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.  

Macstock 2019

While I’m a longtime Mac user, I’ve never been to either of the big gatherings of Apple faithful. I never had the chance to make it to Macworld Expo and not being a developer or Mac journalist I haven’t been to WWDC. However, when I heard about the Macstock conference on some podcasts and read some people’s experiences there on the Mac Power Users Forum, I was intrigued. When they offered tickets for this year’s conference at a substantial discount on Cyber Monday, I decided to take the leap and signed up.

Before the Conference

I flew to Chicago on Thursday and paid a quick visit to some relatives in northern Illinois. After returning my rental car on Friday, I took the L into the city and sampled some deep dish pizza (something that I’d missed on my previous trip to Chicago). I took the train back out to Crystal Lake and hit the Friday night Midwest Mac Mingle Mixer at a restaurant next to the hotel.


Macstock proper kicked off on Saturday morning. There were a bunch of great presentations. The schedule was set up with short 20-minute presentations from each presenter in the morning with longer 45-minute “deep dives” in the afternoon. The morning presentations were all on the main stage, one after the other. The afternoon presentations were split between the main stage and a breakout room, so sometimes you’d have to choose between two speakers (and there were some difficult choices).

Allison Sheridan had a cool presentation that took advantage of links between Keynote slides to tell a series of interlocking stories about her experiences in the Mac podcast space. At the end of the afternoon session, she dove into the technical details of how she set that up. Chuck Joiner spoke on giving great presentations. To show what not to do, he had some good real-world examples of really terrible slides that he’s seen in his day job.

Rosemary Orchard Presenting

However, the highlight of Saturday’s presentations was definitely Rosemary Orchard’s presentations on using Siri and Shortcuts. She had some great demo shortcuts and did an excellent job starting with the basics and ramping up to some really high-level stuff by the end of her deep dive.

Perhaps the most hilarious moment of the day came when an attendee was going down the lunch line asking if anyone had experience taking an iMac apart and ran into Stephen Hackett. As a former Apple Genius and authorized service provider, Stephen was made for this moment. He spent the lunch break completely disassembling the iMac and upgrading the RAM and SSD.

Stephen Hackett disassembling an iMac

The day finished off with the taping of Mac Power Users episode 500, which was in a class by itself. Keen MPU listers will note that as of this writing, the most recent episode is #493. Stephen and David are going to keep this in the can until it’s time for episode 500 to publish in September. Stephen asked the audience not to post any spoilers, so I’ll just say that he and David did an excellent job and they created a fitting 500th episode for this great podcast.

Stephen Hackett and David Sparks recording MPU 500

After the MPU taping, we all shuttled back to the hotel and had a nice catered dinner, followed by lots of great conversation among like-minded folks.


Sunday kicked off with a preview of the Macstock Short Film Fest. They showed a couple of very cool short films that had been submitted by Macstock attendees. The rest of the day followed the same pattern as Saturday, with 20-minute presentations in the morning and longer 45 minute deep dives from the same speakers in the afternoon.

David Sparks presenting at Macstock

David Sparks had an excellent presentation on how to make time to do your creative work. I’ve read David’s Presentations Field Guide and heard him talk about presentations on MPU, but this is the first time I’ve seen him present in person. He did not disappoint (very smooth and very funny). He had some great points on how and why to make time for creative endeavors along the lines of what he’s been talking about lately on Focused.

Mike Schmitz presenting at Macstock

Speaking of Focused, David’s co-host Mike Schmitz followed him with a pair of great presentations on Ulysses. They were about 2/3 tech talk with lots of great detail on how to be productive with Ulysses and integrating it with apps like MindNode, Aeon Timeline, and Deckset (Deckset is particularly tempting, if frustrating since I’ve pretty much switched to the iPad for all my mobile computing needs). The remaining third of his presentations focused on bigger picture issues with doing creative work, including some inspiring words on creativity and creating a writing habit.

