Backup Strategy

When I got my new iMac, I took it as an opportunity to revisit my backup strategy. I’m pretty religious about having good backups and they’ve saved my bacon more than once.1

There are lots of different ways of backing up your data. You can use Apple’s Time Machine, clone your hard drive, subscribe to an online backup service, manually copy data to external drives, back up to network attached storage, and so on. Lots of people will extoll the virtues of one or more of these options. However, rather than starting with the backup techniques themselves, I find it more useful to start by thinking about the problem you’re trying to solve. Decide what threats to your data you are concerned about, then pick backup techniques that address those threats.

So, what threats am I trying to mitigate with my backup strategy?

Oh crap I shouldn’t have deleted that!

The most common threat to my data isn’t theft, or fire, or hardware failure; it’s Command+S. I’ll make a change to a document and save it, then realize that the change got rid of something I wanted to keep. Or I’ll delete a file and empty the trash before I realize that it was the wrong file. Either way my actions are more of a threat to my data than anything else.

The simple solution to this is Apple’s built-in Time Machine software. It lets me go back and resurrect old versions of my data before I mistakenly deleted something.

In the past I’ve run Time Machine over the network, either to an Apple Time Capsule or to a share on my Drobo 5N. Every so often, however, Time Machine reports that it needs to get rid of my old backup and start again. With my move to a desktop Mac I decided to switch over to using a directly attached hard drive for Time Machine. So far this has been working well, but I haven’t really used it long enough to tell whether it’s more reliable than doing it over the network.

Oh crap my hard drive just died!

After my own incompetence, the next most likely cause of data loss is some sort of hardware failure. Either the hard drive dies, or my whole computer fails. Time Machine can help with these sorts of situations but it’s not optimal. I would have to get a new drive (or a whole new computer), reinstall the OS and then restore my data.

A better solution is to clone my Mac’s hard drive to an external drive. This way if I have a hard drive failure I can get back to work right away by booting my Mac off the external clone drive and pick up right where I left off.

I use Carbon Copy Cloner to do this. CCC figures heavily in several parts of my backup strategy, and I think it’s a piece of software every Mac user should own.2 Every night CCC clones my iMac’s hard drive to a 1tb external drive. CCC will make this software a “bootable clone”, setting it up so I can boot directly from the cloned drive (unlike a Time Machine drive).

The one potential issue I have with my current setup is that the external drive I’m using is a spinning hard disk, so when I boot my Mac from the external drive it’s very slow compared to running off my nice fast internal SSD. I’m considering whether it’s worth buying an external SSD as my bootable backup instead.

While my most important files are on my iMac’s hard drive, I also want to make sure all the data on my Drobo network attached storage are backed up. I have CCC set up to clone the Drobo as well. Right now I’m actually using two separate clone drives, one for my iTunes library and one for other data. This is primarily because I outgrew both the original drive I was using for this and the larger drive I got to replace it. So now I’m using both the original drive and the replacement in combination. I use Carbon Copy Cloner to clone my Drobo to these drives on a weekly basis.

Oh crap my house just burned down!

While a house fire is the notional threat here, it’s really a stand-in for any disaster that takes out both my Mac and the various backups on external hard drives I have sitting in my office. It could be a fire, flood, tornado,3 or theft. The solution is to have some sort of off-site backup. For a long time the only way to do this was by physically carrying a backup hard drive somewhere else. This sort of thing is obviously a bit of a pain, so most folks didn’t do it very often (if at all). The advent of high speed internet connections and cheap cloud storage has created a much better solution: online backup.

There are various services out there, some that will store your data for you, others that will back your data up to your own cloud storage service, or even a computer at a different physical location. I use Backblaze, which provides unlimited cloud backup for a yearly, per-computer fee.

One limitation with Backblaze is that it will not back up network attached storage, only drives that are directly attached to your computer. This is where the clone backups of my Drobo come in. Because these cloned hard drives are directly attached to my iMac, Backblaze will back them up. This does mean that my backups of stuff off the Drobo will be up to a week out of date since I only run the Drobo clone job once a week, but the stuff on my Drobo doesn’t change that frequently.

One limitation with online backup is the 1tb per month bandwidth cap that my ISP has recently imposed. I ran into an issue that required restarting my Backblaze backup from scratch when I reformatted my Mac mini, and it will be several months until I have everything uploaded to Backblaze again.

Oh crap I’ve got ransomware!

The most recent threat to my data is ransomware, malicious software that infects computers and encrypts all your data so you can’t access it until you pay the person who coded the ransomware for the decryption key.

