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.

May 1, 2017

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.

April 24, 2017

Getting Things Done

The first in a series on how I deal with task management.

The level of complexity in a task management system needs to be commensurate with the number and complexity of the tasks that you’re managing. David Sparks relates that when he was a student, his task management system was to write down the day’s tasks on the napkin he got with his morning coffee. I never used a napkin, but as the complexity of my life has varied the complexity of my task management setup has waxed and waned from simple checklists (both paper and computerized) to powerful task management software.

Right now I’m at a fairly high level of complexity: my task management system involves two different pieces of software, a notebook, and a whiteboard. I’ll talk about these tools in future posts, but to start with I wanted to talk a bit about the conceptual framework that underlies it all.

That framework is the Getting Things Done system by David Allen. GTD is one of the most popular task methodologies, there are a lot of people out there using it. However, everyone seems to have their own particular take on the system. I sometimes think there are as many was of implementing GTD as there are people using the system. So what I describe certainly should not be taken as canonical. It’s more like, “This is my GTD system. There are many like it but this one is mine.”

Clean Sweep

Of all of the aspects of GTD, the one that was the biggest benefit to me when I first started was getting all of my tasks out of my head and into some sort of system. This is important for a couple of reasons: First, since I am terribly absent minded, any task I just try to rely on remembering is very unlikely to actually get done. I have to get it written down in a place where I’ll come back to it later. Second, (and this is the reason that David Allen emphasizes) having these unfinished tasks bouncing around in the mind is a distraction. It’ll be there, gnawing away until it gets done. Perhaps because I’m so forgetful this has been less of a problem for me.

The cure for both these ills is to get tasks out of my head an into some sort of system. For me, that system is OmniFocus. I’ve got it set up so that it’s extremely easy to get tasks into the software and as soon as I think of something I need to do I’ll pause whatever I’m doing and get it in there. I know from experience that there’s not a moment to waste if I don’t want to forget it.

Next Actions

The next step in GTD is to group tasks into projects and organize them as a series of “next actions”. One of the things I had to learn how to do when I started with GTD was distinguish between projects and actions. When I’m capturing a task, it might go into my system as “learn programming language X”, but that’s not something I can just sit down and do. It’s too big and involves too many different steps to bite off in one go. The next actions might be “Search Amazon for books on programming language X” or “Download programming language X software”.

The critical idea here is that taking a larger project and figuring out the next step requires mental energy. If I have to put in that energy right at the moment when I’m trying to start the work it creates an additional barrier, and the harder it is to get started the more likely I am to do something else. By putting in that thought about what the next step is up front, it lowers the amount of effort it takes to get started with the task when the time comes to actually do it. So when I’m looking at my task list all I have to do is pick one and do it.

While the “action” part of next actions is important, the “next” part is critical as well. One of the things I’ve struggled with is when my task list gets too long, it becomes harder and harder to go through the list and pick something off of it to work on. This makes it important to limit the task list to stuff I can actually do right now. There’s no need to clutter it up with something I can’t start on until next week or tasks I can’t start until I hear back from a colleague. This is where software can make a really big difference. One of the things I really like about OmniFocus is it’s ability to defer tasks (hiding them until a future date) or to make tasks sequential (you don’t even see Task B until you’ve checked off Task A). It really helps keep my list of available tasks manageable.

Contexts

The other way GTD is set up to limit the number of available tasks is by dividing tasks into different contexts. If the task is to fix a leaky faucet at home that’s not something I need to see when I’m at work.

This is one aspect of GTD that I’ve always struggled with, and I know I’m not the only one. When David Allen wrote Getting Things Done back in 2001 the canonical contexts where things like Phone, Computer, Internet, and Office. The idea was on an airplane you could ignore tasks that require phone calls or internet access. If you didn’t have your computer with you didn’t need to see tasks that require a computer or internet access. The problem is the proliferation of mobile devices and cellular data connections have blurred these lines tremendously. Unless a task requires me to be in a particular location, it’s usually something that I could be working on wherever I am.

So, I have three contexts: Work, Home, and Computer. The real divide here is between personal stuff and job related stuff. Work is for everything job related. Personal stuff is divided between Home and Computer. The tasks that require me to physically be at home go in the Home category and things that I can do anywhere I have access to a computing device and an internet connection in the Computer category.

In turn, this means that contexts don’t do a very good job of limiting my available task list. If I’m at home I could be working on everything on my Home and Computer tasks lists and almost everything on my Work task list (with the exception of a few tasks I need to physically at the office to do). This means I’ve always got a ton of different things I could be working on, which makes choosing one of them to actually work on more difficult.

Review

The final piece of the puzzle is to review outstanding projects and next actions every week. It’s really a series of questions about each project: Is this something I still need or want to do? Are there any tasks associated with this project that haven’t made it onto the list of next actions? If I haven’t made progress in the last week, why not?

This is another area that I’ve struggled with and it’s really a critical one. When I fail to do my review for a couple of weeks cruft builds up on my task list and things fall through the cracks. I’ve gotten better about this in part by scheduling time for the weekly review. I review for my personal projects on Sunday evening and my work projects on Monday afternoon. I’m also using an app called Due that’s another part of my task management system to remind myself to do the review on a regular basis. My track record on weekly reviews still isn’t perfect, but it’s getting better.

Getting Things Done has really been a godsend for me. Without it I would be blowing deadlines and missing tasks left and right. It’s really essential for me to be able to function as a responsible adult.

April 17, 2017

I am a very high entropy person

I sometimes describe myself as a high entropy person. My natural state is one of disorganization and absentmindedness.  When I was a kid, my room was always a complete mess. I did poorly in school because I was always missing homework assignments. While procrastination was a factor in this as well, the fact that I had homework often just wafted out of my head almost as soon as I left the classroom (to the disappointment and disbelief of my much more organized parents).

