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My Today at Apple Experience

It took nearly 18 months of Apple’s regular Today at Apple promotions through keynote events and press releases, but I finally had my interest in the program piqued. As I wrote earlier this month, whereas every other Apple product is analyzed to death by writers, podcasters, and YouTubers, the company’s retail stores and Today at Apple program are often ignored by tech media. But Apple’s increased trumpeting of its retail initiatives, in the face of a collective shrug from the press, made me wonder what exactly we’re all missing out on here. I mean, if the company is passionate enough about Today at Apple to host over 18,000 sessions per week, then there must be something special about the program.

So I attended my first session.

Last Monday morning I opened the Apple Store app and booked a session at Apple Fifth Avenue called “Photo Lab: Crafting Your Shot Co-created with Chase Jarvis.” As I suspect is true of most iPhone owners, I love taking pictures with my phone, but I know absolutely nothing about the ins and outs of quality photography. As a result, the Photo Lab session seemed like a great place to start.

Much of the time when Apple promotes Today at Apple, it highlights sessions taking place in its global flagship stores, with beautiful open forums and enormous wall displays. My experience was a lot more low-key, as the Fifth Avenue location is currently approaching two full years in temporary housing as major renovations to its previous location near completion. While the revamped Fifth Avenue store will undoubtedly come with all the beauty and grandeur of locations like Michigan Avenue and Regent Street, for now the site lacks all those modern bells and whistles; rather than taking place in a forum, my Today at Apple session took place around a small table that sat eight participants.

I’m not going to get much into the specifics of the session’s contents, which were solid overall; instead, I want to share three simple takeaways from this first Today at Apple experience. They’re the three main things that were on my mind following the session, and after rewatching portions of Apple’s October event in Brooklyn, I realized that my takeaways actually line up with statements shared by executives at the event.

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iPad Diaries: Typing on the iPad Pro with the Smart Keyboard Folio

iPad Diaries is a regular series about using the iPad as a primary computer. You can find more installments here and subscribe to the dedicated RSS feed.

I have a love/hate relationship with Apple’s Smart Keyboard for the iPad Pro.

On one hand, I’ve always been a fan of its small footprint and ability to almost become part of the device itself from both a hardware and software perspective. The Smart Keyboard snaps itself into place and attaches magnetically to the iPad Pro; it doesn’t require you to even think about charging it as the Smart Connector takes care of it; thanks to the trivial magic of magnets, the keyboard and cover stay attached to the iPad as you carry it in a bag, but can be easily disconnected at a moment’s notice should you need just the iPad’s screen. The software experience is equally intuitive and exquisitely Ive-esque: the Smart Keyboard requires no pairing because it eschews Bluetooth altogether, and it integrates with all the keyboard shortcuts supported by iOS and apps. In the latest iPad Pro, the Smart Keyboard is even Face ID-aware: you can double-tap the space bar to authenticate from the lock screen instead of extending your arm toward the screen to swipe up – a welcome enhancement for those who work with their iPad Pro constantly connected to a keyboard.

There’s plenty to appreciate about Apple’s Smart Keyboard – an accessory designed on the premise of integration between hardware and software, following the same core principles at the foundation of AirPods, Apple Pencil, and (even though some liked to make fun of their peculiar design) Smart Battery Cases. But since its debut in 2015, I’ve been saving a series of small complaints and bigger annoyances with the Smart Keyboard that I’d like to revisit now that Apple has shipped its evolution for the new iPad Pro – the Smart Keyboard Folio.

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Reminder and GoodTask: Third-Party Upgrades to Apple’s Reminders

Reminder (left) and GoodTask (right)

Reminder (left) and GoodTask (right)

Apple has long prided itself on being a company that carefully weaves hardware, software, and services together to offer a holistic user experience. Because of this, every purchaser of Apple products benefits from the built-in apps and services that accompany those products. And on the two most popular sellers, the iPhone and iPad, one of those bundled apps is Reminders.

