Great episode. @Kaitlin is very much a master of #OmniFocus automation.
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Thanks very much for this episode and especially to Kaitlin. V good and interesting. Best wishes
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Great episode! My wife enjoyed listening as well in the car which is high praise from her.
I definitely sympathized with @Kaitlin not having great solutions for the PC at work lifestyle. I’ve tried using the personal iPad at work to use my preferred apps but just never had a good experience with it. I eventually landed on Todoist and Notion as ‘not horrible’ Windows apps to use exclusively for work, but I still dream of finding a Mac-friendly workplace one day.
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Great show and thanks to @Kaitlin for taking the time to share her ideas and workflows!
I also sympathize with a Windows and Mac lifestyle. My work requires Windows and I don’t really have the ability to link any external services (even web ones are VERY limited) to my work machine. And I can’t have personal devices in my workspace. So I have just had to live the “Windows at work; Mac at home” lifestyle.
I will say, it gives me an appreciation for what Windows can do. It’s come a long way, and I don’t despise it like many do. But it really makes me happy when I’m home again on my Mac! 
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I’ll echo that: fantastic show. And I have no interest whatsoever in OmniFocus!
More guests from far-flung places and with different kinds of jobs and workflows, please!
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Au contraire, one of the “benefits” of Windows is you have far less options, as a brief read of topics here will vouch for, considering the amount of “app switching” that goes on! Windows apps may suck but if it’s all you’ve got … 
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One of my favorite guests. I too am not an Omni Focus user but really enjoyed this one. Really appreciated the positive energy.
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Great episode! I was inspired to check out OmniFocus Automation after listening to @Kaitlin discuss her workflows with @timstringer at Learn OmniFocus a few months back. In particular Kaitlin’s “Templates for OmniFocus” plug-in has proven really useful to me, and has encouraged me to engage in an ongoing project to identify what repeating projects I might convert to templates since this plug-in is both so useful and so powerful. Thank you Kaitlin! And I will echo what was said in the podcast itself: if you are an OmniFocus user, you should really check out Omni Automation!
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Another way to make automations if you aren’t comfortable writing them from scratch: ask ChatGPT! There’s a shell script that I’ve been putting off writing for ages, and listening to this episode made me think of asking ChatGPT to write it for me.
NB: Please know what you’re doing so you can see if ChatGPT is making mistakes. And test your script on something not mission-critical.
During the show, David mentioned something about Better Touch Tool and using it to add data to the menubar. Can anyone elaborate on that? I can’t find any mentions of this in the BTT release notes or Google. Thanks!
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I just did nearly four months on a job that required me to use Windows.
For most of my career, I’ve mixed work and personal use on a single computer, but at my job-before-last that was a source of stress for me, so instead this time around I decided to keep work and personal use separate.
In practice, that meant using Microsoft OneDrive to store all my work documents, which I was then able to access from my Mac. But I seldom used that access. I worked 100% from a home office. I did work on Windows, and my Windows laptop was side-by-side on my home office desk with the MacBook.
I tried a couple of KVM switches but I was never able to get them to work reliably. Instead, I just switched the cable between computers when I wanted to switch which computers I used. I also have a Logitech multi-device trackball and keyboard. The Logitech hardware comes with software that supposedly allows you to slide the mouse pointer between machines, and the keyboard and mouse focus will follow. I found that software was unreliable. But the hardware has switches that are easy to toggle. So that was a good solution.
I also used my personal iPhone to access work email, Teams, and calendar. The job required me to install Microsoft device-management software on my iPhone. I hesitated about that for a bit but then said to myself, sure, why not? I’m already trusting the employer with a lot more than my iPhone. And indeed there as no problem; when I left the job I uninstalled the Microsoft MDM software from my iPhone and got on with things.
I used Outlook for email and calendar.
