iPad Life: On a Keyboard Failure Making Me Rethink an Entire Workflow

I have used the Apple Smart Keyboard as my main keyboard for my 12.9” iPad Pro since I bought the device in January 2016. Unfortunately, they are not reliable as I have gone through two of them in that period. I went to Apple to try and plead for swapping out the second carcass but failed.

I love creating on my iPad. It is perfect for writing and drawing with. The Smart Keyboard worked well for me as it was easy to flip around from writing mode to drawing mode and it didn’t add too much weight to the device. It also charged from the iPad and I didn’t need to worry about pairing with Bluetooth.

The Smart Keyboard’s death, however, triggered a long tail of analysis.

The first thought is iOS 13 stands a chance at being a sea change for iPad productivity. I am not sure of two things: whether those changes will make a meaningful difference to how I use iOS; and if those changes work on my iPad Pro. If the answers to both of those are yes, I will likely get something like the Brydge keyboard1 for my iPad and call it a day. If the changes are amazing but don’t work on my iPad, later this year I will look at getting a new iPad Pro2. If the changes don’t improve my use if the iPad, I will take a long look at what the iPad means to my creative life.

There is always a lot of discussion about iPads as laptop replacements, but to get a new iPad Pro setup that mimics what I use now costs about $1,600. That is well towards 13” MacBook Pro prices. If you take out the Pencil, it’s pretty close since the 256GB MacBook Pro is $1,500. At that point, if I drop that kind of money I simply want my iPad to do more than it can now. Little things, like use a mouse and keyboard3, and access data on USB drives. Right now, the new iPad Pros don’t solve $1,600’s worth of problems.

All of the keyboard cases — save the Smart Keyboard — are a form factor that make the iPad more laptop-like, but at the sacrifice of the flexibility of quickly switching to tablet mode. The closest I have seen is the Brydge keyboard, but that one still requires you to remove the iPad from the keyboard to use it in tablet mode. If I am just going to jam the iPad into that style of encasement I wonder if just using my actual laptop is a better option.

Until the WWDC keynote I am not buying another keyboard for my iPad, which means until then I am trying to work off the virtual keyboard as much as possible. Right now it is a tough slog but we will see how that goes. I have a spare Bluetooth keyboard I could use, but I prefer to keep my keyboard and iPad as a singular unit. One thing I do like about the virtual keyboard is just having the tablet flat on the table and not reaching up to use the interface is amazing.

  1. Or, yes, another Smart Keyboard. They aren’t reliable but they work best for the way I use my iPad.
  2. The biggest disappointment would be if USB-drives are only available on USB-c iPads.
  3. The main use case is using our Virtual Desktop system at work.
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On Apple’s Earning Adjustment and Upgrade Cycles

Apple today announced expected revenue for the holiday quarter would fall short of expectations. They didn’t miss by much, only by about $5-7 billion1. Tim Cook blamed a lot of things: China’s slow growth, longer upgrade cycles due to the elimination of cellular subsidies, and that people paying $29 to replace old batteries allowed them to keep their iPhones longer2.

What he didn’t mention was Apple raised the prices on everything over the last few years.

Now, some of the complaining about prices wasn’t justified. The new MacBook Air starts at $1,199, up $200 from the old-model’s $999 price tag. That old Air, however, was outdated. No Retina screen. Old internals. It did have MagSafe and USB-A ports, so for a lot of people it was still worth it.

The price increase on a lot of other items, yeah. I bought my 2016 15” MacBook Pro in March 2017. It replaced as my main Mac a 2011 15” MacBook Pro, and an 11” MacBook Air I bought in early 2015 right before Apple released new upgrades. The 2011 I farmed off to a co-worker; the 11” I still have3. While performance was a driver for the upgrade, a large part of it was getting a Retina screen. The 12.9” iPad Pro really made the older screens hard for me to use. I sometimes wonder if I got a 2014 13” Pro instead if it would still be my main Mac. The dual core processor would likely show its age by now. I still use the Air though, when I need MacOS and an ultra-portable computer.

