My default mental state is that of a lazy, disorganized procrastinator. I have to work hard to trick myself into being the reliable and proactive person I want to be. These apps help me be that person.
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Automation is one of my favorite forms of productivity. I love being above to solve the puzzle of making it work and reap the benefits of computer precision replication of tedious but essential tasks. At its core, I see automation as a way to create time for my future self.
My number one tool for automation is Keyboard Maestro. It is the most powerful and complex tool at my disposal. However, it is only on macOS and has a cognitive barrier to entry, which means it is not my first automation recommendation to someone just starting.
Hazel is another Mac-only tool, but it is an excellent solution for handling complex or tedious file/folder organization. In a slightly round about way, it also allows you to remote control your Mac.
Shortcuts is an iOS/iPadOS app made by Apple that allows you to easily create automations that run the gamut of complexity. Want your phone to go into low power mode every time your battery goes below 50%? Shortcuts can do that. Want to Create calendar entries, send emails, and create an OmniFocus project for your next meeting? Shortcuts can do that too.
After years of searching, OmniFocus is my task manager of choice. It has all the complexity and automation options I need and is also simple enough to use for basic tasks. There is a big up from cost to the app, but once you outgrow Reminders and want a powerhouse app to manage your tasks, OmniFocus is your jam.
If I have to collaborate with someone, I reach for Trello. It’s an awesome kanban based project management tool. I have also used it as the backbone of my personal productivity system (before I landed on OmniFocus). I teach it to my students for project management and use it for dissection documentation, project feedback, and ice breakers.
You might not think there is a lot of room in the calendar app world. You would be wrong! Fantastical is a beautiful and powerful calendar app. If you are looking for the best way to interact with your calendars, Fantastical is it. Fantastical wrangles and synthesizes my personal Google Calendar and my work Office 365 calendars. I can see and manipulate all of my calendars, regardless of platform, from anywhere.