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.

Structure

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.

For calendaring, I rely on BusyCal on the Mac and Fantastical on iOS.

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.

Credit to David Sparks for providing some of the tools that helped me get this up and running quickly and easily.

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.

Final Thoughts

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.

Searching for Hobbies

All work and no play makes Jack a dull boy.

It’s very easy to spend time focusing on work. It has a tangible reward – income! It provides an emotional response – we might love it or hate it (or even just feel meh about it). And, for many, it defines who we are.1

I’ve been taking stock, and have realised that I need to add some more variety to my days. I do my work, I look after my kids, and despite us sometimes being ships passing in the night, I share time with my wife. What has gone missing though, is a third interest. What else can I do? How else can I bring some interest, variety and further meaning to my life?

I don’t want to be passing time here on our earth, responsibly moving projects and tasks forward without having some fun and spontaneity along the way.

It’s clear what my answer must be – I need to find some hobbies!

Ideally, these hobbies will stretch me out of my comfort zone. While I have always been enjoyed technology and basketball, I should move outside these domains to see if I can find something else that is fun and different.

I’ve drafted a list of ideas, with ideas ranging from board games to cooking. I plan on experimenting across a range of areas to see if anything grabs me. And because you can’t manage what you don’t measure, I will try to keep a journal in Day One to track any major hobby events and record my thoughts and impressions of things I try.

I hope I find a new and interesting activity to engage with, but even if I don’t, it will be an interesting life experiment.


  1. This concept of work defining who we are is particularly weird. The work we produce is a product, not a state of being. By defining ourselves by our work we are limiting our potential. The work we do should be a combined result of our skills, traits and personality. The work is achieved because of who we are; it is not who we are.

    Have I just buried the lede in this footnote? 

In Flow

Some days the work just flows. Tasks feels easy, decisions are made, words transfer from the brain to the keyboard with nary a pause; and engaging with people makes you realise the world is full of interesting characters.

These days of flow are generally few and far between. We structure our days such that we have no breathing room. Alternatively, we don’t structure anything and drift through without a clear and achievable goal in mind. If we can happen to find the Goldilocks Zone between those two extremes, and establish a mindset that is engaged yet relaxed, well, I think that’s where the magic happens.

Most days, of course, the work doesn’t flow. Things are a grind and stuff fails to work out as intended.

So the days where flow occurs; embrace it, because there’s no guarantee it will be back tomorrow. Get the most out of this rare and elusive asset!

Replacing Social Media

I joined both Facebook and Twitter many years ago, when they were technical ideas, as opposed to advertising machines driven by algorithms.

Part of the reason for joining in the first place was for me to reserve my namespace. Just like gold rushes of old, it’s always important to claim your username before somebody else jumps in before you and puts their stake in the ground. While Twitter and Facebook took off, I also had my namespaces at long-forgotten sites like Pownce, Myspace and Technorati.

The Halcyon Days

Over the following years, my engagement with Twitter and Facebook increased. Facebook was great for retaining connections with people I knew IRL while on Twitter I built a list of followers that I didn’t know, but whose insights and commentary I enjoyed. This ultimately revolved around my two greatest hobbies: basketball and the Apple IT ecosystem. From around 2011-2015 really were the salad days of these two services.

The problem for them (not me), however, was that I wasn’t paying the bills. Nor were any of the other users. We know how this story goes. As per the trope, if you’re not the customer, you’re the product. There was a realisation that I was certainly the product – being sold as advertising fodder by these services that needed revenue to keep the lights on, and investors invested.1

Addiction

Over time, these services added dopamine to my day. The nefarious social engineering tweaks they built to maintain my engagement were difficult to defeat. Likes, comments, shares, retweets. All these things built in a way that tries to make you feel like you are valued by your audience, but which are all just further measures to build an advertising profile of each of their human products. But it kept me coming back.

My usage continued to grow until a series of events made me question what the hell I was doing. Firstly, most of the Facebook people I realised I either saw in real life — which was much more satisfying — or I never saw them, and didn’t have space in my life to genuinely care about them. The algorithm would occasionally surface them to my feed, then they would bubble down again to be forgotten. On Twitter, there was growing awareness (and evidence) of the hate, vitriol, bile and mistreatment of people, both inside and outside my personal feed.

Downfall

As the services became politicised, they became weaponised. Intolerance grew, they became echo chambers, and the value of what was being expressed was minimised. From link bait to listicles and lame videos, both services were serving up nothing but empty calories. I realised that I was using my most valuable resource — my time — on two services that were giving me nothing back in return for my investment.

Hence, the decision to withdraw my namespace claims. I have deactivated Facebook. I have deleted Twitter.

Reversion

What is great is that I don’t feel I have lost anything. I feel just as informed, and I actually feel calmer. I don’t have this buzz in the back of my brain, like an itch I can’t scratch, knowing that I need to check my feeds. It has freed up the time to do more productive things. I’ve been reading actual books again. I have watched TV shows and movies with full focus.

It’s been great to have more free time to invest in activities that provide mental nourishment, rather than the fast food diet I had become used to with social media. Ironically, I think I had it more right 10 years ago, before the age of social media, where this is exactly what I would do. I would read, learn, converse. I didn’t like, share and tweet. But I think, on balance, I was all the better for it. I’m enjoying this rebalancing I’m going through now, and I hope that it continues.


  1. If you want evidence of just how much you are the customer, be sure to download the document from Twitter that shows just what information they have on you, and how you are linked with a range of brands and services for marketing towards. It’s kind of chilling. 

Deprioritising Facebook

A few months ago I stopped using Facebook. I deactivated my account, deleted the Facebook apps from my iOS devices, and went cold-turkey. I have subsequently had to reactivate my account because of the need to engage with some groups that exist only on Facebook, but I continue to ignore my timeline.

It has been a great change for the better. Facebook adds a huge weight of nothing. It’s empty calories. It uses up time that could be better spent elsewhere. I haven’t missed any news; I don’t feel less engaged with the world. To the contrary, actually. I feel more engaged. I don’t crave the little dopamine hits of likes and comments. I’m still writing and recording aspects of my life, but now they are feeding content that I own, whether it’s on my own microblog, or in my Day One journal, or (heaven forbid) through one-on-one conversations.

It surprised me just how easily I was able to ‘kick the habit’ of using Facebook. I thought I would miss it. As if to emphasise just how hollow the platform is, I’ve not had any of my myriad followers reach out to check if I’m still alive since my departure! That point highlights the disconnected connectedness Facebook promotes. Sure, you ‘like’ somebody’s post, but do you remember it 30 seconds later? Would you notice if it were not there? The evidence would suggest not, and that spot in the timeline would just be filled by something else.

If I could dump the Facebook platform entirely I would. As it is, I will use it as little as possible, and only as required for specific functional tasks. I am not willing to gift my attention to Facebook, for it to leverage into profit. My hours on this planet are too valuable to give you them for free.