Josh Rensch had a great morning presentation. It was nominally about kitchen workflows, but really about effectively bridging the divide between nerds and non-nerds a relationship. It was also a masterclass in a rapid-fire presentation style (246 slides in less than 20 minutes). Unfortunately, I missed his afternoon presentation because it conflicted with David’s.

How do you draw a crowd at Macstock?

A crowd at Macstock

Stephen Hackett disassembling Rosemary Orchard's Mac mini

Disassemble Rosemary Orchard’s Mac mini

Stephen Hackett disassembling Rosemary Orchard's Mac mini as Rosemary looks on

Brett Terpstra (drink!) had a good talk on writing workflows. I missed the morning portion (I was hanging out while Stephen disassembled Rosemary’s brand new Mac mini for a RAM upgrade) but the afternoon portion was very well done. I’m looking forward to seeing Brett and Josh’s full presentations when the videos go up online.

While Macstock was not quite over (there was one more afternoon speaker session and the film festival), I had to head out and catch the train into O’Hare for my trip back.

Macstock was an awesome experience. The talks were great, but the true highlight was all of the great folks in attendance. While I love talking about nerdy stuff online (like on the Mac Power Users forum) I seldom get a chance to sit down and talk with people who have a passion these things in person. Being able to sit down at any table during lunch, or turn to the person next to you in the audience during a break and talk about the tech and productivity stuff we all love is an experience that I really treasure.

I’m definitely planning on going back to Macstock next year.

Personal Retreat – July 2019

I recently did my third personal retreat. I got quite a bit out of my first two retreats earlier this year and I was really looking forward to this one.

Preparing for the Retreat

In his personal retreat video course, Mike Schmitz pretty strongly recommends going somewhere and getting away from the distractions of home for your retreat. Both of my previous retreats have been “offsite” and I think that it definitely helps. Not only does it eliminate distractions, I find it also helps me get a different perspective.

I’ve done my previous retreats in a room at a local hotel and a cabin at a state park. I liked the cabin quite a bit, but in July I figured it might be a bit too hot to enjoy the state park’s amenities (the high on the day I did the retreat was 100 degrees). Instead I found a nice loft on Airbnb just the other side of downtown from my apartment and booked it for two nights.

When I did my first personal retreat I made a last-minute decision to do it on paper, rather than electronically. I’ve kept doing the same for subsequent retreats. I brought the same Studio Neat Panobook I used for my last retreat and a Retro 51 Tornado pen. Though I did the retreat on paper, I also brought my iPad for reference material (and to do this writeup).

I headed over to the Airbnb in the late afternoon and took advantage of the good restaurants nearby to get some sushi for dinner. The next morning I got up early, took a walk, then dove into the retreat process.

For my previous retreats I watched Mike’s videos before going on the retreat and took a bunch of notes. During the retreat itself I just relied on my notes. This time I took advantage of the WiFi at my Airbnb to rewatch the videos while I was doing the retreat.

Core Values

The first exercise in the personal retreat course is to define your core values. Obviously, if they really are core values they’re not something that should be changing every three months, so I could probably get away with just a quick review of what I did last time. Nevertheless, I’ve found it useful to go through this exercise from scratch each time. Mike has some great prompts to get you thinking about what’s truly important to you. Comparing my answers this time around to the previous retreats they’ve been pretty stable and I haven’t made any changes to my core values as a result. However, going through the process has lead me to emphasize different values or parts of particular values each time.

Where are you right now?

This portion of the personal retreat course includes two exercises: listing all of your current commitments and responsibilities, and rating your satisfaction with various areas life in the Wheel of Life exercise. I find listing out my commitments helpful in getting a handle on what my responsibilities are. The Wheel of Life, not so much. This is the third time I’ve done this and I still haven’t found an approach to this that really resonates with me.

