Trying iA Writer

In the past few years I’d been doing most of my writing in a combination of Bear and Ulysses. Bear for note taking and shorter form stuff; Ulysses for long form writing. Both these apps worked well for me individually, but even though I had drawn a pretty clear line between them having two different writing environments did introduce a bit of friction. There are also a few things about Ulysses in particular that rubbed me the wrong way. I dislike the non-standard way it handles Markdown links, for example.

In late 2018 I decided to give iA Writer a try. I picked iA Writer in part because of some of the things Federico Viticci has written about it. I liked the idea of an editor that stores files in iCloud Drive and plays nicely with iOS features like Open in Place. It has both Mac and iOS apps, which is a hard and fast requirement for me these days.

Moving to iA Writer

The first step in this process was to move my existing files from Ulysses and Bear over to iA Writer. Ulysses was simple, I just exported my files to iA Writer’s iCloud Drive folder and they showed up in the app.

Bear was a bit harder because it has a very different metaphor. Rather than files and folders Bear has a flat list of documents organized using tags. While iA Writer supports tags, they’re clearly secondary to the file/folder structure. iA Writer also doesn’t allow for nested tags, which I use pretty heavily in Bear.1

I decided to try to turn my Bear tagging system into nested folders in iA Writer. To do this, I first made sure that everything had a tag of some sort, then exported all of it to a folder on my hard drive. I wrote a Python script that identified the tags by looking for lines starting with a hashtag that was not followed by a space or another hashtag (which would be Markdown headings rather than tags). The script created a folder in the iA Writer iCloud Drive directory for each tag (and within each of those folders for each subtag) and copied the text files into the appropriate folders. I did have to do some manual tweaking afterwards, but I managed to translate my nested tag structure into nested folders a lot more easily than if I’d tried to do it manually.

Likes and Dislikes

Perhaps this is not very consequential, but I don’t think iA Writer looks a nice as Bear. It’s rather monochromatic compared to Bear’s nice use of accent colors.

On the functional side, I like the fact that iA Writer uses vanilla Markdown with some very lightweight highlighting rather than trying to do something fancy and different the way Ulysses does (and Bear, to a lesser extent). One area where I wish they’d go a little further with the Markdown highlighting is to do a better job visually differentiating between different levels of Markdown heading. All headings look the same, and are basically just shown in bold.

I have run into a few bugs. Most annoyingly, the iOS app sometimes freezes when I try to drag and drop text, either within the app or dragging to another app in split view. Copy and paste work fine though, and I really like the ability to move lines (or highlighted blocks of text) up and down with the keyboard. This is especially great on the iPad which lacks some more traditional text manipulation capabilities that you can do with a mouse.

It’s very common for something I write at work to start as a Markdown text document, then get exported to Microsoft Word to share with my colleagues. I like the results of iA Writer’s Word export quite a bit better than Bear or Ulysses.

I may need to rethink my organizational scheme to work better with folders. I’ve got stuff broken up into a lot of different, very specific folders, with lots of folders at the top level and, in some cases, nested quite deep. This worked well with Bear’s tagging system, but I’m not sure this is the best way to do things in a files and folder system like iA Writer’s. Thankfully, iA Writer’s file search capabilities are quite good and very easily accessible from anywhere within the app.

If I do decide to reorganize my file system that will definitely be a task to do on the Mac. Moving files within the app on the iPad is not very intuitive.

On iOS, iA Writer includes a Command Keyboard that can be used to insert common markdown tags, special characters that are hard to get to on the iOS keyboard, etc. There’s a ton of customizability behind this so you can set it up to have exactly what’s most useful to you. I particularly like the fact that it’s available on the iPad even when you have an external keyboard attached.

A change I’m going to stick with

Overall, I’m pretty happy with iA Writer. Having one app for all my writing simplifies my workflow and I like the vanilla approach to Markdown. I’ve gone ahead and cancelled my Bear and Ulysses subscriptions and at least for now, I’ll be using iA Writer as my primary writing app.


  1. A “work” tag with separate tags within it for individual projects, for instance. ↩︎

Doing a Personal Retreat

I’ve been intrigued by the concept of a personal retreat ever since I heard Mike Schmitz talk about it on Free Agents a while back. He described how he goes off on a “retreat” every three months to review, think, and plan. While I was interested, the discussion on the podcast was kind of barebones. When he announced that he put together a video course I jumped on board pretty quickly. Unfortunately, it came along at a very busy time for me, with the holidays and some travel for work, so I didn’t get a chance to actually do the course until late January.

After watching the videos, I was very eager to put this into practice and wanted to get started right away. While I wanted to take advantage of this burst of enthusiasm one obstacle was finding a location on short notice.1 Mike emphasizes not doing the retreat at home or another familiar (and distraction-laden) environment. He also maintains that to give the retreat the attention it deserves, you really need about eight hours, especially the first time you go through the process.

Doing it in the great outdoors was appealing in concept, but probably not in practice in January. I had all sorts of ideas for fun and interesting locations (traveling to a distant city, doing it on a long-distance train trip, etc.) but most were too expensive or required too much lead time. I looked into renting an office or conference room for a day, but that whole process seems unreasonably difficult.2 In the end, inspired in part by CGP Grey, I just got a local hotel room for a couple of nights.3

Preparing for the Retreat

To get ready for the retreat I watched the course videos a second time and took copious notes. If I had one suggestion for Mike, it would be to beef up the workbook to include more of the prompts and advice from the videos.4 There’s a lot of good stuff that didn’t make it into the workbook.

I also listened to an episode of The Productivity Show where Mike talked about his personal retreat practice. This predates the personal retreat course, so some aspects aren’t really as developed, but I still found it useful.

After dinner the night before the retreat I packed up a change of clothes, pens, pencils, and notebooks, along with the course workbook (both printed and in PDF on my iPad). I also assembled some food and drinks so I wouldn’t be distracted by needing to find a restaurant for lunch.5

One of the first things I did after checking in was put my iPad into Airplane Mode and my iPhone into Do Not Disturb (with a strong vow not to open it up and look at it until after I was done with the retreat). Since part of the point of making this, a “retreat” was to avoid distractions, I figured that it would be good to start detaching from my usual diet of digital interactions the night before. Cut off from my usual digital feed, I made an early night of it.