So when my colleagues at work occasionally make jokes about how organized I am, it causes a bit of cognitive dissonance. If I seem organized, it’s because of the systems and practices I’ve developed to overcome my natural state of disorganization.

Every task goes into my task management system because if it doesn’t, its chances of getting completed are miserably low. I keep the number of emails in my inbox at or near zero because if I didn’t there would be hundreds (same for unread items in my RSS reader). My desk at work is clean and organized because if it wasn’t you wouldn’t even be able to see the desktop.

April 10, 2017

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.

April 3, 2017

Doing Deep Work

Sometimes the right book comes along at the right time. It’s not so much that the idea is life-changing but that it reinforces a change that is already going on in your life. Deep Work by Cal Newport was like that for me. ¹

Newport’s thesis is that work requiring sustained concentration that pushes your brain to the limit, is both valuable and rare. Such “deep work” is rare because we live in a culture of constant, distracting, stimulation that rewards busyness rather than productivity. It’s valuable because it is more productive, particularly for certain kinds of creative or technical work.

The book is divided into two parts. Part I is dedicated to convincing the reader that deep work is important, valuable, and rare. Honestly, it didn’t really grab me that much because I was already on this train. Part II, which is about about 2/3 of the book, is full of techniques and recommendations to help you do more and better deep work. This was really what was worth the price of admission for me.

One of the things that Newport emphasizes is that the ability to concentrate on deep work is not something that you either have or you don’t. It’s also not just a habit you can pick up through willpower. It’s a skill that you can train yourself to do.

He lays out four potential philosophies for doing deep work: The monastic philosophy is to isolate yourself from the distractions of the world and dedicate yourself to deep work over a long period of time. Bimodal philosophy alternates days or weeks of deep work with similar time periods dedicated to shallow work. The rhythmic approach is to dedicate a certain time period each day to doing deep work. The journalistic philosophy is to stick short bouts of deep work in whenever you have the time.

I realized that I was already pursuing the rhythmic approach, by doing things like turning off my email client until after lunch. My morning hours are the most productive when I’m trying to do technical or creative work (I’m writing this post on a Saturday morning, for instance). After reading about this I’m going to be more aggressive about defending that time from meetings and other distractions and dedicating it to the kind of deep work that I can do best during those hours.²

For a “productivity” book Deep Work really emphasizes the importance of downtime to recharge your batteries and renew your reserves of concentration. Newport is not at all a fan of putting in a huge amount of hours. His position is that there’s a limit to how much deep work you can get done per day (maxing out at about four hours). The rest of the day can be filled with shallow work, but beyond a certain point adding more shallow work will actually decrease the amount of deep work you can do, making you less productive overall.

I’ve always tried to avoid working late or bringing work home (though not necessarily as a productivity booster). It’s nice to have additional justification for this approach.

An area where Deep Work has lead me to try really changing my approach is scheduling. Newports advocates scheduling your entire day; writing down what you’ll be working on and when. This is advice I’ve heard from other sources but I’ve never put it in to practice because it felt too rigid. However, Newport presents a much more flexible approach to scheduling. He emphasizes that you don’t “win” if you stick to the schedule you laid out or “loose” if you have to change it. The goal is to avoid putting yourself in a position where you have to choose what you’re going to work on in that moment, because that makes it too easy to choose some sort of distraction.

To implement this more flexible approach he advises rescheduling as necessary throughout the day as things change and ignoring the schedule to follow up on interesting ideas or finish something if you’re on a roll. One tool he talks about to help with this is “conditional overflow” time blocks. If you are uncertain about how long something will take, schedule a block right after it that you can either use to complete the first task if it runs long or to work on a second, optional task if you finish up the first one.

Newport has in interesting benchmark to quantify the depth of a particular activity: How many months it would take to train a smart college graduate with no specialized training in the field to do this task? If the answer is relatively short, then the task is not that deep (and probably not all that valuable, since it implies almost anyone can be trained to do it). If the answer is quite long then it’s much more likely to be deep work. He recommends thinking about your various tasks using this benchmark and setting a shallow work budget to limit how much time you spend on these sorts of tasks.

One of the big shallow work time sinks that’s not pure distraction is email, and Deep Work lays out some techniques to reduce the email burden. On one side of the equation, he advocates making the people who email you do more work. If possible, don’t have your email address out there in public. Set expectations that email from people you don’t know may not receive a response. Then you don’t need to feel guilty when you don’t respond. As Newport puts it, “it’s the sender’s responsibility to convince the receiver that a reply is worthwhile.“ Unfortunately, these aren’t really an option for me in the day job. My work email is on our website and part of our job is being responsive to the public.³

Perhaps somewhat counterintuitively, Newport advocates doing more work when you do respond to an email. Specifically, he recommends putting more effort into an individual email (preferably your first one in the conversation) with the goal of minimizing the number of emails needed. So instead of asking someone if they want to meet for coffee, propose a specific place and time up front and avoid the tedious back and forth. I’ve heard this sort of advice specifically around scheduling meetings before, but he advocates this sort of “project” focused email technique more broadly. Think about the end state that you want to get to and use that first email to accomplish (or prompt the person you’re emailing to accomplish) as many of the steps to get there as possible.

As I said in the intro, this book came along at just the right time for me. It provided reinforcement for some of the changes I was already making in my life. It’s also helped me better articulate what I’m doing and why. In addition to the larger conceptual stuff it also gave me quite a few techniques and insights about how to do deep work that are already proving their worth. I’d definitely recommend the book to anyone who does work that requires sustained concentration that pushes your brain to the limit. If you’re still on the fence, Shawn Blanc has a nice podcast interview with Deep Work author Cal Newport.

March 27, 2017