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Welcome back to day three of the Automation challenge. Before we move on to today’s challenge, be sure to complete Day 1 and Day 2.

At this point, you’ve learned that automation can be quite simple. Today we’re going to expand upon that with hidden features that are in Windows and Mac. 99% of people don’t know these features exist, but once you use them, it’ll speed up so many repetitive tasks you do on your computer.


Since Windows and Mac have different hidden features, each operating system user will implement something slightly different but equally useful. Watch the video below to discover how to do that.

Mac users: start at [6:09] (Mac – Quick Actions) where you’ll learn how to use Quick actions.

Windows users: start at [15:45] (Win – Task Scheduler) where you’ll learn how to schedule an automated task. You can get really creative with it, i.e. launch Outlook at 10 am and 4 pm to check email.

Challenge for Mac users:

  1. Annotate a document (can be any type) with a Quick Action.
  2. Comment below that you did it!

Challenge for Windows users:

  1. Create a Diary Prompt like shown in the video to show up every day at 4 pm.
  2. Comment below that you did it!

If you use both operating systems, just pick one.

Let us know in the comments that you’ve done it! It’s important to do this to be eligible to win one of the prizes (Oura Ring, AirPods and Atomic Habits). See you tomorrow for day four! That one will be a challenging one.

Update: Day 4 is now live!

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Last Updated: December 14, 2020

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  1. This is fantastic – I never knew you could zoom in on a document like that!
    I am wondering if there is a way to create my own “add to calendar” quick action – I get stuck on the input dates. Any resources?

  2. I scheduled the accounting software that my firm uses to open at 5 PM daily as a reminder to complete my timesheet.

  3. Done! So cool – had no idea that I could zoom in on a section of document, let alone the quick tool to access document mark-up!

  4. I created my task in windows. I created the diary – really a task to remind me to do a 5 min plan for the next day. I have meetings every Tuesday and Wednesday. I have to pull up meeting notes, reference materials, vacation schedules -etc. Roughly about 5 webpages each time. Most are on confluence. Couldn’t figure out how to pull up just those pages in chrome. What I ended up doing is creating a chrome group to open everytime I open chrome which included those pages. One other issues was that the pages I open up each week are different because we create a new page everytime we have a meeting. I want to be able to open up the last meeting notes. Haven’t figured out how to do that yet. What I’m ending up doing is creating a tab of the location that is the overall meeting area and then still have to make a click over. At least it brings it down to only 2 clicks that I need to do. Other possibility I thought of was to use a different browser so that only those 5 pages open. Still working on it. Again Thanks for this challenge, it kind of feels like I have accountability.

  5. Used the journaling prompt and implemented it when the challenge came out. So far this is quite interesting how it makes a difference in that I actually did journal since then without missing a day.

  6. I’ll have to work on this one with my new work computer. I couldn’t locate the commands to open the apps I wanted. I’ll find the executable files and try again. Also want to investigate using the event trigger.

  7. I set up up a task to check email, and I’ll have to think to see what else I might be able to set up. Very cool!

  8. Done :) Simple and so helpful. I can totally see me using this when my new work computer arrives. For now I am using it to remind me to write in my morning journal

  9. Yeah, I need to think more about my use cases for this. I “know” I should be batching my email, but since I work in sales I tend to leave my Outlook open all the time. I also hear that I should be journaling, but I haven’t started that habit either. Anyway, I pinned Task Scheduler to my taskbar in Windows, so that it is only a click away if I think of something. Or maybe I should create a keyboard shortcut for it? :)

  10. My mac is still on High Sierra. So I don’t have Quick Action. I had to use Automator without it. Thanks for telling me about features in Mojave I actually want.

  11. Update: I persisted even though I don’t have Mojave, which required searching online for Automator with El Capitan (!). I created an automation that takes the selected images and creates one PDF. Done!

  12. The Diary Prompt for Windows is life changing! I just set it up to open Outlook, and open internet browser to the three windows that are part of my morning KPI review routine.

