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. 

Vacation, all I ever wanted.

As I’ve said before, I’m a little late to most nerd parties these days, and this is no different. I’ve been hearing a lot about 2Do for a while now, spurred primarily by Federico’s exhaustive review a few months back. I had first purchased the app back when it was released many years ago, and had peeked at it from time to time since. What started as an opinionated UI with some seemingly odd UX conventions has shifted into a more attractive, highly customizable, and totally flexible app to manage every kind of actionable item you can throw at it.

So when everyone started talking about it, as is my way, I dismissed it as “this is what everyone’s talking about now” and didn’t really bother to dig in. Something about the way the app looked and worked didn’t mesh with the way I thought about my task management. As I’ve mentioned many times before, I’m primarily psychically invested in the OmniFocus way of life, and have been using the app for years. I’ve also used Todoist in a similar way with great success and I’m in there now, for a lot of reasons. And I’m always looking for ways to change things up and increase efficiencies, and just generally make things work better for me. To my detriment, I didn’t explore what 2Do had become, and I wasn’t prepared to integrate it into my workflow.

Last week, after much of the recent fervor had subsided, I had an hour of free time (unheard of these days) and something compelled me to install it and poke at it for more than a few seconds. I can probably attribute that to friends who incessantly discuss its benefits and how it’s totally blown their worlds up in a good way. Whatever it was, I pulled the trigger and spent the hour with the app.

What I discovered was that while I’ve allowed myself to gain comfort and speed in other apps, learning 2Do isn’t like learning another todo system. It’s essentially Drafts for task management–if you want it, you can probably do it. At first, this seemed off-putting to me: like, make some choices, and don’t give the user free reign to do, well, anything, right? Have some boundaries, and fence in your property. That’s just how most things work. Once I surrendered that preconception, I found myself in awe of how utterly malleable the app becomes once you spend time learning and understanding its syntax and its abilities.

I’m honestly shocked at how much I was missing by not taking the time to really dig in. I shouldn’t be, but I guess I’m still whittling away at my own habits in certain areas of my life. I’m glad I allowed myself the time to do it.

I’m not going to write about what the app does. There are many other places to read all that. What I will say is that in my week’s worth of exploration, I’ve discovered ways of managing what I considered to be a completely solidified mental model that I didn’t realize were possible for myself.

No single app (nor switching to an app) is going to physically make you do more stuff. That continues to be on you, and always will be. But being able to visualize different angles around the things you have to do in your life is never a bad thing. There’s something utterly comforting about embracing a system that works for you and never changing and I’ve definitely been there. But there’s also something to be said for making leaps of faith occasionally and trying new things, even if you come running back to your safe place, because it’s allowed you to step outside of the confines of your environment and gain a little distance. It’s why we take vacations, why we like traveling away from home. Seeing things that are similar, but in different ways. Sometimes seeing things that we could not have expected, or that we expected we’d even like. Sometimes those vacations lead us right back to where we belong, but occasionally we end up finding that we’d rather be somewhere else, and we stay.

I’m not sure, after a week of being away, that I’m ready to call the moving company, but I’m sure glad I booked the flight. I’m going to continue exploring the app and really dig in to see how else it can work for me. It’s a bit of an onion, this one, and I’ve only begun peeling.

Person-based OmniFocus context triggers with Launch Center Pro.

During a discussion with some fellow OmniFocus friends in a Slack channel, we talked about how great it would be if contexts that we assigned to people could trigger when we’re with them automatically. While there isn’t a good way to do this yet, I thought about it a bit and made what I would call a halfway decent substitute, all things considered. It combines connecting some hidden OF features on the Mac with Launch Center Pro and OF on iOS. And while it isn’t quite automatic, it’s pretty close, as long as you build a habit around it.

I remembered seeing a post about using OF’s URL scheme support to trigger actions a while back. Some of OF’s features have obvious URL scheme support, but some are a little more hidden. In order to get an actionable URL for a context, you need to have the Mac app open and right-click on the context you want to use. An option called ‘Copy As Link’ will appear. That’s what you want. Unfortunately, there’s no way to do this on iOS, so unless you’re using OF on all platforms, you may be out of luck. But if you’re like me, and you have that beautiful purple icon everywhere, proceed to step two.

With that URL on the clipboard, get it over to your iOS device any way you want. I used Notes.app, because it’s probably the easiest way to do this, as it syncs fairly quickly. With the URL on the iOS clipboard, go ahead and open up Launch Center Pro.

Now you can drop this URL in as a single action, sure, but if you want to really light your world on fire, collect URLs for all the contexts you have that pertain to people. For me, it was about a half-dozen, mostly folks at work, but I also have one for my wife, and one for my parents when I see them. Use LCP’s list format option for your action, adding a label and the appropriate URL for each new item.

When you’re all done, save the action, add an icon, and place it somewhere. You now have a single button that brings up a list of names. If you’re talking to someone for whom you have a context, fire this action off and tap his/her name. OF will open directly to the context and display all the actions associated with that person. Of course, you need to remember to do it. (You could set a notification directly from LCP to fire if you definitely know you’re seeing someone in advance, e.g. for a meeting, to even better safeguard against forgetting to do this.)

Short of having your device know who you’re talking to, as long as you have the sense to pull out your phone and tap that action in the course of the conversation, you’re all set. I have a feeling this is going to help me immensely, especially with people who have very little time and are tough to pin down. Getting all your questions answered or discussion items covered at once is invaluable if time is short. And even if it’s not, you’ve got a nice, quick way to jump to a person’s associated items the next time you sit down together.

Ruthless organization.

I’m really enjoying Relay’s new Cortex podcast with Myke and CGP Grey. While I was familiar with Grey’s work before, this is actually the first time I’ve spent specifically listening to him. I know, Hello Internet is everyone’s favorite show, but I’m a little late to that party, so forgive me.

In this weeks’s episode, Myke and Grey continue to chat about homescreen organization, and Grey reveals that he hides Safari via iOS Restrictions. Although this literally made my jaw drop as I listened (I’m not kidding), I totally get the idea. I’m constantly trying to streamline my phone for the best combination of access to things I want and efficiency, while eliminating things that are just hopeless time sinks. Grey is pretty ruthless about what he allows on his phone, and while I’m not all the way there (I still derive a lot of actual business and personal value from using Twitter on my phone, for instance), it’s an interesting exercise to try.

Sometimes I feel conflicted about spending time thinking about stuff like “in what better way can I optimize the way my apps are displayed”, but I do like going through these steps because I’m constantly reevaluating all kinds of things in my life, and this is just one of those things. I see it as an extension of personal growth and awareness, and as long as it doesn’t get in the way of actual things that need to happen, I think it’s probably fine to reflect on things like this.