Regarding finding open times to meet: Outlook has a fantastic feature called “schedule assistant.” You can see which times are available on another person’s calendar, and just drop in an appointment. Works for group meetings too. At the company where I used windows, people just dropped appointments on other people’s calendars without even talking with them first. At first that sounds rude, but in fact it’s fantastic. Workplace etiquette was that the recipient of the invitation could feel free to ask for clarification or reschedule if the time was inconvenient. Completely eliminates the back-and-forth in email about finding mutually convenient times. So: No need for Fantastical.
For note taking, I tried OneNote but didn’t like it as much as Obsidian. So I went with Obsidian. That worked well. I use a lot of Microsoft Office documents in my career, and Obsidian plays well with those. You can’t edit the documents within Obsidian, but you can manage and open them.
I never found a task management solution I was happy with. Microsoft Tasks was too basic for me. I went with TickTick, but didn’t love it. Todoist is better, except for one feature that I find essential–in a filter view, I need to be able to manually reorder tasks. Ticktick lets you do that, and Todoist does not. When I left the job that requires Windows, I gratefully went back to Apple Reminders.
(I have lately become persuaded by Carl Pullein’s advice that you should stop using your task manager as a project manager, so nowadays if a project is too complicated to manage in Reminders, I put the task list in Obsidian, and simply have “Work on Project X” as a task in Reminders. I’m not rigorous about this–I’m embracing sloppiness in my task management system.
I started a topic on using Windows when I took the job in September.
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I’m glad it worked for you. Something like that would have made my job impossible.
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I was inspired to check out OmniFocus Automation after listening to @Kaitlin discuss her workflows with @timstringer at Learn OmniFocus
Great to hear you enjoyed Kaitlin’s session on Learn OmniFocus. It was a treat to have her as a guest!
In particular Kaitlin’s “Templates for OmniFocus” plug-in has proven really useful to me, and has encouraged me to engage in an ongoing project to identify what repeating projects I might convert to templates since this plug-in is both so useful and so powerful.
Great! I use Kaitlin’s “Templates for OmniFocus” plug-in regularly (in addition to some of her excellent plug-ins). It’s feature-rich, well-documented, and adds convenience and consistency to OmniFocus.
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Sounded crazy to me when I first heard about it, but it was actually an effective way to work. Cut through a lot of back and forth.
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I agree with the sentiment that Windows is…fine. Like I think David said in our conversation, it just lacks a little whimsy. I certainly think I need to spend some more time on window management on Windows (it may be better than Mac, from what I’ve played with so far) and just generally go a little deeper on all things Windows. Realistically my needs are quite simple in a work context, other than the task management piece.
Ah, yes! I am aware of this and should have mentioned it - I use it all the time for setting internal meetings. However, a lot of my meetings involve people outside the organisation (consultants, software providers, etc.) and so that is where Fantastical will likely come in.
My previous workplace worked much like this and I can vouch for the fact that it can work, in certain contexts. I think the approach of where I am - where most people have their calendar visibility set to free/busy and typically invitations can be sent at a mutually free time using Scheduling Assistant, is a happy medium.
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If you want to go a bit deeper in Windows, I recommend installing Powertoys. It’s a free Microsoft utility full of all kinds of power user tools. There’s some pretty cool window management stuff in it I’ve not taken the time to learn yet. My favorite that I do use is just an added keyboard shortcut that stickies a window to the screen even if I click away. It’s super useful to have the calculator or notepad stay on top as I go back to reference a spreadsheet/dashboard.
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And if you’re into yet another approach to automation, AutoHotkey helped make the many years I spent on Windows PCs bearable
EDIT TO ADD: Plus you can get a version of iA Writer which does folding (which I don’t think iA.net ever got around to porting to the Mac).
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Yes, a team using that scheduling system requires folks to keep their calendars up to date, particularly making sure to block off time set aside for personal errands.
If person A wanted information from B, B would often respond, “Put a time on my calendar to talk. My calendar is up to date.”
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I very much like the way windows does window management.
When I had an office, the two software programs that were the basis for our business (estate planning) were Windows software only. We used Parallels on iMacs, and that worked great. The software output to Microsoft Word, and we edited and printed in Mac Word.
I’m surprised I don’t hear of more Mac/Windows users using Parallels on their Macs to run PC software.