The Retreat

The next morning I hit the hotel fitness center and their complimentary breakfast before settling down in my room for the retreat.

Mike based the personal retreat idea off of some of the concepts presented in the book The 12 Week Year. I’d read the book, and I liked the concept, but I found it hard to implement. The core of it seemed like a good idea, but it had some extraneous stuff around it. The Personal Retreat course is a lot more focused.6

Based on what he said on the Productivity Podcast and Free Agents, Mike started doing quarterly personal retreats because he’d had trouble implementing his 12 Week Year goals. It’s intended to provide time to look back at the past three months and ahead to the next three. However, it goes quite a bit beyond just quarterly planning, encouraging you to take a look at your values and long term aspirations and so your plans for the next three months are taking you where you want to go in life.

Core Values

The retreat starts out with the big picture: defining your core values. Mike has some excellent questions to get you thinking about these. I answered all of them, then went back through trying to pick out the common threads by tallying up how often certain things got mentioned and making a mind map of how related ideas clustered together.

I’m usually more of a digital guy, but I made a last minute call to do this on paper in a Field Notes Steno Book, rather than on my iPad.7 Instead, I used the iPad to display my notes (including all of Mike’s prompts and questions). I did this using iA Writer’s focus mode. It highlights one line by graying out everything else, so it helped keep my attention on the particular prompt I was working on.

I ended up listing my core values as short sentences starting with “I am…”. Mike recommends 4-7 core values. I picked 5, but I did cheat a bit by making some of them compound (two related values, like “I am a writer and teacher”).

Between each exercise, I spent a few minutes walking around the hotel to clear my head.8

Where are you right now?

The next exercise focused on the question, “Where are you right now?” It involves an inventory of your commitments and responsibilities and assessing your satisfaction in different areas of your life. I’ll be honest, I didn’t find that this provided quite as much insight as some of the other exercises, though that may just be a product of what my particular commitments are and where my life is right now.

Designing the life you want to live

In contrast, the exercise on designing the life you want to live really grabbed me. Mike has created some great prompts to get you thinking in detail about what you’d like different aspects of your life to be in the future. I almost had too much fun writing about a day in my life five years from now. I probably crammed way more stuff in there than could realistically be done in a day (maybe next time it needs to be a week in the life of my future self).

Retrospective – Accomplishments

From the future, we turn to the past; the next exercise involves looking back over the past three months and listing your accomplishments. I was a bit skeptical when Mike said to allocate 1-2 hours for this, but it did take me over an hour and I filled two and a half pages of the Steno Pad with accomplishments. Not all of these are earth-shattering by any means, but they’re all things that moved the ball forward in one or more areas of my life (making a presentation for work, writing a blog post, etc.).

Thinking of all of these was difficult, but I found a few things that helped. I started by just brainstorming, but when I ran out of steam trying to remember things off the top of my head I looked back over my calendar to see what I’d been doing for the past three months and perused my blog to see what I’d posted there. What really helped was the gratitude journal I’d started keeping after taking Shawn Blanc’s Focus Course. Rather than being a full journal, this just involves writing down one accomplishment and two things I’m grateful for every day. Many of those daily accomplishments are too small for the personal retreat list, but others were large enough to make my quarterly list or prompted me to think of related things that should be listed. One thing I found was that in many cases, the daily accomplishments represented incremental progress on more significant accomplishments that did belong on the quarterly list. I may want to start calling out those bigger things explicitly as I go along, rather than waiting until three months later.9

Retrospective – was What you’re going to change

After a break for lunch, I started up on the second half of the retrospective: thinking about what things you’re going to change. Mike has a nice, structured way to do this involving looking at what went well and what could have gone better and what lead to these outcomes. This, in turn, leads to the three critical questions: What should I start doing? What should I stop doing? What should I keep doing?

For me, this process mostly lead to practices, rather than commitments, which I’m not sure is what Mike had in mind (looking back it’s a bit ambiguous). However, it worked for me, and I think the outcome has been very useful in terms of reinforcing good behavior, discouraging things that are hindering me from accomplishing my goals, and brainstorming ways that I can do better.

Setting your goals

The culmination of all of this, the core values, where you are right now, designing the life you want to live, the retrospective, comes in setting your goals for the next quarter. Mike recommends no more than three goals, and if you’re doing this to the first time, limiting it to even fewer, just one or two. I ended up picking two goals, and I kind of cheated a bit since my first goal, “Spend my time more intentionally” is kind of a cross-cutting issue that affects all sorts of areas. My second goal for the next three months is to write more.

Mike talks about how your goals should be connected to your core values and vision. I actually found it worthwhile to write out for each goal which core values it supports and how and which pieces of my 5-year vision it connects to. I also noted how each goal connected to things I said I should keep doing, start doing, and stop doing. For my time goal, this ended up being quite the task, since how I manage my time ends up touching so many other areas that I filled two and a half pages of my notebook writing it all out. The process really reinforced how being more intentional with my time could have a significant, positive impact on my life.

Another thing Mike emphasizes is breaking each goal down into milestones and daily habits to help ensure you actually accomplish it. The goal is the “what,” the milestones and daily habits are the “when” and “how.” Neither of my goals were all that amenable to milestones, so I didn’t set any. They are ripe for daily habits, however.

For spending my time more intentionally, my primary habit is going to be time blocking every day.10 This is something I’d been doing last year, but I’d kind of fallen off the wagon. After I stopped time blocking it felt like I wasn’t being as productive with my time, which is part of the reason I’d like to start up again.

Essentially, this time blocking practice involves writing out a schedule for each day, saying what I’ll be doing and when. That way I know what I’m supposed to be working on at any given time. It keeps me from having to make a decision of what to work on in the moment and makes it less likely that I’ll fail to decide and end up diddling around on the internet.

