Calendar Management for Productivity & Sanity
I lean heavily on my diary to plan ahead, guide me through my days, and establish a rhythm to my life. The type of work I do has a tendency to drift towards haphazard if not controlled, so a calendar helps me establish and maintain order.
The problem I’ve faced in more recent times is having an overabundance of calendars I need to refer to before being able to commit to something. In simpler times, if I had a gap between 9am and 5pm, it was available to be taken up by a meeting. With the added complexity of kids and a wife who has an even more complex and random schedule than my own, things have reached a point where I need to check about 5 different calendars before I could confirm if I actually had availability for a meeting, irrespective of whether there was a gap in my calendar.
This year I made a personal pact to get better at managing this uncertainty. I’ve considered how I could build a system that works better for me and my family, while maintaining flexibility for my clients. Many of the methods I’ve adopted are not new ideas; in fact, some are a blast to the past when people used paper day-runners and had a personal assistant (secretary?) who would prepare things on their behalf. Alas, I have neither of those, so I have leveraged my skills in process design and automation.
Following is an outline of my diary management workflow as it has developed to date. It remains a work in progress and I expect it will continue to change.
I started by establishing clear and non-negotiable days for which I was available for visiting and meeting with clients. I refer to these as “External” days. The remaining days were locked in as days to spent at the office - my “Internal” days. These days are consistent every week, to help with that rhythm.
When visiting clients a lot of time is lost in transit. By collating these visits into a fewer number of days, I reduce my transit downtime, and have the opportunity to fill those days more effectively.
My “Internal” days facilitate getting into a flow state more often because they aren’t broken up by meetings and appointments. Again, a more productive outcome.
Technology - WhenWorks
My next area of improvement was in the way I was booking the meetings with clients on my “External” days. I had been spending too much time and effort bouncing emails back and forth, doing the ‘availability exchange’ - trying to find a time that works for me and them. I needed to find a better way that was efficient but respected the impact of items on my other calendars.
I started with a trial of Calendly. This cloud-based service provides a method for people to book a meeting time that is subject to the parameters I set. Calendly was good, but had its drawbacks. I use FastMail for email/calendars/contacts and it uses standards-compliant IMAP/CalDAV/CardDAV protocols. Unfortunately, Calendly wants to only work well with Office 365/GSuite/iCloud. My employer provides me with an Office 365 account so I could still make use of the service, but it meant that I had to remember to replicate my Fastmail calendars to Office 365. It worked, but it never felt simple and seamless.
Enter, WhenWorks. After trialling this for just a couple of weeks, I have purchased an annual subscription. WhenWorks is fundamentally an iOS app that is supported by a cloud-based booking platform. By running on my device it improves on Calendly because it can access all my calendars, irrespective of what platform they reside upon. WhenWorks can take into consideration the impact of every single calendar when making times available for others to book.
WhenWorks is simply brilliant. It looks great and offers a full range of options without being overwhelming. Most importantly, my clients have used it without any problems whatsoever.
Automation - TextExpander
For the first half of this year I have been using saved email templates in Cloze to correspond with clients and ask them to select a meeting time using my Calendly service.
Now with my change to WhenWorks, I’m moving away from Cloze and back to using TextExpander to send email using Mail.app instead. With TextExpander I can make a few choices upon snippet execution that lets me customise a boilerplate email. This way the email the client receives is quickly and efficiently tailored to the type of meeting we will have, and will prompt them to schedule a meeting using the appropriate WhenWorks meeting template relevant to that meeting type.
Routine & Preparation - OmniFocus & Daily Papers
The last step is incredibly low-tech, but has made a profound difference to my state of mind at the beginning of each day. It is not a new approach. It is common sense. It is simple. But it requires discipline.
I have set a daily repeating task in OmniFocus that commences at 4pm and is due at 5pm, prompting me to prepare for my next day’s meetings. That’s it; a simple prompt.
This prompt, however, ensures I remember to gather the various documents, information and whatever else I need to have ready to be successful for the events of the next day. Sometimes this process takes 2 minutes, sometimes the full hour.
Since doing this, I’ve found I don’t have stress the next morning, suddenly realising that I’ve got a meeting first thing that I have not prepared for. It creates a calm state of mind for the evening, knowing that I’m ready for the next day. It enables my mind to cogitate on what I have coming up, such that when events unfold I find myself better prepared and ready to roll than I otherwise would have been.
Each of these elements is fairly straightforward in and of themselves. Bringing them all together, though, has improved my flow, and has largely resolved the problem of double-booking and calendar mixups.
Of course this stuff is never done, and it will change with workload and circumstance. For now, however, I feel like it has gotten me closer to the concept of ‘mind like water’ than I was previously.