Keep It Simple

After my big work trip, I immediately loaded the betas of iOS 11 and watchOS 4. I spent the whole summer showing restraint, and I just couldn’t wait any longer. So I backed everything up fully — once to iCloud and once to iTunes — and loaded them on.

What I’ve noticed in two weeks is that there are some small, subtle changes in a few key areas that have a very large and profound impact on how I use my devices. And some of them are really, really great. It’s brought me back to a place I’ve flirted with before, but now I can see my tasks with a new perspective and with a renewed focus. And it started with trying out iOS 11…

iOS 11 on the iPad

Fairly recently, I got an iPad Pro. It changed a lot about how I use my devices, my workflows, and elevated my productivity. I was able to get a lot of things done before; now, with iOS 11, I’ve never been more productive. Having iOS 11 on my iPad is like having an Aston Martin DB11 and adding all of the James Bond gadgets you can handle; it becomes a much more capable machine without changing its form.

The multitasking has taken some getting used to, but I’m constantly flying between spaces and slide over. I’m using different apps in slide over depending on the mode or context I’m in (think social, productivity, finance, etc.), but it feels very freeing now that I have somewhat of a handle on it. As time goes on, I’m sure that feeling will increase even more.

There’s a lot more with iOS 11 – like the new on-screen keyboard that has the flick gesture that I want on the iPhone too – but I’m going to let that be done by the professionals.1 The good news of loading on the beta is that I no longer have a desire to figure out how to sell the 9.7” iPad Pro to get the improved 10.5” model. This thing handles everything that I throw at it, and I don’t have to jump through hoops to get there, which makes me happy.

Management of my tasks is now primarily done on the iPad; there are so many times that split screen has been a godsend for my productivity, and that is the most true when it comes to my daily task management. Having a good watch face to help me through my day had been pretty great before. I often used the Modular face with my task manager’s useful complication and watch app. But with iOS 11 comes watchOS 4, and now there’s a better way…

Siri Apple Watch Face

I’ll admit, when I first saw the watchOS 4 portion of the Apple Keynote, I wasn’t really blown away by everything. As I started working out, there are were some small improvements to how the workout app behaves on the watch. And when I loaded the beta on my Watch, I discovered that I was enamored with the Siri watch face.

A while ago, I created a Today workflow: this workflow would pull all of the information from my calendars, tasks, etc. and put it into my focus for the day. The problem with that was always this: I had to go seek the information, i.e. run the workflow. What I had always wanted was that information to automatically surface when I needed it. What I really needed was an assistant to get me my information and send it to me. I tried using Slack and IFTTT to help me with that, but it never seemed to work out the way I thought it should.

Now I have the Siri Watch Face. It brings up my calendar, the weather, the sunrise/sunset all in the order it’s happening. It still doesn’t bring up my tasks, at least not where I had them.2 I would love to see 3rd-party integrations for task managers or other calendars, weather apps like Carrot Weather or Weather Atlas, and even an Activity card to keep track of my progress throughout the day. Opening this up to the 3rd-party ecosystem will bring powerful new tools to the user, and allow the user to use their default applications in a new way to benefit their daily lives.

Overall, the Siri Watch Face is really fantastic, but there’s one thing that would make it even better: surfacing my tasks for me. And to do this, I need one more thing…

Reminders + Drafts

I’ve been down a road like this before. And there were some things about it previously that didn’t work for me. But there are a lot of things that have improved with the new operating system updates.

What I realized was that although having a dedicated task management app like 2Do, OmniFocus, or Things to house everything can be helpful, I really don’t need to have a complex system. What I needed was a place to house a large list, and then a way to move some of those things that are ready into my focus and apply some triggers (reminders) to execute my next actions. I don’t need a complex set of nested folders and lists; after all, I used to use a piece of paper and a pen for all of this stuff. After I sat down to figure this all out, I ended up just needing a more simple list structure: my master lists in Drafts which provide my areas of focus, my Inbox in Reminders for focus on next actions, and my recurring list in Reminders for when I need nudges for medicine, trash, and the like. And this setup works extremely well for me on the iPad Pro in split screen.