Of course, things come up, and there will be times when I have to adjust on the fly.11 That’s why my second habit to help me spend my time more intentionally is to do a post-mortem every day and look at how I actually spent my time compares to how I’d planned to spend my time. Did something unexpected come up? That’s fine; is it something I could account for in the future or is it something truly unexpected? Did something take longer than expected? That’s ok; how can I do better at estimating how long this sort of thing will take? Did I just blow off the schedule? That’s not really ok.

When I’d been doing time blocking last year I just did it for my working hours. This time around I decided that I’ll be applying it to my entire day. That doesn’t mean I’ll be working 24/7 though. One of my regrets about frittering away my time is that when I look back on how I spent my recreational time I spent a lot of it in ways that I don’t really value (primarily frittering it away on the internet) rather than recreational activities that I value more (reading, playing video games, watching good TV shows). I’d like to change that and blocking time for specific types of leisure is a way to do it.

For my goal to write more, my only habit is to write every day. It doesn’t matter what. Could be fiction, non-fiction, a blog post, a novel, anything. Just as long as I’m spending some time every day moving the cursor.12

To track my progress towards these goals, I’m going to track how many days I time block for, how many days I do a post mortem, and how many days I write for at least 30 minutes. I’m not going to track how much I write, or how many days I stick to my schedule. The goal for the next three months is simply to do these things consistently.

The other aspect of goal setting Mike talks about is looking at your commitments for the next three months and seeing what might interfere with accomplishing your goals. I wrote out my commitments, using the list I developed back in the second exercise, looking through my calendar, and thinking about what else I had coming up. It’s a long list, but a manageable one. In addition to making sure it wouldn’t interfere with my goals, getting these commitments out of my head and onto one sheet of paper was also valuable in and of itself.

Executing the Plan

The final exercise is to plan your ideal week. One of the biggest obstacles to achieving these kinds of goals is not setting time aside to work on them. The ideal week exercise allows you to plan out when you’ll work on your goals for the next 12 weeks. Of course, not every week is ideal, but this at least provides a starting point.

Obviously, this complements my goal of spending my time more intentionally and the time blocking habit quite nicely, so I kind of went whole hog on this exercise. I abandoned my paper notebook and went digital, breaking out the Numbers app on my iPad and using it to block out an ideal week in 15-minute increments. I set aside time for writing every morning, time for planning out the following day, and time for doing a post-mortem on the day every evening. I also made some other adjustments from how I’m currently spending my time (notably, a lot less time on the internet). Everything got color coded as well. Like I said, I really went whole hog.

As a reward for all this effort, I made myself a nice dinner (baked boneless buffalo wings, one of my favorites) and sat down with a drink and the latest episodes of The Grand Tour.13

The Results

I feel like my first personal retreat has been an incredibly useful experience, one that will pay dividends going forward. Of course, where the rubber meets the road is actually going out and implementing these habits and achieving my goals. We’ll see where I stand in three months.

In addition to the quarterly goals and planning, the retreat also helped with some deeper insights. Defining my core values and imagining the life I want to live five years from now are valuable beyond just setting goals for the next three months. Listing out my accomplishments from the last three months was encouraging. For a time in my life that I didn’t feel was very productive I actually accomplished quite a bit.

One thing the retreat helped me realize is that I have a “teacher” itch that isn’t really getting scratched right now. That’s not something I can really remedy in the next three months; rather, it’s something to work on long term (for now I’m going to try to scratch it by writing more).

As I mentioned earlier, I’d read The 12 Week Year and while I liked the concept, some of the other stuff in the book kept it from really grabbing me. Having done the personal retreat (and gotten so much out of it), I feel like I should try rereading the book and see if there are aspects of it resonate more with me now.

One other thing I learned from this retreat was that not looking at the internet when I had my phone out for some other reason was surprisingly hard. It wasn’t even a lack of willpower so much as thoughtlessness on my part. As soon as I was done with what I’d gotten my phone out to do (check my calendar, log some food or exercise, etc.) my thumb just instinctively just went to Safari, Reeder, or Spark. I’m a bit disturbed by just how automatic it was, but it’s a problem outside the scope of this personal retreat.14

Changes for Next Time

I’m definitely doing this again in three months. While it went really well this time I can already see some tweaks, I want to make. For one, I think that I’ll make taking stock of commitments for this quarter a separate exercise of its own, one that comes before goal setting. That way I can take these commitments into account when setting my goals (or change my commitments to accommodate my goals).

Of course, I’m anticipating that there will be differences just because it will be the second time through the process. This is one thing I wish Mike covered a bit more in the course, though I can see why it’s mostly geared towards first-timers. Next time I’ll already have definitions of the core values and vision of my future life (though its probably worth going through the exercises again to see if there’s anything I want to change). I’ve scanned my notes from the retreat and stashed the notebook where I’ll hopefully be able to find it in three months, so I’ll have all of my material from the first retreat available for reference. Of course, the big change will be assessing how well I did on my goals and the associated habits for this quarter.15

One thing I’d like to change between now and then to make the retrospective easier is to do a better job tracking my more significant accomplishments as they happen, rather than having to try to remember them months later.

Something that I won’t change is doing the retreat on paper. That worked really well; it helped keep me focused and slowed me down a bit (in a good way). I did realize about 3/4 of the way through that I need to leave more blank space in the notebook as I write so I can go back and add things that I think of later. I guess I’m too used to doing stuff digitally where it’s easy to insert content in the middle of what I’ve already written.

While the hotel room worked out well, I may consider some other options that more advance planning (and warmer weather) might make possible.

Concluding Thoughts

Doing the personal retreat was a really great experience. It’s already paid off with some great insights, and I think it’s going to continue to pay off over the next three months. I’ll definitely be doing it again.

I really want to thank Mike Schmitz for developing the Personal Retreat course. The way he’s structured the retreat works really well, and it includes some great prompts and questions to really help you get at things that can be hard to pin down, like your core values and a vision for your future. I’d definitely recommend the course and the practice of regularly doing a personal retreat.


