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iOS and iPadOS 13: The MacStories Review

Following years of a judicious union between platforms, it’s time for iPad to embark on its own journey.

In looking back at major iOS releases from the recent past, it’s easy to see how building and positioning these annual updates has become a careful balancing act for Apple.

In last year’s iOS 12, we saw the company focus on improving performance, providing users with tools to understand their device usage habits, and adapting Workflow to the modern era of Siri and proactive suggestions. The strategy was largely successful: iOS 12 was regarded as Apple’s most reliable iOS release of late – a reputation that has resulted in a 90% adoption rate a year later; and the Shortcuts app – the highlight of last year from a user feature perspective – is becoming a built-in (and thus more powerful) app in iOS 13.

For all that Apple accomplished in iOS 12, however, some areas of the experience inevitably had to be put on the back-burner. Besides improvements to Reminders and Files, iOS 12 lacked a long-awaited dark mode (which was rolled out on macOS instead) as well as more substantial tweaks to the ever-evolving iOS 7 design language; chief among iOS 12’s absentee list, of course, was iPad. Even though Apple had trained users to expect major additions to the tablet platform on a biennial schedule (see iOS 9 and iOS 11), the lack of meaningful iPad features in iOS 12 spurred a contentious discussion when it became apparent that new iPad Pro hardware was so far ahead of its software, it legitimized asking whether investing in that hardware was even worth it.

The annual debate that surrounds which features make it into each major iOS release is symptomatic of a complicated truth: iOS isn’t just the operating system that runs on iPhones anymore, and these annual releases are more than a mere collection of updated apps. iOS is the platform for an ecosystem of devices – from our wrists and speakers to cars and TV sets – and its changes have repercussions that ripple far beyond an updated Reminders app or a new icon set.

This, of course, has been the case for a few years at this point, but the nature of iOS as an all-encompassing platform has never been as evident as it is today in iOS 13. For the first time since I started reviewing Apple’s annual iOS updates, it feels like the company is now keenly aware that a new iOS version has to cover an array of themes that can’t be pushed back for scheduling reasons. A single area of attention isn’t enough anymore – not for the Apple of 2019 as an economic, political, and social force, and not for iOS, the engine powering devices that aren’t just screens for apps, but bona fide lifestyle computers.

As a result, there’s something for everyone in iOS 13 and all the recurring themes of Tim Cook’s Apple are touched upon this time around. iOS 13 improves Face ID recognition and promises improvements to app download sizes and performance. Apple is sending strong signals on its commitment to privacy as a feature with a new sign-in framework for apps and enhancements to location tracking controls and HomeKit cameras. iOS’ design language is getting its biggest update in years with dark mode, new tools for developers to express colors and embed glyphs in their user interfaces, updated context menus, and redesigns aimed at facilitating one-handed interactions. We have notable improvements to built-in apps, including the rebuilt Reminders and Health, an overhauled Files app, and hundreds of quality-of-life tweaks that, in big and small ways, make iOS more capable and efficient.

No stone is left unturned in iOS 13 – and that includes iPad too.

The iPad experience has always been largely consistent with the iPhone – particularly since Apple unified core iOS interactions around a screen without a Home button – but also distinct from it. iOS 13 makes this distinction official by splitting itself in a second branch called iPadOS, which uses iOS as the foundation but is specifically optimized and designed for iPad.

It was clear when the new iPad Pro launched in late 2018 that it told only one part of a bigger story about the role of the tablet in Apple’s modern ecosystem. With iPadOS, Apple is ready to tell that full story: while the iPad has always been an extension of iOS, sharing key similarities with the iPhone hardware and software, it’s been evolving – arguably, a bit too slowly – into a different breed of computer that is fundamentally distinct from a phone.

We’ve been able to observe this divergence starting in iOS 9 with Split View multitasking and Apple Pencil, and the transition continued with iOS 11 and its drag and drop-infused environment. It was only natural (and well-deserved) for the iPad to begin advancing in a parallel direction to iOS – informed and inspired by it, but also capable of growing on its own and tackling problems that an iPhone doesn’t have to solve.

From this standpoint, there are two sides to iOS 13: on one hand, an underlying tide that raises all platforms, featuring a distillation of themes Apple comes back to on an annual basis; on the other, a fork in the road, opening a new path for the iPad’s next decade. And against this backdrop, a single question looms large:

Can Apple balance both?

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    Ulysses: The Ultimate Writing App for Mac, iPad, and iPhone [Sponsor]

    Ulysses is a powerful text editor for the Mac, iPad, and iPhone that packs an extraordinary depth of features beneath a simple and clean interface. The app’s Apple Design Award-winning UI allows you to concentrate on your writing distraction-free with the confidence that when you need them, Ulysses’ pro tools are just a click or tap away. Also, because Ulysses syncs using iCloud, you can get your writing done wherever you happen to be and whichever device you are using.