There are some challenges to using it in this way: how can I see everything that relates to my Home list now that it’s split between Reminders and Drafts? Tagging. While I wish that Reminders would get the ability for tags as has been done in Files, I’ll have to run with my own solution for now. It’s something that I’ve seen before,3 and it should help me with a lot of what I’m doing. For each list, I’ll tag it with a x[tag] format: for home, it will be xhome; for podcast stuff, it will be xpodcast. I’ll apply this to the items in my master lists and also the reminders that I pull into my inbox. I can then use Spotlight search to view everything related to that; within the apps, I can search for them. In Drafts, I have a filter created to search for xtasks, which I have put in each focus list I have. It’s a bit more work to type those tags in, but it’s going to be extremely useful going forward when I need to find something quickly.

Previously, I tried using Drafts + I would send tasks over via actions and then apply the date/time to get them done. And while that could have worked then, for one reason or another it didn’t. But now that I’m a little older and little wiser, my mind has been opened slightly and I’m learning about how I operate; what I’ve come to realize is that I need simplicity. So with that in mind, now I can highlight my next actions/tasks in Drafts and drag/drop them into Reminders. From there, I can set all the things I need to do.

Now, I know what you’re thinking: why not use Notes for your lists? That has a lot to offer: search, formatting, rich links, images, etc. That seems like a better solution. And you’re right. Well, for now you’re right. Part of why I want to keep Drafts as my repository for the lists is because I want to future-proof my plan. And I’m hopeful that syntax highlighting comes to Drafts sooner rather than later. On the image below, I have the same list in Drafts and Ulysses, just to show the difference it can make. The visual difference between the two is important. Now I can navigate through my lists with ease. So in the short term, I’ll live with the syntax the way it looks in hopes that the next version of Drafts supports this so that it makes my life easier. If for whatever reason it doesn’t, the good news is that Drafts is extensible enough and I can share this into Notes without a problem.

If in the future I need to expand my lists, I just simply need to create a new area of focus, tag the list appropriately, and add tasks to my Inbox in Reminders. From there, I just have to utilize my watch to help me get things accomplished. The system is good for small amounts, and I’m sure it can handle even my complex projects with ease.4

What it comes back down to is using Drafts as a central place of capture, something I have utilized before. My system has changed once again, but here it is that Drafts is at its core. This small little thing has reduced the mental friction of “where does this go”. I know where it goes. It goes in the place where all of my thoughts start. I might need to send it to another place — via an action, with drag/drop, or simple copy/paste — and then attach a reminder, but that’s ok. I can do that sort of thing on the fly without having to worry about where to start it. And for someone that can often get overwhelmed with how much there is to do with all that life throws at me, knowing that I can start in Drafts is a huge key to any success I have with my tasks life. Using Drafts in conjunction with native apps has led to bigger and better things that I originally had planned.

I’m also reminded of something that Merlin Mann often says on his multitude of podcasts (paraphrasing):

Try just talking to your dingus. Use Siri. Use the new features. Use the apps that you haven’t tried in a long time. A lot of this technology has improved with time.

He’s right. Things have improved with the help of integrations over the years. And while I would absolutely love to see Reminders get the same awesome treatment that Notes has received, it’s still not going to have a ton of nit-picky settings that other task managers do.5 So I should try to use it the way things are intended so that I can see what I can get out of it. Does it mean that I’m going to be able to manage some complex stuff? No. But it can be awesome when you start working within the ecosystem to make it work for you. You might not have a flesh-and-blood assistant, but you can have a better digital one than you’ve had in the past. The more you use it, the more you figure out how to work with it, the more you are going to get out of having this virtual assistant on your wrist.

