This post will be obsolete with iPadOS 13

My transition to using the iPad as my primary travel computer was a gradual one.  It started with leaving my laptop at home on purely personal trips, where I wouldn’t have to get any work done.  From there it gradually transitioned to the point where I haven’t had to travel with a laptop in over a year.

One of the obstacles I encountered along the way was getting files on and off of USB flash drives.  This is something that will get fixed for good in a few weeks when iPadOS 13 comes out with support for external drives in the Files app.  A year ago, when I was considering taking the final leap to the iPad, it wasn’t clear that Apple would ever address this. 

There were workarounds, however.  Sandisk makes the Connect Wireless Stick, a USB flash drive that you can connect to over WiFi.  The Kingston MobileLite Wireless G3 takes more of a Swiss Army knife approach, functioning as a portable charger and a WiFi access point, as well as allowing you to access files on USB drives and SD cards from an iOS device.  

While the Kingston does a lot more, both of these them take a similar approach when it comes to file management.  They each create a local WiFi network that you can connect to.  Once connected, you use their iOS app to move files on and of the device.   

Both iOS apps are serviceable, though I wouldn’t call either of them great.  The process for getting files on the SanDisk is a bit more intuitive; you can drag and drop (though the app does not support Split View) or use the share sheet.  The file gets transferred wirelessly to the drive.  Because the Kingston may not have an external drive attached the process is a bit more complicated.  You can send a file to the app via the share sheet (no drag and drop, though it does support Split View).  However, the file is initially transferred to the Kingston app’s storage on your iOS device.  You then have to use the app to move it to an attached external drive.  

I ended up buying both because they address slightly different scenarios.  The Sandisk covers situations where you need to get files onto or off of someone else’s computer, but it doesn’t help when someone hands you a flash drive with files on it that you need to access.  The Kingston covers both (and SD cards too), but it’s bigger and heavier.  

So why am I writing about this just before iPadOS 13 comes out?  I finally had to actually use it.  I’m presenting at a conference and thanks to a foul-up I wasn’t able to provide them with my presentation far enough in advance to preload onto the computer I’d be presenting from (this also gave me the chance to keep tweaking my presentation right up until I gave it).  I was able to transfer my presentation onto the SanDisk Connect Wireless Stick without any issues.  Just to take the suspenders and belt approach (and because I wanted the chance to try it) I used the Kingston to put my presentation onto a regular USB drive as a backup.  When the time came to give my presentation, I plugged the SanDisk into the laptop that was hooked up to the projector and copied the file to the hard drive.  

The hour of the wirelessly connected USB drive for iOS may be getting late, but I was happy to get some use out of the Wireless Connect Stick before iPadOS 13 made it obsolete.  

Apple News+

Frankly, I never paid much attention to Apple News. I took a quick look at it when it came out in iOS 9 back in 2015, but it didn’t really grab me. I was intrigued by elements of Apple News and decided to give it a try. I think Apple News is going to end up being my primary news source, but for reasons that have a lot more to do with my behavior than the new Apple News features.

For many years my primary news sources have been the Google News page and a collection of news feeds in my RSS reader. When Apple announced their Apple News service, including a 1-month free trial, I decided to give it a go (it also finally got me to upgrade my iMac to Mojave so I could have Apple News available on the desktop).

I find that Apple News doesn’t trigger my completionist tendencies the way RSS does. I have enough RSS feeds that I rarely get through them all. While intellectually I’m OK with this, the big unread count does seem to lodge in the back of my mind and bother me. Apple News doesn’t have an unread count. It has a huge amount of content, much of which doesn’t interest me, so leaving articles unread doesn’t bother me as much.

The other interesting benefit of Apple News is that it doesn’t get updated as often as Google News. I expect part of this is because it’s a curated news source rather than being algorithmically generated like Google. While “not updated as frequently” doesn’t seem like it would be a selling point for a news source, I’m finding it beneficial. Hitting refresh on the Google News page is kind of like pulling the lever on a slot machine. You don’t get new content every time, but you get new stuff often enough to keep doing it. Refreshing Apple News doesn’t result in new content nearly as often. The best way to get new stuff in Apple News is to close it and come back a couple of hours later. This way it pushes me more towards sitting down to read the news a few times per day rather than constantly checking if there’s anything new.

Some minor issues: I find it annoying that the back button is in somewhat different spots on iOS and macOS. The news app on the Mac crashes occasionally (though I never encountered a cycle of constant crashing that some people did soon after the Apple services event).

Overall, I’m surprisingly happy with the Apple News app. The Apple News service, on the other hand, is much more of a mixed bag for me. I didn’t get much out of the magazine content. I don’t subscribe to any magazines and there’s not much in the News catalog that interests me.

The only newspapers that the service offers are the Los Angeles Times and the Wall Street Journal. The LA Times isn’t at the top of the list of newspapers I’m interested in. The WSJ does hold more interest for me. As people have noted, Apple News does not offer access to everything in the Journal, just a selection of articles.  Nevertheless, the vast majority of Wall Street Journal articles I wanted to read were available with the Apple News subscription, but I did run into a few that require a subscription.

At this point, access to the Wall Street Journal would be the biggest selling point for Apple News for me, but I don’t know if I would get $10 per month of value out of that. If I decided to pay for news sources, I’d probably get more out of the New York Times or Washington Post.

