Yesterday I wrote about the task management and your calendar. Today, I’d like to share some of the technology behind how I go about blocking these schedules. Creating calendar items can be tedious. Using a tool like Fantastical makes a big difference, but when blocking a whole week out, you want some automation at your back. For me, it’s been an evolution.

Block and Copy

You can copy and paste calendar events in most calendar apps on the Mac, including Apple’s own Calendar app. Command + C and Command + V are your friends. If you have similar blocks you use throughout the week, you can set them up once, then copy, then paste as many times as needed. You may need to make adjustments to start and end times (or even descriptions), but that is way easier than starting from scratch. Blocking and copying calendar events on the iPhone and iPad are not as easy and more time-intensive. Block and copy is a perfectly acceptable way to set your blocks, particularly if they vary a lot from week to week. As my schedule started getting more consistent, I looked at other options for automating calendar blocks.

Repeating Events

All calendar apps can create repeating calendar events with a high degree of customization. If you want a block every Tuesday at 1 PM or on the last Sunday of every month at 3 PM, you can do that. I tried this for a while but eventually gave up on it for two reasons.

First, I was not too fond of the confirmation box that shows up every time I adjusted a repeating calendar event. It was like hitting a speed bump multiple times every day. It started as an annoyance but quickly became unbearable.

Second, recurring events go into the future, potentially, forever. If you block most of your days going months (or years) into the future, Scheduling anything in the future become more difficult because, according to your repeating events, you are already very busy every day, forever.

Automatic Event Creation

As I explained in yesterday’s post, I don’t want to plan blocks much more than a week into the future. As Yoda said, “Always in motion the in the future.” Blocks planned out more than a week in advance rarely go down as planned. Yet there is enough consistency in my schedule that I’d like to automate the process of generating the 25-ish calendar events I want every week.

The easiest way I found to do this was with a Shortcut that runs through a “Create Event” task for each day in the following week with my standard blocks. You can download a simplified version on your iPhone or iPad with this link. I run this script every Saturday afternoon. It takes just seconds and fills my week with blocks. Since they are not repeating events, I can move and change them at will without seeing that blasted confirmation box. Moreover, since they only go one week into the future, if I’m planning an event for a month from now, my calendar isn’t overly cluttered.

In addition to generating the calendar events, my Shortcut script also inserts alarms for most events to trigger when the block starts. This reminds me to change gears and helps me from getting lost in any particular block.

Daily Evolution

Often, but not always, I need to make adjustments to these blocks as I go through the day. Stuff happens. It’s okay. I do, however, adjust the calendar to reality when that happens. Sometimes it means moving a few blocks around in the coming days. That’s okay too. Regardless, I take a screenshot of my weekly calendar on Sunday night, and I always go back to look the following weekend to see how the week went down compared to my plans. Sometimes I learn a thing or two comparing reality to the theoretical.

The Paper Option

I’ve also tried blocking entirely with paper. For that, I’d recommend a nice pen and a notebook that makes you want to use it. The trouble with doing this on paper for me was that I didn’t have the notebook with me at all times. Digital events are in my pocket, on my wrist, and send me notifications.