Rethinking Reminders

One of Apple’s fundamental strengths is creating software for the masses. You may scoff at this remark, but it’s true. Look at the ubiquity of Messages, Mail, and Notes: there are other apps out there for power users, apps that offer greater functionality, and apps that have better design elements in place.

And while there could be improvements to a lot of what Apple creates in their software, they have been getting better at creating apps that most users will want to use. If we take the example of Notes, we can see the potential Apple has for creating great software for most users. With the added features in iOS 10 and 11, Notes has become a powerhouse app while maintaining the usability for everyone. Over time, Music and Podcasts have gotten better.1 Mail isn’t great, but that might be more a function of email and email providers rather than Mail itself. But one of the most useful apps on iOS is in dire need of a refresh, a reimagining, and a glorious rebirth.

Reminders.

Task Management for All

It’s no secret that I love task management and task management software. And given that I’ve tried a bunch of software, I’d like to think that I have some perspective on the subject. I think a lot of people’s lives can be improved by task management. For years, I’ve tried to get family and friends to see the benefits; sometimes they do, most times they don’t. But that doesn’t stop me from trying.

What I have often found is that the idea of downloading a separate app bothers people. Sure, they’ll have a few dozen free apps – camera and photo editing apps, several social media apps, a bunch of couponing apps – but heaven forbid they get a paid productivity app involved in the mix. The mental friction of having a separate app to manage their lives can be difficult to get over. This is usually the point where I suggest simply using Reminders: it’s basic enough to get the job done, it’s a part of the OS, and they don’t have to pay to try it out. But the app isn’t where it needs to be.

Apple could take Reminders forward as a key app in the ecosystem if they wanted to do it. And it’s not too far off now that iOS 11 has been released. Reminders can improve in a lot of ways to support further use of the app without taking away from its simplicity. It can be made into more of a task management system with some small changes to the layout and features, all while keeping it simple and easy to use. Sure, there might be some better options out there like OmniFocus, Things for iPhone/iPad, 2Do, or Todoist; but each of those options are for different levels and styles of task management, and can be difficult to onboard with someone who has never used a complex app before.

What I can envision for Reminders is a blending of the some commonly used features for these apps, and doing what they do best — create a version that, while not first, is nearly equal to alternatives and is natively a part of the OS. And it can do all this while maintaining one of its own strengths: being native. There are some simple features that could be added without much of a problem, while others might take some re-thinking and redesign in the future.

New Layout and Aesthetic

There are many changes I would like to visually see, as well as adding some new features. Doing so would not only help this app excel, but also by extension help the user better understand his/her tasks and aid in a true task management system. First things first: take the linen paper background and burn recycle all of it.2 In the UI refresh of iOS 11 and the move to the Editorial-style layouts, I am surprised to see Reminders be left behind. It’s dated, serves no purpose, and really limits the possibilities of the interface going forward. If we look at something more modern, say Files or Mail, there are many positive things that Reminders could borrow from its native counterparts: the dedicated side bar and its behavior, sort states that could be modified to fit the task management paradigm, and there is enough space to have clarity and utilize the space to push an updated UI that works for lists and tasks.

Now that we have a better canvas to work with, the view into your task management can be changed. For the most part, keeping lists separate can still work; in fact, for non-power users, this is likely a preferred method of seeing tasks; in a compact view or slide over, it would present in the same way. For power users like myself, I often want to see all of my tasks at once. Sure, you can keep a separate list of your tasks in another app like Drafts or Notes and move them over when you need them; but using a system like this (as I’m currently doing) is a bandaid. It would be nice to keep all of this information in one place.

I think Apple can accomplish this by utilizing system lists, like that of the Scheduled list. It could be in its own section of the app, similar to how Favorites is contained in Files. By adding an All Tasks list, the user can see all of their tasks presented to them. There would be headings for each list, denoted by their color, which separate the tasks; additionally, these can be foldable headings to minimize what is in view. This would also enable drag/drop within the full task view between lists without having to leave the current view. In the future, allowing for the addition of user-generated Smart Lists would be a huge benefit to those with many tasks. There could also be a completed and recently deleted task item for the times you make a mistake so you can recover your work, or if you really want to see what you have completed along the way.

By providing a more modern design, Reminders can have the simplicity it has today while expanding its capability. The utilization of space and information density can be increased with the new UI, while still maintaining the most basic task management. Some of the existing interface for lists can be carried over, namely the color and sharing interface. The task editing can remain the same, but can be presented in an iOS 11 style. It no longer would make Reminders the bastard child on iOS, but would make it part of the new iOS family.

By giving the user an opportunity to view their entire task management structure, it will allow a more-than-casual task management aficionado to really power through a review of what is going on with their entire life, all while using a native solution on iOS that integrates with the entire system.

Tags

Another power-user feature that could be added in an elegant way would be the use of tags. This is already present in Files, and I think presenting consistency across apps would be a huge win for everyone. The tags would be listed off to the side with their color/name; in a single view, these could be shown like a traditional list.