Designing the life you want to live

In contrast, designing the life you want to live is probably my favorite part of the retreat. It asks you to envision the life you want to be leading in five years. Mike has a great set of prompts to get you thinking about what you want your life be like in all sorts of different areas, from your job, to personal relationships, to where you live and how you spend your time. He asks you to envision what a day in your life will be like five years from now. When I did this during my first retreat I got so into it that I wrote out way more than could be done in a single day. Since being overly busy is not the sort of life I want to live five years from now, I’ve taken to imagining an entire week of my future life. This allows me to include all the elements I want to include while having it unfold a more pleasant and realistic pace.

The Retrospective

Having taken stock of where I am now and envisioned where I want to go, the last step before setting goals for the next 12 weeks is to look back at what I’ve done since the last retreat. This process starts with listing out your accomplishments during the past three months.

There always seems to be a mismatch between how little I feel like I accomplished and how much there is when I get it down on paper, but it was particularly acute this time around. I’d done quite a bit of travel during the past three months (I was on the road 24 days during that time). In addition to the time I spent traveling it took me a long time to get caught up after I got back. Nevertheless, I still managed to accomplish quite a bit, including some very significant things at work. It’s easier to dwell on the things that fell through the cracks, so an exercise like this that forces me to acknowledge the accomplishments is very helpful.

After listing your accomplishments, the next step is to reflect on what went well during the last three months and what could have gone better. Dealing with travel, and particularly the post-travel period definitely falls in the “could have gone better” category for me. I fell off the wagon when it came to block scheduling a couple of times and had trouble staying on top of my task management. Both of these definitely affected my productivity. Partway through the quarter I also ended up deciding to basically drop one of my 12 Week Year goals entirely, as I just didn’t have the time to dedicate to it while I was trying to dig out from the effects of travel.

I took a break for lunch at one of the nice restaurants in this part of town before diving into the last part of the retrospective. This involves asking: What should you start doing? What should you stop doing? and What should you keep doing?

Setting Your Goals

Before setting your goals, Mike advises taking stock of your existing commitments for the next 12 weeks. In a good illustration of why this is important, I realized that I’ve got almost as much travel coming up in the next three months as I did in the last three months. Given how much that travel disrupted my productivity and my 12 Week Year goals, realizing how much travel I had on tap led me to pull back on some of my goals.

I did still set three goals. Two of them are carried over from my last 12 Week Year; however, I scaled down a bit to take into account the impact of travel. One is fitness related, while the other is a goal to do better on my time blocking and task management. The third goal is a new one, replacing the one that I dropped partway through the last 12 week year. This new goal is to start the process of getting a professional certification. Getting the certification is going to be a longer term goal (the earliest I would take the certification exam is next spring). Because I’m going to be going through busy periods at work later this fall and again next spring I want to start studying for the exam now.

During my last personal retreat I chose some leading indicators for each of my goals (tracking how often I did the things that would lead to accomplishing each goal). I think that the leading indicators were useful, but I had too many of them, making it difficult to consistently track them all. I cut way back on the number of things I’m tracking this time around. Just four indicators in total (one each for two of the goals, and a pair for the third goal). This should be easier to keep track of and help me keep up with both my tracking and with progress on the goals themselves.

Executing the Plan

The final part of the personal retreat is to lay out your ideal week. This is an exercise that I really dove into the first time around, with a color coded Numbers document showing what I’d do every day of the week. However, I kind of skated on it this time around, just making a few minor tweaks to my existing spreadsheet.

Reflecting on the Retreat

I stayed a second night at the Airbnb (though I did pop back to my apartment for our monthly resident social event that evening) and headed home the next morning.

These retreats are very valuable for me. I continue to be grateful to Mike Schmitz for the personal retreat concept and for his excellent course, especially the great prompts that he’s incorporated into the course to get you thinking.The clarity around the core values and the vision of the future that continues to be very beneficial. In addition to the 12 Week Year goals, I’m also finding that I get other insights from the process.

