Analog Task Management

Third in a series on task management. Read part 1 and part 2.

For many years my task management system has been all digital. Recently, though, I’ve taken to supplementing it with some analog tools.

Field Notes Day Planner

As I mentioned in my post on OmniFocus I have trouble picking out what to work on when my task list gets too long. I try to filter my task list in OmniFocus down to a manageable subset that I use to pick what to work on, but there’s a balance to be struck between getting the list down to a manageable number of choices and not cutting it down so much that things slip through the cracks.

To help deal with this I started coming up with a list of my important tasks for each day. Every day before I leave work I come up with my major task list for the following day. For both technical reasons1 and because I thought it might introduce a bit of deliberation into the process (and a physical limit on how many tasks I could write down for each day) I decided to go analog.

I use a little Field Notes notebook. Each day gets a pair of facing pages. The date goes at the top of the left-hand page and underneath it I write my major tasks for the day. Depending on how full my schedule is and how big I think the tasks are, there are usually 2-5 tasks. One of them is usually a deep work type task that I’ll work on in the morning.

Many of the major tasks are lifted right out of my task list in OmniFocus, but sometimes a major task for the day might represent a series of smaller actions from a project I want to make progress on.

As I go through the day I use bullet journal type markings to check off the tasks I get done and mark those that did not get done and got deferred to a future day.2

The other thing I’m trying out in this analog system is to schedule my time during the day. I’ve heard this advice many times, but it always seemed too restrictive until I read Cal Newport’s explanation of how he does it in Deep Work. This inspired me to give it a try.

On the right-hand page I write the hours of the day every other line, so each line represents 30 minutes. I copy over the “hard schedule” items from my calendar (meetings, appointments, etc.) in red ink. I block out the rest of my day in pencil. When I’m doing this I usually start with the stuff that’s pretty regular from day to day (hard schedule permitting) like doing email after lunch and planning out tomorrow’s schedule before I leave. With the remaining time (and some days there isn’t much of it) I block out time for the major tasks I wrote down on the left-hand page. Sometimes this prompts me to rethink how many of those major tasks I can actually get done in a given day.

Writing the items that aren’t part of my hard schedule in pencil is a deliberate choice. I’m generally a ballpoint pen guy when it comes to writing, but the schedule needs to be flexible because, inevitably, things will come up and it will have to change. Using pencil is both a philosophical declaration that this is subject to change and a practical choice so that I can make those changes without turning the page into a complete mess.

Listing my major tasks and planning out my schedule has been a boon for me so far. It requires an investment of time and effort up front, but I spend a lot less time staring at OmniFocus and trying to decide what to work on next and I’m less likely to get distracted by something if I’ve got a schedule that says what I’m supposed to be doing at that moment.

The Big Board

One of the issues with the way I practice Getting Things Done is that the very task oriented approach doesn’t always give the best high level overview of the project.3 It can take some effort to sort through my list of “next actions” for a project and translate that into where I am with the project as a whole.

I’ve had a whiteboard in my office since I started working at my current job, but rarely put it to any use. A few months ago I decided to see if I could use it to help me get a higher level understanding of where my many projects stood.

I printed out a list of all my projects in a nice big font and taped it up on the left side of the board. On the whiteboard itself I wrote in the next step for that project with the date for that step (if there is one) over on the right side. By “next step” I mean something at a higher level than the GTD-style “next action”. For instance, the next step for a project might be a meeting with the people involved, which would have a series of actions associated with it (do a Doodle poll to set a date for the meeting, reserve the room, set the agenda and send it out, etc.).

Being able to see where I am with all my projects at a glance is very useful. I’m responsible for quite a few projects and many of them are long term who’s deadlines are many months or years away. It’s important to make sure I keep making sufficient progress on these projects and don’t let all my time get sucked up with things that have short term deadlines. The whiteboard does a good job of helping me set priorities for what I need to be doing on these projects to make progress towards the long term goal.

It’s early days yet for both of these analog tools, but so far they seem to be useful additions to my task management system.


  1. OmniFocus only supports one level of flagging (either a task is flagged or it isn’t) and I was already using that functionality to create a 15-20 item subset of my larger tasks list that I draw from for my daily list of major tasks. 
  2. Tasks that are done get an “X” and those that don’t get done and are pushed to a future day get a “>”. 
  3. I should emphasize that this is largely a problem with the way I implement GTD. David Allen has some good stuff in his book on taking a higher level view of your projects (and your life) but that’s part of the system that I don’t really make enough use of. 