  13. Whenever I pay a bill I mark it as ‘Paid’. I do that, normally, with a third-party application like PDFpenPRO . This quick action is much better for these simple tasks. The fact that you don’t have to open an application first, feels very good.

  14. Done! Set up two, one as a reminder to listen to a podcast i love, but tend to miss…

    The other was the diary entry which I set for later in the evening when I’m home,

    Will transfer a few off my phone to computer in the next few days as they make more sense on the computer.

  15. Couldn’t do it. I think it’s because I’m not on my personal computer, and the work computer is seriously locked down so we don’t “accidentally” destroy something. But I can’t access program files at all.

  16. Done.
    Attempted to “Task Schedule” Outlook e-mail check in for 10am & 2pm – locating the Outlook application was the trick.

  17. I don’t remember if I left a comment yesterday, so I’ll leave another. I put in a shortcut key for MS Publisher and will do several more shortcuts since using the mouse is so aggravating to me! Thank you!

  18. So, a day late…
    Had some trouble finding the program to start Evernote on my desktop. Was going to give up, then read some of the comments and tried again. I just put in start Evernote. We’ll see if it works when I start my computer up again… if it does, will have to tweak it. but I’m always intrigued with finding new ways to establish new habits!

  19. Since I spend 10 hours a day at work on my computer there, this will be handy. Home is a morning thing so I set up a diary prompt for 5am.

  20. For Mac: This challenge “annotating a document with a Quick Action” is only possible as of macOS 10.14 Mojave. In macOS Mojave, Apple has introduced a range of new Finder Quick Actions.

    If you are not on macOS Mojave you can create your own Mac Finder Quick Actions via the Automator app, but you are limited to the actions available in the action library.

    For Windows: I added the task to open Onenote as soon as I login on.

  21. This made marking up an image so easy. I was totally unaware of this feature and it actually made me excited to use Automator.

  22. Sorry. The computer I am using is not upgraded to Mojave so does not have Quick Action available. I tried to do this, so I hope I am not disqualified.

  23. Created the journal prompt, but will still need to tweak it a bit to better fit my workflow.

    Considering setting up some other scheduled prompts during the day to keep things flowing.

  24. Hoorah, seems I still can run the (from the run… function) , so I could start the schedular from there (as long as our IT department lets me……)
    So with a workaround mission accomplished 💪🏻

  25. I didn’t create the diary yet, but I realized a real life use case tonight before seeing the challenge… I have to launch Bark everyday from my laptop to scan my daughter’s phone, so I set this up to do automatically at 5 a.m., so we’ll see in the morning if it worked!

  26. Odd… the 3rd and 5th paragraph from my original comment documenting the various complications that arose when I tried integrated my existing AHK workflow and Task Scheduler automation for my journal entries isn’t displaying properly, or got automatically redacted or something?

    Haha well whatever, so long as the part where I said “challenge finally completed” can be clearly seen by the AE team, I guess that’s all that matters…

  27. Hmm… this challenge turned out to be a little tricky to implement. Primarily due to the fact that I already had an automated reminder in place prompting journal entries, but my system relied heavily on an interactive GUI powered by AutoHotKey scripts (at the time I created this script I was attempting to replicate a quick and dirty “nvALT for Windows” type of journaling workflow) rather than a simple system task scheduled to launch a blank text editor.

    At first I thought it would be a simple enough matter, comment out the code that triggers at specific time intervals and just create a scheduled task to take over that function instead. But it turns out that Task Scheduler can’t/doesn’t launch items with the *.ahk file extension for whatever reason. Strange, but not entirely unprecedented. After all, back when I had a Mac I recall being unable to automate launching some of my applescripts unless I explicitly converted those into applets. Turns out a similar solution was called for here, except Windows doesn’t deal with *.app file extensions but rather *.exe

    But even after compiling my Journal.ahk to Journal.exe, launching it via Task Scheduler would repeatedly throw up alerts onscreen asking me to confirm what program to use to run this file and I had to keep manually selecting the “keep using AutoHotKey” checkbox. Again, a bit bizarre considering that .ahk files are automatically associated to run with AHK, so intuitively you feel like a simple compiled_ahk_script.exe should continue that association, but here yet another (admittedly minor, yet annoyingly repetitive) complication arose.

