Today, we published the second part of our Dialog interview with John Gruber of Daring Fireball. You can find the episode here or listen in the Dialog web player below.
Like Federico, John Gruber was one of the first people I thought of when we began planning this first season of Dialog about writers and writing. Daring Fireball was an inspiration for me too, but in a slightly different way.
I first met Gruber in 2012 at the first Úll conference in Dublin, Ireland, where he was a surprise speaker. That was before I built my first iOS app or was writing or podcasting. I went to Úll on a lark to get a closer look at the iOS developer community I’d been following as I started to teach myself Objective-C. By the end of three days chatting with Gruber and other writers and developers at Úll, I knew I wanted to be part of that scene, creating my own apps. It would be almost three years before I launched Blink, my first app that drew any attention, and five before I could quit my old job, but that’s precisely why this second part of our interview with Gruber resonated with me.
Daring Fireball started like many indie businesses: as a labor of love that Gruber wrote on the side while working another job. The site didn’t earn enough to make it a full-time job at first, but over time it grew, and Gruber was faced with a choice. Daring Fireball had reached a point where it had a shot at supporting him and his family, but not unless he quit his day job, which he did.
In the latest installment of Dialog, we continue our conversation about the difficulty of making it as an indie writer online today. Gruber discusses how his priorities have shaped Daring Fireball, the audience for whom he writes, and maintaining the site’s relevance long-term.
Of course, no interview with Gruber would be complete without talking about Markdown. Although we nearly forgot to ask about it, I’m glad we did because it’s not easy to remember that Markdown, which debuted 15 years ago, took a while to catch on. Markdown’s human-readable syntax may not have clicked with writers on the web in 2004, but as more people who didn’t have experience with HTML started their own websites, Markdown gained momentum. Today, it’s used on all sorts of platforms and in text editors, blogging tools, and even Apple’s own Xcode IDE.
As we conclude our first Dialog interview, I want to thank John Gruber for taking the time to be our first guest on Dialog. Next week, we’ll begin a two-part interview with singer-songwriter Frank Turner, who we caught up with as he passed through Madison, Wisconsin on tour last month. I’m excited to share those episodes for a couple of reasons. First, it was a personal thrill to interview Turner, whose music I love. Second, while the conversation is a departure from what you likely hear on a lot of your favorite tech podcasts, there are fascinating parallels between John Gruber’s writing on Daring Fireball and Turner’s songwriting, which is precisely what we’d hoped for when we began this season.
iPad and iPhone users are in for a big treat this fall when iPadOS and iOS 13 launch. Each update is a major release that pushes Apple’s mobile platforms forward in big and small ways, making them more powerful for consumers and professionals alike.
If you haven’t read my iPadOS and iOS 13 overviews yet, the majority of details about each release are documented there. But I’ve been using the beta versions of both systems for a few days now, and while these are just an early look at what the finished releases will be, there are a lot of changes – some very significant, while others are relatively minor – that I’ve been excited to see.
Today, we published the second episode of Dialog Season 1 (called ‘Writers and Writing’) featuring the first part of a conversation with Daring Fireball’s John Gruber.
I’d like to provide some context around this interview as John Gruber was one of the first names I thought of when my colleague John pitched the original idea for Dialog months ago.
When I started MacStories 10 years ago, Daring Fireball was one of my main sources of inspiration: I was incredibly fascinated by the idea that a single person – more than a blogger, a writer – could share his opinions about Apple and technology on a website that was so clearly attached to his name. Gruber’s columns and original in-depth software reviews were the blueprints upon which I modeled my writing for MacStories: at the time, I felt that, even though English was not my primary language, I could at least try to do the same, but for iPhone apps and the modern age of the App Store and iOS developers.
Of course, as I shared for our tenth anniversary coverage in April, MacStories’ style and scope changed throughout the years: I realized I didn’t want to run a single-person website anymore and we expanded to newsletters and, most recently, podcastproduction. However, two of the underlying principles that I observed in Daring Fireball a decade ago still inspire my work and MacStories to this day: MacStories is a website by Federico Viticci and Friends (it’s right there in the logo), and I want to publish longform, personal opinion columns in addition to news, app reviews, and links.
John Gruber and Daring Fireball created a framework for other independent online writers to follow in the late 2000s, particularly in the Apple community. From this very website to 512 Pixels or Six Colors, I genuinely believe we owe a lot to John Gruber’s experiments with online ads, sponsors, memberships, and merch – ideas that, in many ways, he pioneered over 15 years ago when it was uncommon and, to an extent, perhaps even frowned upon – to try and monetize an “indie site” on the open web.
In this week’s episode of Dialog, we asked John to tell the story of his first experiences as a writer (and later editor-in-chief) of the school newspaper at Drexel, where he majored in computer science. That intersection of programming and in-depth, opinionated writing ended up shaping John’s entire career as a freelancer, documentation writer at Bare Bones Software, and, finally, independent writer at Daring Fireball. In addition to contextualizing John’s experiences as a newspaper columnist and editor in the early 90s, in the interview we covered topics such as the role of luck and privilege, how Daring Fireball’s beginnings can be traced back to Apple’s renaissance with the iPod, and, of course, the business of writing online and how he sees the influence of Daring Fireball over the indie Apple community.
I’m happy we were able to interview John for this first season of Dialog, and I like how the entire conversation turned out. It’s inspiring to hear the backstory of Daring Fireball and the core ideas at the foundation of one of the most successful indie websites on the Internet. In Part 2 of this interview, out next week, we’ll continue to dig deeper into the business of Daring Fireball, how John makes a distinction between linked posts and regular columns, his podcast The Talk Show, and, of course Markdown.
My annual practice of deciding which Mac apps qualify as ‘must-haves’ is always an interesting exercise. At the core of this reflection is a simple question: ‘Why?’ Why this app instead of another one? Sometimes it’s an app that stands out from its competitors, making the choice easy. Other times it’s a unique feature that fits well with the way I work. Most of the apps I include in my annual round-ups fit into one of those categories.
Last year though, too many apps fell into a couple of different, troubling categories. First, I tolerate a handful of underwhelming apps because they’re associated with services I like or which are essential to my work. Apps like Slack, Skype, and Trello fall into this category. Second, there are apps like Due and Reeder that I like, but either they don’t get much attention or have fallen behind compared to alternatives on iOS. Fortunately, these apps are still in the minority among the apps I use regularly. For every disappointment, there are apps like Things, Ulysses, MindNode, iA Writer, Screens, and Yoink that are not only a pleasure to use on macOS, but offer excellent iOS apps too.
Still, as I covered in the conclusion of my 2018 must-have Mac apps round-up, the exercise of going through the Mac apps I use left me with an uneasy feeling:
there’s an interesting contrast between what I consider must-haves on iOS and the Mac. On iOS, many of the apps I consider must-haves are compelling because of a single feature that sets one app apart from others or because it fits especially well with how I work. Too often that’s not the case on the Mac. I find myself explaining that I use a particular app because ‘it gets the job done.’ That’s because there are too few alternatives to some apps, which is a shame.
Mac apps are not in a state of crisis, but at the same time, the universe of Mac apps is not nearly as big or diverse as iOS. That’s not surprising given that the number of iOS devices in use is roughly 10x the number of Macs in use. As someone who works on and studies both platforms though, the trends are troubling.
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.
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.
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.
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.
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.
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.
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’sTimery 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.
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.
