How I’m using watchOS 3.

The long-awaited watchOS 3 update dropped last week, and it is–as promised–a marked improvement. I’m sure it’s very impressive on a Series 2 Apple Watch, but even on my Series 0 1 it’s really great. I’ve been spending some time reading the comprehensive review of the update over at MacStories, and I’ve learned a ton. As such, my usage of the Watch has changed dramatically in the past week, and I’m really enjoying this device again.

I still have many, many issues with it, in about a million ways. But the changes are largely positive and between technical adjustments and updates to the user experience, are far and away great steps for the OS to take. I have a much more optimistic outlook for the device than I did a few months back. I’ve always liked it, but let’s be realistic, it was obnoxious for a while.

Anyway, here are the two core things I’ve adjusted that make the Watch better for me on a daily basis. It’s only been a week, so this may change, but it feels solid for now.

Multiple watch faces and ease of switching

This is the most important one, and it has a lot of layers.

I use a “home” and a “work” watch face. “Home” contained an analog face (Utility), the OmniFocus and Drafts complications for capture in the upper corners, and the weather on the bottom. “Work” is a different colored Utility face, with the time in London and the temperature in the corners, and my calendar events on the bottom. Switching between these was always irritating, because so much about the Apple Watch is irritating. Well, I’m happy to report that I am no longer irritated, because a simple swipe changes faces now and I’m whistling like an idiot through my day.

Since apps whose complications appear on your watch face have memory priority, they are quicker to launch. And since the faces are super easy to switch through, I’ve added an extra Modular face in the middle of the home and work faces, solely to use as an app launcher2. So my new layout is:

Home: Activity analog face with subdials (loving this); OmniFocus upper left, Music upper right (I love using the Watch to control audio), and weather on bottom.

[swipe]

Launcher: Modular face; Reminders, large weather in center, Just Press Record, Drafts, Timer

[swipe]

Work: Todoist (work tasks, upper left), time in London upper right, calendar on bottom.

In doing this, I no longer need to keep something like Just Press Record or Drafts on my main face at all times, because they would always get triggered if one of my kids bumped into my wrist, which happens way more than you might think. And although I have weather on my home face, I don’t have it on my work face anymore, which means the current conditions and high/low temp are one swipe away at work if I want them.

That center face–just holding complications as launchers–is freaking amazing. I only use about four third party apps on the Watch at all, but having things so accessible means I literally never need to use the godforsaken honeycomb again. Having the apps launch/refresh more quickly because they’re assigned complications is icing on the cake. And if you don’t mind an additional swipe, there’s no reason you couldn’t add a second launcher face alongside with different apps.

Now Playing and the dock

One thing that sucks is that since Control Center overtook the swipe up to reveal glances (the removal of which I could not be happier about), it means that one of the parts of the Watch I used the most is harder to get to. I would be in and out of Now Playing multiple times a day, whether with podcasts or music. I totally understand the continuity between wanting Control Center to be triggered the same way, but removing the ability to control audio (which of course you can do on the iPhone/iPad) makes this less appealing. I almost never open Control Center on the Watch. I suppose now you can check your battery really quickly, but that’s never been a concern of mine anyway.

Dock apps also get priority in memory, which is good. But… if the handful of apps I need lives in complications, that means I really don’t also need them in the dock too. So I have removed everything from the dock except Now Playing (and whatever was recently used, which I have no control over), which means that while not quite as accessible as before, Now Playing is one button click and a tap away, since it’s always in position (since it’s the only thing in the dock). Not a perfect solution, but working well in spite of the questionable demotion of its position.

These two things have drastically changed how I use my Watch on a daily basis. I’m extremely tempted to go check out the Series 2 at the store, but the change even on the original Watch is incredible. It’s actually far more useful now. Add in all the other little bits, like the changes to replies in notifications for Messages, and my most frequent activities have experienced a palpable reduction of friction. Which is exactly the reason this device exists in the first place. If Apple keeps this trend going in the right direction, the Watch will quickly graduate from a “yeah it’s cool, I guess” to a “I can’t imagine going through my day without this” kind of device.

I’m excited to see where this is headed.


  1. I will not refer to my launch day Apple Watch as a Series 1, because it contains the old, busted chipset, and not the new bumped one. No, I’m not bitter. Why do you ask? (I will probably continue to be a giant infant and get a new Watch eventually, but I’ve held off for the time being.) 
  2. A bunch of people were super excited about this idea and were thanking me for being such an innovative person, but in all honesty, this idea came directly from the MacStories review. I read it and was like YES and then immediately implemented it. I let everyone know on Twitter but figured it was worth an additional footnote. So go thank Alex, because I stole it from him. 

Summer explorations, part three: Resolution and refinement.

