Mastering the Art of Calendaring: My Weekly Routine
When you don't realize you have a conflict until the day-of, I'm judging you for being disorganized.
Every Thursday, I have a routine task I like to call “calendaring,” where I review my calendar for the upcoming two weeks. It’s a simple but essential habit that helps me stay ahead of any potential scheduling conflicts and keeps my work and personal life running smoothly.
You probably have conflicts
Here’s the thing: When you send out a last-minute note of “double booked at this time” or when you don’t show up to a meeting, you look bad. When you don’t decline a meeting when you’re not going to be there, when you’re late because you didn’t realize you were double booked, and when you show up unprepared, you look bad. When you don’t keep your calendar up to date, when you are cavalier about showing up to meetings, you look bad. You look irresponsible. You look like you’re wasting everyone else’s time. Be the most prepared person on the call, and people will find excuses to work with you. Fly by the seat of your pants, and people will dread working with you. Show up and put in effort.
If you put in 15 minutes every Thursday to manage your calendar proactively, you will find that those 15 minutes transform your weeks.
Tools I Use
I rely on a couple of great tools to manage my time.
First, Reclaim helps me block off personal time on my work calendar without revealing individual details, like dinners, shows, or events. To others, it just shows as “busy,” so my colleagues don’t see specifics.
Second, I also Fantastical for day-to-day calendar management, which syncs across all my calendars (I actively use three Gmail accounts).
Finally, my tried-and-true Todoist reminds me every Thursday to actually do the “Calendaring.” I never worry about it, and I never think about it. Every Thursday, I’m reminded to take 5 minutes and look at the next two weeks.
Lean into Recurring
Here are some of the recurring events on my calendar:
5 AM to 8:30 AM is blocked off M-F with “Morning Routine”
5 PM to 5:30 PM is blocked off M-F with “Ask before booking”- I might be able to meet at this time, but I also need to shut down for the day, so I want people to ask before booking.
5:30 PM to 7:50 PM is blocked off M-F with “Witching Hour”
6:30 AM-7:30 AM Monday-Thursday is blocked off for my CrossFit class
The 30 minutes before is blocked off for “Travel to”
The 30 minutes after is blocked off for “Travel from”
I have an all-day “No meeting Wednesdays” event on Wednesdays from 8:30 AM to 4:50 PM.
Fridays are also blocked off until the week of, when I remove the block. I want to save a place on my calendar for things that need to be handled ASAP. (This is not visible in the screenshot.)
Picking up my CSA (Community Supported Agriculture) box, the cleaning lady coming, and other activities that happen regularly at a specific time are captured in recurring tasks with the correct cadence in the event. Don’t keep these things in your head!
It’s not quite a recurring event, but in that spirit, do some bulk planning, too. For example, I want to have all of the Army Football games on our calendar for the fall rather than trying to remember when each game is as it’s coming. Last weekend, I spent 10 minutes adding all the season’s games to my calendar, including the TV channel the game will be on!, and inviting my husband to the calendar events. These aren’t exactly recurring events, but they’re events you shouldn’t be thinking about all the time.
My Process
Check for overlaps: First, I look for duplicate or overlapping events on my calendar. For example, I might be double-booked for a work call and a recurring meeting, so I’ll reschedule to avoid conflicts.
Adjust & reschedule: I then make any necessary updates. Whether moving a call to a better time or ensuring my personal plans don’t interfere with work, I tweak the schedule as needed. I also adjust recurring events to ensure they fit seamlessly into the week.
Plan ahead: After I’ve cleaned up my current week, I look ahead to the next two weeks. This helps me catch any potential issues in advance, like meetings that fall during times I’ll be out of office. If I notice something that needs changing, I fix it right away to avoid future headaches.
Identify what you need to prep for: Monthly 1:1 with your skip level coming up next Monday? Big presentation is next week? Holiday Monday in three weeks means you should also expect half the team to be out in two Fridays (even though no one has put it on the calendar yet)? Look at the big picture and the little picture. Understand what you need to put in work on. You don’t need to solve these problems now- you need to identify them. Add them to your other tasks to stay focused on getting your calendar right.
Calendaring is a quick, less-than-15-minute task that gives me peace of mind and helps me stay organized. By dedicating time to this process, I avoid surprises and can focus better on my work and life.
Seriously, I timed it this morning. This week, it took 8 minutes.