With all of these changes, I can now manage all my tasks using my iPad Pro or iPhone running iOS 11 – my master list in Drafts, my focus list and recurring tasks in Reminders – and have it all surface for me on my Apple Watch on the Siri watch face. It puts it all there for me to look at in one scrollable view so that I can make sure I’m focused on the right things. The information I’ve stored is being surfaced to me. I’m letting go of the preconceived notions I had about what I should be using, and thinking about the way I want to work. I’m pleasantly surprised by how well this is working, and it’s only been a couple of weeks. How long will this last? Who knows. But I really like where this all is headed. I think I’ll set a reminder for next September: “Hey Siri, remind me in September to keep it simple.”

This post was originally a “Piques of the Week” post. I have taken most of that post and turned it into this one. Apologies for those that are re-reading some of this again, but it was the right thing to do.

  1. It’s a fantastic review that you can read in chapters on the web. Or download the ePub. Or listen to in audiobook form. It’s just very, very well produced. I hope to eventually be as good as Federico and the team. Bravo!
  2. I was using Things for iPhone and iPad for most of the summer. Fantastic app. I’m still using Todoist for my work tasks.
  3. I think I saw Gabe do this first, but it could have been from Merlin Mann as well. I can’t remember. Whomever it was, thanks.
  4. My life is complicated, more than a lot of others. However, most of the tasks that I do are simple and don’t require a lot of steps to be written down.
  5. Please, anyone at Apple that reads this: please make this happen. Reminders could be great, but it needs a bit of love. It’s not that far off, and I have ideas. Perhaps I’ll write them out. But it can be done. And I hope that you do it.

Piques of the Week – Volume 13

This time it’s all about my luggage.

In preparation for my upcoming trip, I wanted to make sure I had the right stuff for travel. Being that travel preparation is so important, I wanted to make sure I had the right stuff. I wanted to travel light, small, and better than I have previously ever done. In my research, I found these items:

Dash Hardside Carry-on by Brookstone

I’ve wanted a piece hardside luggage for a while. From what others have shared with me, it can allow you to pack more while using less space. And while there are many travel professionals out there with their ultra-fancy suitcases, I didn’t need that much for travel. I ended up finding the Dash Hardside Carry-on by Brookstone as a perfect carry-on bag.

Why a carry-on? A couple of reasons. First, I tend to overpack.1 But I need to travel extremely light for the trip I’m undertaking. I can also do laundry when I’m there, so I’ll be good. Second, I wanted a bag not only for this trip, but for future family trips where that can be our carry-on bag. The Dash is designed to fit into any overhead bin. With the 360° spinning wheels (which I love so much), it’s going to be great for going through the airport.

This bag is light-weight at 7lbs thanks to the polycarbonate shell, and I’ve been able to pack a lot of things in there thanks to the expansion zipper and some other travel accessories which I’ll get into below. I’m all packed and ready to go for this trip, and I’m thankful I’ll have this bag with me.

Eagle Creek Garment Folder

Packing a lot of clothes in your suitcase can be tricky. And even though some bags allow you to compress the items within, there are some other options to help minimize the space certain garments take up. Enter the Eagle Creek Garment Folder.

This folder comes with a helpful folding board with instructions. The two wings on the sides offer compression of the clothes to help minimize wrinkles and save space in your bag. And at 12″ x 18″, it fits perfectly inside my 20″ carry-on.

Packing Cubes

I’ve never really thought of using packing cubes. But for one reason or another,2 I ended up finding some to try out. First, there are a lot of options. But I ended up going with the Mossio Packing Cubes: there are 3 cubes, 3 laundry bags, and 1 shoe bag. And for $15, this seemed like the best deal for me to try.

While they are inexpensive, these bags are hardly cheap in feel. They use YKK zippers stitching, and have a thicker nylon fabric. The bags and cubes come in small, medium, and large sizes. The cubes fit nicely in the bottom of my bag, arranged neatly. Next to them are the laundry bags that also contained some items. I was able to place the garment sleeve on top of these, and the entire other side of my suitcase was left open.