OmniFocus

Second in a series on task management. Read part 1 here

In my previous post I talked about how I use David Allen’s Getting Things Done system for task management. You can implement GTD in many different mediums, from pencil and paper to a wide variety of software. When I first started with GTD I ran my system on vertically ruled index cards. However, I discovered that I had enough complexity in my life that it quickly overwhelmed my index card based system. I moved over to OmniFocus and I’ve been there ever since.1

OmniFocus is specifically built for GTD and it implements all of GTD’s fundamental concepts: projects, contexts, weekly review, etc. One of the most important features for me is that it’s available on the Mac, iPhone, and iPad and syncs seamlessly between them.

Quick Entry

One of the things that’s important to me is making it as easy as possible to enter tasks. On the Mac OmniFocus does a great job of this right out of the box. It has a quick entry box feature that will pop up ready to receive a task when you press a particular key combination (mine is Ctrl + Option + Space), regardless of what app I’m in at the time. Sometimes I’ll enter all of the details of the task in the quick entry box (Context, Project, defer or due dates), but often I’ll just put enough in there to remind me what the task is supposed to be. OmniFocus will hold the task in it’s inbox until I get around to processing it and adding all of the details.

OmniFocus has a quick entry feature on iOS as well, but it’s nowhere near as useful. Rather than just a quick keyboard combo, I’ve got to open the app and hit the quick entry button before I can start typing. Entering additional details requires navigating through lists of projects and contexts and using the iOS date picker. It’s well designed and uses iOS interface elements well, but for a long time I wanted an experience more like what I could get on the Mac.

Recently I switched over to entering my tasks using the Drafts app. Launching Drafts automatically opens up a new document with a blinking cursor ready to type. It integrates with many different apps, including OmniFocus; allowing me to send whatever I type to OmniFocus as a new task. I actually have two actions set up to send to OmniFocus, one just adds the task, the other specifically adds it to my Work context..

It’s possible to include a due date with a task as well, by putting “@due(today)” after the task (the “today” can be replaced with a specific date or a number of days or weeks). The problem with doing this in Drafts is that the parenthesis and “@“ symbol are more difficult to access on the iOS keyboard. Thankfully, Drafts supports TextExpander snippets. I set up a snippet that replaces “xdue” (which can be typed without any special characters on the iOS keyboard) with “@due( 5pm)” and places the cursor right after the opening parenthesis. So I can type “xdue” and then enter a specific due date or the number of days.2

Defer Dates and Dependencies

One of the best features of OmniFocus is the ability to defer a task. By giving a task a start date sometime in the future it won’t show up in the task list until that date arrives. This is a great feature for keeping stuff that I can’t do anything about right now out of my main task list. I use it all the time when I need to follow up with somebody in a week, or when a task can’t be started until some future time.

OmniFocus also offers the ability to make all of the tasks in a project sequential, so the second task in the project won’t appear in your task list until the first task has been done. This is useful when you’ve got dependencies where a subsequent task can’t be started until you’ve done the previous one. I do wish they had a more flexible system for this, allowing me to make one task dependent on another, rather than having to make the entire project sequential.3

Triaging the Task List

One thing I’ve always struggled with is keeping my task list manageable. OmniFocus can hold huge numbers of tasks, but I can’t deal with that many at one time. When I get too many things on my task list it makes it hard to pick out what I need to be doing right now. I find my limit is about what OmniFocus can display without having to scroll the task list to see everything (15-20 tasks depending on screen size). Defer dates and sequential projects can help with this, but I still have more things that I could be doing right now than I can easily choose from.

The solution I’ve found is to prescreen my task list and create a subset of tasks that I’ll actively consider when deciding what to work on at any given moment. I’ve tried a bunch of different ways to implement this concept in OmniFocus and they’ve all had issues. As Churchill reputedly said, “Americans can always be counted on to do the right thing…after they have exhausted all other possibilities.”4 I can’t say I’ve gotten around to the right way of doing this, but here are some of the other possibilities that I’ve exhausted:

My first approach to this was to use defer dates. I would go into OmniFocus every morning and defer all of the tasks in my task list that weren’t in the subset that I wanted to work on that day. This was rather fiddly and time consuming. In particular, it was hard to implement on iOS, where you have to defer one task at a time (on the Mac you can select a bunch of tasks and defer them simultaneously).

After giving up on the mass defer option, I started using due dates to create the subset of tasks that I was going to pick from. I’d go into OmniFocus in the morning and set the tasks I was interested in to be due that day. This was a bit less fiddly because I only had to set dates for the smaller subset of tasks that I wanted to pick from, but it was still pretty fiddly. It also made it hard to distinguish stuff that had an actual hard deadline from stuff that I had given an arbitrary due date to.