Parts one and two of this series are here and here.


I know this all seems like a tremendous waste of time, and in some ways I’d agree. I get a little sad when I think about how many other ways I could have spent the time I’ve sunk into task management and this kind of thing. Moving from one app to another. Thinking about perspectives, and filters, and tags. Talking to friends about what they do. Experimenting, tweaking, and returning to the starting point.

But if you’ve read this far, you’re likely the kind of person who sees some value in the process. And that’s part of my point.

I see two things very clearly now. The first is that this really has become a hobby, which is a little weird, but whatever. My hobby is playing with task apps and organizing information. This should come as no great surprise to anyone, given my previous statements. And for all the hand-wringing it causes me, I do like it. It’s fun. It’s like doing a jigsaw puzzle over and over again, but the pieces’ shapes change ever so slightly each time, so it’s familiar, but not exactly the same. It’s oddly delightful.

The other thing is that for better or worse, the way I feel about myself is intrinsically tied to how I feel about the information I manage in my life. I’ve discovered (re-discovered?) that I feel great about myself when I think I’m completely on top of things and not so great when I feel like things are slipping through the cracks. I suppose this is slightly better than tying your feelings of self-worth to something like your personal appearance or fiscal status, which may not be as easily managed.1 At least this way, I have a relatively manageable way to climb back out of whatever emotional abyss I find myself in from time to time, and can reason out why I might be feeling that way at that time.

I’ve found there’s something almost Konmari-esque about switching task apps after a certain amount of time. Each time I do this process, it takes less time than before, because I get serious about pruning things that have been floating around in my system that I have no intention of ever really getting around to. I shed a handful of things that were being maintained and adding to the overhead and re-prioritize some other things, forcing myself to take a good look at what I want to get out of the switch. It feels… cleansing, if we’re being honest. And I like that feeling a lot.

After all this, what have I learned?2

  1. I’m not going to feel guilty about doing this stuff. It’s fun, and it serves a purpose.
  2. I have great friends for humoring me as I go through this. Of course, they’re as bad as I am.
  3. Splitting work and personal data, while initially somewhat challenging, has yielded some interesting things both in how I use apps, but also in how I think about getting things done.
  4. If this is what I have to do to make me feel good about myself, things could be a whole lot worse.
  5. I should spend more time with my kids.

That last one pretty much applies to all aspects of adult life, but as you crest over the hill of “yay, I feel like I’ve settled into my new task app” it starts to kind of assert itself a little more.

So that’s it. Summer lovin’. Happened so fast. See you in about a year when I manage to get myself knotted up all over again about something else. Or the same exact thing. Either way.


  1. “No offense if that’s your bag, it just isn’t as important to me,” he said as he ate a third helping of dessert and drove away in his modest five-year-old mid-size vehicle. 
  2. The other thing I’ve learned is that it’s tremendously helpful to read my old blog posts. It’s like talking to myself in a private (except that it’s published publicly on the the internet) therapy session. 

Summer explorations, part two: The serpentine path of satisfaction.

Part one of this series is here.


As I said in the last post, splitting task data was something I’d not done before, and it became a very interesting scenario. I toyed with the idea back in July, but it was purely a theoretical thing, a thought technology and not much more. It didn’t stick then. In fact, it took seismic shifts in my daily routine and workload to precipitate the change and have it remain intact. But that happened in the past few weeks, and now I’m using two separate apps for work and personal tasks as opposed to filtering those things in a single app.

Once that decision was made, the next thing that happened was a realization that the way I think about “work” and “home” are drastically different–but I was managing them the same way, with the same overhead, filtering, tagging, etc. It didn’t make sense anymore. When everything is in one app, you start playing with filters and views to separate things you don’t need to see in reasonable ways. Eventually you hit on something that works, and you’re happy. But what I realized as I broke this data apart was that the things I want and need to accomplish in my personal life are vastly different from the things I need to accomplish at work. More importantly, the way I think about these things and the way I set about trying to do them really ought to be different too.

So I stepped back, with two disparate data sets, and thought about it. Todoist is a perfect tool for work, with team collaboration, web integrations, and cross-platform support. But what’s the perfect tool for everything else?

I’d been using 2Do for the past few months, and I’m a big fan of the app. It totally changed the way I think about information, how I organize it, and how I access it. I was late to that party and I’m far from the only fan, so if you’re interested, I encourage you to read these other great posts.

But 2Do started to feel (as flexible as it is) like more than I needed for this. So I did what any rational person would do in this position. I tried 47 other apps.

I began with redefining the things that happen in my personal life: there are “reminders”, which are things I need to remember, usually at a certain time. And there are “tasks” which can be things that need to get done but have no date—or things I’d like to get done, whether tactical or aspirational. I took anything without a date and created individual lists in Notes. I told myself I’d refer to them on a regular basis.

