of interest.

Here’s my current roster.

#alerts – high priority notifications, Google alerts I’ve set up for various things,1 and I watch a specific Dropbox folder for collaboration alerts, since they usually show up a few days late or not at all.

#blogposts – each time I post something, the link to that post is dropped into this channel. Mostly just a quick reference if someone asks for one.

#clipboard – multi-device snippets and pasteboard sync. Still love it and use it constantly.

#daily – this is a new thing I’m trying. I’ll explain in a minute.

#deliveries – I mostly just buy things on Amazon, so I don’t use this all that much, but I will occasionally throw a tracking number/link in here if I need to refer to it, eliminating the need for a dedicated app.

#ebay – if I’m searching for something, it pops up in here as it appears on eBay.

#edc – RSS entries on cool gadgets from everydaycarry.com. I have a problem with small tools, and this is how I indulge myself.

#home – I have some shared lists in Wunderlist with my wife, and I get the update notifications sent here.

#photo – I have a few different RSS feeds pointed here, with the simple goal of seeing nice things on a semi-regular basis. Currently, NASA’s photo of the day (via IFTTT), and Unsplash (love this site.)2

#pricedrops – alerts on app sales from MacStoriesDeals and AppShopper.3

#reading – this is my “read later” channel. I toss random links I plan to read here and come back to them whenever.

#rss – I keep a small collection of low-volume feeds that I want to ensure I read each day, so they don’t get lost in the din of other news and the RSS combing I do for work. Blogs by friends, and a few other sites I enjoy.

#snippets – a channel that just holds blocks of text, links, images, etc. I may use frequently or not so frequently. I don’t use this channel all that much, but I like that it’s here.

#starwars – a channel devoted to Star Wars news, articles, and general nerdery.

#town – alerts from the local police department about events, hazards, etc. Supremely–and surprisingly–useful.

#twitter – since effectively abandoning the network on which I used to set fire to piles of my personal time, I created a channel for a handful of accounts that I’d still like to see updates from, without subjecting myself to the misery funnel that Twitter’s become in many ways.4 I also get notified here if someone mentions me, or if certain search terms hit a match.

#video – think “read later” but for stuff you’d watch. YouTube links, etc.

#weather – forecasts and severe weather alerts.

#workflow – a channel devoted to iOS automation, piping in new items from r/workflow and the Drafts Action Directory as they appear. I think I might have a few other things pointed here as well too.

#yankees – news and info on the baseball team I grew up with.

So that’s the current run, and I’m still thinking of new ones.

Which brings me to the idea behind #daily. I have a pretty standard routine (I’d imagine many of us do at this point) of waking up, grabbing for my iPhone, and beginning the Early Morning Badge Clear Game. What often ends up happening however, is that I get into my work inbox, or start reading something I don’t have time to finish in the news, or whatever. You get the idea. The #daily channel was supposed to be an experiment to collect things that I would definitely want to see first thing in the morning, all in one place, give me a jump on my day, and get me mentally prepared for what I need to do–quickly.

The first thing I did was move the morning weather forecast from #weather into this channel, since I always want to see the forecast for the day first thing in the morning. Then since I’m old and can’t always stay up late anymore because kids are soul vampires being a parent of small children can often leave one very tired, I sent the RSS feed for Meh in there, so I can see what stupid thing they decided to sell overnight. This doesn’t work so great for when they have those freakout sales on Fukubukuro boxes of nonsense, but since they’re tweaking the way they do things, may prove more useful to me as time goes on.

But what’s really useful is seeing what I need to focus on that day. My tasks, calendar, etc. all shoved into a nice little summary. A daily brief. That’s where my mad scientist friend Tim comes in.

We’ve been going back and forth on this idea, and we’re in the middle of creating a Workflow5 that will take a whole bunch of personal information (calendar, tasks), add a field for impromptu notes, and throw the weather forecast in for the day, format it in a decent way, and send it directly to Slack. I do this before bed, and the next day, I just scroll up and read through the brief I sent, and then anything else that wound up in the channel overnight. I’m thinking about maybe using Workflow to insert some news headlines6 and other things that can get my brain going while I’m laying in bed, wishing I was still asleep.

Tim has done a lot of work tweaking this idea and building functionality into it, so check out his post. He’s got a bunch of explanation and links to multiple variations on the Workflows.

I’m really into this daily briefing idea. It’s new, and I think it has some legs. I plan on exploring it a lot more.

There’s a theme throughout my use of Slack, and my ideas for what I can do with it, and it’s similar to how I think about Workflow. I’m most interested in using these tools to either a) pull information to me in some useful way so I don’t have to look for it, or b) replace a single-use app of some kind with a similar and (hopefully) comparable set of functionality. Those two use cases continue to drive my experimentation with both apps, but primarily with Slack. Using dedicated channels in an app I already have installed, I can replicate the primary functionality of a handful of small apps that I would have otherwise installed. Will it do everything those apps do? No, not by a long shot. But for the major use case(s), it’s almost always good enough, and that continues to drive me to think of other ways to extend it. The more I use it, the more I want to use it, and find new ways to do so.