The problem with ransomware is, depending on how cleverly it’s written, it can potentially corrupt any backup that can be reached from your computer, including network attached storage, external hard drives, and even online backup. The solution is to have a backup that’s not attached to your computer.

The most recent addition to my backup strategy is a “rotating shelf backup”4. I have two large external hard drives and every week I’ll connect one of them to my iMac and clone the iMac hard drive and my Drobo 5N. Once the clone is done, I’ll disconnect the drive and put it on the shelf. The two drives alternate every other week. By using two drives, I ensure that even if I was hit by ransomware while doing the clone, I’ve still got a copy of my data on a drive that’s not connected to my Mac.

Oh crap I forgot that file when I reformatted my hard drive!

Most of these backup strategies are intended to make sure I have as recent a copy of my data as possible. However, there are times where I want to make sure I’ve got an old copy of my data. Whenever I decide to nuke and pave5 I’ll use CCC to back up the computer to a a disk image on my Drobo. This gives me a copy of my data that can hang around for months or years, long after my Time Machine, clone backup, and online backup have been written over with data from the newly formatted drive. This has saved my bacon a couple of times when I realize that there was an important file stored in some odd location that didn’t get copied over to the newly formatted hard drive. I’ll do the same thing when I get rid of one of my computers.

Do I really need to do all of this?

The truthful answer is probably not. This is a pretty heavily optimized backup strategy. Most of these techniques protect against multiple threats. If a hard drive dies you can recover from Time Machine or an online backup, for instance. A clone backup is easier to recover from, but it’s not the only way. You could protect against all of these threats with just Time Machine and a clone backup that you stash at a friend’s house. But that isn’t going to be as quick or seamless as having strategies optimized for each threat, nor does it provide as much redundancy.

I’m trying to have the best possible solution for each of these potential issues. This means when I do have a problem, I’ll be able to get back up and running with a minimum of fuss, but it’s more effort on the front end.

I would say that as an absolute minimum, you ought to have two different types of backup, one of which should be offsite. There’s nothing like suffering a hard drive failure and then finding out there’s a problem with your backup. As the saying goes, “two is one and one is none.” The easy button for most people is probably Time Machine and a service like Backblaze. Regardless, have a backup strategy and test it periodically.


  1. For instance when I unexpectedly needed to erase and reformat my Mac mini. 
  2. SuperDuper has a similar feature set, but I prefer Carbon Copy Cloner. 
  3. Here in Kansas anyway. Depending on where you live substitute in a hurricane, earthquake, wildfire, or whatever the local natural disaster is. 
  4. Does that make it a “lazy susan backup”? 
  5. Reformat my hard drive and set that computer up from scratch. 

My Multi-Monitor Setup

I have always been interested in getting as much screen real estate as I can on my computers. In the early 2000s, when dual outputs on video cards1 were first becoming widely available I ran a pair of 19” CRT monitors and ever since my main machine has had at least two displays. My new iMac has given me the opportunity to create something pretty close to my ultimate setup.

The iMac can support one 5K external display or two 4K displays. I opted for the two 4K displays, both because that provides more screen real estate for less cost, and because it allows me to create a symmetrical arrangement (the iMac in the center with a secondary monitor on either side2).

4K displays are available in 21”, 24”, and 27” sizes. The 21” seemed like it would be a bit small for displaying two apps or webpages side by side, especially since the secondary monitors would be further from my eyes. I’ve read several places that stretching 4K over a 27” monitor doesn’t look as nice as the smaller displays. The sweet spot for 4K displays seems to be 24”.

I went with the Dell P2415Q, a 24” 4K display recommended by The Wirecutter and [Katie Floyd](katiefloyd.com/ P2415Q). It’s a nice monitor. The picture is very crisp, though the color and brightness can’t compare with the iMac’s built-in display. After playing around with the scaling in display preferences it does a good job showing two side-by-side apps, showing the full content in each app while not being too small to read comfortably. I’m very happy with them so far.

One of the keys to using a big multi-monitor setup like this is to be thoughtful about how you place your apps. Don’t just spread windows out willy-nilly. Each part of my desktop has a particular role.

The center screen is obviously where I do most of my work. It’s usually home to either one maximized app that fills the entire screen or two apps running side by side (often Reeder and Safari).

The right half of the left-hand monitor and the left half of the right-hand monitor are for my supporting apps. While I’m doing something on the center screen I might be using one of these positions to take notes in Bear, move cards around in Trello, or reference an email.