I’m so happy with these, that I’ve ordered 3 additional sets: one for each member of our family, each in a different color. This will be very helpful for longer family trips: we can cut down on the number of bags we take, and use the packing cubes to distinguish which close belong to which person. For $60 total, we will be more organized as a family. I’m all for this.

I’m traveling for 2 weeks straight. And while there will be an opportunity for me to do laundry, I’m going to be happy that I’m able to pack everything I could need into my new suitcase and my backpack. Bon voyage!

  1. I like being prepared
  2. That other reason being Amazon Prime Day and a bunch of them were on sale

Piques of the Week – Volume 12

Smart Cover for iPad Pro

When I first purchased my iPad Pro 9.7, I immediately wanted to get the Logitech Create Keyboard Case. That has served me very well, and something that I have really enjoyed. But there are a lot of times when I’m just going around the house where the added heft of the functional case really didn’t work well. I started to remove the iPad from the case fairly often, but lost some functionality.

That’s when I thought to pick up the Smart Cover for iPad Pro 9.7. Not only does the Smart Cover allow for protection of the screen, but it also can prop up the device in two modes: the “viewing” mode and the “typing” mode.1 The viewing mode allows me to FaceTime with family, watch a show or two, or read the news if I feel like screaming into the void. The typing mode allows me to respond to people without having my device in a heavier case; this does require me using the on-screen keyboard, however. I can also pair the device with my magic keyboard for longer writing, which might come in handy for a large fall review that I’ll be working on.

I’ll even store my pencil up at the top, which is secured by the magnets. The pencil also fits in the groove on the front of the Smart Cover, but I’m nervous about it falling off and me losing it; it’s not something I often do while moving about, but while it’s on my desk or on my counter, I will keep it around.

If I had the choice to do it over again, I might have picked up the Smart Keyboard, but I like having the options. Using the on-screen keyboard has showing me that the larger devices might be better suited for that use case; either way, if I upgraded to the larger size, I’d likely get the Smart Cover for the 10.5 / 12.9. Highly recommended for sleek carry and around the house use.

Akwox Silicone Cover for Siri Remote

With multiple devices around the TV, there comes multiple remotes. And while I could get some sort of universal remote for everything, I much prefer using the remotes that come with the devices.

We have a small remote caddy at home, but one remote we have the most problems with is the Apple TV Siri remote: it’s always getting misplaced, and because the face is black, there’s a risk of it being lost. So rather than continuing to look around, I thought I would get a smarter solution – to Amazon!

I did a quick search for Apple TV remote silicone case, and arrived at the Akwox Silicone Cover for Siri Remote. There are multiple color options, but if we are going to see it in our house, I wanted to get something bright. I settled on a bright orange color for easy visibility. The case is a nice fit, and even helps point which way is up. For $7, I won’t have to worry about losing the expensive remote any longer.

  1. This is just my nomenclature for these. I can use the typing mode for note taking or drawing with my pencil, if I wanted.


Usually every summer, I’m going through a clearing of my life. It initiates in the spring, continues through summer, and then I start getting things back in order in the fall. I’m not sure why this happens, but it does. Rather than trying to fight it, I have learned to go with the ebb and flow of it all.

One big area of this is apps. I always try to reduce the number of apps that I use at any given time and cutting the reliance on multiple services when and where possible. I started using Slack as a personal information center last year, which prompted me to create a workflow that put my daily agenda front and center (when I would remember to run the workflow at night). That evolved when I got my watch, where I modified the workflow to run that morning to give me today’s agenda. And that worked well for a while.

Then, there was a change to the way Slack ran groups: the ability to delete archives went away. For one reason or another — ok, multiple reasons — this didn’t sit well with me, especially when I’m pulling in personal data into it. I’m not going all tinfoil-hat paranoid on this one, but if it’s going to be my personal Slack channel, I’d like to have the control to wipe out channels without archiving them.