The other thing I’ve come to enjoy is the separation of topics of my interest (or functionality) by channel. Instead of an RSS app with a bunch of feeds in folders, I can send different feeds to different channels, and mix that content with other notifications and integrations to create a new experience. This level of flexibility is what gets me really excited about continuing to explore the tool and talk to other people who are thinking along similar lines.

Slack has become an integral part of my day, and continues to deliver a ton of value for me on a personal level well outside of its intended business-based use cases. Having a team all to myself is really fun, and gives me a great outlet to fiddle with iOS automation and web services without too much fussing. I’ve seen other people exploring this kind of thing too, and they’re doing some great things as well.

If you’re doing something cool with Slack outside of work, I’d love to hear about it.


  1. You can create an RSS feed for a Google alert and then use Slack’s RSS integration to get it into a channel. 
  2. If you have any other suggestions for things that send nice pictures, please do let me know. I love this channel and want more of it. 
  3. IFTTT has a channel that does this too, for AppZapp, but I found it to be too high volume (even with my tweaking) and not relevant to my general interests. YMMV. 
  4. I’m still way happier not being there, in case you’re wondering. 
  5. I had the idea, Tim is actually doing all the heavy lifting, because he’s like, WAY better at Workflow than I am. 
  6. But if I’m being honest, this almost sounds like a terrible idea, because it’s usually just more misery, and I can do without that first thing when I get up. 

Dalliances and deviations.

So I returned my iPhone SE.

I know, I know.

I was so into it. Last time I talked about it, my mind was made up, I was forging ahead, I had everything I needed and my resolve was strong.

To be honest, it was a great few weeks. I really like that phone a lot. It is an incredible, compact, able little thing. And I would absolutely recommend it to anyone who asked about it. There is absolutely nothing wrong with that phone. I truly adored it while I was using it.

But after watching the WWDC keynote, my mind started wandering. Although I wasn’t much into 3D Touch this time around, it seemed to be extending in pretty interesting directions. The iOS 10 UI made me pause too. I looked at the changes to layout, fonts, and other elements and realized that while it would work on a smaller screen, it wasn’t designed for a smaller screen.

That’s when it hit me: going against the grain of whatever direction Apple is moving in is not a great idea.

I started to realize that if I wasn’t using the de facto hardware (read: 4.7″ and up), I was not going to be getting the best experience. The changes coming to iOS are built for new hardware, with a typical inclusive nod to the previous year, making the update almost fully accessible, minus whatever secret hardware features are lurking, waiting to be revealed in the fall.

Most importantly, I wasn’t planning on buying a new phone this fall, and even if I was, I couldn’t see Apple refreshing the 4″ size so soon, if at all. I’d like to think that it caught them a little off guard, given that it was a bit hard to get one if you were just strolling in to a store for a while there. Tim Cook even noted that the demand was “much beyond what we thought” during the Q2 earnings call.

Still, the phone I had wasn’t able to take advantage of all of iOS today, let alone tomorrow. So I made the call to go back up to the 6s, and that was that.

But like a pre-teen romance at summer camp, I’ll remember the few weeks we had together fondly. Preferably against an 80s-style montage of Peter Cetera and soft-focus shots of me holding the phone wistfully.

The similarity of differences.

Google held its annual I/O conference recently, and unveiled some extremely interesting developments for the year to come. Focused ever more heavily on data processing and machine learning, its AI initiatives are being inserted into many of their products, and creating some new ones in the process.

One of the most notable new additions is Google’s Assistant, which replaces the Google Now functionality. Available throughout Android and new products like Google Home, Assistant will use context to present you with relevant information across many apps and services, allowing users to have a more fluid conversation with their devices, using the natural language patterns they’d ordinarily use talking to people as opposed to specific syntax queries.

Quite honestly, it’s very impressive stuff. I watched the I/O keynote in its entirety this week when I found some time, and I was blown away by some of the things Google is doing, right now, today.

I know a lot of people who enjoy it and use it daily, but for me, Siri has been inconsistent at best, and infuriating at worst. I can attempt the same, simple operations on different days and get wildly different results. Features have been added over the past few years, and on paper, it looks terrific. In reality, it is a crapshoot as to whether or not the small task I need to perform will actually get done in any possible way that would be faster than me using my phone manually. Using it on the Apple Watch is an abject nightmare. Your experience with it might have been nothing but unicorns prancing through fields of wishes and dreams, but it’s a broken system as far as I’m concerned.

Consistency is a huge part of good user experience. If, as a user, I have doubt, or reservations of any kind that the thing I need to do isn’t going to happen the way I expect or want it to, that creates friction. Friction eventually erodes trust, and without trust, I cease to be able to do the things I want in the way I want them done. I’ll find another way.

Siri has long struggled to mature under Apple’s development since the technology was acquired several years ago. I’m sure there are many, many good people working on it, and it pains me to feel the way I do and say these things, but it is simply not something I enjoy using–or use at all for that matter, anymore. There’s been quite a bit of talk lately about Apple’s ability to deliver compellingly (and consistently) in this new, shifting, data-driven landscape. Now famously having taken a stance in favor of localizing personal data to the device and protecting it in every way possible (a stance I am quite fond of), lots of questions as to whether or not the company is even prepared to meet this challenge–one that Google has been tackling for many years now–have arisen.

