Using Drafts, Reminders, and Slackbot as a task management system.

I know, this sounds like a fever dream. Stay with me. I promise it’s headed somewhere.

Over the summer, I made the decision to split my work and personal tasks between two separate systems for a lot of reasons. It’s stuck, and I’m really happy with that decision.

I also decided that in terms of thinking about personal tasks, a basic hierarchy is all I need. There are things that need to get done by a certain time, and then there’s everything else. I was using OmniFocus for this to great success.

But if I’m honest with myself, I’m still over engineering things. Work stuff, ok, there’s other people and dependencies, and lots of other things at play. But my life? At home? I essentially need lists, and that’s about it. Simple, basic lists. With the occasional nudge to do something once in a while.

I’ve also been (re)drawn to the idea of using as much of the stock OS as possible, which means I’m looking at Reminders for things. I’ve been down this road before.

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.

iOS 10 seems to have fixed a lot of the weird behavior I noticed previously. Also, if I’m not forcing Reminders to be a system it’s not–i.e., using it for what it’s actually good at–I can actually derive an incredible amount of value from it. Here’s what it does well: it reminds you to do stuff. If an alert fires, and you don’t dismiss it or complete it, it hangs out on your lock screen until you do. Every time you look at your device, it’s there, like “hey, yeah, hi, don’t forget this thing”. Simple, quiet, persistent. I like this behavior.

So anything with a date/time/location goes in Reminders. Easy enough. But what about this part:

what it doesn’t do is allow you to make changes to those items easily and quickly

Well. I had a good think about this, and realized that if I’m using this tool correctly, chances are I’m not making changes, but I do still need a little flexibility in assigning those dates and times. So as always, I turned to Workflow. In minutes, I had built an “add reminder” action that I can trigger anywhere from the widget that asks for input and either presents a list of my most common times for an alert or one of three most-used locations (home, office, pharmacy).

I can add a new reminder, with the right alert, in about half the time. It’s freaking great.

That brings me to all the stuff that doesn’t need an alert, but has to get done at some point, or at least should. From that same post:

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.

Once again, I was trying to make a tool do something it shouldn’t. So I changed the way I thought about these lists. I need to keep these lists handy, and they don’t always require action but I need to remember to check them (in GTD, this is a “review”) occasionally. I’m in Drafts all day long, for a million reasons. I’d never tried filters before, so I decided to give this a whirl.

Not one list, but a few key ones. See, if these things are always accessible, in a tool I’m already using all day, I think I’m more likely to idly scroll through and do several quick reviews, and potentially cross some things off. This is definitely the big variable in this new system, and I’m waiting to see how it feels. So far, so good.

Drafts doesn’t have line spacing controls, and one of the other things I wanted was a little more padding in the list views for ease of reading while I scan quickly. So I added a very basic Unicode character that creates a little bit of space between lines, allowing for a nicer view. I added that to an action key, and made an action list to send the draft to the right list.1 This is also good because I can filter against that same Unicode character, and keep things where they belong, keeping my inbox cleaner and actionable.

Within the lists themselves, I can use the native link mode and line re-ordering functionality Drafts has to move items around (or delete them when complete) or view a URL I add to a task. Works pretty well.

But what happens if I have an item in this list that I decide I need a nudge for? I took that same Workflow action I’d built, and modified it slightly to take a selected line of text from Drafts and send it through the same flow. It kicks it over and runs the same super fast steps and dumps it into Reminders for me, to ping me at some future point.

So I’ve covered basic lists and the escalation point where I need an alert to move something along. I also mentioned Slackbot. My love for Slack is well-documented at this point. I’m always looking for different ways to use it. I decided to try using Slackbot for a certain class of nudge that is absolutely not mission-critical—one that I didn’t feel like seeing in a list every time I opened Reminders—as a test. So I have a handful of recurring reminders I’ve asked Slackbot to yell back to me every now and then.

I have a “home” list of stuff we need to do around our house. Totally not urgent, has no time sensitivity. Every Saturday at 9am, Slackbot goes “hey check your home list and see if you can do anything today”. I don’t need to mark anything as done, and if I want to hear about it again, I can defer the reminder for later or the next day. This is only for stuff I kinda don’t really care about, but still want a poke for occasionally. So far, so good. And you can review what you’ve told Slackbot to track with a simple /remind list slash command. I’m still exploring this one, but it’s been fun so far. I’m currently trying to think of other little nudges that I don’t necessarily need to take action on, but that I’d like to see now and again.

That’s pretty much it for now. For… now. Every time I change this system up, I feel like I’m losing my mind a little more, but I also feel like in restructuring everything, I keep learning about what’s important to me at different times in my life. And I’ve decided that this is my hobby. I really do like playing with these things. I have almost no free time, and a busy work and family life, and this stupid crap actually makes me happy. It’s not getting in the way of doing stuff, and that’s the important thing.