For instance, while I’d known all the travel really threw me for a loop, the Retrospective part of the retreat helped me really appreciate the impact that it had on my productivity. Going forward I think I need to have a post-trip plan to help me catch up after being gone and I need to set aside time specifically for those post-trip activities. Another non-goal thing I got out of the retreat is that I need to do a really deep cleaning of my OmniFocus database. There are a lot of tasks and projects in there that need to be dropped or put into deep freeze.

All in all, another successful retreat!

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.

Second Personal Retreat

I got a ton out of my first personal retreat back at the end of January. It helped me define a long-term vision for my life and had a significant impact on how productive I’ve been during the past three months. Now that three months have gone by it’s time to do it again.

For my first personal retreat, I decided to go whole hog and follow Mike Schmitz’s recommendation to do it “off-site,” away from home. I found a lot of value from getting away from familiar, distraction-laden environments. Back in January, I rented a hotel room for a couple of days. While the hotel room worked well, I thought I had a good chance of getting good weather this time of year and reserved a cabin at a local state park for two nights.

Preparing for the Retreat

Ahead of the retreat, I reviewed all my notes from Mike Schmitz’s Personal Retreat Handbook video course. I also finished up rereading The 12-Week Year (which I was reading for my Masterminds group).

I brought all of my notes from the last retreat but deliberately decided not to look at them ahead of time. Since I’d be at the state park cabin, I packed plenty of food and drink and a sleeping bag, along with my usual tech gear.


Last time I had made a last minute decision to do the retreat on paper, using a Field Notes Steno Book I had in my backpack. I liked the analog experience, so this time I planned for that in advance. I brought a Studio Neat Panobook notebook. I’ve had the Panobooks since the original Kickstarter, but I haven’t used them much because they seem too nice for just day to day use. The personal retreat seemed like an excellent opportunity to put them to work on something ‘special.’

I headed out to the cabin mid-afternoon on Thursday. After a stop at a local grocery store for some supplies, I enjoyed a nice dinner. I finished rereading The 12 Week Year while waiting out some rain showers then took a nice walk at sunset.

The Retreat

After breakfast and an early morning walk, I got started on the retreat.

Core Values

The first exercise is to define your core values. Rather than starting by reviewing what I’d written at my first retreat, I decided to go through the exercise from scratch. I thought it would be interesting to see how consistent my responses were. After all, core values should represent things that don’t change radically every few months.

Mike’s course has a great list of questions to help prompt you to think about what you value. After going through these, I opened up my notes from last time and compared them. They weren’t exactly the same, but I covered a lot of the same ground. I ended up keeping the same set of core values, but I refined the wording a slightly, merging two of the values together.

This time, rather than walking up and down the hallway of the hotel between exercises, I was able to get out and spend a bit of time enjoying the park by taking a short walk (I saw a trio of wild turkeys).

Where Are You Right Now?

The next exercise has you list out all of your commitments and rating your satisfaction with different aspects of your life. I found my responses were fairly similar to last time. The numeric values differed (it seems like I had been more willing to assign extreme ratings back in January) but the areas that had been highest continued to be highest, and the ones that had been lowest continued to be lowest.

Designing the life you want to live

Next up was an exercise involving thinking about your life five years from now. The Personal Retreat Handbook has a nice list of prompts to help you think about what you want your life to be like in the future. This is one exercise I really dove into at the previous personal retreat; I did the same this time.

The course asks you to write about a typical day in the life.  Last time I did this I ended up with a tremendously overstuffed day to fit in everything I wanted to write about. Since being insanely busy is not one of my ambitions, I decided to do a week in the life this time. That allowed me to fit more of what I’d like my life to be like at a much more realistic and relaxing pace.

The Retrospective – Major Accomplishments

After another break, I came back for the first part of the retrospective, listing your major accomplishments. I’d been making an effort to track my accomplishments better over the past 12 weeks, so this went a lot more smoothly than it did the first time. I was able to fill an entire page in the Panobook in fairly short order. Even before this exercise I felt like I’d had a productive quarter, but seeing everything listed out definitely drove home how much I’d gotten done. It was a very heartening experience.