    Under the hood, Ulysses has all the functionality needed to manage and produce all of your writing projects. The Library sidebar is perfect for organizing a large number of documents into groups that can be nested. The app also features writing goals, powerful search and filtering options, support for keywords, in-line images stored locally or remotely on a server, and much more. Ulysses is constantly being updated with new features too. Recently, the iPad version added a split view, which allows you to view and work on two documents at once. Publishing to a Ghost blog was also recently added, and you can export your final product in a wide variety of formats including, plain text, Markdown, TextBundle, rich text, DOCX, ePub, HTML, and PDF, or publish to a WordPress or Medium blog.

    Ulysses is a free download on the App Store and Mac App Store, so you can try it before deciding whether to subscribe for $4.99 per month or $39.99 per year. Students can subscribe for six months at a time for $10.99. However, Ulysses has a special deal just for MacStories readers. For a limited time, use this link to learn more about Ulysses and get the first year of an annual subscription for $19.99, a 50% discount off the usual price.

    Our thanks to Ulysses for sponsoring MacStories this week.


    Introducing a New MacStories Podcast: Dialog, Where Creativity Meets Technology

    Federico and I are excited to announce a new MacStories podcast called Dialog. The show is a seasonal podcast featuring weekly, in-depth conversations with special guests about the impact of technology on creativity, society, and culture.

    You can subscribe here and listen to the first episode on Apple Podcasts.

    You can also listen to the first episode on the Dialog website here.

    Each season will be organized around a central theme and include in-depth discussions with guests with expertise in the season’s topic. To kick things off, season 1 is all about writers and writing. You’ll hear from a combination of familiar and unfamiliar voices, all of whom are accomplished writers with backgrounds in journalism, songwriting, fiction, screenwriting, and more. Since we began recording episodes, it’s been fascinating to hear guests share their unique perspective on writing, the creative process, and the business of writing and discover areas of overlap between very different kinds of writing.

    Seasonal Format and Future Guests

    Dialog is a sort of spin-off of AppStories, our podcast about the world of apps. The interviews we’ve done on AppStories are some of the most popular episodes we’ve produced. However, over time, we realized that AppStories’ format is too constrained to do justice to many of the interviews we want to do. The self-imposed time limit of that show and its topical focus became a barrier.

    That led me to sketch out the contours of what would become Dialog during our annual MacStories winter holiday break. To overcome AppStories’ constraints, I decided we needed to flip that show on its head both structurally and topically.

    Structurally, Dialog’s conversations with guests are far more in-depth than we could accomplish in a 30-minute AppStories interview. Dialog’s interviews will run as long as two hours but will be split over two episodes to keep each episode to about one hour long. It’s a format that also provides headroom for Federico and me to participate more fully in each episode; less like a traditional interview and more of a conversation with our guests.

    Topically, Dialog’s focus is also broader than any interview we’ve done on AppStories. Of course, you can expect Federico and me to come at each season from a tech angle, but that’s the lens through which each season will be viewed more than it is the subject matter of the seasons themselves.

    Although Dialog is different than anything we’ve done before, its roots are also firmly grounded in MacStories’ character. We enjoy the apps and hardware we try every day, but what we love the most is telling the stories of the people who make those things, exploring how they empower creativity, and reflecting on their impact on the world around us. Dialog is a natural extension of our approach to technology.

    The first episode of Dialog, which you can listen and subscribe to here, introduces the topics we will cover this season. Federico and I talk about our backgrounds in writing, how we got started, our approach to writing at MacStories, the business of writing online, and a lot more.

    Next week, we’ll be joined for a two-part conversation by our first guest, John Gruber of Daring Fireball, who will be followed by singer-songwriter Frank Turner, and other guests throughout the summer. At the end of the season, Federico and I will wrap up what we’ve heard and learned from the writers we’ve talked to before taking a break to plan season 2.

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    Beyond the Tablet: Seven Years of iPad as My Main Computer

    For the past seven years, I’ve considered the iPad my main computer. Not my only one, and not the most powerful one I own, but the computer which I use and enjoy using the most.

    I’ve told this story on various occasions before, but it’s worth mentioning for context once again. My iPad journey began in 2012 when I was undergoing cancer treatments. In the first half of the year, right after my diagnosis, I was constantly moving between hospitals to talk to different doctors and understand the best strategies for my initial round of treatments. Those chemo treatments, it turned out, often made me too tired to get any work done. I wanted to continue working for MacStories because it was a healthy distraction that kept my brain busy, but my MacBook Air was uncomfortable to carry around and I couldn’t use it in my car as it lacked a cellular connection. By contrast, the iPad was light, it featured built-in 3G, and it allowed me to stay in touch with the MacStories team from anywhere, at any time with the comfort of a large, beautiful Retina display.