At its core, Reminders is a simple list and to-do app that can be surprisingly powerful thanks to features like repeating tasks, location-based reminders, collaborative lists, and note support. Many times over the years Reminders has been my primary task manager and served me fairly well. It may not be as capable as alternatives like Things, but the app remains an appealing tool for those whose needs are light, and who value the ease afforded by Apple’s built-in ecosystem.

Unlike most of Apple’s other iOS apps, Reminders is built on a framework that’s accessible to third-party developers. Though developers can’t build apps that hook in directly with your Messages or Notes databases, Reminders is a different story. The underlying system powering Reminders is calendar-based, meaning it’s not tied to a single first-party app. Just as Fantastical and Timepage offer access to your existing iCloud calendars, developers can similarly build entire replacements for the Reminders app utilizing your existing collection of lists and to-dos. Two such apps, Reminder and GoodTask, serve as perhaps the best third-party Reminders clients on the App Store.

Each app takes a different approach to enhancing Reminders, with one focusing on modern design while the other offers power user features and flexibility; both, however, retain some of the benefits of staying in the Apple ecosystem while improving upon the first-party Reminders app.

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iPad Diaries: My First 48 Hours with the New 12.9” iPad Pro

Two days ago, I walked into my local Apple Store and bought the new 12.9” iPad Pro along with a Smart Keyboard Folio, second-generation Apple Pencil, and LG’s UltraFine 4K display (plus, of course, AppleCare+ because these iPads don’t come cheap). As I shared on Twitter and the Connected podcast on Wednesday, I went for a 1 TB configuration (with cellular) in Space Gray, and the display is the monitor I’ll primarily use with a new Mac mini I also plan on buying very soon. It’s been a busy couple of weeks in our apartment: we’ve been doing some renovations and buying new furniture, including a larger desk for my “office” (read: a section of our bedroom). As I’ve shared on my various podcasts for the past few months, getting a bigger desk with a Mac mini and 4K display that would support both macOS and iOS was always part of the plan.

While in previous years I was able to offer reviews for the new iPad Pros before launch day, that wasn’t possible this year. For this reason, I decided I didn’t want to wait several weeks to prepare an in-depth review of the new iPad Pro and avoid questions from MacStories readers until the story was finished. So in a break with tradition, I’m trying something different this time: as part of my semi-regular iPad Diaries column here on MacStories, I’m going to share a collection of shorter and more topical articles about the new iPad Pro over the next few weeks.

I believe this generation of iPad Pros is one the most exciting changes to the iPad line in years, and I want to jump straight into the discussion by detailing, step by step, my ongoing experience with the new iPad Pro from the perspective of someone who’s been using an iPad as his main computer for the past five years. I plan to write about iOS, apps, and my iPad Pro workflow soon, but today I’d like to start by explaining my purchase decision and sharing some initial impressions about the iPad’s hardware. Let’s dive in.

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Choosing Your Markdown Editor: A Comparison of Ulysses and Drafts

One thing the MacStories team loves to do is constantly try new apps, compare the serious contenders in each app category, and settle on the app that suits us best. Most of the time this app evaluation process takes place on a merely private level, for personal purposes, but today I wanted to share in public an in-depth comparison and analysis of two excellent writing apps: Drafts and Ulysses.

These two apps have been on my mind a lot in recent months. To share some context, I have used Ulysses as my primary Markdown editor almost exclusively since early 2016. During that time I’ve been very happy with the app, even through its transition last year to a subscription model. I’ve continued trying out the latest updates from Ulysses’ competitors, of course, but nothing else has stuck for me. However, there’s one app I’ve long wanted to give a serious look at, but hadn’t been able to until recently: Drafts 5.

Tim Nahumck’s review of Drafts was the first tug on my interest, causing me to follow updates to the app with a close eye. Then Federico had a successful experience writing his iOS 12 review in Drafts 5. Ultimately, I couldn’t resist giving the app a serious shot any longer.

Drafts and Ulysses are very different apps in many ways. However, they share in common being powerful Markdown editors. In this article I’ll walk through their similarities, divergences, and ultimately share which app I’ve decided to write in going forward. The goal is not to say which app is better, as the answer to that question is entirely subjective. Instead, I want to help you decide which app is likely best for you.