For now, at least, I canceled my Apple News subscription before the trial period ended. I may come back if they add more newspapers in the future. It would also be an appealing addition to some sort of Apple services bundle, but as a standalone product, Apple News isn’t worth it for me.

The Apple News App, on the other hand, is an unexpectedly good fit. I’ve deleted most of my general purpose news feeds out of my RSS reader, and I’m opening up Apple News once or twice a day instead.

Review of the 2nd Generation AirPods

I love my AirPods. In fact, I just about loved them to death. By the time they were about two years old, I had used them so much their battery life had declined to the point where I was only getting about 90 minutes of listening time out of them. One of my uses for them is going on 2-hour walks, so this was a problem.

I use my AirPods every day: walking to and from work, exercising, taking longer walks on the weekends. They’re one of my most used devices. I use them enough and find the advantages over wired headphones big enough that replacing them if they were lost or broken would be a top priority.

Given how much I use them and the state of my original AirPods I was definitely in the market for some new ones. I hoped that I could nurse my existing pair along until Apple announced an updated version, but if it got to the point where my original pair became truly unusable, I would have bought an identical set of replacements.

So when Apple released the 2nd generation AirPods I hardly even bothered looking at the spec sheet. I just went straight to the Apple website and ordered a pair. The only real decision was whether to splurge on the new wireless charging case (they’re available both with a Qi-compatible wireless charging case and a regular case). I was a bit uncertain about whether the extra $40 would be worth it, but I decided to give it a go.

The new AirPods look identical to the old ones. The wireless charging case is slightly different, with the LED indicator migrating from inside the case to the front of the case and the hinge now being made out of aluminum rather than stainless steel.

On the inside, the new AirPods support “Hey Siri” to activate the Apple voice assistant. They’re also advertised as having longer talk time, but I hardly ever use mine for phone calls.

Qi charger in my mud room
Qi charger in my mud room

I’m glad I got the wireless charging case. I bought another Qi charger and set it up in the hallway/mud room where I leave my stuff when I come home. It’s much easier to just drop the AirPods case on the charger every day than it is to try to keep track of how much battery life the case has left and remember to plug it into a lighting cable every couple of days (with my old AirPods I’d been caught out by forgetting to charge the case a couple of times).

When you put it on the charger, the LED comes on momentarily, but it doesn’t stay on. It would be nice if that would display colors indicating “charging” and “charged” like the old MagSafe connectors on Mac laptops.

The “Hey Siri” functionality works well. While I still feel self-conscious about it, I may be more apt to use “Hey Siri” in public than I was to activate Siri manually. The activation phrase makes it obvious what I’m doing in a way that tapping an AirPod did not.

On my old AirPods I set it up so tapping the right AirPod brought up Siri while tapping the left one skipped forward (which was set to skip ahead 30 seconds when listening to a podcast in Overcast). Now that I can rely on voice activation for Siri, I have tapping the right AirPod skip forward and tapping the left one skip back. Having both forward and back is useful for navigating podcasts.

Given the state of my old AirPods, perhaps the biggest feature of the new ones is their battery life. The advertised listening time isn’t any different on the new models, but by merely being fresh out of the box their battery life is much greater. On my old ones, 90 minutes of listening to podcasts was enough to give me a low battery warning. The new AirPods are still above 65% after an hour and a half.

I’m very happy with my new AirPods. Of course, aside from battery life, I was happy with the old ones. Features like “Hey Siri” and Qi charging are just gravy.

Time Blocking and Bullet Journaling

One of the goals that came out of my personal retreat was to be more intentional about how I spend my time by time blocking every day. I’d recently bought The Bullet Journal Method by Ryder Carroll, along with one of the nice Bullet Journal Notebooks, so naturally, I decided to implement this using a bullet journal.

Time Blocking

My time blocking practice evolved out of some of the things Shawn Blanc talks about in The Focus Course, mixing in some ideas from the “Ideal Week” exercise that Mike Schmitz covers in his Personal Retreat Handbook, and some of David Sparks’ posts on scheduling his day (see posts here, here, and here.

The basic idea is to plan out a schedule for each day. This serves a couple of purposes. The main reason I first tried time blocking a couple of years ago is that I don’t have to make as many decisions about what to work on in the moment it lowers the “activation energy” to get started on a task.

Before time blocking I often found myself looking at my long list of tasks in OmniFocus trying to decide what I should work on next. Not only did these decisions take time, they also seemed to draw on the same reservoir of mental energy that’s required to do Deep Work. With time blocking I can make these decisions in advance. All I have to do in the moment is look at my schedule, and I’ll see what I’ve decided that I should be working on.

The other major benefit of time blocking is to help me be more intentional about how I spend my time. I’d been time blocking my workday for most of 2018, but towards the end of the year, I kind of fell off the wagon. I not only found this made me less productive, but I ended up spending a lot of time diddling around on the internet rather than getting stuff done. Often, this is because rather than expend the mental energy to make a decision about what to do I’ll just end up going online instead.