Several years ago I was running a pair of 24” monitors on my work machine I usually sat in front of the right-hand monitor and I often found that the left half of the left-hand monitor often ended up “out of sight, out of mind”. I didn’t want that to happen with this setup, so I try to be very thoughtful about what goes on either end of my desktop. I use the left half of the left-hand monitor and the right half of the right-hand monitor for apps that I want to be able to see at a glance, but don’t need to pay continuous attention to, like the Sonos controller app.

Multimonitor screenshot medium size

One important thing to note is that while different parts of my desktop fill different roles, apps aren’t necessary confined to a single role or position on my monitors. For instance, OmniFocus usually lives at the extreme right side of my desktop (the right side of the right-hand monitor) so I can glance over and see my task list. However, when I’m doing my weekly review OmniFocus takes center stage and moves over to my main monitor. Similarly, when I’m using Bear to take notes, it lives on the left side of the right-hand monitor with whatever I’m reading on the center display. When I’m using Bear to write or edit an article like this one I’ll move it over to the iMac (and often maximize it).

This sort of flexible approach means I need good tools for moving apps and arranging windows. I’ve used several different window managers over the years. My current favorite is Magnet. It’s just a quick key combination to move and size a window to cover the left or right half of the current monitor, maximize it to cover the whole display, or move it to the next monitor. I got a Magic Trackpad with this iMac, which has lead me to incorporate Better Touch Tool into my window management. I have it set up so a force press on the upper right or left corners of the trackpad will move the current window to the left or right monitor, respectively. A force press on the lower right or left corners moves the current window to that half of the current display. If I’m typing on the keyboard and need to move a window, I’ll use Magnet. If I’m using the trackpad, I’ll use Better Touch Tool.

Being able to have a ton of windows on the screen can be a huge productivity boost for some activities. For others it can be a huge distraction. To help combat the latter, I often use HazeOver. This app grays out everything on your screen(s) except for the current application. You can set how opaque you want this to be, all the way up to pitch black. I have it set to about 90%, which does a great job helping me concentrate on the task at hand when I need to.

Running a setup like this does have some implications for some of the OS’s built-in features. For many years I ran the dock on the side of my screen to save precious vertical screen real estate.3 With three widescreen monitors like this that would mean an awfully long trip to reach it, so I’m back to the default position at the bottom of my center display. Apple added the ability to jiggle your mouse back and forth to make the pointer expand so you could find it in El Capitan, but I never found the feature that useful until I had this much screen real estate to loose the cursor in.

I’m very happy with this three-monitor setup. The iMac display does most of the work, but the ability to have supporting apps to either side and apps I can glance at easily on the extreme ends is really nice, and helps with productivity.


  1. VGA and DVI! Talk about a blast from the past. 
  2. The true ultimate setup would be an iMac flanked by two 5K displays, something that will be possible with the iMac Pro, coming out later this year, albeit at tremendous cost (~$8000). 
  3. I still run the dock on the left side of my monitor on my laptop. 

First Impressions of the new 2017 5K iMac

I am now the proud owner of a brand spanking new iMac!

What I got

This is the first time that I’ve bought an iMac (or any all-in-one desktop). Before I’ve always had desktop machines with separate monitors. Since such a big portion of the value of this computer is in the screen I ordered a fairly high-end machine so that hopefully I’ll be happy with it as long as possible.

Apple offers their usual three “good, better, best” configurations on their website. The higher end configurations have slightly better processors and the “best” machine has more storage; they also have three different graphics cards. Notably, starting with the higher base model is the only way to get better graphics on this machine; you can’t configure the GPU separately.

I started with the “best” configuration and bumped the processor up to an i7 (better multithreading and a faster clock speed). Unlike a lot of Macs, the memory in the 27” iMac is user replaceable rather than being soldered to the motherboard. With non-upgradable machines I tend to max out the RAM when I buy it, since there’s no way to add more later. In this case, I bumped it up to 16gb, but if I feel the need in the future I’ll be able to upgrade it all the way up to 64gb (and do so for a lot less than the $1200 Apple would charge me).

The other big upgrade I made was getting a 1tb SSD. I fell in love with SSDs when I bought my bought my current MacBook Pro back in 2012. After using it for a while anything with a spinning hard disk just seems soooo slooooow. The other storage option on this machine is a Fusion Drive (a spinning disk plus a small SSD for cacheing frequently used data). While the Fusion Drive mitigates some of the disadvantages of the spinning disk, I’m willing to spend the extra $$$ to have fast access to all the data on my machine. However, I decided it didn’t make sense to spend $1400 for a 2tb SSD. I keep the really big stuff like my iTunes and Plex libraries on a network attached Drobo. The drive in my computer is basically apps, my photo library, and dropbox, plus whatever larger files I’m working on at the time. Honestly, right now I could probably get by with a 512mb SSD (the one in my MacBook Pro has been doing fine) but since the SSD is not easily replaceable, I figure 1tb will help future-proof this machine.

