Productivity Hacks: Timeboxing and the macOS Automator

Alastair Christian
Alastair Christian
Published in
5 min readFeb 13, 2020
Photo by Mateusz Kapciak from FreeImages

We all know that focus matters and attempting to multitask is a productivity killer. In a perfect world you would be able to focus on a single task until it is completed and then move onto the next one. I don’t know about you, but this utopia is still a little way off for me. On any single day I may have the following types of task on my plate:

  • Communications with staff, suppliers, clients and potential clients;
  • Working on marketing material for DataDIGEST;
  • Writing for my personal or DataDIGEST blog;
  • Writing code for a client project (could be one of any number of technologies, each with different tools);
  • Undertaking training, usually online with Pluralsight.

In the past I have experimented with setting aside a whole day each week or fortnight for things like writing and marketing. Unfortunately, the real world tends to encroach upon those ring-fenced days and things don’t get done. I’ve also found that I struggle to form good habits when tasks that aren’t in my current comfort zone occur so infrequently. I’m ashamed to admit that having missed a couple of days of writing, selling or going for a run is not something that makes me feel guilty. In fact, it gives me more reason to miss another one: “I’ve already missed three weeks this month, I might as well miss the fourth and try again next month.”

So I’ve learnt that for me it makes more sense to set aside buckets of time each day for all the different activities I have to perform. I’ve written before about my dabblings with the Pomodoro technique and I still find that I am most productive when I am working in timeboxes. But I kept running into a distraction problem. There would often be applications left open from a previous task that interfered with my focus on the current task. For example, if I had been working on a training course from Pluralsight and then switched to working on the marketing plan for DataDIGEST, catching a glimpse of the training slides, or the demo I had been working through, would knock my mind out of marketing mode and back into learning mode. Context switching is hard enough without distraction landmines being scattered about my workspace.

I decided to see what macOS provided to help me. Like most Mac users, I was already habituated to using Spotlight to open whatever application I was looking for. It occurred to me that rather than using Spotlight to open each individual application I was going to use (and each task might involve 3 or 4), it would be good to use Spotlight to say “I am going to start writing” or “I am going to start .NET coding” and have it open every application needed for that activity. The Automator utility within macOS provided an easy way to achieve what I was looking for.

Let’s use my writing activity as an example. I need 3 applications open when I am writing. Bear, to actually write in; a timer/pomodoro app (currently Tomato 2, but I change my preference here as often as my son changes his mind about whether he likes nachos); and Microsoft To Do (which in this case contains any ideas for writing I’ve jotted down). What I want to be able to do is command-space “start writing” and have only those applications open.

Step 1: Open the Automator app.

macOS Automator initial dialog

Step 2: Click on the “New Document” button.

macOS Automator new document dialog

Step 3: Choose “Application” as the document type.

macOS Automator new, empty Application document

Right, we are now in the Automator utility. In the left hand pane is a Library of available actions. For this simple automation, we are going to be interested just three of these actions: “Quit All Applications”, “Get Specified Finder Items” and “Open Finder Items”. These are all under the “Files & Folders” node, but if you know what you are looking for the Search box at the top of the Library pane is the fastest way of finding things.

macOS Automator searching for “Quit All Applications” and adding to workflow.

Step 4: Locate the “Quit All Applications” action and drag it into the Workflow area to the right. We have some options to configure. I generally want to be prompted to save any changes in existing applications, so I check the “Ask to save changes” option. If there are some applications you always want open, you can add them to the “Do not quit” list.

Step 5: Locate the “Get Specified Finder Items” action and drag it into the Workflow area. For this action, we want to select each of the applications we want to open, so we click on Add… and browse to the Applications folder and select Bear, Microsoft To Do and Tomato 2.

Step 6: Locate the “Open Finder Items” and drag it into the Workflow area. Since we are opening applications we can leave the “Open with” option as “Default Application”.

macOS Automator showing full workflow with Quit All Applications, Get Specified Finder Items and Open Finder Items.

Step 7: Now we just need to save our Automator document. I call mine “Start Writing.app” and save it in the Automator folder in my iCloud Drive. This way the automation is available on both my laptop and desktop.

To use the automation, simply command-space and start typing “Start Writing”. Spotlight will find the application and execute the automation. The only gripe I have with this setup at the moment is that in macOS Catalina I’ve lost the ability to assign applications to specific displays in my multi-monitor setup, so there is a bit of window arranging that has to be done.

That’s it. Automator is pretty simple to use and quite powerful. It has definitely aided my context switching and focus, in addition to shaving a second or two off the process of opening applications. What productivity hacks do you use? Or do you have favourite workflows that you use in macOS? Sound off in the comments.

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