    The tipping point came when I had to be hospitalized for three consecutive weeks to undergo aggressive chemo treatments; in that period of time, I concluded that the extreme portability and freedom granted by the iPad had become essential for me. I started exploring the idea of using the iPad as my primary computer (see this story for more details); if anything were to ever happen to me again that prevented being at my desk in my home office, I wanted to be prepared. That meant embracing iOS, iPad apps, and a different way of working on a daily basis.

    I realized when writing this story that I’ve been running MacStories from my iPad for longer than I ever ran it from a Mac. The website turned 10 last month, and I’ve managed it almost exclusively from an iPad for seven of those years. And yet, I feel like I’m still adapting to the iPad lifestyle myself – I’m still figuring out the best approaches and forcing myself to be creative in working around the limitations of iOS.

    On one hand, some may see this as an indictment of Apple’s slow evolution of the iPad platform, with biennial tablet-focused iOS releases that have left long-standing issues still yet to be fixed. And they’re not wrong: I love working from my iPad, but I recognize how some aspects of its software are still severely lagging behind macOS. On the other hand, I won’t lie: I’ve always enjoyed the challenge of “figuring out the iPad” and pushing myself to be creative and productive in a more constrained environment.

    In addition to discovering new apps I could cover on MacStories, rethinking how I could work on the iPad provided me with a mental framework that I likely wouldn’t have developed on a traditional desktop computer. If I was in a hospital bed and couldn’t use a Mac, that meant someone else from the MacStories team had to complete a specific, Mac-only task. In a way, the limitations of the iPad taught me the importance of delegation – a lesson I was forced into. As a result, for the first couple of years, the constrained nature of the iPad helped me be more creative and focused on my writing; before the days of Split View and drag and drop, the iPad was the ideal device to concentrate on one task at a time.

    Over the following couple of years, I learned how to navigate the iPad’s limitations and started optimizing them to get more work done on the device (I was also cancer-free, which obviously helped). This is when I came across the iOS automation scene with apps such as Pythonista, Editorial, Drafts, and eventually Workflow. Those apps, despite the oft-unreliable nature of their workarounds, enabled me to push iOS and the iPad further than what Apple had perhaps envisioned for the device at the time; in hindsight, building hundreds of automations for Workflow prepared me for the bold, more powerful future of Shortcuts. Automation isn’t supposed to replace core functionality of an operating system; normally, it should be an enhancement on the side, an addition for users who seek the extra speed and flexibility it provides. Yet years ago, those automation apps were the only way to accomplish more serious work on the iPad. I’m glad I learned how to use them because, at the end of the day, they allowed me to get work done – even though it wasn’t the easiest or most obvious path.

    When Apple announced the iPad Pro in 2015, it felt like a vindication of the idea that, for lots of iOS users – myself included – it was indeed possible to treat the iPad as a laptop replacement. And even though not much has changed (yet?) since 2017’s iOS 11 in terms of what the iPad Pro’s software can do, the modern iPad app ecosystem is vastly different from the early days of the iPad 3 and iOS 5, and that’s all thanks to the iPad Pro and Apple’s push for pro apps and a financially-viable App Store.

    We now have professional apps such as Ulysses, Agenda, Things, Keep It, and iA Writer, which, in most cases, boast feature parity with their Mac counterparts; we have examples of iOS-only pro tools like Pixelmator Photo, LumaFusion, Shortcuts, and Working Copy, which are ushering us into a new era of mobile productivity; and both from a pure iPad-hardware and accessory standpoint, we have more choice than ever thanks to a larger, more inclusive iPad lineup, remarkable Pro hardware, and solid options to extend the iPad via keyboards, USB-C accessories, and more.

    Seven years after I started (slowly) replacing my MacBook Air with an iPad, my life is different, but one principle still holds true: I never want to find myself forced to work on a computer that’s only effective at home, that can’t be held in my hands, or that can’t be customized for different setups. For this reason, the iPad Pro is the best computer for the kind of lifestyle I want.

    However, the iPad is not perfect. And so in the spirit of offering one final update before WWDC and the massive release for iPad that iOS 13 will likely be, I thought I’d summarize seven years of daily iPad usage in one article that details how I work from the device and how I’d like the iPad platform to improve in the future.

    In this story, I will explore four different major areas of working on the iPad using iOS 12 system features, third-party apps, and accessories. I’ll describe how I optimized each area to my needs, explain the solutions I implemented to work around the iPad’s software limitations, and argue how those workarounds shouldn’t be necessary anymore as the iPad approaches its tenth anniversary.

    Consider this my iPad Manifesto, right on the cusp of WWDC. Let’s dive in.

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      10 Years of MacStories

      Later this week on Saturday, April 20, MacStories will turn 10 years old.