First Impressions

Out of the box my first reactions was “wow, this is big”. I’ve run a 27” monitor at work, so the size really shouldn’t have been a surprise. However, unlike a monitor the “chin” beneath the screen adds considerably to the impression when you’re sitting in front of it. It also makes the machine fairly tall. I like my monitors elevated fairly high; I’ve been running the monitors on my desk at home on a 10” tall monitor shelf for a long time. In this case, however, putting the iMac on the shelf made it way too high. The shelf had to go. For now I’m using a few reams of paper and a book, putting the bottom of the iMac’s “foot” about 7” above the desk. This puts the screen in the proper ergonomic position (with my eye level just below the top of the screen).

The big 5k screen is just fantastic. I am completely blow away by how bright and sharp it is. I’ve had retina displays on my laptop and iOS devices for years now, but thanks to it’s size this is just in a whole different category. It’s also tremendously bright. I’ve got it on the middle brightness setting and it’s still brighter than the 24” monitor I have next to it, even with the brightness on the external monitor cranked all the way up.

Lots of people say that once you’re used to a retina display you won’t be able to stand a non-retina screen, but in the past I hadn’t found this to be true. My retina MacBook Pro spent most of it’s lifetime right next to a standard definition 24” external display. If you looked hard, it was obvious the laptop screen was better, but I didn’t think it really made the external monitor look bad. Putting that same 24” display next to the iMac made it look horrible by comparison. I had been planning to get a pair of 4k monitors to go with the iMac, but seeing just how bad the standard def display looked definitely made that more of a priority.

This is a very fast machine. Not that my MacBook Pro was pokey by any means, but the difference is quite noticeable. While the processor and memory are both substantially faster, I think the faster SSD is a big contributor to the perceived increase in speed. Going from the SATA connected SSD in my MacBook Pro to the PCIe connected drive in the iMac isn’t as big a difference as going from a spinning disk to an SSD, but it takes a lot of things that were short waits on my MacBook Pro and makes them effectively instantaneous. Stuff that took a long time is noticeably quicker: for instance, when I run DaisyDisk on my iMac’s SSD it runs in a fraction of the time that it takes on my MacBook Pro.

I haven’t had a chance to do a lot of real processor intensive stuff, but it’s no slouch in that department either. The iMac cranked through the photo recognition on my large Photos library quicker and with less disruption to my other work than on older machines.

So far, the only games I’ve played on the iMac are Civilization VI and Kerbal Space Program, neither of which are graphics hogs even with all the settings maxed out. The GPU in this machine is mid-range by PC standards, but in these games it’s just loafing along.

I also got the new Magic Keyboard with Numeric Keypad (the numeric keyboard option is new1). Normally I’m a click-clacky mechanical switch keyboard guy.2 The Magic Keyboard is similar to the keyboard in my MacBook Pro, with much less key travel (though still more than the recent MacBook and MacBook Pro keyboards). I’m giving it a try, but I’m not sold yet. I may end up going back to my big, wired keyboard. One minor annoyance is that the Magic Keyboard doesn’t have the double-height “+” key that I’m used to, so the “-“, “*”, and “/“ keys are each one position off from where my fingers think they should be.

Another feature I really like that’s new to me is the ability to unlock the Mac with my Apple Watch. This actually came out last fall as part of macOS Sierra, but my MacBook Pro was too old to take advantage of it. It’s probably a bit faster than typing in my password, but not by a huge amount. I’d still really like a desktop keyboard with a TouchID sensor (that might be enough to get me to give up my mechanical switch keyboard for good).

Overall, I’m very happy with the new iMac. The speed and the big, gorgeous screen are a big upgrade from my 5-year old MacBook Pro. I’m also happy to have a dedicated desktop machine. As I said in an earlier article, for my current circumstances having a desktop at home and a laptop (or, increasingly, an iPad Pro) that I can take to work or on the road makes more sense than doing everything on a big beefy laptop. I’m looking forward to many years of enjoyment from this machine.


  1. It’s also a bit hidden when you’re ordering in the Apple online store. Rather than being one of their usual click boxes or drop down menus, it’s hidden behind a text link that says “Change”. 
  2. My daily driver is a Das Keyboard Professional 

Laptop vs. Desktop

For most of my computing life, I was a desktop and laptop person. A desktop machine at home for heavy duty tasks and gaming, and a laptop for presentations and getting work done on the go. This pattern survived my transition from Windows PCs to Mac, where I ultimately ended up with a Mac Mini and a first generation MacBook Air.