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Why Shortcuts Matter for Accessibility

Since it was announced at WWDC over the summer, the lion’s share of conversation around shortcuts has been about getting things done quickly and efficiently. Apple’s marketing message focuses on how shortcuts in iOS 12 help “streamline the things you do often” using Siri and/or the Shortcuts app. The company also recently put out a press release highlighting top App Store apps that have integrated shortcuts to extend their functionality, touting them for “making [users’] favorite apps even easier to use with a simple tap or by asking Siri.”

While the convenience factor of shortcuts is appreciated, an important aspect to their utility is accessibility. It’s a crucial aspect of the story around shortcuts, because while everyone loves a time-saver or two, these workflows also have the potential to make iPhone and iPad more accessible. In an accessibility context, shortcuts can be lifesavers in terms of reducing cognitive load, excessive swiping and tapping, and other common points of friction often met by disabled users.

Shortcuts, Past and Present

Before considering shortcuts as an accessibility tool, it’s important to understand their roots in order to properly frame them into perspective. The idea that shortcuts, or workflows, can prove valuable as an assistive technology isn’t a novel one.

Workflow, on which the Shortcuts app is based, was acquired by Apple in early 2017. Two years earlier, however, Apple selected Workflow as an Apple Design Award winner primarily for its integration of iOS accessibility features. Ari Weinstein, who joined Apple to work on Shortcuts post-acquisition, told me in an interview at WWDC 2015 that he and his team received feedback from several blind and visually impaired users who were curious about Workflow and wanted to try it. As a result, the team felt adding VoiceOver support was “the right thing to do,” Weinstein said.

To paraphrase Kendrick Lamar, Shortcuts got accessibility in its DNA.

Given the history lesson, it’s not at all far-fetched to think the Shortcuts app would have appeal to disabled users. Like Overcast and Twitterrific, Shortcuts is an app built for the mainstream, yet it has the care and design sensibility to carry relevance for a variety of use cases, like being fully accessible to a blind user via VoiceOver. This isn’t small potatoes; given Apple’s commitment to the disabled community, it’s certainly plausible Workflow’s ode to accessibility made the app all the more desirable.

More Than Just Productivity

As I reported during WWDC, Apple’s focus this year, software-wise, marked a departure from how they’ve traditionally approached accessibility enhancements. Unlike past years, there were no new discrete accessibility features for any platform. (AirPods with Live Listen is close). Instead, Apple chose to hammer on the idea that the tentpole features (e.g. Group FaceTime in iOS 12, Walkie-Talkie in watchOS 5) can be enabling technologies. The overarching theme of the conference was that the new features were so well designed that they brought inherent accessibility gains.

Siri shortcuts is another of those features. In my briefings with Apple at WWDC and since, shortcuts has been one of the first items they wanted to discuss. Like Group FaceTime and others, the company firmly believes in shortcuts’ potential as an accessibility aid. Their enthusiasm is warranted: for many users with certain cognitive and/or physical motor delays, the consolidation of tasks can reduce friction associated with remembering how to perform a task and then doing it. In this way, shortcuts are the inverse of task analyses; rather than extrapolating tasks into their individual parts (e.g. tapping a series of buttons in an app), the Shortcuts app’s automation turns them into a single step. (You break down steps when creating your own workflows, but that’s beside the point being made here.) Lest we forget about Siri; being able to use your voice to activate shortcuts is a boon for people with motor delays, as the “hands free” experience can be empowering.

For disabled people, shortcuts’ focus on speed and accessibility can open up new possibilities in terms of what they can do with their iOS devices and how they do things. Throw in system accessibility features like VoiceOver and Dynamic Type, and the Shortcuts app becomes far more compelling than simply being a sheer productivity tool.