  1. Hopefully next quarter around I can set things up further in advance. ↩︎
  2. Most of these places don’t even list their prices online, making it hard to tell if it’s even a reasonable option. In this day and age making someone interested in buying your product submit their contact info as a sales lead and wait for someone to get back to them is awful. ↩︎
  3. Check-in and check-out times mean that if you want eight uninterrupted hours in a hotel room you really need to stay for two nights. ↩︎
  4. It would be nice if the videos were downloadable. ↩︎
  5. I’d booked a hotel room with a kitchenette, so I had a decently sized fridge and cooking facilities. ↩︎
  6. Or is that Focused? ↩︎
  7. In retrospect, I really wish I brought one of my Panobook notebooks. It would have been perfect for this. ↩︎
  8. This made me glad I went with a hotel room rather than the cabin at one of the state parks I’d been considering. It was 18 degrees this morning, so going out for a walk would have meant getting all bundled up every time. ↩︎
  9. Around this time it started snowing outside. I’m really glad I didn’t decide to do this outdoors. ↩︎
  10. David Sparks sometimes calls this “hyperscheduling,” though I don’t really like that term. ↩︎
  11. As David Sparks puts it, “A calendar is a soup rather than a puzzle.” ↩︎
  12. This post is a down payment on that habit. ↩︎
  13. There’s no better contrast to all this deep thinking than a good dose of Clarkson, Hammond, and May. ↩︎
  14. This does have me thinking about Cal Newport’s new book Digital Minimalism, which seems like it would be on point. ↩︎
  15. The work I’ve done on this post means I can check the writing habit off for today. ↩︎

 

Review of Build Your OmniFocus Workflow

I’ve been using OmniFocus for a long time. In fact, OmniFocus was the very first paid iOS app that I paid bought back in 2008 when the App Store debuted. At this point I’m definitely not a novice user, but I’m always looking for ways to use OmniFocus to manage my tasks more effectively. It plays a central role in my ability to get my work done so any improvement will pay dividends across a wide variety of areas.

In that vein, I recently read Build Your OmniFocus Workflow by Ryan Dotson and Rosemary Orchard. The book offers a comprehensive guide to using OmniFocus to manage your tasks, with an emphasis on how to fit OmniFocus into a larger system of task management.

Thanks to its customizability, OmniFocus has always been a bit of a “build your own task manager kit”. With the addition of tags, OmniFocus 3 leans even more in this direction thanks to the many new options for how to use the app. What started out as a fairly vanilla GTD app has become a very powerful and flexible piece of software that can be used to support many different takes on task management. As the book puts it: “There are two keys to getting started using OmniFocus: understanding the software and developing a workflow.”

Build Your OmniFocus Workflow does a great job of looking beyond the four corners of the app to talk about how to fit it into a broader context. It’s really a cross between a software manual and a higher level treatise on task management.

While the overall emphasis is at the system level, Build Your OmniFocus Workflow starts with the absolute basics (setting up the software, using the interface, and fundamental concepts) and builds up from there. As a guide to the apps, it’s quite comprehensive in exploring pretty much every feature, both on the Mac and iOS (there’s also a short section on OmniFocus for the Web, currently in beta).

Despite being a long-time user of OmniFocus on both platforms I still learned quite a few new things about the app. For instance I had no idea that on iOS you can drag the “add to inbox” button to add a task in a specific place. I also have to say that Rose and Ryan’s explanation really made me get how a single action list differs from a regular project, which is something that I’d never really understood despite a decade of using the app.

As one would expect from Rose, there’s quite a bit of material on automation. Everything from AppleScript, to IFTTT, to Shortcuts. There’s also an appendix listing and explaining all of the rules you can use to create custom perspectives. This is nice since not all of these rules are necessarily obvious.

Interwoven with the software guide are Ryan and Rose’s thoughts on how to build your larger system. Again, it starts with a very basic workflow (capture, process, review, and do) and builds on that. They talk about what does and doesn’t belong in OmniFocus, how to define effective projects, what to do when you get overwhelmed or fall of the wagon when it comes to keeping your system up to date.

I really appreciated their thorough take on the review process, not just using OmniFocus to review your projects and actions, but also reviewing your system as a whole. Another tip I really like is to tag actions that you’re procrastinating on so you can go back and think about why (Is the action unclear or not well defined? Is there some obstacle that prevents you from doing it? Is it really something you need to do?).

Finally, Ryan and Rose wrap things up by laying out their own workflows as examples, explaining how they use the app and the systems and practices they’ve built around it.

The book comes in PDF, ePub, and .mobi formats, so there are plenty of reading options. I read the ePub version on my iPad using the Books app.1

Build Your OmniFocus Workflow has definitely helped me get more out of OmniFocus, both in terms of running the app and thinking about my task management system more broadly. Not only is it a great guide to using OmniFocus effectively, I think it really encourages a thoughtful approach to setting up your task management system. I definitely recommend it.

Comparison with the OmniFocus Field Guide

One question I’ve seen asked on the Mac Power Users forum is how Build Your OmniFocus Workflow compares to David Sparks’ OmniFocus Field Guide. I think the two are quite complimentary. Some of this is just the differing format; it’s easier to get certain things across using video while other things are easier to explain textually. However, this is also a product of differing perspectives on OmniFocus and how best to use it; there are areas where Ryan and Rose have a different view than David.

In some areas one goes into more depth than the other. The book delves deeper into review, for instance, while the Field Guide has a considerably more thorough treatment of tagging systems.

Both encourage using OmniFocus to build your own unique task management system. Build Your OmniFocus Workflow takes a somewhat broader view of OmniFocus as one element embedded in a larger system while the Field Guide concentrates a bit more on building a system within OmniFocus. They also take a somewhat different approach to presenting these systems. The book mostly lays out a series of options throughout the text that the reader can assemble into something that suits them, then details Ryan and Rose’s workflows as examples at the end. David presents six different systems (in varying levels of detail) giving the viewer a look at several widely varying approaches. He also spends a bit more time talking about the pros and cons of various ways to use tools or features within OmniFocus, and why one approach might fit a particular set of needs better than another.

Both Build Your OmniFocus Workflow and the OmniFocus Field Guide are quite good, and I think that if you get a lot out of one of them, you’d get a lot out of the other as well.


  1. One nice thing about the Books app is it makes it much easier to copy text than the Kindle iOS app. I did this quite a bit to take notes while I was reading. ↩︎

Three months with the iPhone XS

Now that I’ve had my new iPhone XS for a few of months I feel like I’ve used it enough to have an informed opinion on it. Rather than burying the lede, I’ll start out by saying I really like this phone.