This is not something that’s confined to the workday either. When I was doing my personal retreat one of the things that came to the fore was the amount of leisure time I was spending on “low-quality recreation;” activities that just aren’t that interesting or rewarding but that I end up doing by default. I’d really like to be spending my leisure time on stuff that I find most enjoyable, rather than whatever’s easiest. When I picked time blocking back up after the personal retreat, I decided to do my entire day, every day, rather than just the workday.

While those are the big two, there are other benefits as well. Among them, time blocking helps me maintain a realistic idea of what tasks I can accomplish in a given day. If I’ve got lots of appointments or other obligations, I can (indeed, I’m forced) take that into account during the scheduling process.

For me, the key to making time blocking work is flexibility. I seldom have a day go precisely the way I planned it out. Stuff happens. Sometimes a task takes longer than anticipated. Sometimes something new pops up that needs to be done that day. Sometimes I find I can’t even get started on a task because I’m missing something critical.

When this happens, I just have to “roll with the punches” and adapt. I’ll push another task off until tomorrow, substitute a shorter task for a longer one, or drop something entirely. As David Sparks put it, “A calendar is a soup rather than a puzzle.” Sometimes you have to stir the soup.

That said, more often than not, my actual day is pretty close to the schedule I laid out. Even if I have to adapt, I find that starting with a schedule works better for me than doing everything on the fly.

Bullet Journaling

When I first started time blocking last year, I incorporated a few elements of Bullet Jounrnaling. This time around, inspired by Ryder Carroll’s excellent book, The Bullet Journal Method, I decided to dive deeper into the bullet journal system.

The bullet journal method is a system using pen and paper to track tasks, appointments, and notes. It’s a nice blend of structure and flexibility that’s very adaptable to individual needs. The system is very modular; it’s built around daily, monthly, and yearly logs, collections of notes on particular subjects, and an index to help you find important notes.

While I’m using much more of the bullet journal system than I was in the past, I’m not using it as my primary task management system. OmniFocus is still the source of truth when it comes to what I have to do.

My implementation

I’ve adapted the Bullet Journal Method’s Daily Log format to do my time blocking. I use a two-page spread in the bullet journal notebook with my schedule on the left-hand page and my most important tasks and daily log on the right.

The schedule uses half an hour per line, from 5:30am to 9:30pm. I’ve found that I generally don’t need more than half-hour resolution; I’m not trying to schedule everything down to the minute. Indeed, I’m finding that the fact that I can only easily schedule in half-hour increments is a benefit rather than a drawback since it adds flexibility for breaks, diversions, small tasks that come up, etc. It kind of leads naturally into a pomodoro-like way of working.

As I mentioned earlier, I don’t use the Bullet Journal as my primary task management system. However, I do write the 3-5 most important tasks for the day in my daily log on the right-hand page of the day’s two-page spread. This is not everything I have to do today, just the biggest and/or most critical tasks.

Underneath the list of tasks, I have space to take notes about how the day went. I’d like to turn this into more of a daily journaling practice, but for now, it’s more of a random assortment of notes and events.

Finally, at the end of the day, I’ll use that right-hand page to note down one thing that I accomplished and two things that I’m grateful for. This is a habit that I picked up from The Focus Course, and I’ve been doing it for several years now. I find it’s useful to help me reflect on the positive things that happened during the day, even if that day didn’t seem to go well overall.

I’m using the Bullet Journal’s monthly log for some habit tracking (at the moment mainly noting days that I write and that I’ve time blocked for). However, I’m not getting a whole lot of use out of the yearly log or collections from the Bullet Journal system. Those sorts of things tend to go into my calendar or my notes app, respectively (Fantastical and iA Writer).


I’ve been back on the time blocking train for about two months now. It’s definitely helped me be more intentional with my time. I find myself spending less time randomly messing around on the internet and more time doing productive things or high-quality recreational activities. I’ve gotten more done at work and read many more books.

Overall, I think time blocking has been well worth the effort I’ve put into it. Doing it in a bullet journal format is something I’m not entirely sold on. Much as I like the nice Bullet Journal Notebook (and the Retro 51 Tornado pen I’m using to write in it) I’m intrigued by some of the stuff David Sparks and Mike Schmitz have been doing with PDF templates that you can use in GoodNotes on the iPad with the Apple Pencil. That could be an alternative to toting around a paper notebook. For now, though, I’ll stick with paper at least until I fill my current notebook.

Inventorying my tools in 2019

Back in 2017, I wrote an article on Inventorying my Tools, going through the software I use to get work done on a regular basis. Now, about two years on I thought it would be interesting to go through and see what’s changed.

This list focuses on work (and side project) related apps. It excludes purely personal and recreational apps like Reeder and Paprika. It also only covers things that I think of as “real apps” as opposed to menu bar applications or little utilities like Yoink or TextExpander (though that line is kind of fuzzy, given my inclusion of 1Password).