My theme for 2019 Evaluation. For the record, I’m not looking at making major life changes. I am, however, evaluating the devices, apps, and services I use. For now, it’s a lot of data collection. What do I use my Mac and iPad for? I say I want to use x app more, but over the year I use y app instead. I promised myself it was unlikely I was going to upgrade any of my devices. Some of this is price. The increased price of the new iPad Pro may not have completely turned me away, but also needing to buy a new Smart Keyboard and Pencil (also at a roughly 20% price premium) surely did. The same with my iPhone. I used my 6 for three years, and I expect to get 4-5 out of my 8 Plus. New iPhones are more expensive and my existing one works just fine. For me to upgrade I need to see real-world improvement; not just benchmarked improvement.

As Patrick Rhone would say, a lot of people are finding out their current phones and devices are enough.

  1. Since this is the internet, I feel I need to mention I am being sarcastic.
  2. I am not making that one up.
  3. It’s on my desk next to me, actually.

iPad Life: Moving the Goalposts

Any discussion of using the iPad as productivity tool — be it a primary or secondary device ends up with: “Until x application is on the iPad, it can’t be a ‘real device.’” Said application is usually Photoshop. Adobe recently announced plans to bring Photoshop to the iPad. Naturally, the anti-iPad crowd folded their tents, admitted you can now do “real work” on an iPad and the argument ended.

I will give you a few moments to catch your breath from laughing so hard. The MacRumors forums — where most of the arguments I see take place — the big discussion point is that clearly it’s not the real full version of Photoshop, and here are all the reasons it will fail without even looking at the app.

This is the problem I have with people saying you can’t do “real work” on an iPad. Most of the arguments are from people who have never used the iPad for such tasks. They immediately dismiss the idea, and insist until the iPad is exactly like a Mac, it is but a child’s toy. Maybe they feel threatened that Apple will one day stop making the Mac. Maybe their fears will come true. My own issues going to an iPad-only life are well-documented. Which is why the only opinions in these arguments that matter to me are the people who have attempted to use the iPad for more than surfing the web.

Photoshop coming to the iPad is a big deal. While apps like Affinity Photo & Designer, Procreate, and Pixelmator are quality apps, Photoshop is the standard for any photo editing. It’s great to see Adobe finally realize they need to bring their apps to the iPad.

.plan Files and Tracking & Thinking About Personal Goals

For working on some of my personal projects that have longer timelines than “install this tool on my Mac”, I’ve been struggling with how to track and report on progress. Things, which I love, isn’t good for these. These efforts aren’t really something that can be broken down to task levels. A good example is learning about security tools. I have a task in Things to remind me to install a tool on my Air. But tracking progress, notes, and high-level tasks I need something else. The same for working on coming up with a side-hustle and secondary revenue streams.

I was thinking of how John Carmack of id software used to maintain .plan files. It used the finger protocol as a type of blogging engine, but I liked the simple, text-based structure. As I was thinking about tracking some of my personal stuff, I debated between a separate Ulysses sheet, or using Apple Notes, or just Day One Journaling. I ruled against these because I don’t want it to be in my face. I didn’t want a constant reminder that I hadn’t gotten to those projects because work, school, and life got in the way. I also want to keep it private. I did want the ability to edit the file on Mac or iOS, so that sort of limited the app I would use.

So, I decided on keeping a sort of .plan file in Byword. It’s a simple text file. It’s out of the way since it’s not an app I use a lot. It’s just one file now named “plan” and I will be keeping some notes and goals over time there. Maybe it’s close to bullet journal, but I just wanted a separate way to track a lot of this.

iPad Life: A Post-iPad-Only Life and Rendering Unto Caesar

I have largely abandoned the idea that I can go iPad-only. While I never actually thought it would work for me, and admire people like Matt Gemmell who can, I have come to the grudging realization I cannot join their ranks.

In the parlance of many failed relationships, it’s not the iPad; it is me.