      It was Monday, April 20, 2009 when, fresh out of a job from which I had gotten fired, I decided to publish the first official post on my self-hosted blog after a few weeks of running a free WordPress.com website. I was 21. My English was terrible and, at the time, MacStories was written in two languages, English and Italian – probably to hide my discomfort as a non-native English speaker. If you want to hear this story (and my entire background) in much greater detail, John interviewed me on this week’s special episode of AppStories.

      Since that first post about web browsers, MacStories has been on my mind every day and it remains the most important thing I’ve ever built in my adult life. In many ways, MacStories has come to define me.

      As you might guess, I’ve struggled to come to terms with the meaning of this anniversary. I don’t like celebrating work-related anniversaries. I don’t think our readers appreciate excessive self-congratulatory content and I’d rather focus on getting work done every day. I prefer to let other people compliment us if they ever feel compelled to do so; otherwise, I just want to focus on providing a service to our audience, because that’s what I’m ultimately here to do: to make sure that MacStories and our related properties can be useful and inspiring for our readers around the world.

      Ten years, however, does feel like an extremely long time in Internet years. For this reason, when I started thinking about this looming milestone sometime last year, I knew I had to do something special for this anniversary – just this once – to look back at the past decade of MacStories, reflect on the things I’ve learned along the way, and plan ahead for the future.

      Here’s the short version: this week is going to be extra special on MacStories. We’re launching our first official merchandise today (macstoriesmerch.com) and there will be a series of retrospectives published on MacStories throughout the week (keep an eye on this tag). In addition, we will be launching a couple of new perks exclusive to Club MacStories members.

      Now, allow me to share some thoughts about creating MacStories and what this website has meant for me over the past 10 years.

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      My Must-Have Mac Apps, 2018 Edition

      Last year when I wrote about my must-have Mac apps, I was coming off a tumultuous year that started with a daily commute into Chicago for my old job and ended with me working from home. As the year came to a close, I was exploring what that meant for the way I work on the Mac.

      That process continued into 2018. With the number of new things I took on in 2017 and the transition to indie life, I made the conscious decision to step back and settle into my new life. That wasn’t easy. There’s a natural tendency to take on everything that crosses your path when you go out on your own, but I’ve seen too many people fall into that trap in the past. Instead, I concluded that 2018 would be the year to improve the way I already work by refining existing workflows and reevaluating how I get things done, including on the Mac.

      Three events led me to work on my Mac more in 2018. The first was the 27-inch LG 4K display I bought in January. It was a big step up from the 23-inch 1080p one I had before and, combined with a VESA arm, improved working at my Mac substantially.

      The second factor was our MacStories coverage of the App Store’s tenth anniversary. For it, we produced seven extra episodes of AppStories that were released in the span of one week, which kept me in front of my Mac recording and editing for long periods of late May through June.

      Third, just after WWDC, I destroyed the screen of my iPad Pro thanks to the trunk hinges that invade the interior of the 2016 Honda Accord.1 I decided to hold out for the new iPad Pros, but that meant writing for four of the busiest months at MacStories without a good iOS work solution. I used a current-generation 9.7-inch iPad some, but it couldn’t compete with my LG display.

      As 2018 comes to a close, the changes I’ve made haven’t been dramatic despite the extra time I’ve spent in front of my Mac. Instead, I’ve fine-tuned existing workflows and added new apps for specific tasks.

      Below, I’ve broken down the 49 apps I use roughly by activity and function. I’ll mention where Apple’s apps fit into my workflow as I go because without them there would be a few big holes in the landscape of apps I use, but the focus of this roundup is on third-party apps, not Apple’s.

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      1. I’m right there with you on this one John. ↩︎

      Drafts 5.5, MultiMarkdown, and CriticMarkup

      Tim Nahumck, writing about the latest Drafts update for iOS:

      One thing that is included with MultiMarkdown as an option is Critic Markup. Looking through the guide, there are several helpful elements that can be used for editing my writing utilizing Critic Markup. I can highlight some substitutions, additions, and deletions. I can highlight text to show something I might want to work on later. I can also add a basic comment somewhere that won’t be shown in a preview. And with this action, I can easily add any of them with a tap and a text entry, which inserts it in the proper format. This is helpful for creating and previewing the documents in Drafts, and gives users the flexibility to mark up files and save them back to a cloud service. I can see myself using this a lot for longer posts or large reviews. I’ve even modified my own site preview action to render the MultiMarkdown via scripting, as well as updating both my standard and linked post WordPress publishing actions to do the same.

      I’ve always been a fan of CriticMarkup but have never been able to get into it as it wasn’t integrated with the text editors I used on iOS. Considering how Drafts is my favorite option when it comes to writing and editing certain annual long-form stories, and given how I came up with my own syntax in previous years to embed comments in Markdown documents, I’m going to give this a try.

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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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