A Calendar is the Last Great Frontier

Workflow wise, I’m pretty set on many things. I love the Studio Neat Panobook and Totebook for note taking. Both are amazing and I can’t see myself ever leaving them. Task management wise, I used to live in Things and then Todoist and then Things again. But that process taught me one thing about todo lists. They are the worst way to measure your life. They create anxiety and unrealistic goals because they are islands on to themselves. The fix for me was creating a daily goal list the night before and put that in my Panobook. Then I can check those off with a pen and life feels wonderful. For those reminders that need a little reminding, I just use Apple’s Reminders app which does all I need.

Email is awful, but there is no help in sight (maybe Hey will solve this). I suppose Slack owns the chat space. But Calendar is what just fails me every time. I’ve tried all the products. Fantastical, Google Calendar, Timepage, you name it. The simple fact that I can’t list more than a couple here really shows what the problem is. There is nothing to innovate.

I feel like I use a calendar in a couple ways; I put events up such as “Meeting with Bill” or “Connor’s Lacrosse Game”. I put up blocks of time, “Work on proposal for the Queen”. I put up out of office notifications, “Vacation in Hawaii”. The problem with calendars as they are used today, is they all treat those three ways of measuring something the same. Start time, end time, notification. Then we throw up some blocks like a Kanban board and try and find time to get it all done.

I feel like an optimal calendar would be the opposite. Rather than have a blank board to put things on, you should be carving out time to work on things that matter to you. My best work is done in the white space of a calendar and rarely gets recorded (unless I’m charging time to a client).

I probably don’t need a new app to do this. I could obviously start putting time in the calendar to capture these moments of focus. I wonder if the dynamic of thinking of a digital calendar as an old fashioned paper calendar is where we should be. As I said, shame this space hasn’t been explored as well as todo and email apps.