When the focus of my non-day job stuff was writing and drawing, the iPad was perfect for that. Even architectural drawings, while I can’t do full AutoCAD on the iPad, I could still draw buildings and have some fun with that. Schoolwork was a little more challenging where I’d run into some limitations with Word, I could still get around them on the iPad. It was when my career path diverted into information security the wheels fell off the iPad bus. There are some discovery and recon tasks I can do on the iPad, but the tools I use require access to the Unix parts of macOS I don’t ever expect iOS to allow.

I wrote earlier about how I carry too much crap with me and did some data analysis on how I use my mobile devices. While the numbers clearly point towards the iPad as my primary mobile device, they don’t tell all the story. There is a line from the Bible I like which is Render to Caesar the things that are Caesar’s… and a variation of this applies here. While I cannot go iPad-only, the iPad is still pretty much my primary mobile device. Unless I really need a program only available on the Mac, I only bring my iPad with me. I’m writing this post now at lunch at work on my iPad. I bring the iPad to to take notes, read materials, write, and draw. The reasons I outlined in A Year of Using the iPad as a Laptop Replacement for using the iPad as my primary mobile device still apply. But, I felt like my quest to either go Mac-only or iPad-only were causing me to focus on the negatives of each system, rather than the positives. By accepting I need each device in my life freed up a lot of mental energy. I love writing and drawing on my iPad. I love using Unix tools on my MacBook Pro. If that means I leave the house with both of them in my bag some days, well, so be it.

The “I Carry Too Much Crap” Edition

From Ben Brooks:

My rule here is very simple: take a phone and one other device. Unless you have a major reason why you need three devices, take only two. For me the second device is my iPad Pro, and before that it was my MacBook. If you need a Mac, take a Mac and use your phone for anything else. But decide if you even need that second device — I take mine strictly because if I can squeeze in writing time, it is worth having the iPad Pro. But I could do it all with my iPhone if I wanted

I’ve been in a weird state where I’m straddling a few tech lines and as a result I’m leaving the house frequently with both my iPad Pro and my MacBook Pro. The short version of a long story is I can’t really go iPad-only, but, I also can’t really go MacBook-only at the same time. My primary, non-day job, yet productive, tasks are: writing, drawing, photo editing, and security analysis. I’m oversimplifying here, but the iPad is best at drawing and the MacBook is the only platform I can do security analysis with. The other tasks I can do close to equally as well on either platform.

Ben’s post helped illustrate a growing frustration I have with my daily load-out: I routinely leave the house with my iPhone, MacBook Pro, and iPad Pro. That is one device too many. I’ve made my peace with the fact that I need a powerful Mac, an iPad Pro, and an iPhone as part of my technological setup. What I struggle with is why I feel I need to bring both the iPad and MacBook Pro with me. Core apps I use (Ulysses, OmniGraffle, Affinity Photo) are reasonably feature complete between iOS and macOS1. The iPad-only apps are Procreate for drawing, and the macOS-only apps are my security toolsets.

The practical answer is to just go back to a MacBook Pro. It’s a more flexible platform and the walls I hit are fewer than on iOS. Drawing is the least-performed of my activities. Even today I ran into a weird iOS limitation. I needed to export a multiple-canvas Omnigraffle document to png files. On the Mac, there is a checkbox to export the entire document. On the iPad, no such checkbox exists. [UPDATE: I have since learned there is a workaround] Practicality is not the only driver, though. I really like using the iPad Pro. Typing on the Smart Keyboard is a dream and I love the portability of the device. As with creative work, security work when away from my home is also a rarity.

Since I can’t decide, and impulse and emotions aren’t good points to base decisions on, I’m falling back on my analyst mindset. I created a spreadsheet where I will record on a high-level my device usage. Three columns: Date, iPad, MacBook. The value will be Date (obviously) and for each device row I am using a 4-point grade: 0, did not use the device; 1, used the device lightly; 2, used the device heavily; 3, did something I can only perform on that device. As an aside, this is only for when I leave the house. I don’t care too much right now about my day-to-day usage at home. I will also take care and not cheat the data. If I brought my MacBook, have it on the desk, and the thing I want to do can be done on either the Mac or iPad, unless necessary I won’t drag out the iPad just to give it a checkbox for the day.

