Way back in 2016, in the era of iOS 9, I laid out the tentpole features I wanted to see come to iOS and the Mac. Now, three years later, so many things from that wishlist have become a reality that it’s probably a good time to revisit the topics that haven’t yet come to pass, and plan a new wishlist for the years to come. I originally planned this list to have a Developer/User split, but it became clear that the two go hand-in-hand; if you’re doing complex things on iOS today, using the various automation apps, you are but steps away from needing the same things that developers do.
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WWDC, A Wish List (2019 Edition)
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.
Timery for Toggl: The MacStories Review
I have a long, rocky relationship with time tracking. For years I tracked my time because I had to; clients were billed by the hour. I hated the tedium of it. A big part of that was because I didn’t have access to time tracking apps. Instead, I kept track of my time in a notebook or a plain-text document. When I left that job, I celebrated, figuring that I’d left time tracking in my wake. I was very wrong.
No sooner had I started writing and podcasting full-time than I found myself tracking every minute that I work again. There was a difference this time though. I was doing it for myself to ensure I spent my time wisely; no longer was I just feeding the back-end to an invoicing system.
Time tracking helps me weigh the value of the time I spend on every project, identify inefficiencies in the way I work, and acts as an early warning system to avoid burnout. Tracking for my own benefit has made all the difference in the world, but it didn’t make keeping up with the habit any easier. For that, I needed a better set of tools than a notebook or text file.
The service I decided on was Toggl, which Federico and a few other friends were already using. It’s perfect for anyone tracking their time for their own purposes because the service has a generous free tier. If you want more extensive reporting, advanced features, or project and team management though, there are paid tiers too.
Toggl also offers a rich web API. That was important when I first started using Toggl because early versions of its iOS and Mac apps weren’t great. Those apps have improved, but early on, I switched to using Federico’s Toggl workflows which evolved into his current set of Toggl shortcuts alongside the Toggl web app running in a Fluid browser instance on my Mac.
I’m still using Toggl in a Fluid browser on my Mac, but since last summer, I’ve been using the beta of Joe Hribar’s Timery on iOS and loving it. In fact, Timery is so good that even when I’m at my Mac, I find myself turning to it to start and stop timers instead of the web app. There are additional features I’d like to see Timery implement, which I’ll cover below, but for flexible, frictionless time tracking, you can’t beat Timery. The app has been on my Home screen for months now and gets a workout seven days a week. Here’s why.
An Interview with Khoi Vinh, Principal Designer at Adobe
Earlier this week I had the opportunity to sit down with Khoi Vinh, Principal Designer at Adobe who leads its Design Practices group and author of Subtraction.com. Vinh, who was in Chicago to speak at the HOW Design Live conference, talks about how Adobe is using Adobe XD to integrate UX and UI design and prototyping into the product creation process for everyone from freelancers to big companies. He also discusses designers’ role in addressing the problems social media is facing, how artificial intelligence is beginning to play a role in design, and his podcast, Wireframe.
(The following has been condensed and edited for readability.)
Tell me a little bit about what you’re working on at Adobe these days.
Adobe XD is one of the main priorities at Adobe. We’re really passionate about the experience design space; really passionate about how product designers, UX/UI designers, they’re really kind of leading the way for how professional creativity is changing and XD is more than just an app, it’s a platform to help us build what designers need. So we see it as more than just a design app. It’s also prototyping and sharing, and so it’s really meant to help designers, and also the people who work with them, get more value out of the design process and be more productive in general.
My MacStories Story: How iOS Automation Changed My Life
Six years ago I was a senior in high school – a laughably short timeline compared to the immensity of growth and change which took place within it. Graduation, all of college, and a lonely move across the country; a career imagined, pursued, and achieved; friends and relationships come and gone. Not many threads of life make it all the way from the start of your late teens through the end of your early twenties, but those that do feel special in a way not much else can. MacStories is one of mine.
This week we’re celebrating MacStories’ 10th anniversary, and this year marked the fifth anniversary of my first article on the site. It boggles my mind to think that I’ve been part of this incredible team for more than half of MacStories’ life, but that’s nothing compared to the feeling of when it all began.
A Brief History of The Prompt and Connected
“I think we should talk to Federico about joining the show.”
With that, my podcasting career – and life – got a lot better.
This was the spring of 2013. Myke Hurley and I were packing our bags at Myke’s original podcast network, heading over to 5by5. He and I had been publishing a weekly Apple show named “The 512 Podcast,” but we wanted to do something bigger and better, and Myke had the idea to wrangle Federico into things.
How MacStories Instigated My iPad-First Journey
When I started reading MacStories, the site had already shifted its focus from the Mac to the iPad – and that’s what drew me in.
I’ve been an Apple admirer for as long as I can remember, but in my younger years the company’s products were simply outside my budget. It wasn’t until the age of 18 that I owned my first Apple device, an iPod, which was followed a couple years later by a second-hand MacBook. In both of these cases, it was the surprisingly short lifespans of my previous non-Apple MP3 player and laptop that led me to finally splurge and pay the Apple premium. I quickly discovered that, for me at least, it was well worth it.
Despite loving my iPod and MacBook, I didn’t start diving deeper into the Apple ecosystem until after the iPad’s release in 2010. At that point the iPhone had been around for a few years, but in frugality I had stuck with a cheap flip phone and evaded the smartphone era as long as I could. After the iPad, though, things quickly changed.
Shortly following the launch of Apple’s tablet, my boss at the time purchased that very first iPad for me, which was the gateway that led to an iPhone 4 later that year, a MacBook Pro the year after that, and many more Apple products since then. The iPad catalyzed my deepening interest in Apple, and it was the iPad that also, several years later, led to my discovery of MacStories.
MacStories’ Heart
Ten years is a long time on the Internet. So many companies have come and gone in that time, making it worth considering what it is about MacStories that has endured.
Having worked with Federico for roughly a third of that time, I can’t claim to be objective, but before I joined the team, I was a long-time reader of MacStories and a developer who pitched an app to Federico. That’s given me a perspective on MacStories that goes beyond my current role, so it will probably surprise no one that I have a few thoughts on the matter.
The Perfect Side Gig
MacStories was a big part of my life for over five years, from January 2011 through November 2016. I only vaguely recall emailing Federico about the possibility of writing for MacStories, though I do remember sending him two sample articles – one of which was about the iPad (naturally!). Federico was happy to give me a go and I started pretty much straight away.