”We see huge accessibility potential with Siri Shortcuts and the Shortcuts app. It’s already making a difference — helping people across a wide range of assistive needs simplify every-day tasks like getting to work, coming home, or staying in touch with friends and family,” Sarah Herrlinger, Apple’s Senior Director of Global Accessibility Policy & Initiatives, said in a statement. “We’re getting great feedback about how powerful the technology is in streamlining frequent tasks and integrating multiple app functions with just a single voice command or tap.”

How I Use Shortcuts

I am far less prolific in my adoption of shortcuts than some people. Others, like Federico and Matthew Cassinelli, are far more well-versed in the intricacies of what is possible and, more importantly, how you chain certain commands together.

My needs for shortcuts are pretty spartan. The shortcuts I use most often are practical, everyday ones I found in the Gallery section of the app. I currently have thirteen shortcuts; of those, the ones that are the most heavily-used are the laundry timer, tip calculator, and one for texting my girlfriend. While I have enjoyed spelunking through Federico’s work for esoteric, power user shortcuts, the reality is my work doesn’t require much automation. I typically don’t need to do fancy things with images, text, and the like. That isn’t to say these tools aren’t cool or valuable; they’re just not necessarily for me. For my needs, quick access to, say, the laundry timer is worth its weight in gold because I always forget to move my clothes.

Consider another shortcut of mine, Play an Album. I’ve been listening to Eminem’s new album, Kamikaze, virtually non-stop since it came out at the end of August. Rather than manually launch the Music app, find the album in my recently played queue, and hit play, I can utilize the Shortcuts widget to play it with a single tap. The manual method is three steps which, while not tedious for me in any way, is more work. Going back to the task analysis analogy I used earlier, not only is Play an Album faster, it particularly helps me conserve precious visual energy I otherwise would have expended finding the album. For fine-motor skills, the shortcut also saves on potential cramping in my fingers caused by my cerebral palsy. Again, what can take multiple taps can be condensed into a single motion. For many, that’s a huge win.

The same concept applies to sending iMessages to my girlfriend. Using the shortcut, what would normally be a multi-step process is reduced to a single step. The advantage for me is a matter of kinetics, but for others, the advantage very well could reduce cognitive load and increase executive function. Not insignificant.

The Bottom Line

As is the case with stuff like Markdown and Apple Pay, technologies not built expressly for accessibility’s sake, the Shortcuts app is so well considered and approachable that anyone can use it, regardless of ability. There are no complicated settings or special modes; as Apple designed it, it just works as they intended it.

That’s what makes Shortcuts’ star shine brighter. Yes, Apple is pitching it for speed and convenience. Yes, shortcuts can be as pedestrian or as nerdy as you want them to be. Above all, however, the Shortcuts app is accessible. It’s an app that’s reachable to the widest possible audience, turning its utilitarianism into something far greater.

Examining Dark Mode Implementations of Mac Productivity Apps

As I noted in my review of macOS Mojave, there’s a lot more going on with Dark Mode than dark gray window chrome. There were two sessions at WWDC dedicated to Dark Mode. Some apps are easier to adapt to Dark Mode than others from a technical standpoint, but beyond the coding, developers have to grapple with many design issues that affect apps differently.

As with many new features Apple introduces, there’s the way the company would like to see Dark Mode implemented and then there’s the way third-party developers use it in practice. Part of the variety you find is driven by the particular needs of each app. Other differences reflect compromises that are necessary to adapt existing designs to Dark Mode. Sometimes, however, developers intentionally ignore Apple’s recommendations, choosing to take a different path.

In my Mojave review, I collected some representative examples of apps that were ready with Dark Mode implementations when the OS update shipped. Since then, many other apps have been updated. I’ve spent time with many of them and have begun to see some design and implementation patterns among the early adopters that are interesting to compare to similar system apps by Apple. It’s also useful to consider how these variations will impact the experiences users have with these apps.

In the sea of dark gray floating before my eyes, I’ve identified a handful of app categories that illustrate some of the subtle differences between the apps I’ve tried. There are many other good examples, but email clients, task managers, text editors, and note-taking apps are categories that best illustrate how Dark Mode is being used by the first wave of developers to put the feature into practice.