  1. There are edge cases on things like some filters for Affinity Photo, but for the purpose of this article we can call them feature-compatible and not get too far down in the weeds.

iPad Life: My iPad Pro Usage post-MacBook Pro Purchase

Fraser Speirs — a long-time iPad-only advocate — is leaning towards getting another MacBook Pro. Fraser is famous for a piece he wrote about going iPad-only entitled: Can the MacBook Pro Replace Your iPad? It was an interesting reverse take on the whole “Can your iPad replace your laptop” argument that is bandied about.

I am both glad and disheartened to hear this. I was glad because it’s easy to get into a situation where taking a stance on something like going iPad-only is tough to back off from. Your identity can be wrapped up in “that guy who went iPad-only”. Inevitably, you hear from all the people who gave you grief about it two years ago with an extra helping of “told you so.” So, being able to publicly and critically assess whether a tool works for you, and change course if it isn’t, is a good trait. It’s disheartening that Fraser feels that iOS 11 doesn’t meet his needs anymore and he needs to use a Mac again.

There are four people I follow on Twitter that are iPad-only folks. Not sorta-iPad only, but full-time, only use an iPad people: Matt Gemmell; Ben Brooks; Fraser Speirs; and Federico Vitcci1. CGP Grey is also a heavy iPad user so he deserves honorable mention here. Of these five, two of them are either using the iPad less after iOS 11 or are thinking of moving back to a Mac. CGP Grey needs a Mac to create his YouTube videos, so he’s always straddled that line. iOS 11 was supposed to be the big start of iPad productivity, but instead people I follow who use the iPad heavily are leaning towards walking away from it.

I am happier with iOS 11 than I was with iOS 10, but not drastically. I think the new Files app is a great step forward. Drag and drop is pretty useful. iOS 11 has helped me not use Workflow app as much as I used to. However, iOS 11 has some weird bugs that are driving me nuts. I’ve been having a lot of rotation issues where I unlock my iPad and the rotation is stuck until I engage the gyroscope again. The Apple Smart Keyboard has been flakey and I need to snap it on and off again to get it work. That said, I think the drag and drop, the Dock, and the new Files app are a net win. I wouldn’t go back to iOS 10. I don’t think I can do tasks I couldn’t do on an iPad before iOS 11, but some of the suffering around those tasks has declined.

Fraser’s comments made me think a little more about my iPad usage after I got the MacBook Pro in March. Has my iPad usage increased or decreased? Unfortunately, I don’t have any data to back up my theories. The best example is my iPad usage last night when I was working on my schoolwork for the week. I’d been taking part in an informal case study on a MacRumors post regarding using iPad Pros for school. Like any thread about iPad productivity it devolved into a thread of half-truths, assumptions, lies, and bold statements of what you can and could not do on iPad. So, when this semester hit the midpoint I posted my findings about 5 weeks with the iPad. I considered the experiment closed at that point. I haven’t gotten any responses to that thread in a few days, so I guess a lot of people consider the experiment closed as well. I could go back to using my MacBook Pro for school and not think twice, or feel I had sold out the cause. Instead, when I got down to the business of doing this week’s assignments I just picked up my iPad fired up PowerPoint and worked on the assignment. When I was done, I uploaded it to the shared Google Drive folder and emailed my classmates.

Was this inertia from having a rhythm of working on school work this way for the last 5 weeks? I don’t think so. When I was doing some writing this weekend I found myself always reaching for the iPad first. For a lot of creative work like drawing and writing, the iPad is such a natural fit now for how I do that work. That’s not to say the MacBook Pro will sit unused. My beloved Topaz filters only work on my Mac. I use Tableau a lot and there is no iPad version. Sometimes I need the might and power of the full Office suite. Today I am working remote and need to connect to our virtual desktop system to do work. That type of work is still best done with a pointing device you can right-click on easily.

So, in conclusion my iPad use hasn’t really changed for the core work.

  1. Federico uses a Mac to record his podcasts, but that is it.