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Happy New Year! 

I hope your holiday festivities were heart-warming and restorative. My wife and I started ours with our car dying the night before we planned to hit the road, though the holidays did get better from there and we are thankful for a few days with family. 

I don’t usually make New Year resolutions. I think that is largely due to a fear of failure, and of not knowing how to actually implement these goals and aspirations. Change is hard. But I have been thinking recently: if there is one thing I could change this year that would have a significant impact on my life, what would that be? I have decided that that one thing is to make friends with my calendar.

What do I mean by that? Why do I often feel like my calendar is my enemy, or at least a puzzle that is impossible to decipher? There are a number of reasons. Especially as my business has grown in the last few years, I have often felt like my schedule controls me. I feel like I need to work on evenings and weekends in order to meet deadlines, which means making trade-offs with other activities that are also meaningful. I realize this may not be so much a scheduling problem so much as an I’m-accepting-too-much-work kind of problem, but either way it boils down to feeling out of control and overwhelmed.

The problem goes deeper, however, as I have struggled with setting schedules for myself since university. This seems counterintuitive, as I actually thrive on routine. And therein lies the problem, I think. My tendency, when I devise a schedule for myself, is to stick to it as rigidly as possible. Interruptions or other unplanned changes cause me to panic and get disoriented, and eventually I abandon the schedule for a more reactive, and stressful, mode of being. I seem to be in a bind where not having a schedule is not serving me well, yet my typical approach to scheduling and calendars is also not serving me well. I need to find a better way. 

So how do I become friends with my calendar? I mentioned this resolution to my wife, and she astutely pointed out that it is quite an abstract goal. 

I agree with her, and I am okay with that. I am realizing that my relationship to my calendar and schedule is multi-faceted. There is coming to terms with my years of fears, anxieties, and frustrations with schedules. There is learning how to productively handle changes within a schedule. There is finding a scheduling framework that seems to work for me. There is understanding my own biorhythms so that I am working with myself, rather than trying to cram myself into an artificial construct. All of this will take time to figure out and understand.

One book I have read recently is Make Time: How to Focus on What Matters Every Day, by Jake Knapp and John Zeratsky. What I appreciate so much about their book, compared to some others I have read about calendars and schedules, is their acknowledgement that everyone is different. They offer eighty-seven tactics to try, but fundamentally their approach is to experiment and be reflective about what works and what doesn’t. I found it incredibly freeing to realize that I don’t need to have the perfect schedule right away, but I can take time to develop it, and that setbacks along the way are part of the process. Indeed, as I age and other life events happen, my schedule will probably continue to evolve. 

The book also discusses a scheduling technique from Cal Newport, who wrote the book Deep Work. In this technique, you write a new schedule for yourself every day, and leave room to revise the schedule as needed. This provides a mechanism—which I have been sorely missing—to thoughtfully acknowledge that change can and will happen, and to recognize that the remaining time can still be reallocated and used productively. I’ve been trying this for a week now, and it has been a helpful tool for reflection. I have handled interruptions better, and on the flip side, it has also helped me stick to my schedule when I’ve been tempted to change for no good reason. 

Another new initiative I’ve been using for about six weeks now is to put up white board wall stickers in my work space. This has been a fantastic change for me. I think I am still learning just how tactile and visually-oriented I am, as I am enjoying both seeing my work on the wall and the physical labour of writing, crossing out, and erasing. Borrowing the concept of sprints and burndown charts from a book I indexed, I list all of my current projects for a two-week period so I have the constant visual reminder of what I need to accomplish. I also graph my progress each day, so I can see where I am with each project. The whiteboard is also a great space to brainstorm, to write notes, and to make lists. I use it every day.

I already have some ideas for what else I want to try this year to become more comfortable with my calendar. I am happy with some of the results so far, and I am sure more ideas will come up as I experiment and reflect. I am hopeful that 2019 will be the year I finally get a handle on my schedule. I wish you all the best in your endeavours this year too.

What are some of the ways or resources you use to keep your calendar in order?