So yeah, that’s this month’s experiment. I’ll let you know how it goes.


  1. And naturally, Tim improved it by combining everything into one action, so if you want to play with this stuff, just use his instead. It’s tight. 

Things I like this week, volume 29.

Twenty Thousand Hertz

This is a new podcast that I discovered thanks to it being featured on a recent 99% Invisible episode. It’s all about telling “the stories behind the world’s most recognizable and interesting sounds” and is exactly the kind of stuff I adore–people examining something that permeates our consciousness and culture at a deep level. Great storytelling, great production value.

And the latest episode is literally about one of my favorite things: 8-bit sounds. I had the biggest grin on my face as I listened to it.

A delightful show, and I can’t wait to hear more.

Twenty Thousand Hertz

A return to form.

I type a lot. Hundreds, if not thousands of words, every day, across various devices. I’d say it’s a primary interaction model for most of us at this point. It’s changed the way I think about information, because since I can type, I often do, and it means that since I can type pretty quickly, I can capture quickly too.

Along the way, I’ve used lots of different notebooks as well. That was a vestigial practice–held from college, I’d wager–where I was never without one. But in my professional life, I could just never get it to stick the way I could in my personal life. I’d use a Moleskine or some Field Notes for a while, and then inevitably gravitate back to my Mac in most cases.

And I’ve tried to blend these ideas in the past, with various degrees of success. I’ve drastically increased my usage of iOS across personal and professional activities, but I’m still typing. A lot.

Earlier this year, I got the 12.9″ iPad Pro and an Apple Pencil. I enjoyed the novelty of finally having a digital handwriting tool that almost exactly matched my writing style on paper. But I still wasn’t using it much for this. I’d pull it out and open Paper to sketch something quickly or explain an idea, or annotate something, but I just didn’t make the mental shift to embracing it as a real input method.

But in October, I attended a conference for work. And I decided to try something different: I would sit in sessions and meetings and just listen and only write down something that stood out to me as interesting or important. What happened as a result of this decision should surprise exactly no one: I listened more attentively and actively, as opposed to simply trying to capture every detail of what was communicated. The things I did capture were of more value because they were most likely the important aspects of the information, and the act of capturing them more deliberately by hand allowed them to gestate in my mind a little more.

This isn’t a new discovery. In fact, I already knew this to be the case, even on a personal level. But blending the idea of the digital notebook along with the act of handwriting triggered something new for me. Since then, I’ve been keeping daily handwritten notes in an app that was recommended to me by a friend. Each day, I start a new notebook, log anything I need to during the day, and at the end I export a PDF to Box for archiving.

The act of more consciously listening and being present in a discussion has been transformative for me. I think that for a long time, I felt obligated to log as much as possible but what’s really more important is engaging in the discussion when it’s actually occurring.

To the extent that this is a digital activity as opposed to paper-based, in doing it this way, I allow myself a quick and easy way to backup my notes and share them if need be. I can drop images in and annotate immediately, or record the entire session and take notes alongside. Distinct advantages over a paper notebook, but the biggest one is that I have one thing to carry and I can do everything with it, as opposed to a computer and a notebook, which I’d then want to scan in some way, adding another activity to the chain of events.

I’m dealing with information differently now, and I’m really pleased with how it’s been going. It’s been about a month, and I really enjoy the act of writing again, which surprises me. It might not be as efficient a method of capture, but part of that capture process is understanding what it is I’m keeping for later—and slowing my mind and allowing that information to breathe as it moves around has been a real change.

Of course this all led me to buy a second iPad too, but that’s a story for another time. 😉

Things I like this week, volume 28.

Apple News

I’d been using it for light reading with a few sources before (not as an RSS replacement), but as of iOS 10, I’ve left the “Top Stories” stuff turned on and it’s become one of my most-used apps. I like the new look of the app, but still think it’s a bit odd on the iPad (I find there to be strange formatting issues with too-small fonts, odd layouts within articles, and photos that are huge and cropped in totally weird ways). On the iPhone however, it’s fantastic. I’m in and out of it all day, every day.1

Handwritten notes

Hopefully I’ll have more to say about this soon (working a post out in my head for the past few weeks) but for now, suffice to say I’m rediscovering how slowing down the ways in which I listen to and take in information can actually help my brain. Using the Pencil/iPad instead of typing, and reshaping how I do things.


  1. I mean, it’s mostly bringing me abject misery all day, every day, because 2016 is a goddamned emotional black hole, but I’m still enjoying the app. ↩︎

Things I like this week, volume 27.

I realized I haven’t done one of these since August, and that made me sad. Part of the reason for doing it at all was sharing fun stuff, but the other part was to make sure I was writing. Things have been extraordinarily busy this fall, but that’s no excuse. I can find 10 minutes to write a paragraph about a fun thing.