Every Day

  • OmniFocus
  • iA Writer
  • Microsoft Word
  • Safari
  • Chrome
  • Outlook
  • Spark
  • iPhone Mail app
  • Fantastical
  • Toggl
  • 1Password
  • Dropbox
  • Files
  • Luna Display
  • Bullet Journal Notebook


  • Goodnotes
  • Drafts
  • Shortcuts
  • Excel
  • Numbers
  • PowerPoint
  • OmniOutliner
  • Jump Desktop
  • Field Notes Steno Pad

Occasional But Vital

  • ArcGIS
  • TransCAD
  • Python (IDLE)
  • Sublime Text
  • Kaleidoscope
  • OmniGraffle
  • Typora
  • My office whiteboard

Changes from 2017

A fair number of apps have gone by the wayside. Bear, Byword, Ulysses, and Scrivener have all been replaced by iA Writer. Toggle has replaced Hours, and Sublime Text displaced TextWrangler. And, of course, Workflow has turned into Shortcuts.

There are some outright additions that represent categories that I didn’t even have on my list two years ago. Many of these are iPad apps like Files and Goodnotes, a consequence of my increased use of the iPad as a work and travel device. Others like Luna Display and Jump Desktop are related to my Mac mini home server.


As I said two years ago, I think part of the value of this exercise is not just listing the apps, but thinking about why I use these apps and whether there are any changes I could make to get my work done more effectively.

Are there some of these where I would benefit from learning to use them better? Which ones do I want to use more often? Which ones do I want to use less often? Are there tools that don’t fit my needs anymore? What tools aren’t I using that I might benefit from?

For instance, last time around I’d expressed a desire to transition Word from something I use every day to an app that I use more occasionally. While I’ve probably reduced the amount of time I spend in Word, I haven’t been able to cut back as much as I would like. My writing generally starts in a text editor, but at the point where I need to share things with other people at work, it makes the transition to Microsoft Word.

One area where I have made progress since the last inventory is in reducing the number of text editors I use. Byword and Scrivener were already on the way out, but for most of that period, I divided my writing between Bear and Ulysses. Now that I’ve switched to iA Writer I’m down to one app for writing prose (with Sublime Text for writing code). That simplifies things in a lot of ways.

One area where I’m still in the midst of a transition is going from taking all my handwritten notes on paper to doing more of it on the iPad Pro using the pencil. The Field Notes Steno Pad still gets plenty of use, but probably about half of my notes are made on the iPad in Goodnotes. I’d like to continue to move in this direction.

I still don’t feel like I’m getting as much as I could out of Drafts or the Shortcuts app. My primary use case for both of them at the moment is as a front end for OmniFocus: Drafts as a quick entry tool and Shortcuts to set up templated projects. I think I’d benefit from delving deeper into these (as well as Scriptable, which didn’t even make the list).

Due to some changes in my work, I’m not doing as much coding as I used to. I’d like to exercise that muscle a little more, even if it’s just as for some sort of side project.

In addition to notebooks (Field Notes and Bullet Journal), the other analog tool on the list is the whiteboard in my office at work. A couple of years ago I was using it to keep track of progress on the many projects I was responsible for, but that has kind of fallen by the wayside as more and more of my time has gotten sucked up into one big project.

Taking a big picture look at what apps I’m using and why is definitely a useful exercise. I carried through on some of the changes I made two years ago, and I’ve got some more in mind that I want to make based on this new inventory. If anything I need to do it more often than every two years.

iPad on a Stick

In an earlier article I related my experience spending a month using my iPad Pro with an external monitor. The external display has some real ergonomic benefits, putting the screen up at eye level rather than down on the desk. However, it does create an odd and unnatural divide between the display, where I can look while I read or type, and the iPad itself, where I need to look to swipe or tap.

The next stage of my iPad experimentation has been to get a tall stand for my iPad, raising it up to about eye level. In this case, I’m using the iPad Stand for Desk, Aluminum Height Adjustable Swivel Stand and Holder for iPad Mini Pro Air Tablet Up to 12.9″ iPhone Galaxy Phone iPad Bussiness Office Kitchen Display Charging Dock Accessories.1 This stand was recommended by Myke Hurley on Upgrade. While this is a very tall iPad stand, I’m still using a ream of paper underneath it to raise it a little higher. I’m also still using the Apple Magic Keyboard with the numeric keypad.

iPad stand
iPad stand

My initial reaction was that after spending a month with my iPad’s screen on a 27″ monitor, even the 12.9″ iPad seems tiny by comparison. It’s by no means too small to use, but there’s definitely a different feel to it than using a big external display with the iPad (or my 27″ iMac, for that matter).

Of course, the biggest change to interacting with the iPad on a tall stand is the need to reach up to interact with the screen. With the iPad in a Smart Keyboard Folio or the Elevation Labs DraftTable that I used with the external monitor reaching the screen is a matter of moving my hands a few inches. With the tall stand, it’s more like moving my hands a few feet. This is definitely “zombie arms” territory.

In contrast to using the iPad with an external display, there’s no confusion about where to look. As a display device, when reading or typing, the iPad works just fine. Once I got over my surprise at the size difference the screen was plenty large enough to read easily.

An advantage of having it on a stand like this is the ability to rotate it into portrait mode. The “sheet of paper”-like experience of working on a text document in portrait mode is quite nice. It might be one of the best ways to do extended writing in a single document on the iPad.2

The flip side of the ability to rotate into portrait is that it can be a bit of a challenge to get the iPad exactly level and centered in the stand. Maybe it’s just my OCD’ish tendencies, but I find this bothers me quite a bit. It’s also more trouble to get in and out of the stand. With the Elevation Labs DraftTable, I could just flip the Smart Keyboard around the back, set it on the stand and plug in the external monitor. With this stand, I have to take the iPad out of the Smart Keyboard Folio and go through a somewhat fiddly process to get it into the spring-loaded rubber clamp that keeps the iPad in place.

