Notes On WWDC

I was traveling the day of the Apple event and the WiFi on the flight wasn’t quite good enough to stream the video live. So it took me a couple of days before I could watch the entire keynote. The following is my miscellaneous notes and observations taken while watching the full replay:

tvOS 13

  • I’m glad they finally showed off a teaser trailer for one of their Apple TV+ shows. I’m not sure if “For All Mankind” is something I would enjoy watching in full, but it does seem quite compelling.
  • Multiple user support sounds really nice, but what if multiple people are watching TV at the same time, which I expect is quite common. How do you track that? Is there any way to tell the TV that there’s more than one person watching and have that sync back to their respective iCloud accounts? Or are you only able to have a single person viewing at a time?
  • Adding support for Xbox One and DualShock 4 controllers is a huge deal, but I still wish Apple would design and release their own controller.
  • The new Apple TV dock looks nice, but I’m curious to see how it works with existing applications that have Top Shelf extensions. There is already a limited number of top-tier apps with that functionality and introducing a new iteration of Top Shelf doesn’t give me hope that more apps will implement it.

I’d still like to see a bit more movement on the Apple TV front. The updates they introduced sound great, but I would feel more confident in my decision to go all-in on Apple TV if they pushed it a little bit further.

watchOS 6

  • New Apple Watch faces. They seem neat, but none of them look like they’ll knock Utility, Modular, or Activity Digital off of my setup — they’re the three best watch faces and it’s not even close.
  • I like seeing Calculator come to the Apple Watch. I’ve been using Calzy, but I’m not positive that it’s the best calculator experience possible on the Watch. I’m hoping Apple will help to raise the bar for this category.
  • Independent apps could be a huge deal for Apple Watch because there won’t be any need to build a companion iPhone app. But I’m more excited about the streaming audio API. The experience of listening to podcasts on the Watch at the moment isn’t great, but I hope these two features give developers the opportunity to improve it greatly.
  • App Store on the Watch goes hand-in-hand with the independent application capabilities, but I can’t imagine it being a good experience. Who wants to sit there and browse applications on their wrist?
  • Activity Trends is exciting — it’s the type of information and coaching that I’ve always wanted to see from the Watch.
  • I don’t think too much about my hearing and likely am surrounded by dangerously loud environments far more often than I realize. I look forward to a time when I’m notified to move further away from the source or consider using ear plugs to protect my hearing.

Apple continues to do a great job of improving the Apple Watch year-over-year and I’m happy to see this continue. The most exciting aspect of watchOS 6 is the new streaming audio API — I’m hoping that developers will make some great apps with this.

iOS 13

  • I’m interested to see the real world implications of the new application bundle slimming they’re using. Apps launching twice as fast is an impressive feat — if they can pull it off, it’ll be a big deal.
  • I don’t care about dark mode and don’t understand why anyone else does. I just don’t get the appeal.
  • I’ve never even tried a swipe-style keyboard before, so I’m interested to give it a try. I don’t expect I’ll use it long-term, but we’ll see.
  • I like that Mail is finally getting robust text formatting options, but I’m a little worried that this will mean an uptick in the amount of emails I receive with colored text and font size adjustments. That will not be an improvement in my eyes.
  • The new Maps app looks nice, but I think the most important new feature for me is the shareable ETA. I expect I’ll use that all the time.
  • I’m happy that Apple is making strides at fixing the social login issue. It’s such a convenient feature for users, but the privacy implications are larger than the average user realizes. Being able to use Sign-in with Apple is going to be a boon for user privacy. The randomized email address announcement received a huge applause and it deserves it.
  • I’ve thought about purchasing a HomeKit camera for our backyard, so we can keep an eye on our pool when we’re not home. But the privacy implication of an internet-connected camera kept me from actually purchasing. I might pull the trigger when some of these HomeKit Secure Video cameras hit the market.
  • HomeKit for routers is neat, but wouldn’t it be cool if Apple was the company that was building these routers? I guess our only hope is that Eero will add this functionality to its existing routers so I won’t have to spend another few hundred dollars on a new setup.
  • It didn’t take long for Vignette to get Shrelocked by the new Messages app, I guess.
  • I hope the new photo editing features won’t muck up the interface in a way that makes it difficult for novice users. I don’t want to mess with too many advanced settings, I just want to adjust a couple of sliders and call it a day.
  • There are so many instances where my wife and I want to listen to the same podcast or YouTube video. We end up sharing a set of AirPods and each of us wear one, but being able to share audio to multiple AirPod sets is going to be fantastic.