Let’s get back to it, then.

Zinio for Libraries

I’ve known about Zinio as an online magazine service for a while. And I am a huge fan of our local libarary, which has terrific kids’ programs and lots of digital media. I’ve been borrowing ebooks for a while now, but I completely forgot they also have a magazine service through Zinio.

This is different than standard Zinio, and you’ll need to make sure your local library supports it, but if they do, you’re straight bonkers if you don’t avail yourself of this. Here’s how it works.

You need a library card. Do that if you haven’t already. You’re paying taxes, you might as well have it. It’s worth it.

Then, download the app–this app, not the regular Zinio one–because it has a special login function that connects to your library’s system.

You visit a page on the web in Safari where you can see current and back issues of lots of different magazines. You pick the one you want. Then you go back to the app, refresh, and boom. You’re reading the latest issue of whatever you want in seconds, like a real grown up person.

This app shines on the 12.9″ Pro too, I’ll add–if you want the truest experience, hold it in landscape and you can see both sides of the magazine like you’re holding it for real. But if you rotate into portrait, while the device is enormous and bizarre, you get a massive, full-size page to read, no zooming required. This may be the only use-case I’ve yet found for the 12.9 in portrait mode, but it’s solid.

I’ve just been doing this in the evenings, lazily flipping pages in some magazines I like, and I don’t feel guilty about spending several bucks on a paper issue I’ll barely read, because it’s totally free, and if an issue sucks? Who cares. Delete it and get something else. Instantly.

Totally great, and a lovely complement to Apple News (another thing I’ve really come to enjoy with iOS 10) as a casual way to read.

Zinio for Libraries

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.

Summer explorations, part one: A feeling of relative control.

Summer traditionally seems to be a great time to muck around with my systems and workflows. Lots of people are away, so the office gets these nice little lulls where I can sit quietly for bits of time and ruminate. We’re on the cusp of a new iOS release–and new hardware–but nothing is happening quite yet, so I’m thinking about it, but also can’t act on anything. Year after year (if I read back through blog posts and journal entries), I end up tugging on threads in my setups over and over again, exploring things I’ve used for months or years, trying new things, generally comfortable with upending everything, knowing in September I’ll be wiping everything and installing iOS fresh.

This summer’s been no different, apart from me being way busier than normal at work. But ironically, it’s been this shift that’s precipitated probably some of the biggest changes and realizations about the way I organize and deal with information in my life. In fact, the changes in my responsibilities have triggered a chain of events that will likely alter the way I deal with information for a long time.

It came in phases. Phase one involved creating a calculated division between my work and personal worlds, which didn’t exist before. Phase two built on phase one and is all about how I think about doing things in my personal life, and how I structure the things I need to remember, the things I want to accomplish, and just about everything else that makes its way into my brain.

But I’ve come out (what I think is) the other side now, and the crazy part is: sure, I’ve played with some apps and done some reconfiguration of tools, but in doing the things I’ve done this time around, I’ve uncovered some things that I didn’t expect to.

We’ll get to that.

This is all probably too long and meandering to walk through in one post, so I’m going to break it up. Gotta get those 16 page views somehow. Fair warning, this is some nerdy-ass stuff.

Let’s begin.


Since joining a much larger company, the things I need to do–and subsequently keep in my mental RAM–have changed dramatically. I interact with many, many more people, on a global scale, across time zones, in different disciplines, and with greatly varying agendas and goals. It’s actually been an incredibly good experience for me as a person because it’s opened me up to thinking about things in new ways, and given me the opportunity to work with lots of personalities I might not have been exposed to otherwise. All good things.

Along with this comes a lot of new stuff I need to do and think about. I lead a small team doing interesting projects, but I also play roles in other parts of the company as well. I have to span a lot of different activities in the course of any given day, and I may not have time to cover everything I need to. I have had to learn to delegate and share some of the load, which honestly was a challenge for me, but utterly necessary in order to keep my sanity. Luckily for me, my team is amazing and is more than willing to help out with anything.

So instead of keeping my tasks in a silo by themselves, we’re all using Todoist together now. It has been transformative, mostly because I’ve never used it with anyone before. 1 I’ve used it extensively myself, but the service begins to take on a whole new life when you use it with other people. So we all have the app installed, and the team has access to just about every project in my personal list. This way, they can see everything I’ve got going on, can jump in and handle things if they see an opportunity to do so, and I can assign tasks to them as I work through setup of projects on calls and in meetings. I get notifications when things get done, and we can comment on tasks, attach files, and chip away at large bodies of work all at the same time. It’s been terrific for feeling like we’ve got a handle on everything we need to do, and I’m glad I kept my premium account active, because it’s really been quite handy.