One minor annoyance is that in the stand I’m not able to put the Apple Pencil in its usual spot atop the iPad Pro. Always having the pencil available and ready to go is one of the best features of the iPad Pro. If I were to go with this sort of setup long-term, I’d definitely want some kind of pencil holder on my desk so that there would be a spot for it. For now, I’m just putting it on the desk between the keyboard and the base of the stand.

When I first started my experiment using my iPad Pro with an external display, the question I was trying to answer was “can an iPad Pro replace a Mac on my desktop at work?” Given that I’ve gone two months without needing to do anything substantiative on my Mac3, the answer seems to be yes.

Unlike a lot of people, my main challenge in using the iPad as my primary work computer was always ergonomic rather than about the software. Things I use my Mac for at work (editing text in iA Writer, managing tasks in OmniFocus, browsing the web in Safari, and reading and replying to email in Spark or Apple Mail) can all be done on the iPad. Any other tasks can be done on my work-issued PC. The challenge has always been that, for me, working for an extended period using an iPad in a Smart Keyboard (or a traditional laptop for that matter) was never that comfortable for me. I want better ergonomics, with a display up at eye level. Both using an iPad with an external display and putting it in a tall stand solve this ergonomic issue.

At another level, however, neither if these iPad setups really feels optimal. Using the iPad with an external display creates an awkward blend of direct and indirect manipulation. Using it on a tall stand requires my hands to come a long way up from the keyboard to manipulate the screen. If I had to pick one, it would probably be the external display, but it’s still a compromise. These disadvantages are significant enough that now that the experiment is over, I’m planning on going back to my MacBook Pro hooked up to a nice, ergonomically placed external monitor as my daily driver at work.

If my MacBook Pro were to die, though, that would put me in a difficult spot. Are the disadvantages of using the iPad in this role significant enough to justify dropping over a thousand dollars on a new Mac? That’s kind of a hard sell either way. The Mac definitely provides a more natural, compromise-free desktop experience, but a new laptop or Mac mini would be a pretty substantial outlay compared to an external display that I could use with the iPad Pro I already own.

At this point, I hope that my MacBook Pro will hold out long enough for Apple to make improvements that would make the iPad Pro a better fit for this kind of role. This could be support for external pointing devices, but it could also be better support for keyboard shortcuts (by both apps and the OS) so that I could get more done without tapping and swiping on the screen.

  1. Yes, that entire thing is the name. And yes, they misspelled “Bussiness.” ↩︎
  2. Maybe that weird iPad Keyboard Dock for the original iPad was on to something. ↩︎
  3. Keeping in mind that I do have a PC sitting right next to the iPad that can shoulder some of the load, even if I prefer using iOS and macOS rather than Windows. ↩︎

iPad Pro with an external display

One of the questions that have occupied me recently is whether an iPad Pro can replace my Mac laptop.1 One of the ways I justified spending a lot of money on one of the new 2018 iPad Pros was that it would help me avoid replacing my even more expensive MacBook Pro. I’ve already concluded that the iPad Pro is a workable replacement for my MacBook Pro as my travel machine. I’ve taken several long work trips with just the iPad and gotten by just fine.

The other role that the MacBook has long served is as my workplace Mac. For many years I’ve had one of my personally owned Macs on my desk next to my employer-issued PC.2 There’s some specialized software I use for work that’s Windows only, but for lots of general tasks like writing, outlining, and task management I prefer Mac/iPad apps.

Federico Viticci’s article on the many setups of his 2018 iPad Pro got me wondering whether the iPad Pro could replace my MacBook Pro on my desk at work. A lot of “can an iPad replace my Mac?” questions really boil down to “what software do you use?” In this case, software is not the problem. My work Mac is primarily used for writing text files (currently using iA Writer), managing tasks using OmniFocus, and browsing the web in Safari. I’ll also manage email in Spark or Apple Mail and occasionally outline things in OmniOutliner. All of these have iOS equivalents.3 Basically, anything I can’t do on the iPad is stuff I’d be doing on the PC anyway.

So for me, the question of whether the iPad Pro could replace my work Mac was not one of software, but ergonomics. I find it very uncomfortable to spend an extended period working on an iPad in the Apple Smart Keyboard or any 3rd party stand that puts the iPad in a similar position. I always end up with a crick in my neck. Laptops are just as bad, which is why I always used my MacBook Pro with an external display whenever I was at my desk. Federico’s article got me wondering if I could do the same with my iPad Pro.

My setup


My first obstacle was finding a suitable external display to test this with. I started with an old 19″ Dell monitor that had been hooked up to my work PC. Not only was it easily available, but the 4:3 aspect ratio meant that unlike a widescreen monitor the iPad output wouldn’t be pillarboxed.4 Unfortunately, the iPad looked terrible on it. Not just “this obviously isn’t retina,” but blurry enough that I’d get a headache if I used it for any significant length of time. A 24″ HD monitor suffered the same issues. The iPad looked great on one of the 24″ 4K monitors I had hooked up to my iMac at home, but I didn’t want to bring one of them in to work. Eventually, I tried it on a Dell 27″ U2719D that’s usually attached to the work PC. It’s not 4K, but it’s 2560×1440, which is somewhere between a standard definition monitor and retina. On it, the iPad’s output was clear and sharp. As is my usual practice, I used several reams of paper to get the monitor up to a higher elevation.

