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.

Embracing contexts and perspectives in OmniFocus Pro.

Over the past few weeks, I’ve been really trying to take my OmniFocus use to the next level. I know that I haven’t been applying the true power of the application to my workflow, and so I’ve been making a concerted effort to learn about and implement the aspects of it that I’ve either not understood fully (defer dates) or underused (perspectives, contexts). What I’ve found through reading and discussion with some friends and fellow users is that (surprise) there’s an entire other world within the application once you embrace some of those more complex concepts.

I’m by no means an expert user, even at this point (I’d give myself “advanced”, though) but as I explore it, I’m often compelled to share things I discover. I think there’s something interesting about this app too, similar to other professional tools like Photoshop or Logic/Pro Tools that encourage users to share tips and flows with one another. As an audio engineer might tweak settings to get something just perfect in Logic and then share that discovery, productivity apps like OmniFocus have a similar base of interest.

Note: before we go further, it’s worth mentioning that in order to create custom perspectives and do the things I’m about to describe, you need to upgrade to the Pro version of the application(s). It is seriously worth it, though, because as good as it is by itself, you can truly make it your own with this additional functionality. If you’ve been holding off making the jump, my advice is to consider it. Also, Omni is a great company full of great people and you should support them so they can continue being great.

The Problem

I manage everything in OmniFocus. Personal tasks, work projects, home renovations, writing activities, et. al. I have tightly organized project structures, but feel that I need to focus on critical tasks in specific scenarios, e.g., I don’t need to know that the trash goes out tonight if I’m standing in my office.

The Process

In order to understand what and how I wanted to see things to ensure I was always performing the right set of tasks without interference, I needed to explore some things I’d avoided, namely flagged items and defer dates. I’ve used contexts selectively in the past, but never managed to make them really stick. By combining all three of these features, I was able to create a set of perspective rules that always show me:

  1. What I need to do right now
  2. Things I need to do soon that require some level of follow up

And to ascertain how to do that, I needed to clarify where and how I think about things:

  1. At work (in my physical office, and during the work day)
  2. At home (any time I’m not in the office)
  3. Any other time (primarily the weekend, since the other time blocks are covered)

The Solution

Three new contexts, three new perspectives, and a clear way to see only the essentials no matter where I am.

First, I created three new contexts: “9am-5pm”, “5pm-9am”, and “Weekend”.

9am-5pm covers my workday. When I’m standing in my office, what are the things that need to happen before I leave? This includes work-related tasks, but is not limited to that. Sometimes I need to call a bank or run an errand at lunchtime. Personal tasks under this context also appear here to be bound within that timeframe.

5pm-9am covers all the time I’m not at work. This includes things that can only be done at home (take out trash, give our kids baths) and/or work tasks to be accomplished after hours.

Weekend is a wildcard. I apply this context to anything that I think I want to tackle on Saturday or Sunday, when I assume (haha, small children) that I’ll have a modicum of free time.

I also made the decision to start using flagged tasks to indicate dated or undated tasks that require a follow up activity either on my part or the part of someone else. (Some people use a “Waiting” context for things like this, but I could never make that stick either.)

Then, combining these new groupings, I created three new perspectives.

See if you can figure out where I’m going with this.

9am-5pm is a perspective that collects:

  • anything in the 9am-5pm context that is due or flagged and available (not deferred)
  • anything that needs to happen as I leave the office for my home in the evening

5pm-9am is a perspective that collects:

  • anything in the 5pm-9am context that is due or flagged and available (not deferred)
  • anything that needs to happen as I leave my home for the office in the morning

Weekend is a perspective that collects:

  • anything in the 5pm-9am context that is due or flagged and available (not deferred)
  • anything dated or undated in the Weekend context

Now, you might be thinking “but… you’re home between 9 and 5 on the weekend, so your whole plan is shot and you’re a shortsighted person who really didn’t think this through” and you’d be sort of correct. But I don’t really care. The main purpose of that context is not so much to bind me to the hours as it is to block the day up the way I need to think about it, primarily during the work week. Certainly I could have called these “Office” and “Home” but it didn’t really feel right to me, since I think about my day in terms of time and not so much location. Location is a modifier on time. I could be working from home one day–in which case I’m not really in the office, but need to accomplish tasks between those hours. It just made sense to me. Also, I realize I kinda contradicted myself in explaining all this, since the weekend time blocks don’t apply, but let’s just keep going. It’s working.

I also made a few other new perspectives to collect all the undated stuff between work and personal projects at a glance, so I can browse them in between weekly reviews if I feel like it. Useful if you find yourself with a little extra time and want to try to accomplish something.

I think the next logical step for me is going to be time estimates. It’s something I haven’t felt the need to do, but as I follow this process to its logical end, I’m going to want to (I assume) get even more granular at points.

Maybe you’re reading this and freaking out because it’s like a bolt of lightning for you. Maybe you’re reading it and rolling your eyes. In the case of the latter, well, I’ve got nothing for you. I like exploring this stuff because as I’ve discussed in previous posts, it keeps my brain happy and is interesting to me. It’s a rabbit hole, and you can certainly waste endless amounts of time tweaking and not doing. But tweaking enough to do more is a truly exciting feeling to a certain kind of person like me and an incredible positive feedback loop. And if you’ve read this far (or any of those other posts), you’re probably that kind of person too.

Now get to work.

OmniFocus for iOS / OmniFocus for Mac (MAS) / OmniFocus for Mac (Omni Store)