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macOS Mojave: The MacStories Review

I went to San Jose this June not expecting much from macOS. After all, it’s a mature OS that already did what I need. My expectations were reinforced by rumors and leaks that Apple would introduce a Dark Mode and the fact that High Sierra introduced several significant foundational changes to macOS. I concluded that Mojave would focus primarily on a design refresh.

I was wrong. Dark Mode is the most visible and one of the most significant changes to macOS, but Mojave is much more than a UI refresh. Dark Mode and Mojave’s other system updates include productivity enhancements that have made meaningful improvements to the way I work on my Mac.

It took some time to acclimate to Dark Mode, but now I prefer it. As much as I like Dark Mode though, the most important changes to macOS have been those that surface existing functionality in new places making them more useful than in the past.

Mojave adds a collection of Desktop, Finder, and screenshot tools that are notable for the way they meet users where and how they work. It’s a functional approach to computing that has had a bigger impact on my day-to-day workflow than other recent updates to macOS, even where the Mojave updates provide new ways to do things I could already do before.

There’s a lot to cover in Mojave, so I’m going to dive right in and dispense with explaining how to set it up. Apple has a whole page devoted to the topic that you can explore if you’d like. Instead, let’s start by considering how Mojave’s Dark Mode.

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watchOS 5: The MacStories Review

watchOS had a bumpy first few years. Some poor decisions and perhaps a premature initial launch forced significant design changes to be in order right away. It wasn’t until last year’s watchOS 4 release that it finally felt like the waters had calmed. Apple seemed to have solidified the brunt of its focus around fitness and audio, while also debuting a healthy backdrop of first-party apps, new watch faces, and machine learning features. The Siri watch face was the big addition for both of those last two categories, and while its initial introduction was underwhelming, the ideas behind it were intriguing. The redesigned Workout and Music apps along with background audio during workouts were excellent additions to the Apple Watch’s core foundation. All things considered, Apple pushed a great update last year, and it only got better as the year progressed.

While it didn’t ship in time for watchOS 4’s launch in September, streaming from Apple Music was released late the next month in watchOS 4.1. The ability to stream music in the background during workouts freed runners and other athletes from being tied to their phones while they exercised. Paired with the redesigned Workout app – which put live statistics front and center while keeping Now Playing and workout controls just a swipe away – watchOS 4 established a truly better fitness experience for Apple’s smartwatch.

The audio story that Apple told last year felt much less complete. Despite receiving a significant amount of attention in Apple’s marketing efforts, the Apple Watch’s music improvements seemed almost strictly geared toward workouts. Background audio was limited to workout apps and withheld from the platform as a whole, the first-party Now Playing screen continued to monopolize possession of volume controls, and the Music app only gave manual access to preselected songs instead of the full music library on your iPhone1. Audio on the Apple Watch had received some strong improvements, but the scope of those positive consequences felt unnecessarily limited.

Thankfully, Apple seems to agree. This year’s watchOS 5 update, released today for all Apple Watches Series 1 and later, fills in the gaps of the watchOS audio feature set. Third-party audio apps can now run in the background, and full audio controls including volume adjustment via the Digital Crown have been made available to them. watchOS 5 also introduces the first-party Podcasts app, which supports automatic syncing of new episodes that you’re subscribed to and streaming of any show in the iTunes podcast directory.

Beyond audio, watchOS 5 also builds on the solid fitness foundation with activity competitions, expanded Workout types, automatic workout detection, and advanced running statistics. Siri has continued to receive attention as well, introducing third-party integrations to the Siri watch face and a raise-to-speak feature which truncates the inveterate “Hey Siri” prefix for the first time on any platform. A new Walkie-Talkie app marks the first return to novelty Apple Watch communication methods since Digital Touch, but this time I think Apple might have tapped into a legitimate, albeit niche use case. Top things off with improved notifications, the introduction of web content, and NFC-powered student ID cards and we have a substantial watchOS update on our hands.

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  1. This last decision always felt senselessly arbitrary, and indeed Apple finally reversed it in watchOS 4.3 last March. ↩︎