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.


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.

  1. I first heard about Deep Work from Shawn Blanc
  2. It would be nice to dedicate days or weeks (or years) to deep work, but my job and schedule wouldn’t really allow it. 
  3. Thankfully, what we do is boring enough to most people that we’re hardly deluged. 

The Never Ending Battle: Fighting Email Distractions

If I got a ding every time I got a new email, I’d go insane. So whenever I get a new device or try a new email program, the first thing I do is turn off the audible alert it makes when I get a new email. If I didn’t, every email would be at least a momentary interruption as my mind registers the ding. What’s more, it makes the arrival of each new email a moment of temptation; a chance for me to get off task and into my mail app checking on whatever new email arrived.

Apple has made going this route a little easier with it’s VIP feature. I’ve set it to alert me when I get an email from someone on my VIP list, so only emails from the most important people are an interruption. Importantly, I’ve been able to keep my VIP list short and the people on it are not ones who are emailing me constantly.

For many years now I’ve run my devices with the email ding turned off, but I still had the rest of the notifications options turned on. Oddly enough it wasn’t the more obvious notifications like the lock screen notifications or the banners that pop up when a new email arrives that made me realize this was still a problem, it was that badge on the app icon with the number of unread emails. Every time I was on the home screen of one of my iOS devices, that little red circle tempted me to just pop over to my email app and see what was in there.

I went ahead and turned off the app icon badges (and all other non-VIP notifications). While I was at it I turned off badges for all of my home screen apps except for Due, OmniFocus, Messages, and Drafts. In addition to helping with distraction this also increased the visibility and importance of alerts for those apps. When the red badge indicating tasks that are due soon in OmniFocus is one among many on my home screen it blends into the background. When it’s the only one it really stands out.

After I turned off the notifications on my personal devices it got me thinking about my work PC. Initially I was just going to turn off the desktop alert that popped up for new email, but I got to thinking about a couple of things:

  • I do my best, most productive work in the morning, particularly when it comes to technical tasks or high quality writing that requires intense concentration.
  • I seldom receive any email so urgent it couldn’t wait until after lunch.

So I’m trying an experiment: Outlook gets turned off before I go home at night and it doesn’t come back on until after lunch the next day.

So far I haven’t had any irate colleagues coming up to me and complaining I didn’t respond to their email fast enough (thankfully, the email culture at my workplace is not one that requires immediate responses).

I have run into a couple of issues though: Outlook is both an email app and a calendaring app. This means that I can’t open it up to look at my calendar at the beginning of the day without also catching a glimpse of my email. Now I do think my willpower is strong enough that I could keep myself from reading any email when I’m in there, but sometimes even seeing the sender and subject line can distract me into thinking about the email when I’m trying to spend my most productive time on another task. So I’m trying to develop the habit of checking my calendar in the morning on one of my iOS devices, where I have separate email and calendar apps (currently the excellent Timepage).

The other issue is that sometimes the task that I’m working on in the morning requires me to send mail and there’s no good way to do it without firing up Outlook and seeing my mailbox. This has me wishing for an email client that would allow you to send mail, but not read it.1

One way or another email has been an issue for me for a long time: Checking it too often, letting it build up in my inbox, allowing particular messages that I need to do something with (usually something unpleasant) to sit there and fester. I hope that the measures I’ve taken recently will help me make some progress, but I’ve got no illusions that these represent any sort of final victory. It’s a never ending battle.

  1. And also wishing for the flexibility to use a desktop email client other than outlook with our locked down email system, but that’s a different subject. 

Inventorying my Tools

One of the things I’ve been inspired to do lately is to take an inventory of all the tools I use to get work done. 1 To help bring some order to this I’ve broken it down into tools I use every day, tools that I use often, and tools that I only use occasionally, but are vital for particular tasks (within each of these categories tools are listed in no particular order).

