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

An update on how I’m using my private Slack team.

Almost a year ago, I began using Slack by myself, having created a private team with a bunch of purpose-based channels. If you want to know more about how that experiment started, check out that post.

People ask me from time to time if I’m still using it, and the answer is a resounding “yes”. In fact, Slack continues to improve and offer great integrations with lots of other services, and it’s even easier than before to send information into a Slack channel from almost anywhere. It’s blossomed into an indispensable organizational tool that I spend a great deal of my day in, browsing, working, and pushing information into and out of the team.

The addition of Safari View Controller to the app has made a lot of these things I’m pulling in faster to access, and provided a more centered experience. I’ve refined my channels a little bit since I started, and added some new ones, centered around other topics of interest.

Here’s my current roster.

#alerts – high priority notifications, Google alerts I’ve set up for various things,1 and I watch a specific Dropbox folder for collaboration alerts, since they usually show up a few days late or not at all.

#blogposts – each time I post something, the link to that post is dropped into this channel. Mostly just a quick reference if someone asks for one.

#clipboard – multi-device snippets and pasteboard sync. Still love it and use it constantly.

#daily – this is a new thing I’m trying. I’ll explain in a minute.

#deliveries – I mostly just buy things on Amazon, so I don’t use this all that much, but I will occasionally throw a tracking number/link in here if I need to refer to it, eliminating the need for a dedicated app.

#ebay – if I’m searching for something, it pops up in here as it appears on eBay.

#edc – RSS entries on cool gadgets from everydaycarry.com. I have a problem with small tools, and this is how I indulge myself.

#home – I have some shared lists in Wunderlist with my wife, and I get the update notifications sent here.

#photo – I have a few different RSS feeds pointed here, with the simple goal of seeing nice things on a semi-regular basis. Currently, NASA’s photo of the day (via IFTTT), and Unsplash (love this site.)2

#pricedrops – alerts on app sales from MacStoriesDeals and AppShopper.3

#reading – this is my “read later” channel. I toss random links I plan to read here and come back to them whenever.

#rss – I keep a small collection of low-volume feeds that I want to ensure I read each day, so they don’t get lost in the din of other news and the RSS combing I do for work. Blogs by friends, and a few other sites I enjoy.

#snippets – a channel that just holds blocks of text, links, images, etc. I may use frequently or not so frequently. I don’t use this channel all that much, but I like that it’s here.

#starwars – a channel devoted to Star Wars news, articles, and general nerdery.

#town – alerts from the local police department about events, hazards, etc. Supremely–and surprisingly–useful.

#twitter – since effectively abandoning the network on which I used to set fire to piles of my personal time, I created a channel for a handful of accounts that I’d still like to see updates from, without subjecting myself to the misery funnel that Twitter’s become in many ways.4 I also get notified here if someone mentions me, or if certain search terms hit a match.

#video – think “read later” but for stuff you’d watch. YouTube links, etc.

#weather – forecasts and severe weather alerts.

#workflow – a channel devoted to iOS automation, piping in new items from r/workflow and the Drafts Action Directory as they appear. I think I might have a few other things pointed here as well too.

#yankees – news and info on the baseball team I grew up with.

So that’s the current run, and I’m still thinking of new ones.

Which brings me to the idea behind #daily. I have a pretty standard routine (I’d imagine many of us do at this point) of waking up, grabbing for my iPhone, and beginning the Early Morning Badge Clear Game. What often ends up happening however, is that I get into my work inbox, or start reading something I don’t have time to finish in the news, or whatever. You get the idea. The #daily channel was supposed to be an experiment to collect things that I would definitely want to see first thing in the morning, all in one place, give me a jump on my day, and get me mentally prepared for what I need to do–quickly.

The first thing I did was move the morning weather forecast from #weather into this channel, since I always want to see the forecast for the day first thing in the morning. Then since I’m old and can’t always stay up late anymore because kids are soul vampires being a parent of small children can often leave one very tired, I sent the RSS feed for Meh in there, so I can see what stupid thing they decided to sell overnight. This doesn’t work so great for when they have those freakout sales on Fukubukuro boxes of nonsense, but since they’re tweaking the way they do things, may prove more useful to me as time goes on.

But what’s really useful is seeing what I need to focus on that day. My tasks, calendar, etc. all shoved into a nice little summary. A daily brief. That’s where my mad scientist friend Tim comes in.

We’ve been going back and forth on this idea, and we’re in the middle of creating a Workflow5 that will take a whole bunch of personal information (calendar, tasks), add a field for impromptu notes, and throw the weather forecast in for the day, format it in a decent way, and send it directly to Slack. I do this before bed, and the next day, I just scroll up and read through the brief I sent, and then anything else that wound up in the channel overnight. I’m thinking about maybe using Workflow to insert some news headlines6 and other things that can get my brain going while I’m laying in bed, wishing I was still asleep.

Tim has done a lot of work tweaking this idea and building functionality into it, so check out his post. He’s got a bunch of explanation and links to multiple variations on the Workflows.

I’m really into this daily briefing idea. It’s new, and I think it has some legs. I plan on exploring it a lot more.

There’s a theme throughout my use of Slack, and my ideas for what I can do with it, and it’s similar to how I think about Workflow. I’m most interested in using these tools to either a) pull information to me in some useful way so I don’t have to look for it, or b) replace a single-use app of some kind with a similar and (hopefully) comparable set of functionality. Those two use cases continue to drive my experimentation with both apps, but primarily with Slack. Using dedicated channels in an app I already have installed, I can replicate the primary functionality of a handful of small apps that I would have otherwise installed. Will it do everything those apps do? No, not by a long shot. But for the major use case(s), it’s almost always good enough, and that continues to drive me to think of other ways to extend it. The more I use it, the more I want to use it, and find new ways to do so.

The other thing I’ve come to enjoy is the separation of topics of my interest (or functionality) by channel. Instead of an RSS app with a bunch of feeds in folders, I can send different feeds to different channels, and mix that content with other notifications and integrations to create a new experience. This level of flexibility is what gets me really excited about continuing to explore the tool and talk to other people who are thinking along similar lines.

Slack has become an integral part of my day, and continues to deliver a ton of value for me on a personal level well outside of its intended business-based use cases. Having a team all to myself is really fun, and gives me a great outlet to fiddle with iOS automation and web services without too much fussing. I’ve seen other people exploring this kind of thing too, and they’re doing some great things as well.

If you’re doing something cool with Slack outside of work, I’d love to hear about it.


  1. You can create an RSS feed for a Google alert and then use Slack’s RSS integration to get it into a channel. 
  2. If you have any other suggestions for things that send nice pictures, please do let me know. I love this channel and want more of it. 
  3. IFTTT has a channel that does this too, for AppZapp, but I found it to be too high volume (even with my tweaking) and not relevant to my general interests. YMMV. 
  4. I’m still way happier not being there, in case you’re wondering. 
  5. I had the idea, Tim is actually doing all the heavy lifting, because he’s like, WAY better at Workflow than I am. 
  6. But if I’m being honest, this almost sounds like a terrible idea, because it’s usually just more misery, and I can do without that first thing when I get up.