I connected the iPad using the Apple HDMI adapter that I bought to use for presentations. It has pass-through charging, so my iPad gets charged as well as connecting it to the monitor.

To hold the iPad, I used an Elevation Lab DraftTable stand. This stand is big, heavy, and rock solid. I’m running it in the highest position, which holds the iPad at about a 45° angle. I started off with it off to the left of my keyboard (I’m left handed), but I quickly found that centered underneath the monitor worked much better for me.

Speaking of the keyboard, I used the same Bluetooth Apple Magic Keyboard with the numeric keypad that I’d been using with my Mac at work. It works fine, but if I decide to go with a setup like this over the long term, I’ll probably switch to something different. For one thing, I’m a mechanical keyboard guy. I like clicky switches and lots of travel. For another, I think Bluetooth is actually a disadvantage in this role. The problem with a Bluetooth keyboard is that if I disconnect the monitor and want to use the iPad in tablet mode, it retains the connection to the keyboard so the on-screen keyboard won’t come up when I need to type. Several times I’ve had to turn off Bluetooth in order to type on the iPad. It would be better to have a wired keyboard plugged into the same hub as the monitor. That way disconnecting the monitor would disconnect the keyboard as well.

The experience

Using the iPad with an external monitor is a bit of an odd experience. It’s not the same as using a laptop with an external display because the iPad’s touch interface still requires direct manipulation. This means dividing my attention between the monitor and the iPad. When I’m reading or typing, I can look at the external monitor, but if I need to tap or swipe I have to glance down to make sure I hit the right touch targets. Glancing down is not really a problem, but I do find that I sometimes forget to look back up and end up just using the iPad screen rather than the external display. While I can still use the iPad that way, it kind of negates the ergonomic benefits of using an external monitor.

Contrast this to using macOS on a laptop. Because the trackpad manipulates the screen indirectly, there’s not the same requirement to look at the laptop screen rather than the external monitor. Trying this configuration does have me hoping that Apple will add some sort of pointing device support to iOS, though I don’t know how likely that is in the short term.

FaceID works fine in this configuration. In fact, if anything it reinforces how much better having FaceID makes iOS. Rather than having to type my master password into 1Password, all I have to do is glance down at the iPad and my password will get filled in. I really can’t wait until FaceID comes to the Mac.


When I started this experiment to make sure I gave the iPad with the external display a fair shake I vowed that I would do everything I possibly could on the iPad and use my Mac at work as little as possible. Since the beginning of January, the only thing I’ve used my Mac to do at work is to make some changes to a Gantt chart I made in Typora.5 Other than that, the only reason I’ve booted up my MacBook Pro has been to do maintenance tasks on it (to run backups and software updates).

That said, the fact that this sits right next to my work-issued PC does provide a bit of a safety valve. I may have done a bit more on Windows in the past month than I would have if I’d been using the Mac rather than the iPad (particularly when I need to tweak a Word document or PowerPoint).

Overall, I think this has been a successful experiment. I clearly can get by with the iPad Pro and PC at work. That said I don’t know if I’m entirely sold on the iPad plus an external display. Dividing my attention between the iPad and the monitor is kind of awkward, and I’ll often find my attention captured by the iPad and forget to look back up at the display, negating the benefits of having the external monitor. It tends to work best for reading and typing, less well for anything requiring more sophisticated touch manipulation.

That kind of leaves me in limbo. If I were to commit to this configuration, I’d want to buy another external monitor for the purpose so I could move the 27″ back to my work PC.6 I don’t know if I’m quite ready to go that route though. For the moment I’m trying a tall iPad stand so I can see if elevating the iPad itself on a stand is a better ergonomic solution for me than an external monitor.

  1. Unlike some folks, I’m nowhere near ready to go iPad only (I love my iMac and my Mac mini home server). ↩︎
  2. Most often this has been my MacBook Pro, but at times my late Mac mini has filled that role as well. ↩︎
  3. Having both Mac and iOS versions is getting to be a hard and fast requirement for me to adopt an app these days. ↩︎
  4. Pillarboxing is when there are black bars on either side of the display when you display 4:3 content on a widescreen monitor. ↩︎
  5. Typora lets you create Gantt charts in Markdown, which is a bit fiddly but I found worked better for me than any other software I tried. I use it seldom enough that I could just use Remote Desktop to access my Mac when I need to update this Gantt chart, but I really ought to find a Gantt application I like on the iPad. ↩︎
  6. Ideally a USB-C monitor so I could have a single cable connection ↩︎

Mac mini Home Server

I recently replaced my Drobo NAS with a Mac mini. The initial impetus for this came from the fact that my Drobo was running low on space. All of the drive bays were full, so I couldn’t just throw another drive into the machine. This was not an insurmountable problem; these were mostly old 3tb drives, so I could have just replaced a couple of them with newer, larger drives and had plenty of space. However, it got me thinking about what I wanted out of a NAS and whether the Drobo was really the best way to fill that need.