The advantage of having these items laid out in this way is that it also gives a view (or a perspective) based on a tag when selected. If you could have a person or a place as a tag, this could be useful for when you see someone or near a place; it could further be expanded by allowing a tag to have a contact or address applied, ideally using drag and drop. Having the ability to filter your tasks on a tag brings a power-like feature to casual users. Additionally, searching in spotlight for a specific tag would also present items in Files, Reminders, and — if it were added — Notes. The user would only have to remember the name of the tag to find what he/she needed across the system.

When in a view with a sidebar, a user could drag a task over to a tag and apply it, just as in Files. The frameworks for creating these options are already there: they just need to be applied to Reminders.

Drag and Drop

Speaking of drag and drop, I would love to be able to drag anything over to be reminded of it. Think of the “Hey Siri, remind me of this” feature, but without using the voice. I can do this already with a link from Safari or an email. But what about a specific Note? Dragging over a specific note currently copies the entire text contents of the note, rather than a link back to the note itself; I can, however, ask Siri to remind me of this note later, and a link to the specific note is inserted. The difference in behaviors is maddening. Unifying them, or at the very least presenting a user with the option to import a link to the note or the text using a contextual menu, is better for the user in every way.

Additionally, drag and drop could bring some other features into Reminders. The ability to add documents, images, etc. to any task is now possible thanks to drag and drop. Having the option to add additional contextual information to a task would be immensely helpful. Need to get a grocery store item, but want to make sure you get the right thing? Now you can take a picture, and drag it right onto the task; the image would be added into the notes section of the task. Want to be reminded to take action on a specific file? Simply drag it from Files, and a rich link to the file would be created. You can tie the important information into a task from multiple sources across the system.

Other Features

Sorting is badly needed in Reminders. The UI elements are there today in Files, and they could be presented in Reminders in the same fashion. Having the ability to sort lists based on due dates, priority, tags, and name are basic functions that any good task manager should provide. If they are provided in other Apple apps, why not this one?

The repeat features of Reminders have been greatly improved over the years, but there’s room for improvement. Most 3rd-party applications have options for repeat after completion, weekday/weekends, and other custom repeats. Going forward, having a pause option for repeating tasks3 would be a fantastic feature to implement; it is a great feature for the user going on vacation.


One of the biggest benefits to making these changes in Reminders is the additional benefits of a native solution. This will play well with Siri, the Siri watch face, and all of Apple’s 1st-party apps. I don’t have to figure out how to mispronounce the name of the app I’m using, I can just speak what I need to do. It can utilize all of the newest frameworks and APIs that Apple releases. It also means that some of the existing features, like list sharing, and can be applied to tasks as well. How great would it be to have native, 1st-party collaboration for task management right out of the box in iOS?

I could go deeper into this, but I’m leaving a lot open for Apple to figure out. The mockups that I have created — all using Pixelmator on iOS — are just a start of what could be; I would love to see some small UI differentiation while still maintaining the overall aesthetic that is found throughout iOS. Maybe they have a better solution in mind, but I hope that they take some key elements from amazing tasks management apps out there, while simultaneously combining it into their own solution that works across the operating system. It needs a functional and visual overhaul, and with the new Editorial UI that has been put into the system, now is the time to make that change.

Presenting new users with a deep-linking paradigm in a non-complex manner will help them better understand what is possible with their operating system and allow them to explore new options. Giving users the options to view their tasks in multiple ways by making things extensible using existing system-level interactions is the best way forward for Reminders. If it is built into the system from the start, there’s a better chance that users will utilize its functionality to enhance their lives, which is something that Apple as a whole strives to do with their products.

It’s time to rethink Reminders and give it the update it so desperately needs and deserves.

  1. I know there are some out there that would argue this point and say that Spotify or 3rd-party podcast clients are better. But this isn’t about the tech users, but rather the general user.
  2. Grab Notes and do the same, while you’re at it.
  3. Steal inspiration from Things here.

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 + Reminders.app. 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.

The Sum of the Parts

This summer opened my eyes to trying new things with task management. I had a great, wonderful system, and then split it in two. Then I tried Reminders instead, and loved it even more when I got my Apple Watch. And life as I knew it was going along just fine. Until something just felt off.

I couldn’t put my finger on it. I was accomplishing what I needed, and there wasn’t really a hole in my system. Life had just gone from chaotic to simplistic. And maybe that’s why things felt wrong. I can’t explain why, but it just didn’t feel right anymore. I’m sure it’s a bit of a sickness, but I have come to realize I need to have some complexity in my life.

So I started thinking of what to do next. Did I need to try a new system? I’ve tried OmniFocus, Things, Due, etc. and nothing really stuck, despite those apps being great in their own ways. I thought about what made the Reminders experiment so great: the simplicity. But yet, when I needed to look at everything going on, it was cumbersome at best. I tried to make something work, but it just felt wrong to me. So maybe it wasn’t a problem of the tools I have and what I’m using, but rather how I’m using them (or not).

And it’s led me to a strange, crazy place.
Continue reading “The Sum of the Parts”

Basic

Over the summer, I experimented with a lot of different app configurations. I tried too many task management apps to see how different things fared. I loved my solution, but I wanted to see what else was out there. Then I bifurcated my tasks and used two apps. Splitting my brain in this way was tough, but has been extremely rewarding.

A few months later, I found myself with an Apple Watch. Continue reading “Basic”