So back to Google.

They’re pushing forward with machine learning, using massive amounts of collected data–data that Apple has said it won’t take and doesn’t want–to create entirely new user experiences. The more it works, the smarter it gets. In the aggregate, all this data and use strengthens the product and allows users to do more things. It’s not an app, it’s an entire layer within the OS, working around what you’re doing with your device, affording you additional skills and options.

Earlier this week, prior to watching the keynote, I was having a conversation with some friends in Slack. Using my high-level glances at what Google was doing, and without really thinking too deeply into it, I said the following:

AI/bots may or may not be the future of computing. But data analysis and the kind of power Google has with those capabilities most definitely is.

That’s where Apple can’t catch up. This isn’t about phones. This is about what software is becoming and where the things we do with software go.

And I talked at length about why I thought this was true. I wasn’t spouting apocalyptic proclamations about Apple; they could set fire to piles of money today, every day for months, and still be in better shape than almost any other company on Earth. But I did express some real concern for the platform I enjoy and prefer not being able to keep up, and how the tradeoffs Apple is making to keep users safe (good) could potentially preclude it from delivering more compelling and timely experiences that people will come to expect from their devices (not so good).

Then I watched the keynote.

What became apparent to me, seeing everything myself and hearing the Google presenters talk about the technology, was that Google and Apple aren’t even competing in the same space anymore. Both companies are engaged in selling mobile devices, but they’re coming at personal technology from such different perspectives, they’re almost not even comparable. A few years ago, it seemed like the companies were at odds on the same field. But they’re not even playing the same sport.

If we’re going to distill it down to a focused, philosophical difference, I think it might look like this.

Apple’s world centers on hardware. It designs and builds amazing and transformative devices. Software is paired with hardware, and the integration points are tight, able to take advantage of hardware optimizations and tuning in crazy ways. Apple’s general perspective today on data is that they don’t want to know certain things, and want to obfuscate others. It’s a very individual-centered and -minded approach.

Google is all about that data. It eschewed hardware for its mobile OS initially, insisting that other companies provide it, following the Microsoft model of the recent past. It’s edged toward unifying software and hardware in a way similar to what Apple does, but doesn’t seem to be interested in pursuing that to its logical end. Hardware is a vehicle for software and data, passing in and out.

Apple and Google, in the eyes of the general public and many tech bloggers, have been at war for many years, and in vague terms, both companies sell fancy mobile phones. But the implications of those businesses are so far beyond the face value of what we see. And what I’ve realized is that they aren’t zero-sum or mutually exclusive. What I’ve come to understand is that the more the two companies seem to have been battling, the more the individual directions of each company become unassailably concrete.

Let’s use healthcare as an example, since that’s been the focus of segments in both companies’ recent presentations.

Apple: ResearchKit and CareKit. Centered around individuals, reporting personal data. Assembling tons of it, and allowing for better personal follow through on long-term treatment, and more individualized reporting for research purposes. Gathering of this data is done through traditional channels, but by allowing users to have agency in these processes, Apple affords people the ability to contribute to a large data set, but safely remain an identifiable component variable.

Google: machine learning to aggregate data against the treatment of extremely difficult ailments (diabetic retinopathy was the example presented in the keynote). Very few doctors can detect it accurately, and it’s very hard to do right/well. And this small number of doctors can’t be everywhere at once. But put enough data into a machine and it can pattern match the very intricate details–perhaps better than people, and everywhere at once (since people can only be in one place at a time). Throw incomprehensible amounts of information at an enormous amount of computing power and basically brute-force a treatment protocol that functions better than humans ever could.

Two fundamentally different approaches, two similar goals.

It’s a very interesting and important time in personal technology. Data moves through our lives like air. We want to protect it (some of us, anyway), but we want the value that sharing it can provide us. We want the future we were promised in our childhoods, but the changes we find occurring around us can be discomforting. This kind of change is everywhere, and it continues to move like perpetual motion, unstoppable. It’s beautiful and frightening. But it is inevitable.

I’m delighted that Apple wants to protect my information and is loudly standing up to the degradation of that idea in public and within the legal system. They may even be able to pull off the things I’m hoping for, without the compromises I’m looking to avoid. I’m also really excited to see what Google can actually do to advance the entire industry and provide new ways of solving serious problems. I think there are a lot of ways that these two approaches can exist together, in complementary layers, that can give us more of the future we’d hoped for. I’ve been becoming increasingly jaded about technology in the past few years, but I feel like I’ve been shown possibilities this week that may set me back in the other direction. Of course, there’s still time for things to go horribly awry.

The world will create a narrative of opposition because our nature is to set forces against one another. I no longer see this as a competition. And along with things like VR (which I have become obsessed with, in terms of non-gaming applications), for the first time in a while, I have real hope for things beyond my whatever my next phone might be.

That feels really good.

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.