I’m coming from an iPhone 7, so many of the features that make me like the XS so much aren’t really “new”, though they are new to me. First and foremost is Face ID. This has been awesome. It really is like going back to the days of my iPhone 3G when I didn’t have a passcode on my phone: just slide to unlock.

Face ID has been pretty close to 100% reliable for me. The only situation where I consistently have issues is when I’m not wearing my glasses or contacts (at night in bed, for example). My vision is quite bad so when I’m operating without corrective lenses I end up holding the phone very close to my face; too close for the Face ID sensors to work correctly. Once I remember to hold the phone further away at a more normal viewing distance it will unlock. The only other time I had issues was one morning where it simple failed immediately every time I tried to authenticate (a reboot got it back to normal).

Contrast this with Touch ID, which was usable, but never great. I often had to put my finger on the sensor several times before it would unlock. If my hands were too wet or too dry, the fingerprint sensor wouldn’t read correctly. In particular, during a trip to Montana last fall the cold weather dried out my hands dried out so much that my success rate with Touch ID plummeted pretty much to zero. In contrast, when I went out there on a hunting trip this year just after getting the new phone I didn’t have any issues. The only time it failed to unlock was when I had my face covered on a very cold morning.

I’d been anticipating that Face ID would be a really big feature of the iPhone XS for me. The impact of Qi charging has been more of a surprise. Initially I was skeptical about the utility of wireless charging, but since it was a feature of my new phone I decided to give it a go. It’s surprising how much easier it makes it to top off my phone. Plugging in the cable was just one more point of friction that I don’t have to deal with any more.

At this point I’ve got three Qi chargers. One sits on my nightstand and charges my phone overnight. While this Anker charger isn’t the least expensive, it offers the ability to turn off the light that indicates the phone is charging, which is important to me in a bedside accessory.

I’ve also got Qi charging stands that hold the phone up at a nice viewing angle on my desk at home and at work. I initially bought an Anker charging stand for my desk at work. Unfortunately, the stand is tall enough that it contacts the camera bump so the phone sits somewhat unsteadily in it (this probably wouldn’t be a problem with the XS Max). I brought the Anker stand home and replaced it with this charger from Samsung. The circular design means the camera bump clears the top of the stand, making it much steadier (the rubberized material on the stand helps too). I use the one at work quite a bit. The one at home, not so much, in part due to the inferior stand, in part because I just don’t have as much call to constantly have my phone out on my desk when I’m at home. Both stands hold the phone at an angle that makes Face ID fairly easy to use.

The XS’ camera is definitely an upgrade from the iPhone 7. This is the first dual-lens phone camera that I’ve had, and I’ve found the 2x lens quite useful. On the other hand, I don’t really get much out of portrait mode, largely because I take few pictures of people. The front-facing camera on my phones has never gotten much use, and the one on the iPhone XS is no different (aside from FaceID).

Frankly, I thought going to the OLED screen would be a bigger deal. I’d heard lots of great things about the iPhone X screen. It’s a nice screen, but in day to day use I don’t really notice it. The notch doesn’t really bother me. I think part of this is because my phone spends the vast majority of it’s time in a portrait orientation.

I’ve always been a “small phone” guy. I really think the iPhone 5 was about the ideal size for a smartphone, largely because I primarily use my phone one-handed (if they made an iPhone X style phone in that size I’d be all over it). Like the iPhone 6/7 size phones the XS is a bit large for my taste, but workable. It’s still mostly a one-handed device for me, but I do find myself bringing up a second hand to help stabilize the phone more often. This is not so much because the phone itself is bigger than the iPhone 7, but because the larger screen means some things are a longer reach.

I’ve gotten used to the new gestures and the lack of a home button. Tap to wake is great and swiping to go home works well. I really like the ability to swipe right or left on the home indicator to switch between apps. It makes quick app switching much more accessible on the phone than it was on the iPhone 7.

Finally, this is a very nice looking phone. This is the first time since my original iPhone 3G that I’ve bought a white iPhone (all of my others have been space gray or black). I like the look of the pearlescent white back and the stainless steel outer band. Mine is currently careless (though I do have a screen protector on the front glass, as well as Apple Care).

Overall, I really like the iPhone XS. I know a lot of folks weren’t all that excited by it, but coming from the iPhone 7 it’s been a very worthwhile upgrade. Well worth the cost.

 

2018 12.9″ iPad Pro First Impressions

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When I got my 1st generation 12.9” iPad Pro back in 2016, my overwhelming impression was of how large it was. Compared to the iPad Air 2 that I had previously, it seemed huge. With the new 12.9” iPad Pro, my first impression is how small it is. Some of this is coming from the old 12.9”, of course. I don’t know how someone coming from a 9.7 or 10.5” would feel. Compared to the old 12.9”, the new one is about an inch narrower (in landscape) and a quarter of an inch shorter. It feels quite a bit lighter as well; both because it is about an ounce lighter and because the smaller size means the center of gravity is closer to your hand when holding it in landscape. I was already fairly comfortable using my old iPad Pro handheld, but it’s noticeably easier with the new one.

I really like the design. The slim bezels seem like the natural design for the iPad. The squared off edges look nice and don’t create any issues when I’m holding it.

FaceID rocks! I know some people have had issues with it on the iPhone, but in my month using it on the iPhone XS, it’s worked very well for me. So far, the iPad has been similar. I’m still getting used to making sure I don’t cover the camera with my thumb, however. That will be a matter of training myself on where to hold it (yes, “You’re holding it wrong” is still a thing). It may just be setting up a new device and having to log in to a bunch of stuff, but I’m finding Face ID to get into 1Password almost as useful as Face ID to unlock the iPad.

I really like tap to wake too. If anything tapping the screen to wake up the device seems more natural on this than it does on the iPhone. Being able to double tap the smart keyboard to open great, though I’m not at the point where that’s second nature yet. As an aside, I’ve heard this describes as “double tap the spacebar”, but for me, it works with any two taps in succession (even two different keys). The first keypress wakes the iPad, allowing FaceID to do its thing. The second slides the lock screen out of the way.