Mm hmm.

I went back to Reminders, like a gentleman. Built-in, deeply integrated, and simple as can be. Set up a few lists. The perfect place to store the things I need to be reminded about. Even does those cool deep-link things between apps as of iOS 9. The Notes idea, however, quickly became a weak spot, so I pulled those items into a single note in Drafts, which I am in all day, every day. Figured if it’s right in my face, I can see it and take action. I would look through that list each day and if I saw something I needed to do that day, I would highlight it and send it right to Reminders for attention-grabbing. It was flawless! Until it wasn’t.

Reminders is great because of what it does, which is exist on all your devices without a bunch of extra effort and mostly capture things in a reasonably expedient manner. But what it doesn’t do is allow you to make changes to those items easily and quickly. Or sometimes sync reliably (I had weird duplication of tasks, and stuff marked as done come back from the dead multiple times). All it takes is a few cracks in the facade, and I’m running. So while in principle, having all those unchanging things (bills, medication alerts, household stuff) always available on any new device via iCloud, it just didn’t feel like enough to take the throne.

More disappointingly, even though I adore Drafts more than life itself, it really isn’t the place for me to house my tasks and take action on them. The idea of a single Markdown list of the things I want to do was intoxicating, but it didn’t fit with my mental model of how I manage things I actually need to do.

Then I went back to Wunderlist, which I’ve used in the past. Wunderlist is cool because like Todoist, it’s web-based, so you can do some cool stuff with it. The app’s come a long way and features excellent things like natural language capture now. But between some syncing weirdness, some UI glitching on the iPad, and general malaise, I decided within a few days that it wasn’t going to be the winner either.

Then I snapped entirely and put everything back in 2Do. I wiped all my previous data one Sunday morning and decided it was the right place. I told myself I would change the way I think about organizing things (more capture, more action, less fiddling, less overhead) and I was convinced I was done.

Until about 45 minutes later, when I re-downloaded OmniFocus, installed it, and put everything in there too. OmniFocus, my longtime on-again, off-again girlfriend, with whom I share history, with whom I am not truly complete, despite my weary wanderings.

For the next 36 hours or so, I had all of my personal life in those two apps. And then I just freaked out. No, seriously, I did. I had a baby anxiety attack, quickly righted the ship, realized I’m a total asshole, thanked the heavens that this was my biggest problem right now, and just said fuck it, it’s going to be OmniFocus again, and that’s that.

The more I thought about it, the more I realized that the way OmniFocus organizes and displays information is what I was looking for right now. It does bulletproof reminders and due times. And with what I learned about not using due times and surfacing things at the right time when I need to see them, I figured out what I needed to do.

If you’ve made it this far, I truly am sorry. And thankful. We should hang out.

So.

Anything that either has to happen at a certain time or should happen by a certain time gets a due date in OmniFocus. Everything else sits across a handful of projects. Flat hierarchy (for now), no folders, no sub-projects, none of that. Simple. Barely any contexts. Contexts are a luxury now. I only create one when absolutely necessary. I have four perspectives: “Today” (due and flagged), “Available” (everything without a due date), “Wait Up” (stuff I’m owed or stuff I owe – good for work and personal life), and “All” which is just everything, in case I ever need to dive in. I can use Drafts and Siri for capture everywhere, and things like MailDrop and calendar integration as well.

The idea is: things I need to do each day (due) show up no matter what. In addition to that, I comb through “Available” each morning and choose one or two things I really want to get done–and think I can during the course of that day–and flag them so they show up. I have to be brutally honest with myself, and only pick those one/two, but it’s made me start to plan around how I want things to get done a bit more, instead of just making lists and never actually doing them. Last week alone, I cleared about four or five little things that had been hanging around just because I pushed myself.

And therein lies the big lesson.

This isn’t about apps, or systems, or UIs, or web integrations. It’s about getting serious and allowing myself both the flexibility to do things, and not do things as life dictates. It’s about changing the way I think about work projects and the way I think about my personal goals, so that both get accomplished in the best way possible. By changing the way I visualize and organize, I’ve been able to reset what my actual goals are, and start clearing items out. But it wasn’t the apps. It required a serious mental shift, and I had to be ready to do it. I wasn’t before. Things changed, and conditions became favorable, I acted on it, and I’m pleased with the results. I still have lots of work to do to move through some longtime lists I’ve been carrying around, but the new ideals I’ve created will lay the foundation for how I manage those things going forward.

Final chapter: after all this nonsense, what does it all mean? I realize some things about myself (again) and crystallize how I want to think about things for the future.