The Retrospective – What you’re going to change

After lunch, I did the second half of the retrospective exercise, looking at what went well and what could have gone better during the previous quarter. While there were a lot of things I feel I did well, there were also quite a few areas for improvement.

Setting Your Goals

Finally, where the rubber meets the road. This time I set three goals, rather than the two that I set at my first retreat: one health-related, one around learning a new skill, and one around improving my task management. The skill goal, in particular, is also more ambitious than my previous goals.

One area where I part ways a bit with Mike is his suggestion that you concentrate your goals on the areas you rated lowest back in the “Where are you right now” exercise. The health and learning goals are actually in two of the areas I rated most highly. They’re highly rated because both areas are very important to me, so even though I’m doing well in them, I felt like I’d get a lot out of pushing them even further.

Rereading The 12 Week Year helped clarify the difference between goals (what you’re trying to accomplish) and tactics (how you’ll go about achieving that goal). These were somewhat muddled together in my first round of goals. This time they’re more clearly defined.

The other thing that rereading the book led me to change was to take a more quantitative approach to some of these tactics. I established leading indicators for all the goals (essentially how much of the time I’m performing the tactics compared to how often I said I would). Two of the goals have lagging indicators as well (real world numbers that the tactics should move the needle on).

One important aspect this time around was assessing my existing commitments for the quarter. I’ll be traveling for two full weeks, plus a few additional weekends. Recognizing this lead to some weasel wording in my tactics and indicators saying I’ll do them “when I’m not traveling.”

Executing the Plan

After a break, I picked up with the last exercise of the day. The main activity in this exercise is to create your “ideal week.” Last time around I dove into this, spending a lot of time creating a color-coded numbers spreadsheet laying out my ideal week. The spreadsheet was still mostly good to go, so this time I just tweaked it to accommodate some stuff related to my new goals.


With that, I finished my second personal retreat. I took another walk and made dinner (boneless buffalo wings, which is turning into a tradition on these personal retreats). Then played some Stardew Valley and binge-watched The Tick.

The next morning I enjoyed the state park a bit more, then packed up and headed home.


I feel good about my second personal retreat. It wasn’t quite as revelatory as the first one, but that’s really an experience you can only have once. I got more out of the retrospective this time around (and I think I’ll get even more out of it next time, with more ambitious goals and better-defined tactics). The goals this time around are much more ambitious. I’ll need those well-defined tactics to help achieve them. Come July, we’ll see how I did.

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.

Morning Routine

Something I’ve found myself doing lately, almost by accident, is having a much more consistent morning routine. Rather than setting out with this in mind, it’s been a side effect of two of the goals that I set at my last personal retreat.

First off, I set a goal of writing every single day. No specific target for how much, or what to write. It could be 5 minutes working on a blog post or an hour working on a novel (or vice versa). The goal is just to sit down and spend some time moving the cursor every single day (and if you look at the number of blog articles I’ve published in the past few months it’s obvious that it’s having a positive effect on my output).

The hard part was finding time to do this. I already established a habit of exercising every morning (it was pretty much the only thing in my morning routine that was consistent). I didn’t want to give that up. While I don’t have a fixed time when I’m required to be at my desk at work most days, I didn’t want to push that any later than I was already doing. I did have a bunch of time that I was spending messing around on the internet (including reading through the overnight posts on the MPU forum). I found that this aimless messing around online was often the monster that ate the rest of my morning routine. Imposing a bit of order on that could help me find some time to write, but not as much as I wanted.

I decided to bite the bullet and move my alarm back from 6am to 5:30. The extra half hour, combined with imposing some discipline on my morning internet usage, would give me some time to write.