    I suppose at this point I should’ve just given up on trying to force this to work. I could just as easily have created a simple task to launch an empty text editor and commented here that I completed the challenge… but I already HAD a working solution! I just couldn’t get it to work with Task Scheduler nicely for whatever reason lol. So maybe call it tenacity or perhaps call it stubbornness or call it whatever else you will, but after pulling my hair out and some more super-sleuthing online I finally came up with the workaround of putting quotes around my Task Scheduler entry and connecting my actual Journal automation script to the executable for AutoHotKey itself… and if that doesn’t make sense, simply put, I had to do this number: “C:\Program Files\AutoHotkey\AutoHotkey.exe D:\jvtho\Dropbox\Apps\Editorial\Journal.ahk”

    So now I can get rid of the Journal.exe I compiled earlier, which is great since I prefer to get hands on and tinker with optimizing my script once every few weeks or so and having to recompile an executable copy each time would’ve been a chore. Just before commenting on here I also realized that I could drop the quotes and just paste the Journal.ahk script as the argument parameter in Task Scheduler once AutoHotkey.exe is launched from my Program Files folder. So there, after much trial and error I finally completed the challenge! I’ll be honest though… I most likely will just unfreeze the segment of code I commented out which handles the timed launching of Sublime Text whenever I get around to tinkering with the script next. Till then, I’ll let Task Scheduler handle it for the next few weeks and see how it goes, but it just makes more sense not to bifurcate how I automate my journaling triggers, with the script now only handling the keyboard combo that aspect whereas Task Scheduler now handles the timing trigger.

    In any case, that’s how I completed this challenge to augment my existing workflow that automatically launched my preferred text editor of choice, loaded with my date/time stamped journal entries in the sidebar, before offering a GUI prompt onscreen for Title entry, tags, etc… by literally still doing all of that, except now having it launched via Task Scheduler rather than directly from my Journal.ahk script :)

  28. Done. Quick Actions was what I found most interesting in the video and it was good to experiment with using them. The PDF splitter is really useful. Ii tried setting up a merge action (merging PDFs is something I quite often have to do) but I couldn’t find a way to specify a save location – any suggestions?

    Best, Paul

  29. Well…that was certainly easy. I didn’t have a use for the document I annotated today, but I’m sure this will work great in the near future. I’ve always opened up PDF files in Preview and annotated from there, so I’m excited to reduce the number of steps needed to get this done quicker.

  30. Done! That was certainly easy and convenient. I knew of annotation via iOS, but not on the Mac. I have a feeling this will come in ultra handy in the next few weeks.

  31. I created a Task in Task Scheduler: at 11:00 AM every day, my Year to Clear Journal will open for that day’s entry.

  32. Done! Also, ended up creating another quick action to extract highlights that I usually do in my PDFs. Hooray!

  33. Annotated pdf’s. Good. I do this on a regular basis. Automator is also good. Could not find specific workflows that are applicable to me. However, I see how this works and will be thinking about what I can automate through Automator.

  34. Set up to launch outlook at 10 am and 4 pm everyday on my work PC to try out the “twice a day focused email time” approach in the book “Make Time”.

  35. Use quick actions all the time to annotate images. In this case I had an application screenshot with errors in the GUI used the annotation to highlight the label that needs to be changed

  36. Created a Diary Prompt. I am toying with the idea of an automated email to remind me to complete my workday shutdown every day also!

  37. Did the diary prompt even when I don’t need it. Can’t think of anything useful for me right now but the time will come… Have to check out in detail what possible is. Certainly an interesting tool. Thanks.

  38. I wish I could say done, but I’m using an older Mac OS for compatibility with music-making apps that I use. When those apps become fully compatible with Mojave, then I’ll consider changing my OS. Saving this tip for that day. :)

  39. Completed on Mac. These new found apps are really great.

    This 5 day challenge of breaking things down into each of the elements we learnt about on Monday has been great to clarify where I still have gaps in knowledge and ensuring that I can practice applying the knowledge several times to help it become embedded. The reinforcement of listening to the short clips more than once has been helpful.