Based on the last iOS-related slide, there seems to be a ton of new features that were never showcased on stage. I’m most excited about the advancements to Shortcuts that weren’t discussed, but I’m sure there are several dozen other little improvements that will be nice to see as well.


  • Pinning widgets on the home screen is going to be amazing and it’s likely the first thing I enable when I install iOS 13 on my iPad. I’m a big fan of widgets, but was never in love with how tough they were to access. There was a time when the system would remember that you accessed your widgets last and present you with those when you swiped down from the top of the screen, but that was lost a few major updates ago. I’m glad we’ll have a quick and easy way to always access widgets again.
  • I’m happy to see that they’re adding the ability to use split-view with multiple instances of the same application, but I don’t expect I’ll actually use it in practice.
  • The app exposé and slide over app switcher look quite nice, but I am a bit concerned that this will add an additional layer of complexity to window management, which will inevitably get in the way of productivity. I’m curious to see how it will play out when you’re actually using the device.
  • Support for thumb drives and external disk drives is going to be a major deal. It was one of the things I mentioned to my wife after the event and it will be a big win for her. She recently switched to an iPad as her primary home computer and having the ability to throw a document on a thumb drive so she can take it to work is a major improvement.
  • Hearing a WordPress shoutout during the Safari segment was pretty cool.
  • I’m not too sure about the new gestures for text manipulation. I think I’ll get the hang of the new copy and paste gestures relatively quickly, but I’m concerned that the new text selection gestures are going to feel a little odd at first. There’s a lot of potential for conflicts — how does the system know I’m selecting text or moving the cursor instead of trying to scroll, for example? There were a couple of snafus during the demo, which doesn’t fill me with confidence.
  • The full page markup functionality is kind of amazing. I’m sure this has a ton of applications for web designers and developers, as well as teachers and print publishers.

Apple really hit it out of the park with iPadOS. This has been my primary home computing platform since I first purchased my iPad Air 2 in 2015 and it just continues to get better each year. I’m still a far cry from being able to do my day job from my iPad, but that’s mostly because of some specialty software that isn’t available on the platform yet. Maybe in a few more years, the system will get to the point where I can start pushing our developers toward releasing apps for iOS as well.

Mac Pro and Pro Display XDR

  • I think the new Mac Pro has a snazzy design. It might not be as elegant as an iMac or a MacBook Pro, but it has a powerful, utilitarian look that I love.
  • The machine is incredibly powerful out of the box, but they really gave themselves a ton of headroom to expand and upgrade the machine down the line as necessary. This is exactly what pro customers have been waiting for.
  • The new Pro Display XDR is an incredible piece of tech, but I wish they announced multiple models. A 32-inch display is massive and I’m sure there are plenty of pro users that would have liked to have an option that was a bit smaller, maybe 27- and 24-inch options as well. Even if it meant cutting down the features a bit on the smaller models. This would have been especially nice for users that prefer to have multiple displays instead of one giant display.

The Mac Pro and Pro Display XDR are expensive. Really expensive. I understand that this is aimed at the pro market, but I would have liked to see Apple offer these at lower pricing with significantly reduced specs. Long gone are the days of Mac Pros that can be purchased for $1999 and upgraded over time. And that’s a real shame.

I’ve been looking to upgrade our home server to something new because the 2011 Mac Mini that we had been using is a bit long in the tooth. It would be nice if I could have replaced it with a Mac Pro so that all of the storage was internal and the ability to rip/convert DVDs and Blu-ray discs was faster than the Mini is capable of. I hate the fact that if I want a ton of storage connected to our Mac Mini, I have to use a bunch of external drives that leave the whole setup looking like a mess.