Speaking of the keyboard, think the Smart Keyboard Folio is an improvement on the old Smart Keyboard. It’s considerably more stable than the older version. While most of my brief use so far has been on a desk or countertop, it does seem more “lappable” as well. I’m not finding the more vertical ”desk” angle very useful, however. Some of that may be due to my height (6’5”). If I were 6” shorter the more vertical position might be better for me (I know @macsparky complained some about the angle of the old Smart Keyboard, but I never found it to be a problem). As it stands, I think it’s going to live at the less steep “lap” angle (which is almost exactly the same as the old Smart Keyboard).

The typing experience is almost identical to the old one. If you liked the old model, you’ll like this one. If you didn’t like the old one, I doubt you’ll find this one any better. Personally, I liked the typing feel of the Smart Keyboard. While it’s not as good as a nice mechanical keyboard, I do think it’s the best keyboard Apple currently makes.

One minor affordance that I just read about today is that when you have the keyboard folded around to the back of the folio (“tablet mode” basically) it has some magnets to keep the keyboard part of the folio in place, rather than flopping around the way the old one did. I’ll still probably take it out of the folio most of the times that I’m not actively using the keyboard, but leaving the folio attached in tablet mode does seem like it will be less annoying than with the old one.

I haven’t really spent enough time with the Pencil to say much about it. The pairing and charging seem to work well. I tried the double tap gesture to get the eraser in Apple Notes and it is a lot easier than switching tools.

The last “accessory” is the new 18-watt power brick. It seems surprisingly big. Since the prongs don’t fold it’s actually a bit longer than Apple’s 29-watt MacBook Adorable power brick (smaller in the other dimensions though). Honestly, I don’t think I’ll be using this much. I’ve got a bunch of MOS bricks which have 2 USB-A ports in addition to USB-C, as well as one of the MacBook bricks. All have folding prongs, which are nicer in a bag and while the 18-watt brick is smaller, it’s not that much smaller. I know a lot of people were eager to get a more powerful iPad power brick from Apple, but I’m not that impressed.

Power brick aside, I’m very pleased with the hardware. On the other hand, the software experience was a bit rougher. I restored mine from an iTunes backup and it stalled right at the end of the initial sync process. I did a restart and it seems like all of my content got synced over.

Once I got past that obstacle, every single app stalled with the progress circle about 2/3 of the way around. Restarting did not fix this, so I ended up deleting apps and redownloading just the ones I really needed. Doing this has the potential to delete local data, but I was pretty confident that everything important was in the cloud, plus I’ve still got my iTunes backup (and until I send it in to the Apple Give Back program I could always pull data off of my old iPad too).

Partway through this process, the logjam broke and the rest of my apps started downloading. I figure there must have been a few apps that were gumming up the works and once I deleted those the rest were able to download. Since I was getting rid of so many apps that I hadn’t used in years (if ever) I went ahead and completed the process of winnowing out old apps, so some good did come of this frustrating experience.

My only other issue so far was not with the device, but with my AppleCare+ coverage. When I got the Proof of Coverage email from Apple it appeared to list two iPads, rather than one. One of the serial numbers matched my new device, but the other did not. It also said both were 1tb models when I had the 512gb version.

I wanted to make sure there wouldn’t be any issue with my AppleCare coverage if I have to use it, so I gave Apple a call. The first rep I called looked into it (using screen sharing to take a look at the email I received and the serial number of my iPad) and passed me on to a person from the AppleCare team. She did some research and was able to explain that the second “iPad” listed was actually my Apple Pencil. She couldn’t say why it listed my iPad as the 1tb model, but she assured me that it wouldn’t affect my coverage. The Proof of Coverage email is rather confusingly drafted, but the Apple support reps I talked to were very helpful.

Despite the somewhat rough start on the software side, I’m very happy with my new iPad Pro so far (for the all of five hours that I’ve had it). I want to spend more time with the Apple Pencil, using it for notetaking and other tasks. I’m also planning on trying some stuff to put the A12X through its paces (probably some video editing in LumaFusion). We’ll see how long the honeymoon lasts.

Omni Focus Field Guide, Third Edition Review

I have long been a fan of David Sparks’ MacSparky Field Guides. These originally started out as a series of Apple iBooks that used the unique characteristics of the iBooks format to combine text and screencasts to cover technical topics like Paperless workflows, Presentations, and, most recently, the iPhone. The iBooks Field Guides were brimming with content, often pushing up against the 2-gigabyte maximum size for the format. Along the way, David also started making Video Field Guides, which were shorter, video-only products covering topics like Hazel, Photos, and OmniFocus.

Recently, David announced that given the uncertainty about Apple’s commitment to the format, he wouldn’t be putting out any more of the iBooks Field Guides. Instead, he set up a website at learn.macsparky.com to host video courses. While this was initially populated with streaming versions of the existing Video Field Guides, he quickly added two new ones: the Siri Shortcuts Field Guide and the OmniFocus Field Guide, Third Edition. While these share the all-video format of the Video Field Guides, in spirit they’re much closer to his iBooks Field Guides. They’re truly massive, with over three hours of content in the Shortcuts Field Guide and more than five hours in the OmniFocus Field Guide.

The OmniFocus Field Guide, Third Edition is an all-new product, covering OmniFocus 3 for both iOS and Mac. As you might guess from the length, it’s very comprehensive. That said, it does not feel at all padded out. Instead, it has a clear progression from simple content for users who are new to OmniFocus, ramping up to power user features and in-depth discussion of how to set up a system in OmniFocus most effectively to get your work done.

I’m a long-time user of OmniFocus 2 (and OmniFocus 1 before that), so I’m more on the power user end of the spectrum. However, I’m also just now making my transition from OF2 to the new OF3. I held off on OmniFocus 3 for iOS until the Mac version also became available. It was released last Monday, as was this Field Guide, so it came along just at the right time for me.