The Drobo/home server fills a couple of roles for me. Primarily, it’s a big pot of storage where I can throw large files that I don’t need to access frequently and take up a lot of room on the primary drives of my computers. It also stores my Plex and iTunes media libraries, making them available over the network to any device in the house.

For the most part, the Drobo has served me well over the past six years, but there are definitely some downsides to using a NAS rather than having direct access to your data from a computer. Network shares aren’t always mounted when you want them to be.1 Certain things are much slower or less reliable when doing them over the network.2

For quite a while I’d assumed that when I eventually replaced my Drobo, I’d get a Synology NAS. However, I realized that many of my issues were with network attached storage in general, rather than the Drobo in particular. While a Mac mini was more expensive than a Synology, I could also reuse some external hard drives I already had on hand rather than having to buy new drives to populate the Synology, meaning a Mac mini would actually be a bit cheaper up front.


I had been planning to initially try this out with an old mid-2011 Mac mini, but the old mini gave up the ghost just as I was getting started with this project. So I went ahead and bought one of the new 2018 minis.

For the home server role, I probably could have gotten by just fine with the base model. However, one of the great things about the Mac mini is how flexible it is. My 2011 mini has, at various times, been my main home desktop, a headless server, and a secondary desktop machine at work. I thought the base model might be too limited if I even wanted to use it as a desktop. In order to future proof this machine a bit I bought the higher-end configuration with a 6-core i5 processor and a 256GB hard drive. I did stick with the stock 8GB of RAM, but that can be upgraded in the future (albeit with some difficulty).

It’s not really very consequential in the grand scheme of things, but I do like the space gray color. I think it suits the mini rather well.


The mini runs headless, without a display attached.3 As a server, it trundles along without my intervention most of the time, but I do need to get on it occasionally. I’m using Jump Desktop4 to provide remote access. It allows me to log in to the mini from anywhere using an application on my iMac or iPad.

However, the most common way for me to access the mini when I’m at home is using Luna Display. Luna is a hardware dongle that plugs into your Mac and lets you use an iPad as an external display. While the original use case mostly focused around using the iPad as a second display for a laptop to get more screen real estate the release of the 2018 Mac mini created a lot of interest in using Luna and the iPad as the primary display. This is how I’m using it. Unlike Jump Desktop, this only works when I’m on my home network. However, Luna is a lot faster, less laggy, and has better resolution than a remote desktop app. It really is like having a screen plugged right into the mini.

Luna Display also allows you to use the touchscreen to manipulate the macOS interface on the mini. This is a two-edged sword. While it’s convenient, it also makes clear why Apple has resisted adding a touchscreen to Mac laptops. Many of the touch targets are just way too small.5 The Apple Pencil helps with this since it’s a lot more accurate than my big fat fingers. I’ll often grab it off the top of the iPad when I need to minimize a window (don’t want to accidentally hit the red button instead of the yellow button) or another similarly precise task. Scrolling and right-clicking are a bit troublesome as well. However, the most significant limitation is probably that with Luna display you can only enter text on the remote computer if you’re running an external keyboard. It won’t bring up the software keyboard on the iPad. My iPad Pro spends so much time I the Smart Keyboard Folio that this isn’t really an issue for me.


I gave serious thought to running the mini very stripped down as far as software goes, but in the end, I decided to install my usual suite of apps. A big reason for this is, so I have the option to use Jump Desktop on my iPad to log in remotely when I’m on the road without a laptop. Having this option is a nice safety blanket that makes it easier to leave the laptop at home and go iPad only when I travel. It also means that if my iMac were to go down the mini is all set up to take over right away as my primary desktop.


One of the critical tasks for a home server is keeping everything backed up. A real advantage of the Mac mini over Drobo is that Backblaze will back up directly attached external hard drives but not network drives.6 A disadvantage is that I no longer have the built-in redundancy in the event of a drive failure that the Drobo provides. Instead, my data gets backed up from my two main external drives to another pair of external drives every night. Combined with weekly backups to “shelf” hard drives that don’t stay connected to my machine, I’m feeling pretty good about my backup.7


I’ve taken this opportunity to move my printer into the spare room where the mini lives. I print seldom enough that I don’t really need to have the printer within arms’ reach all the time. It’s shared over the network so I can still print from my iMac, and using Printer Pro I can send stuff to it from my iPad as well.8

Concluding Thoughts

I’m very happy with my decision to ditch the Drobo and use a Mac mini as my home server. Having my data on a machine that I can log into directly rather than just a network share makes lots of things simpler and faster. It gives me options that I just didn’t have with a Drobo, particularly when it comes to remote access.

The new mini is a very slick machine. It’s been fast and responsive and has handled the fairly heavy load copying data off my Drobo and doing initial backups to cloud services. I’m really glad that Apple decided to update the mini and keep it in the lineup.