    I also learned about the use of chapters when viewing the material which I had not been aware of.

    Thanks so much for this free guide to personal automation and the associated challenge to help us move from guided practice to independent practice. So many high fee online courses fail to include these two important elements to ensure transformation can take place.

  40. Jeremy – you can always use the search option to find notepad.exe – it’s a little easier and faster than spelunking through the file system.

  41. Created diary prompt – worked like a charm. 99% of what I do in my job is online, and when I tried to have it open a specific website for a specific time/reason…. IT blocked me. Sadness.

  42. I’ve set this up. I use Windows for work and for my family computer at home; however, my office computer is Linux. I’m currently looking for counterparts in Linux – it takes a little more searching and setup, but so far, so good.

  43. This was the second thing I made when I back home from work (after kissing my family members! 😉) I had to set on my personal PC as my company Windows laptop is totally blocked to changes by my IT department. I set a prompt to check my Image gallery every time I turn on my PC and share some pic to my iPad on Dropbox to populate my DayOne journal backwards with significant moments spent with my family!

  44. OK, 3rd day. Really lost. I think I must be the only one because everyone who has commented seems very happy. I haven’t upgraded to Mojave so Quick Action appears to be out. I tried Automator instead. I had a couple of ideas: 1) send all photos attached to email to Photos or 2) convert selected webpages to Word documents. I couldn’t figure either out. Then I thought I’d try (3) putting together PDF pages into one PDF. Couldn’t figure that out, either. Just spent an hour on this, have a terrible headache, and I guess I’ve “flunked” today.

    s there any help in addition to the tutorial in doing these exercises?

  45. Yup, did it. I suppose that the real power comes from modifying these to my needs. Sadly, the quick menu is not appearing in third-party apps.

  46. Done for Windows! I set it for 12:45 so I could test it. It works! Now I’ve reset it for 4 pm daily. Many thanks for this great tip!

  47. Handy tip for automator usage – worth some more exploration (the sample is interesting, but not something I expect I’d use all the time).

    I’m a big fan of Hazel (as covered elsewhere) and use it to automate a whole load of folder watches to manage downloads / music / video intelligently. Fun, and useful!

  48. Done.

    I created a little Windows Forms app that shows the message “Don’t forget your journal entry” that will pop up every week day at 4:00PM.

  49. Done for Windows. Created a diary prompt and also a prompt for stretch breaks between work sprints. Seems like some form of the Pomodoro method could be signaled with automated prompting.

  50. Ok, I have to say this feature is the coolest! I listened to a podcast a while back on listening to good focus music. So I have set up Spotify to automatically open for me every day. It sounds so simple but I often find myself struggling to take that one extra step to open spotify every morning as I sit down at my desk and see how much other hot priorities I have during the day. This will help set the tone for my day! Love it!

  51. Hey, Productive people, great to connect with you again.
    I already set up my Diary prompt yesterday.
    I was just wondering if any of you could guide me a way to open my Word with this prompt instead of “notepad”.
    Thanks for this tip

  52. Done! I also created a scheduler task that triggers whenever I log in/unlock my Windows machine which opens my Todoist window, as a way to remind me to look at my to do list when I sit down at the computer.

  53. Set mine up to remind me to start my end of day routine. Maybe that will help me leave on time for a change.

  54. I just did a markup on an image. I have wanted to do this for so long and can’t imagine I’ve spent over 10 years owning a Mac without knowing this! THANK YOU!

  55. Done! I just automated in windows a daily task that opens a file with my affirmation/motivation phrase from the week. =) Its fun and useful.

  56. That was fun. I have paid many $ for the ability to do that with other apps. I needed to remember to switch my views in Finder, since I’m usually in List view.

  57. I’m not a daily diary/journaling person, so this particular automation exercise was purely for practice. It will be more useful at work for specific weekly tasks.

  58. I have a common workflow that involves resizing images to a certain size, then opening them with ImageOptim, which shrinks them down further. Used to run it as a shell command but it’s even easier as a quick action from Finder.

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