  • Catalina is an excellent name.
  • I’m glad they’re finally unbundling iTunes into separate applications. And I’m even happier that they’re doing this after I’ve moved on to Plex for managing my media library. I just feel a bit better about the transition knowing that it will take place without me having to really feel any of the pain points associated with it. I still maintain an iTunes library for iTunes Match, but that’s far less important to my media workflows than our main library is.
  • Sidecar seems like a really nifty feature. It’s just a shame that they had to Sherlock an entire class of applications in the process. But I’m not someone that has really spent much time using multiple displays for any of my workflows. I tend to have my iPad propped up next to my MacBook Air while I work, but that’s mostly for managing music playback and occasionally testing a webpage issue on a different system. I’m curious to see if Sidecar changes that for me.
  • The Find My app seems like a massive upgrade from the previous iteration, with the separate Find My iPhone and Find My Friends Apps. I love that they’re utilizing other people’s iPhones to help you find your devices wherever they may be.
  • Project Catalyst is something that we’ve already heard about, back when it was called Marzipan. I’m hoping it will mean less Electron apps in my Dock and more native applications on my machine.

macOS seemed like less of a step forward compared to the rest of Apple’s platforms. Which makes sense, since the Mac is a much more mature platform. But I guess a large portion of their efforts in that regard went toward developer-level improvements with things like Swift UI and their AR endeavors.


This was one of the most impressive WWDC events that I can remember. The entire keynote was just packed with little announcements that will have a real impact on Apple device users’ lives. I think they probably could have cut a bit more from the keynote, giving us a more streamlined, compact event. I’m not sure if Swift UI and the AR segment really needed to exist within the main WWDC keynote and might have been better suited for The Platform State of the Union later that day.

But I look forward to getting my hands on all of the new software that they introduced during the event. I’m not sure if I’ll end up installing iPadOS or iOS 13 on my main devices, but it’s tempting. Perhaps I’ll take the plunge when the public beta releases this Summer.

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Tech Travel Kit

This past week, I traveled to New Orleans for a work meetup with my Happiness Engineer team. It was an incredible experience with a lot learning, amazing food, and games. I learned that Overcooked is an excellent game and there are actually legitimately good team building-type exercises.

This was my first time traveling for work and thought it might be useful to share the tech-related items that I brought with me during the trip. Not just because I’m obsessed with this sort of stuff, but because I’ve learned a bit about what I actually need and more importantly, what I don’t, when traveling.

I kept the majority of my tech items inside my carry-on, which was a Tom Bihn Pilot. It might be the best bag I’ve ever owned and it was roomy enough to hold all my gear while still remaining fairly compact. It has a vertically oriented water bottle/umbrella pocket with a metal grommet at the bottom, which will let water leak out instead of soaking your bag. I also made good use of all the o-rings inside of the Pilot to attach keystraps and various Tom Bihn pouches to organize my kit.

Here’s the full list of gear that I kept in the Pilot:

  • MacBook Air (2018): it’s a fantastic machine with a severely flawed keyboard. I still run into issues with duplicate or missed key presses, but hopefully I’ll have a chance to get the keyboard replaced with the latest iteration soon. I love every other aspect of this machine, though, and am glad I chose it instead of one of the Pro models.
  • iPad Air 2: It’s over four years old for me, but is still my primary machine for non-work tasks. Writing, browsing the web, watching video, and reading are at their best on the iPad. At least for me. Armed with my essential Shortcuts, I can do just about everything I need to do.
  • Nintendo Switch: This is an item that I don’t expect I would bring next time I travel. Two or three of my teammates also brought their Switches and I never ended up taking mine out of its case.
  • USB-C Charging Cable: I just use the standard USB-C cable that came with the MacBook Air, nothing special. I do have a fancier Anker cable, but It’s about six inches shorter than the Apple cable. I probably would take the Anker in the future because it’s a bit thinner and easier to wrap up and store. In practice, the length difference wouldn’t have mattered.
  • USB-C to Lightning Cable: I have this one from Anker, mostly because I’m a big fan of their other Lightning cables. It’s nice and durable and is great for charging my AirPods or iPhone while I’m working from my Air.
  • Magic Mouse 2: I might eventually replace this with a more ergonomical alternative. But until I find one that I like, it’s a nice, portable option that gets the job done.
  • Anker PowerPort Atom PD 1: The existence of these ultra-compact, relatively high power output chargers is one of the major reasons why I went with the Air. This charger can power my device without a hiccup and is much smaller and lighter than the default charger.
  • Sandisk USB-C Thumb Drive: This serves as my portable Time Machine Backup that I leave in my suitcase while I’m out and about with my laptop. This way, if anything happens to my Air, I can get back up and running quickly after acquiring a replacement.
  • Tile Mate: If I ever get separated from my bag, I can use the Tile app to trigger the unit’s audio tone to help me find it or make use of the map feature and rely on other Tile users to track it down. I started using these last year and don’t plan on looking back — every bag I own needs a Tile.
  • AirPods 2: The best headphones available. You might notice the omission of “wireless” in that last sentence and I can assure you, it was intentional. The battery life is great, they’re more pocketable than just about anything else on the market, and can switch devices is a snap.
  • Lighting Cable: A standard USB-A Lightning cable from Anker that serves as my primary charging cable for iPhone, iPad, and AirPods. It’s sturdy and does the job well.
  • Watch Charging Cable: I typically don’t travel with my Apple Watch, but thought I was going to do enough walking during the trip that it would be worth the extra gear in my bag. I ended up appreciating it much more than I initially expected. The ability to receive notifications on my wrist so I can keep in touch with my wife and having a timer that I could use without disturbing those around me were quite handy.
  • Anker PowerPort Mini: My go-to bedside charger, which typically powered my iPhone and Apple Watch. Every couple of days I’d use it to top-off my AirPods and iPad while I was working in the hotel or getting ready to head out in the morning. It’s the most compact two-port charger I’ve seen and the primary reason I haven’t dove head-first in to USB-C yet.

I also ended up with a small collection of tech kit in my checked bag. It was all the items that I didn’t expect I’d need or want on my travel days and consisted of the following:

  • Tile Mate: Again, there isn’t a bag I own that doesn’t have a Tile inside of it now. Having one in my checked bag was especially neat, I could often launch the Tile app and see that the unit was connected from inside the plane, which confirmed that my bag made it on the flight.
  • Lightning Cable: An additional Lightning cable that I could use for charging my devices. I never ended up using this item, so I might leave it at home the next time around.
  • Twelve South Compass 2: This is my go-to stand for the iPad, but something I never touched during my travels. I think I’ll keep it in my kit, though, because I did find myself using my MacBook and iPad simultaneously a few times. In hindsight, I should have grabbed the Compass, which would have made these situations a bit more comfortable.
  • Lightning to HDMI Dongle: Another item that never left my bag. I brought this in case I had some time to watch YouTube or Hulu before falling asleep, but I never had time. At night, I threw in my AirPods and listened to a podcast while I was getting ready for bed. That was the extent of my hotel room entertainment.
  • Apple Watch Woven Nylon Band: I like to switch out bands frequently and wanted to give myself the option to do so during my travels. I would definitely bring one again because I switched twice throughout the week of the meetup.
  • Switch Accessories: My portable dock (using this shell), power adapter, and Joy Con Straps never saw the light of day — I just didn’t end up using my Switch at all.
  • HDMI Cable: This served as a way to connect my Switch and my iPad or iPhone to the TV through the HDMI to Lightning adapter. I plan to leave this off my packing list next time as well.

As an aside, I used an Away suitcase as my checked bag for the meetup. I bought the medium sized model in asphalt. It’s a joy to use with all sorts of nice little features, but the built-in lock ended up breaking during my travels. The slider mechanism will release the zippers regardless of what combination you enter — that’s not exactly ideal.

I don’t want to give the bag up, though, and wouldn’t mind adding another to our luggage collection for when my wife and I go on trips together. I plan on contacting Away within the next couple of days to see if they can offer a replacement or if there is some trick that I’m unaware of to get it working as expected again.

One last thing to note, Automattic will have me traveling at least a couple of times each year. So if you’re as fascinated by gear as I am, you can expect I’ll be publishing articles like this again the future.


—May 3, 2019

Prism for iOS

—April 11, 2019

In-App Opt Out

—March 17, 2019

macOS Menu Bar Apps

—January 21, 2019

MacBook Air

—January 6, 2019

December Home Screens Update

—December 24, 2018

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