My current method is to use OmniFocus’ flag feature to create my subset. It’s less fiddly since I only have to set the flag for a task once, rather than having to create the subset anew every day. The disadvantage is that since I’m not forced to actively curate the list every day it has a tendency to grow over time, which kind of defeats the purpose of having a small subset of my task list. I’ve recently taken to supplementing this by using a paper notebook to plan my day better, including both tasks and my schedule, but that’s a different article.

An Essential Tool

OmniFocus has really become an essential tool for me. Going back to grade school, things like remembering homework have always been a struggle for me. Since then my life has grown a lot more complex, and having a powerful task management tool is the only way I can keep thing from slipping through the cracks.

Next up in the task management series: analog task management with a notebook and a whiteboard.


  1. Nine years. 
  2. The “5pm” is in there because when you send OmniFocus a task from Drafts with a due date, the default time for the task to be due is 12am (unlike when you enter a task in the OmniFocus app and the default due time is 5pm). So I’ve set up the TextExpander snippet to pre-populate a 5pm due time. 
  3. Although you can set up a subproject inside of a project and make just the subproject sequential, it’s a bit clunky. 
  4. I was disappointed to find the attribution to Churchill is probably apocryphal. It seems like a very Churchillian thing to say. 

PDF Reading Workflow

One of the things I’ve been rethinking recently is how I handle PDF documents. There’s a larger story here that covers long term archiving and search, but right now I want to concentrate on just one particular workflow: receiving and reading PDFs.

Previously I was rather ad-hoc about this, but if my practices could be distilled into a workflow it would have gone something like this:

  • Receive an email with an attached PDF or a link to a PDF document online.
  • Use the OmniFocus Mail Drop to create an OmniFocus task with either the link as a note or the PDF document itself as an attachment.
  • Open the PDF from the OmniFocus task and read it (on one of many different devices and apps).

This had a couple of disadvantages. If I attached the PDF, it took up space in my OmniFocus database. If I linked to the PDF online, it might move or be taken down in the (sometimes substantial) time between creating the task and when I got around to reading the document. There was no permanent archive of PDFs that I’d read, they were scattered around different apps on my iPad and Mac.

For some of those larger reasons mentioned above I was looking at using DEVONthink as my primary PDF repository. As part of this process I was casting about for a way to easily add PDFs it and create corresponding tasks in OmniFocus. The difficulty of this was compounded by the fact that my initial contact with email containing PDFs is usually on my work PC, a machine that can’t run either DEVONthink or OmniFocus.

But I think I’ve found a solution.

  1. Dropbox – My work PC does run dropbox, so I can save the PDF to a folder in my work Dropbox account. When I do this I also rename the PDF to something sensible (the filenames of many of the PDFs I receive are pretty cryptic). This folder is shared with my personal dropbox account on my Mac.
  2. AppleScript – On my Mac, that Dropbox folder has a Folder Action Script attached to it. The script adds the PDF to DEVONthink and gets the x-callback-url of the item. Then the script creates an OmniFocus task. It names the task “Read” followed by the PDF filename and includes the DEVONthink x-callback-url in the notes field.  You can find the AppleScript here.
  3. DEVONthink – Eventually I’ll file the the PDF in the appropriate group in DEVONthink. Importantly, moving the document around within DEVONthink won’t break the x-callback-url (it’s associated with that particular document, not that document’s location within DEVONthink).
  4. OmniFocus on iOS – When I’m ready to deal with some of my accumulated reading material I’ll open up OmniFocus on my iPad and find the task synced over from my Mac. Opening up the notes field and touching the x-callback-url will launch DEVONthink To Go.
  5. DEVONthink To Go – The URL will take me directly to the PDF in question. While I could read this right in DEVONthink I’ve been enjoying LiquidText (particularly the new 3.0 version with advanced Apple Pencil support). So I use the share sheet in DEVONthink To Go to send the PDF to LiquidText.
  6. LiquidText – In LiquidText I can read the PDF, highlight, excerpt relevant portions, make notes, etc. When I’m done I can share updated document with my markup back to DEVONthink To Go using the share sheet.
  7. DEVONthink To Go – DEVONthink To Go is smart enough to recognize the marked up PDF as a modified version of the original. It gets synced back to DEVONthink on my Mac.
  8. OmniFocus – I check off the task to indicate I’m done reading that document.

This workflow improves on what I’ve been doing it a couple of ways. It automates the OmniFocus task creation, it gives me a local copy of the document tied to the task while storing the PDF someplace more sensible than my OmniFocus database, and it creates a pathway for long term storage of both the original PDF and my notes about the document.