  1. Especially a problem for things like scheduled backups that happen when I’m not sitting in front of the computer ↩︎
  2. iMazing backups of iOS devices seem to work much better when the destination is on a local drive than a network share, for instance. ↩︎
  3. I used the USB-C to VGA adapter I bought for my iPad to temporarily connect the mini to an old display to get things up and running. ↩︎
  4. I also tried out Screens, but ended up settling on Jump Desktop for my remote access needs. ↩︎
  5. Jump Desktop for iOS has some affordances for this, including different mouse pointer modes and support for specific models of Bluetooth mice. ↩︎
  6. I had a workaround for this (clone the Drobo to an external drive attached to the iMac), but it was kind of kludgy and meant the data on the Drobo only got backed up to the cloud once a week. ↩︎
  7. Much more on my backup strategy can be found here. ↩︎
  8. My printer predates AirPrint. ↩︎

Three months with the 2018 iPad Pro

I’ve been using the new 12.9″ iPad Pro for a few months now, and I thought it was time to update my first impressions. Overall, it’s probably my favorite (and most used) Apple device right now.

A smaller big iPad

Compared to my previous 1st generation 12.9″ iPad Pro the smaller overall size is really noticeable. The new 12.9″ is much nicer to use in the hand as a tablet (as opposed to in a stand on a desk). The reduced size and weight mean it’s also easier to carry around. I’m finding that I tend to bring it with me more often than my old 12.9″. Some of this difference may be down to the excellent Sutter Tech Sling that I got at the same time as the new iPad Pro, but the smaller size and lighter weight of the iPad itself plays a role too.

Face ID

Much like my experience going to the iPhone XS from an iPhone 7, FaceID is really the headline feature. If anything it’s even better on the iPad. It works in any orientation, and I mean any. Not just the four cardinal directions, but even when holding the iPad at an angle.

The one annoyance with Face ID is that I sometimes wind up covering the camera with my hand. This is a particular issue for me as a left-hander since, in landscape mode with the pencil charger at the top, the camera is on the left. I wish Apple had just made this a landscape mode device and put the camera in the bezel of one of the longer sides. One thing I like is that when FaceID fails the iPad definitely does a better job than the iPhone telling you why it failed (usually it’s either distance or having my hand over the sensor).

Combined with the ability to double tap the keyboard1 to wake and unlock the device, FaceID makes the iPad the device I’m most likely to use when I need to hop on for a quick task.


I really like the Smart Keyboard Folio. I think it’s the best keyboard that Apple makes at the moment (though that may be damning by faint praise). While there’s nothing like a mechanical switch keyboard with lots of key travel, for a low-travel portable keyboard I think the Smart Keyboard Folio is quite good. While it is thicker than the old Smart Keyboard, it makes a much more solid stand. I think the fact that it’s the same thickness across the entire surface is an aesthetic improvement over the “thin part/thick part” design of the older model. However, the multiple angle options don’t really do much for me. I never really use the more upright angle; it’s just too steep.


While I still use the keyboard the majority of the time, I’m getting far more use out of the new Apple Pencil then I ever did out of the old one. The old pencil was always buried amid all the clutter on my desk or stowed away in a bag somewhere, not worth getting out unless I had a big “Pencil job.”  Now, I make a point of grabbing the pencil every time I get the iPad out of my bag so that when I’m using it, the new pencil is always right there, magnetically attached to the top of the iPad. That’s the real game changer.

I’ve found myself using the new pencil quite a bit when editing text (which I have always felt was a weak point of iOS).  With the pencil I can double tap with the pencil to select a word, then use it to drag the blue dots at the end of the selection much more precisely than I can with my finger.  It also allows much more precise placement when dragging and dropping text or images.

I’m also using the pencil quite a bit for taking handwritten notes. I started out doing this in the Apple Notes app, but I think I’ve settled on GoodNotes for this role. While writing on glass doesn’t feel the same as using a pen and paper, it works well enough and the advantages of having my notes digitized from the get-go and not having to worry about filing them or finding them again later more than make up for that.

Display, battery, and USB-C

The display is excellent, but I can’t say I really notice improvements from my old iPad Pro like True Tone and Pro Motion in regular use. There are still some apps that haven’t gotten with the program and updated for the new resolutions, so they still display with a black border around them. It’s pretty seamless (just looks like the bezels are a bit thicker), but it annoys me that I’m not getting full use out of this display.

Battery life is excellent. I used the iPad Pro for notetaking at a conference last month, and despite heavy use, I really did get all day battery life out of it. Using chargers that support USB-C power delivery tops the battery off quite quickly.

USB-C on the iPad is still a story of unrealized potential. At this point, I’m not really using it for anything that I couldn’t have done with Lightning with the right set of dongles and cables. Even the quick charging was something I was doing using a USB-C to Lightning cable with my old iPad Pro. I really hope we get support for things like external storage in the next version of iOS.

The best iPad yet

If you just look at specs on the page, it doesn’t seem like the 2018 12.9” iPad Pro should be all that big a jump from the 1st generation 12.9”. It’s slightly smaller, swaps Touch ID for Face ID, and it gets a faster processor and a place to charge your Apple Pencil. In practice, I’ve found that the new iPad Pro is a significantly better device, one that’s changed how I use my iPad and how I divide different computing tasks among my various devices. I’m nowhere near ready to give up my Mac, but I do find I’m not using it as much lately, and that’s largely thanks to the new iPad Pro.

  1. This sometimes gets described as “double tap the spacebar to wake,” but you can do it with any key. ↩︎

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. ↩︎