David starts with the basics, installing the software, setting it up, and walking through the various areas of the user interface. Throughout the course, he gives fairly equal weight to the iOS and macOS version of OmniFocus 3. If there is a bias, it’s not leaning towards one OS or the other, but that within iOS he tends to spend a lot more time demonstrating the iPad version than the iPhone version.

He doesn’t just confine himself to telling you how to twiddle the buttons, however. As he steps through how to capture and process tasks he’s also introducing the fundamental concepts that drive OmniFocus (and doing a bit of an introduction to the Getting Things Done system that OmniFocus was originally designed to implement).

There’s quite a bit of content on Tags (about 45 minutes by my count). These are a new feature in version 3 of OmniFocus and David spends quite a bit of time talking about how to use them effectively. Making the transition to tagging tasks and projects is going to be the biggest change for me moving from OF 2 to OF 3, so I appreciate the comprehensiveness of his coverage.

He also spends a lot of time talking about various perspectives. Perspectives are a tool that allows you to slice and dice your project and task list using various criteria to pull out specific tasks. They’ve only gotten more powerful and flexible with the addition of tags in OmniFocus 3. This is an aspect of OmniFocus that I know I haven’t been using to its full potential, so I was happy to see it covered in depth. One area David is clearly opinionated about is the benefits of custom perspectives available in the Pro version of OmniFocus. While he talks about how to make good use of the built-in perspectives in the standard version, you can tell his heart is really with the custom perspectives of the Pro version.

One area I thought could have used a bit more depth is review. David goes through the mechanics of reviewing projects and talks about how he customizes the review intervals to suit the needs of different projects. He also talks a bit about “meta-reviews” where he goes through at a higher level and thinks about his system and workload as a whole. Despite this, I do think the course could have gotten further beyond the mechanics of the project reviews to a more in-depth discussion of what you should think about when reviewing a project.

As befits one of the hosts of the Automators podcast, David spends quite a bit of time talking about how to automate OmniFocus. He starts out with very simple automation using tools like Text Expander, or even just copying and pasting templates from a text editor, all the way up to much more complex automations using the Shortcuts app on iOS.

Unlike some other task managers, OmniFocus is not a very opinionated piece of software. While it started as a very traditional GTD app, it’s always been very customizable and amenable to being used in a variety of ways. If anything it’s gotten even less opinionated in version 3, as tags enable even more flexibility (and allow you to get even further from traditional GTD methodologies). This lends a bit of a “do it yourself” vibe to OmniFocus. In some ways, it’s a toolkit for building a task management system rather than a fully-fledged task management system itself.

David embraces this aspect of the software by discussing six different task management systems you could set up OmniFocus to implement. He covers a system built around defer dates, one based on flagging tasks, and one that leans heavily on the new tagging features. He also talks about using OmniFocus 3’s enhanced forecast perspective as the center of your task management (though this is less of a full-fledged system than a technique that could be applied to defer date, flag, or tag based systems). He also briefly covers a system built around higher level tasks (as opposed to the concrete “next actions” of classic GTD). Finally, David talks about his own system, which leans heavily on tags, but also blends in elements of flags and defer dates.

Not just in this section, but throughout the Field Guide, David talks about various ways of using OmniFocus, even if they’re not how he personally uses the software. He clearly has some opinions about the best way to use it, but he realizes that what works best for him won’t necessarily be best for everyone. He does an excellent job of laying out the pros and cons of various strategies.

As with many of the Field Guides, if you’re looking for a laugh, it pays to keep an eye on the example tasks and projects David is using. His OmniFocus database seems to indicate that David is some sort of mad scientist.

If there’s a unifying theme in this field guide, it’s “The Manager and the Maker.” This is the idea that OmniFocus can be the manifestation of our inner manager, organizing what we have to do and getting it out of our way quickly so that we can do creative work, letting out our inner “maker.” Some folks don’t think that OmniFocus or GTD really work for creative pursuits; that they’re just meant for salesmen and CEOs. David seems to have a bit of a chip on his shoulder about this. He uses OmniFocus to manage the creative work of his MacSparky empire, including articles, blog posts, and this very field guide and he makes clear that he thinks OmniFocus is very useful for creative work.

The OmniFocus Field Guide, 3rd Edition is a great resource. I think anyone looking to get started with OmniFocus or get better at it is going to get a ton out of it, whether they’re a new user or a power user. I know that I’ll be totally redoing my system to take advantage of OmniFocus 3’s new tagging features and a bunch of other strategies that I learned from this course (I’ve got an article on my new system brewing too). The productivity benefits of a smoothly functioning task management system and the complexity of my job (and life) make both the Field Guide and the OmniFocus software a real no-brainer. If you’re finding that the complexity and volume of your tasks mean things are falling through the cracks or taking a lot of time to manage, you should check out OmniFocus and the Field Guide.

The Multipad Lifestyle

David Sparks is a bad influence. The idea of having multiple iPads first got into my brain listening to Mac Power Users #317 when he confessed to Katie Floyd that he had bought a 9.7” iPad Pro to go with his 12.7” one.1

My path to multiple iPads was a little different. For many years I ran 9.7” iPads. Originally, of course, 9.7” was the only choice. I was never really tempted by the iPad mini, not so much because of screen size, but because my iPads tended to spend a lot of their time connected to external keyboard cases. While some manufacturers make keyboards sized to the mini, they’re really too small for effective touch typing (even 9.7” sized keyboards are on the cramped side).

The iPad Pro

When the original 12.9” iPad Pro came out, I thought it was interesting, but not something I’d really be interested in. It was so big, and I had a fairly new iPad Air 2 that I still really liked. Then my Air 2 was stolen and I had to figure out what to replace it with. After quite a bit of debate I ended up getting a 12.9” iPad Pro.2

I really do like the big iPad Pro. The big screen is great, especially for watching video and it does split view multitasking much better than the smaller iPads. The Apple Pencil has been useful, but not anywhere near as big a deal for me as it has for some other folks. I use it mostly for occasionally marking up PDFs rather than drawing.