One of the ways I’ve imposed that discipline is my goal to time block each day. In fact, the morning has become by far the most consistent part of my schedule (particularly on weekdays). On weekdays I could basically copy and paste everything before 9am and only have to deviate from it a couple of days per month.

With the help of multiple alarms on my phone and a clock radio across the room, so I physically have to get out of bed to shut it off, I get up at 5:30 every morning. The “every morning” bit is important. I am not naturally a morning person. If I sleep late one morning, it throws off my sleep schedule for days afterward.

From 5:30 to 6 I drink a glass of water and read the MPU forum and the news on my iPad. At 6 I pry myself away from the internet and do my morning exercise routine. This generally takes a little over an hour. Throw in a shower and some breakfast and about 7:45 I’m ready to start writing. I’ve got 45 minutes to write before I have to head out the door to work.

As morning routines go, this is certainly nothing earth-shattering. Exercise, shower, and breakfast are about as typical as you can get. What I thought was interesting is how consistent it’s become without explicitly making consistency a goal. It’s really been a side effect of the writing and time blocking goals.

Is time blocking right for me?

Recently I posted about how I schedule my whole day using time blocking. This sort of thing can be controversial, and it clearly doesn’t work for everybody. Some of the conversation around this got me thinking about what makes it more suited for some folks than others.

I think a lot of it has a lot to do with what kind of work you do. Think of work as a spectrum: On one end of the spectrum is work that’s completely interrupt driven. For instance, a manager who spends all of his time responding to emails and phone calls from other people and dealing with urgent issues as they come up. On the other end of a spectrum is work that’s completely predictable and consistent. Say, assembly line work.

If your work is very interrupt driven, where most of your day is spent reacting to stuff that comes in, time blocking probably isn’t going to be very useful. There’s just not enough predictability to plan out your day in advance.

It might seem that time blocking would be helpful for very routine work, but if the routine is totally consistent time blocking isn’t really that helpful. There’s no reason to sit down time block each day if all you’re doing is repeating the same schedule over and over.

Where time blocking really works best is in the middle of the spectrum. The work is variable enough that planning is useful but consistent enough that planning is possible. This really boils down to lead time. If you can’t know what you’ll be working on 15 minutes from now, time blocking is impossible. If you know what you’ll be working on at any given time next week or next month, time blocking is unnecessary. The sweet spot is when you can plan out the rest of the day or tomorrow’s work with reasonable certainty.

Of course, this is an oversimplification. Lots of people’s work is a mix of different types. There are times when you get interrupted even in the most consistent of jobs. And even in very interruption-driven jobs, there might be some things that are totally consistent, like weekly meetings.

While time blocking is most useful in situations where most of the work falls on the middle of that spectrum any time blocking system needs to be adaptable to some level of interruption and some level of consistency. Of these, dealing with consistency is much easier. Those regularly scheduled events can be the skeleton that you build your time blocks around.

Interruptions are trickier. At a basic level, it may just amount to staying flexible and not getting too committed to your time blocked schedule. If it’s a quick interruption, you may be able to deal with it and get back to your planned time block, but sometimes you just have to roll with the punches blow up the schedule. I like David Sparks’ description that, “A calendar is a soup, not a puzzle.” Sometimes you need to stir the soup.

Another alternative might be scheduling your interruptions. “Scheduling interruptions” may seem like an oxymoron, but depending on how time sensitive the interruption is, it may be possible. If most of your interruptions can wait a few hours, you might be able to do something like scheduling a block of time at 11 o’clock to deal with all the interruptions that came in that morning (this is effectively what the advice to only check your email twice a day is doing). Similarly, you may be able to set up “office hours” when you’ll be available for walk-ins from colleagues and others while walling off other time in your schedule to do deep work.

Time blocking isn’t for everyone. Depending on the type of work you do it may or may not be suitable (not to mention other issues, like whether it fits your personality or how much control you have over your work). Even for those who find time blocking suits them, it’s not going to work the same way for everyone. That said, it can be a very adaptable practice.

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.