Then about 5 years ago I got a job where I needed a beefy machine at work to do video editing and photo manipulation. Rather than spending the cash to keep both a desktop and a laptop up to date, I decided to go with one powerful laptop and move it back and forth from home to work. At the time, the Retina MacBook Pro had just came out, and I ended up going with a top of the line 15” model. I got a couple of external displays to satisfy my passion for screen real estate and was good to go.

I did not go entirely laptop-only, however. Although my Mac Mini had been eclipsed by the MacBook Pro as my primary computer, I kept around as a home server, running my iTunes library, handling online backups, and other tasks. This helped me retain the advantages of having a desktop at home without the expense of keeping up with new hardware (who cares if it’s slow when I only log in once every couple of months).

I love the 15” Retina MBP and that machine is still going strong today. However, my circumstances have changed. I no longer do a lot of heavy duty tasks on my Mac at work; rather than editing movies and photos, the most stressful thing I’m doing is some light Python scripting. On the flip side, the 5 year old MacBook Pro and Mac Mini are getting rather long in the tooth for some of my needs at home. The MBP isn’t able to run some of the games that I’d like to play1 and the Mini has started getting a bit flaky.2

All of this lead me to decide that my next Mac would be a desktop machine; I settled on one of those big, beautiful 5k iMacs. I actually made this decision late last year, but since the then-current iMac was over a year old at that point and lacked USB-C or Thunderbolt 3, I decided to wait and hope for an updated model. I was hoping for new Mac desktops at their November event, but when that brought only new MacBook Pros, I feared it would probably be Fall 2017 before we saw any new iMac models. Then WWDC 2017 brought an unexpected gift: new iMacs with USB-C and Thunderbolt 3 support! I jumped on the opportunity right away and now I’ve got a new top of the line 5K iMac on the way. I expect I’ll have plenty more to say about this machine when it arrives.

For now, my old MacBook Pro soldiers on in the laptop role. I still tote it to work every day. It’s under threat from a couple of different sides, however. Since I no longer need a ton computing horsepower in a laptop, I’m tempted by the ultralight MacBook. The touchbar has me drooling over the new MacBook Pro as well, and the 13” model would still be quite a bit smaller and lighter than my current MBP. The biggest threat may not be a new laptop at all, however. The 12.9” iPad Pro has already replaced my laptop more and more often when I travel, and with the new enhancements to iOS that were recently previewed at WWDC, I can foresee it taking on a larger and larger role in my life. Perhaps the next phase for me is a beefy desktop at home and an iPad everywhere else?


  1. Civilization VI 
  2. It got to the point where it wouldn’t boot and I had to reinstall the OS. 

Due and Time Sensitive Tasks

Fourth in a series on task management. Read part 1, part 2, and part 3.

OmniFocus is a great tool for capturing and organizing tasks, but when it comes to getting certain stuff done I need a bit more of a kick in the pants. That’s where Due comes in.

Due is a very persistent reminders app. By default it will sound an alert not only at the date and time you set for the task, but every five minutes thereafter. It’s great for things that need to get done at a certain time, like taking the trash can out to the curb on trash day.

While you can use it for one-off tasks, most of the stuff I’ve got in there are repeating tasks. Due has a very powerful system for this that goes beyond just the daily and weekly repeats you see in other apps. It allows you to set a task to repeat on a certain day of each month, or just on weekdays, etc. The only repeat interval I think is missing is one for a certain number of days before the end of the month (which would be useful for things like mailing my rent check that needs to arrive by the 1st of the following month).

I use Due for things like reminding myself to back up my iOS devices to a Mac every week, to top off the charge on a USB battery pack every month, and even to call my parents on their birthdays. One of the most critical things I have in there is a reminder to do my weekly GTD review in OmniFocus. I have a tendency to skip that, so it’s great to have an app as persistent as Due to get me to do it.

Due is a great looking and well designed app on iOS. The Mac version is not nearly as impressive (and has a completely different look). It basically seems kind of phoned in on the Mac, the iOS version is definitely the flagship. I’ve got it installed on my laptop just so I get the reminders, but I don’t usually interact with it much on the Mac (the reminders sync back and forth via iCloud or Dropbox).

I resisted Due for quite a while, relying on the built-in iOS reminders app, but it has become a critical piece of my task management system.

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.