For me, though, the real killer feature is the Smart Keyboard. As I mentioned, I’ve run external keyboard cases3 with my iPads almost from the very beginning. While I’ve found them much better than the onscreen keyboard, cases sized for 9.7” iPads have always been a little cramped to type on. The larger size of the 12.9” is finally enough to fit a real, full sized keyboard layout. The magnetic connection makes it much easier to get the keyboard on and off the device, so I can easily swap back and forth between typing and just using the iPad without the keyboard to watch video or browse the web. The Smart Connector is a big advance over Bluetooth in that the keyboard is always on. With Bluetooth keyboards if you haven’t typed anything in a while you have to wake the keyboard up before typing.

While I have not gone nearly as far down the route of making the iPad my primary machine as folks like Fraser Speirs or Federico Viticci, the 12.9” Pro has allowed me to go further in this direction than I previously thought. These days I don’t usually take my MacBook Pro with me when I travel unless I think I’ll have a particular need for it.

As much as I love the 12.9” iPad Pro, there have been some disadvantages to it. When I had a 9.7” iPad, it was pretty much my constant companion. With the help of a Tom Bihn Ristretto4 I had it with me almost all the time. I don’t carry the 12.9” around nearly as much. The extra size and weight make it easier to just leave it and only bring my phone. It’s not really a “take everywhere” device for me the way the 9.7” was.

The big iPad is also sometimes awkward around the house. It’s great for working at a desk or table, or sitting on the couch watching a video, but it’s big enough to be a bit awkward to hold in one hand and tap or type with the other.

Thinking about a smaller iPad

Initially, these disadvantages had me thinking about getting a larger iPhone. Ever since the iPhone line split into the regular and plus sizes, I had stayed with the smaller phone. Since my phone was effectively taking on some of the roles that the 9.7” iPad had filled for me, it had me considering whether an iPhone 7+ would make sense. In the end, though, I just couldn’t do it. The bigger phone just wouldn’t fit in some of the places where I keep my phone, and it’s not really friendly to one handed operation.

Eventually, I came round to the idea that the only way I could fill the gap left by the 9.7” iPad was another iPad. Unlike David, however, my solution to this was not a 9.7” Pro, but a iPad mini. I thought the mini would nicely split the difference between the big Pro and my iPhone.

I’d been thinking about going this route for quite a while, but part of the reason I decided to jump on it was the signs that the iPad mini might be on the way out. Apple recently dropped all of the mini models except the 128gb size, as well as undercutting it price-wise with the new $329 iPad. If I wanted the new one, this might be the time to do it.5

While buying a second iPad is pretty much the definition of a splurge, I did economize in a couple of ways. This is my first iPad without cellular data. I relying on wifi and tethering to my iPhone for this one. I also went with just a 32gb model, which is the smallest amount of storage I’ve ever had in an iPad. I figure that the big iPad Pro is going to remain my primary platform for watching video and I don’t sync my music library to any of my iPads, so all I really need is enough space for apps. While Apple isn’t selling the 32gb iPad mini any more, it was still available from other sellers. I found a good deal on one from Walmart. It had evidently been sitting on the shelf for a while, since it came out of the box with iOS 10.0, rather than the then-current 10.3.1.

The iPad mini

This was the first time in a long, long while that I’ve set up an iOS device from scratch. Usually, when I get a new iPad or iPhone I just restore from my old device’s iCloud backup. Thinking about it the last iOS device I set up completely from scratch was probably the original iPad.

That said, cloud services make getting all my data on a new device pretty easy. Download the apps and set up iCloud, Dropbox, and a couple of app-specific syncing services (like OmniPresence).

There are some aspects of the smaller iPad that take some getting used to. The touch targets are all a bit smaller, for instance.

The keyboard is really way too small for touch typing. I find myself doing a lot more hunt and peck, often with the mini in my right hand and typing with my left. Holding the device vertically in both hands and typing with both thumbs is probably the fastest way to enter a non-trivial amount of text. When I’m using the mini I also find myself missing the number key row from the iPad Pro onscreen keyboard (though the flick keyboard in iOS 11 may mitigate that). The mini clearly isn’t going to be a machine for serious typing, compared to the iPad Pro or a Mac.

I use Split View quite a bit on my iPad Pro, but it definitely isn’t as useful on the mini’s smaller screen. I find myself using Slide Over when I need to access data in a second app (I did this with 1Password quite a bit during the setup process when I needed to enter credentials in other apps).

So far I find myself using the iPad mini quite a bit as a secondary screen. It’s what I grab when I’m doing something else and want to look something up on the internet or check email. If I’m sitting down to concentrate on one task I’m more likely to use the big iPad (or the Mac).

Accessories

When I got the mini I did some hunting for a shoulder bag that really took advantage of the mini’s small size. Getting the smaller device in putting it in a bag sized for the 9.7” iPad seemed like a waste, so I really wanted something designed for the mini, but those are few and far between. I ended up getting a nice Waterfield Design iPad mini sleeve with a shoulder strap. This is about as minimalist as you can get (if anything I wish it had a bit more space for extra gear than the one very flat outside pocket that the sleeve sports). I’d link it, but it looks like Waterfield isn’t making the iPad mini sized one anymore.

The other piece of gear that I got for my iPad mini was a cheap folding stand. Frankly, these are not very high quality (though I haven’t broken one yet), but they are the lightest and most compact stand that I’ve been able to find. Everything else would be bulkier than the iPad mini itself. This little stand slips nicely into the flat pocket on the Waterfield case (though it doesn’t always want to stay there).

Was it worth it?

I haven’t ended up using the mini as often as I thought I would, in part because around the time I got the mini I cut down on how often I went out for lunch, which was one of the main times I figured I’d be using the mini. Still, I think it was worth it, even if it is clearly a secondary device for me.


  1. He’s not the only one, of course. I know other people are doing the same thing, notably Myke Hurley and CGP Grey. 
  2. A few months later the 9.7” iPad Pro came out. If it had been out at the time (or if I had known it was coming) I probably would have gone with the smaller size and never known how well the 12.9” Pro would work for me. 
  3. First Zagg, then Bridge
  4. An older model Ristretto specifically sized for a 9.7” iPad that they don’t make any more. 
  5. Before buying new, I did check Gazelle and some other sources for used models. I could only find 16gb or 128gb models, and even those only seemed to be available in the gold color (which I detest).