However, now that I’m sharing all this stuff in Todoist, I’ve discovered that I want to have the things I’m tracking in my personal life somewhere else. The other part of joining a large company is stuff like IT policies and compliance, and I’ve found that having a clean separation of work and personal data on my company-provided laptop is the most comfortable way for me to work. It also gives me another reason to bring my iPad to work every day, which is essentially my personal laptop now anyway.

So I’ve split my world: email in different apps (Mail for work, connected to Exchange, Airmail for personal), files (Box for work, Dropbox for personal, along with my Synology), and tasks (Todoist for work and a million freaking things in the last month for personal stuff). For some reason, my calendar is the only thing I don’t mind blended, although I tried that too for a while (Calendar for work, Fantastical for personal).

I’ve never done this before; work and personal life was always together, and not in an unhealthy way. When you help start a company, it kind of happens. You don’t draw those boundaries the same way you might when you’re not personally invested in something. It never bothered me to see that stuff all mashed up–in fact, I really liked figuring out how to filter and sort in creative ways. Some of my best tinkering has been around how to use my favorite tools to show me exactly what I wanted when I wanted it. Now I’ve realized with all the things I’m tracking, the best way to do that and accommodate my personal wishes to keep work and personal life connected but separate means I take that information and split it right down the middle.

With certain data, like email, this was easier than I’d expected. I always thought having a unified inbox was wonderful, until I was sifting through dozens of work emails to lift out the actually important personal email about my mortgage that I absolutely couldn’t afford to miss. So I bought Airmail and haven’t looked back. It got a great update right around the time I was making this change, so it was rather fortuitous.

Files were easy too. I keep one folder from Dropbox on my work machine called “Sync” and it only contains a dedicated 1Password vault I use for work stuff, and my Alfred data. Everything else on that machine is work stuff and so it lives in Box.

Tasks. That’s where things take a real turn. Big surprise, I know.

Next post: the clouds part, I go a little crazy, and land right back where I always start, a little more enlightened for the journey. As it should be.


  1. Federico has written quite a bit on using Todoist with his team at MacStories, and they do some very cool stuff over there with it and a few other tools. 

Things I like this week, volume 26.

Catalyst Case for Apple Watch

I’m a longtime fan of Casio G-Shock watches. I have an Apple Watch because I like the idea of smartwatches, and because it works with my iPhone the best. I’ve never particularly liked the way it looked, but I was willing to make a fashion trade off for functionality. It obviously has the best feature set of any watch I can pair with my phone, but it looks like a space lozenge. I mean, if you’re a fan of watches, it really probably isn’t doing anything for you. But it does do a lot of crap.

Anyway, I found this and it’s basically the exact kind of style I want in a watch (chunky, rugged, metal + plastic, colors optional; round) but isn’t out until this fall. It does surf forecasts (yes!) but runs Android Wear (I can use that with an iPhone, sort of, right?!), which may or may not provide what I need/want from my smartwatch. It’s also as much as an Apple Watch, so I’m not sure I want to take that dive. Maybe. I don’t know.

In the meantime, I’ve made an aesthetic upgrade to my setup, by adding this chunky-ass case. I’d heard of Catalyst, because I always buy waterproof cases for my phones (usually Lifeproof), primarily for beach/vacation action, but was unaware they also made a product of similar pedigree for Apple Watch.

I wanted a (smart)watch I could take surfing with me, but they explicitly say you shouldn’t engage in “high-velocity water activities” with the case. I don’t know if two-foot waves on a longboard at the Jersey Shore qualify as “high-velocity”, but hey, who am I to challenge a manufacturer on their product constraints. But I thought I might be able to get away with it, since most of the time I’m not surfing, and it definitely beefs up the Apple Watch in a decent way.

Overall, I think it’s pretty great. I definitely like having a bigger watch, and it is a bit more rugged looking. Because of the shape of the Apple Watch, it’s limited to a larger version of that vertical rectangular layout, but it adds a nice extra bulge on the side where the crown and button sit, which does change the overall shape in an interesting way. I’m not in love with the band, which is soft silicone–don’t get me wrong, it’s insanely comfortable but because of the finish of the rubber, it slides out of its loop quite a bit (the little ring that holds the extra bit of watch band down, I mean), so I end up flappin’ in the breeze a little more than I would like.

But it’s more in line with the kind of look I want, and it does add some extra water resilience, so I’m pretty pleased with it. Not too bad to take on and off, but you definitely won’t be switching bands quickly. You’ll need a few minutes to undo the case and get the watch out, but it’s not hard: a single tiny screw and a pair of snap hinges, and you’re done. I haven’t put it through its paces in terms of durability because it’s so new, but for looks, it certainly meets my criteria.

Catalyst Case for Apple Watch