This got me thinking about what I’m really using my personal channel for, and it really came down to several key things:

  • Alerts for Calendar events on Google Calendar.
  • Alerts for my local township news.
  • Image sources (NASA, Unsplash, etc) to get some cool images.
  • My RSS and feeds.

All of the rest that I was using it for didn’t seem so important. There was a sense of tinkering that I enjoy like when I used to build with Lego when I was a kid. I liked putting all of the pieces together because it was fun. And maybe the Slack thing was ultimately more fun than useful with all of the tinkering I needed to do to make it right.

So, I started looking around for other ways that I could accomplish those specific items. I realized that I probably couldn’t just use a single app for this, and although I like minimizing my apps, this sat well with me. What I started to realize that I was doing some tinkering again, but this time with the built in features of iOS. We’ve been accustomed to having dedicated apps for things that we often overlook the built-in solutions that have come a long way.

So to satisfy my needs and my desires, I started tackling these items one at a time.


I’ve wanted to get away from using Google Calendar for a while. So the timing seemed right, and I moved my entire family over to iCloud calendars. With this change, I get the alerts where events have been added, changed, deleted, etc. There isn’t any special integration that I have to pipe in, and I don’t have to wait a while for the notifications to arrive. The speed of iCloud sync appears to be faster. I’ve removed the Google Calendars from my devices now, and things are going smoothly.

RSS & News

I’ve used RSS readers in the past. The problem with them is that I wanted two different things: a curated list of specific websites I want to follow, and the news. I don’t subscribe to a plethora of websites in my RSS, so using a dedicated app didn’t seem right.1 Up to this point, I had never tried using the Safari Reading List feature. Within the bookmarks area of Safari, there are two other options: Safari Reading List and Subscriptions.

I took all of my RSS feeds from Slack and have started to use the Subscriptions feature. Now I have my curated list in a single place, and I can add and remove them as I need.

For my read-it-later service, I’m using the Safari Reading List. Not only is this a native part of the OS, thus eliminating a need for a separate app like Instapaper, but I can also add a link to the reading list from nearly everywhere, including from This means that when I get the Club MacStories newsletters, for example, I can tap and hold on the link in the email, add it to my reading list, and continue on processing my email.

I’m also using another native app — — for getting the news. I have thoughts on this, but I’m going to save that for another post. But in short, I like using it, even if I need to get better at doing so.

Local Alerts

Apparently my township website has a handy link to alerts; they have a service for text alerts through a service called Nixle. There aren’t too many messages that get sent, but if there’s an accident and I need to avoid a specific area, I get a text. If there are downed power lines, a fire, or some other emergency, I get notified through that system as well. It relies on the men and women in our police and fire departments to send in the alerts, but they are really excellent at doing so. I’ve also added the local government RSS feed to my Subscriptions so I can stay up-to-date on township news.


I don’t usually subscribe to an image of the day type of service. But with all of the exploration to Pluto and Jupiter as of late, the images of space are amazing to see. We are witnessing some history, and I like seeing that as often as it comes. So I’m using the subscriptions feature in safari to handle this also. Image sources are piped into Subscriptions and are bookmarked as well.

Dismantling my personal Slack has been an interesting endeavor. I’m usually a fan of single apps, piping in a bunch of information. But as the native apps have gotten better and better, I’m starting to utilize them more often. I’ve replaced the complexity of Slack with Safari, News, and Calendar – three native apps. I’m not relying on a middle-man anymore, and that feels better to me. Even with my current task manager, Things 3 for iPhone, iPad, and Mac, I can use the Reminders integration with Siri and Drafts actions, which feels more native than a custom sync solution.

As time is going along, I’m finding that in general, the basic solutions work for me. I don’t need complicated workarounds. Even though the same information I was gathering before in one place has now spread amongst several places, my perception is that it’s lightweight, cleaner, and better. Sometimes your perception of something being better is all you need to make it reality.

  1. And it would ruin the Feng Shui of my homescreen.