Every Day

Microsoft Word
iPhone Mail app
Field Notes


My office whiteboard

Occasional But Vital

Python (IDLE)

The list itself is kind of interesting, but I think the real value here is to reflect on the tools individually and as a set. Are there some of these where I would benefit from learning to use them better? Which ones do I want to use more often? Which ones do I want to use less often? Are there tools that don’t fit my needs anymore? What tools aren’t I using that I might benefit from?

I’d really like to move Drafts up the list and make it an app I use every day. I know I’m not using it to it’s full potential right now. On the flip side, I’d like to use Microsoft Word less often. It’s in the “daily” category because I use a PC at work and almost all of the folks I collaborate with don’t write text any other way except in Word. I’d much rather use a simpler Markdown enabled text editor (several of which you’ll see on the list). I doubt I can get it off the list entirely, but only having to open it a few times a week seems doable.

One of the tools that’s helping me diminish my reliance on Microsoft Word is Bear. It’s can export content as a Word document and, using Dropbox, I can get the exported .doc file onto my work PC fairly easily. When I initially made this list, Bear was in the “often” category, but by the time I got around to writing this article it had jumped up to “every day”.

Among the things this list has me thinking about is whether Byword is going to stick around for me much longer. It’s been a mainstay for me on both iOS and the Mac for a long time. But when I look at all of the text editors on the list I have to wonder how much room there really is for it between Bear on one hand and Ulysses on the other. About the only thing Byword has going for it right now is when I need to make some edits to a text file on the filesystem of my Mac (since both Bear and Ulysses want to store their own documents internally).

Many of the apps in the occasional category are problematic. They serve a vital purpose, but I don’t use them often enough to really achieve a level of mastery. There are a few of them like ArcGIS that were everyday apps for me in the past and enough of that knowledge has stuck around that I can still make them dance when I need to.

For some of them I probably just need to decide if a more specialized app that I seldom use is worth the overhead compared to a more general tool that I use less often (Ulysses versus Scrivener, for example). For many of them, though, I really don’t have a good alternative. It’s just not a problem I’ve got a solution to at the moment.

In addition to all the apps, you’ll notice a pair of analog tools on the list (Field Notes and my office whiteboard). Initially this list was going to be focused on just software tools, but these are important to my getting things done. In particular, the Field Notes Steno books that I use for all my note taking in meetings and the like is probably one of the most vital, and most used tool on the list.

Overall, I think this was a useful exercise. It got me thinking and caused me to make some changes to how I use certain apps. I’d encourage others to give it a try as well. It’s probably something worth doing on a regular basis.

  1. I’ve excluded personal stuff that I use purely for recreation, like Reeder and Sonos. 

Why am I doing this?

I am completely incapable of learning something new and not feeling the urge to write about it.

This has been most evident in my hobbies1, but lately I’ve felt the urge when it comes to certain tech and productivity related topics. Part of this is probably because I’m a bit of an insufferable know-it-all and I can’t seem to resist occasions when I can speak from a position of authority. However, over time I’ve come to realize that a big part of this is that the process of writing is beneficial to me.

When I write up something it forces me to organize my thoughts and think more deeply about what I’ve learned than I would otherwise. If it’s something from a class or a book, it forces me to take better notes (or to take notes, period) and to engage more with the subject matter. Just about anyone would probably be better off taking good notes and doing some review/organization afterwords. Most of them don’t necessarily feel the need to make that process public. But for me, at least, a key part of the motivation to follow through on those things is the fact that it will be out there for all the world to see. Hence, this blog.

In short, the reason I’m doing this is because writing about something I learn helps me learn about it better. I’m no productivity guru2. I have no ambitions of becoming the next Shawn Blanc or David Allen. Consider this more of a journey of self-improvement, and if you’re on that journey too, consider me a fellow student.

  1. For instance, I’m a gun guy, and a detailed summary of every firearms training course I take seems to end up online. 
  2. As you’ll see soon enough a big part of the reason I’m interested in organization and productivity is because I’m naturally so bad at it.