Work Year Wrapped
Leverage the calm of the holiday pause
There is a magical moment on your work calendar that you probably didn’t even notice. Most employers give Christmas Day as a holiday. And if you’re lucky, you also get Christmas Eve off. But the less recognized spot on your calendar are the two workdays before Christmas Eve. These are your “Reflect & Refine” days.
It’s pretty common for people to take the entire period between Christmas and New Year’s off. It’s also common for people to add more days onto their vacation on either end of those holidays. This creates a window where the office is a ghost town, in the best kind of way. Rather than following everyone else out of the office doors at the end of the year, try sticking around for these two days when no one else is there.
Reflect & Refine is a two-day period where there are no distractions, interruptions, or surprises. You don’t even have to operate your Triage Shield1, because there is no incoming mail, no incoming chats, and no meetings. There is just you.
And being the last work days of the year, it’s the perfect time to execute the higher level version of your Weekly Review2. Here is the process I’ve followed for the last two decades to close out my current year strong, feel more prepared for the year ahead, and more fully enjoy the holiday break from work.
Day 1
1.1) Step back
Come into the office, but don’t turn on your computer. If you have any other chair in your office besides your desk chair, have a seat in that. If the only chair you have is your desk chair, then first roll it away from your desk to the other side of the room, and then sit there. Set a timer for 10 minutes3, and then start getting yourself in the right mindset for what’s ahead. Tell yourself, “Today isn’t a typical workday. Today I don’t care about the email, and the high priority issues on my plate. I’m not here to get any work done. Instead, I want to think about how work overall is going.“
When the timer goes off, get up and take a couple of minutes to do a slow walk of your office hallways. When you return to your office, turn your computer on. If there are distractions on the screen, close them all down. Bring up your External Brain4 and create a “2025 Reflect” page. Alternatively, if you have the whiteboard space and prefer to brainstorm with markers and boards, then do that.
Over the course of the day, you will be referring to both your External Brain and Your Team’s External Brain5 to help remind you of the year gone by. The trick is to make sure that you don’t get sucked into present day problems as you do it. For instance, when you remember a relevant conversation that happened in email, you’re going to open your email. At that moment, you may easily fall into the habit of commencing email triage. Fight it. This is where I will commonly remind myself before even opening my mail, “I’m only opening mail to find this conversation. I don’t care about any other mail. I’m opening mail, going straight to the search back, and typing to find the conversation I want. Then I’m closing the app.”
1.2) Take stock
Use an established set of questions to help guide you through a “year in review” exercise. Here are the questions I use:
What has worked well for me in the last year?
What hasn’t worked well for me in the last year?
Have I made the amount of progress I wanted to make on my mission? Why or why not?
Do I feel satisfied with my scope of work? Why or why not?
Do I feel satisfied with my own performance? Why or why not?
Use my list as your starter list, but you should definitely make this list your own. Add or delete until you have a list that sufficiently stirs your mind.
Don’t treat this list of questions as a survey, where you answer with the first thing that comes to your mind and move on to the next item. Instead, spread all your questions out on the screen in front of you, or on your whiteboard, and give yourself the time for ideas to come. I commonly capture all of these questions, read over them a couple of times, and then do another slow walk through the office hallways. I just want to give the questions time to sink in deep in my brain. When I return to my desk, I then start writing.
Don’t feel obligated to answer these questions in any order. Move back and forth between questions, adding items as they come to mind. This is when you’ll be leveraging your External Brain and your Team’s External Brain. One perfect example is that you should read over your performance reviews for the last year and see what details emerge that belong somewhere in your “2025 Reflect” notes.
Plan on this process taking you until lunch. So when the ideas start coming in slower, don’t try to rush yourself out of this stage. Know that you’re in this until lunch, and then just let the time pass. Keep resetting yourself to create the opportunity for new perspectives. You can take more walks around the hallways, maybe even a fresh air loop around the building. Or you can take a move out of Mr. Keating’s book from Dead Poet’s6 and stand on your desk so that you can, “Look at things in a different way.”
1.3) Enjoy your lunch
Now go take a break and eat lunch, anywhere other than in your office. Take a pen and pad with you, as you will undoubtedly think of more things as you eat. Just scribble enough so that you don’t lose the idea, and then resume your munching and thinking.
When lunch is done, return to your desk and add in whatever scribbles you came up with at lunch.
1.4) Refine your plan
You should at this point have no shortage of notes to leverage. It’s now time to make a plan for the year ahead. The key here is not nuking everything and starting over. I don’t believe in New Year’s Resolutions, but I do believe in New Year’s Refinements. Some questions that help frame the afternoon:
What has been working for you, that you want to take to the next level?
What habits have grown a little sloppy that need to be tidied up?
What one corrective measure would have the most ROI (Return on Investment) towards advancing your mission?
With your refinement questions in in your head (and captured on the computer or on the whiteboard), reread all of your notes from the morning. Look for ways that you can leverage your highlights to mitigate your lowlights, going forward.
Day 2
2.1) Refresh your memory
Return to the office and go immediately to your computer or whiteboard for your day 1 notes. Reread all of your notes from day 1 to page everything back in. Then give yourself 10-15 minutes to make any “upon further reflection” edits.
2.2) Take a first step
Now ask yourself, “What is the next action I can complete by the end of today that would most set me up for success in the new year?”
For each possible next action that comes to mind, write it down, and measure it against your plan. Does it address one or more aspects of your refinement plan? Can you with 100% certainty complete that action by the end of the day?
Once you have a list of 5-10 possible next actions that pass the test, score them by degree of positive impact on your plan. Take the first item, and pull the trigger.
If your next action is a “reduce my debt” action, such as cleaning up your mail inbox or getting through pending code reviews, then please consider the following. No clean up action should be without a “clean up the process behind it” step. So, if you do choose to try to tackle your email inbox drudgery, make sure you give equal time for “tweaks to reduce future drudgery.”7 Perhaps spend some time on your email filter rules. Or figure out what conversations have been happening in mail that need to be better captured in Your Team’s External Brain.
If you’re looking for suggestions for your next action, a standard suggestion I give is, “I bet your calendar could be tidier than it is,” with my rationale being that prescheduled time silently steals more of your attention and ability to produce than you realize. This opinion was cemented for me in my 2004 Reflect & Refine. We were three years into an extended project where the recurring meeting count just kept ticking up, month after month. But because it was happening incrementally, like the frog in the pot of heating water, I hadn’t realized just how much of a dent these meetings were making in my day.
I took a look at my calendar and counted 32 hours per week of recurring meetings! My team members had presents from me waiting in their inboxes when they returned in January of 2005: I had done a culling of all the meetings I owned, and had provided suggested adjustments to the owners of the other meetings. By the end of January, I was down to 20 hours per week for recurring meetings on my calendar, which for my architect role at the time gave me the perfect balance between connection with the team and time to advance my own efforts.
2.3) Take a second step
If you get done with 2.2, and still have enough time left in the day, grab the second item off your list, and pull the trigger.
Stop when there is not enough time left in the day to complete the next action. Don’t overcommit. As my friends always said when we were shooting hoops, “End on a made bucket.”
2.4) Call it a year
You’ve done your due diligence. You took adequate time to assess the health of your work and have taken steps that will enable you to hit the ground running next year. Note your stress level when you walk out of the office. If there was a cloud hanging over your head before, that should have dissipated, at least slightly. You should be feeling more peace. You may even break into a few bars of “Silent Night”, or the Christmas-neutral “Feels So Good”8.
Now you can go enjoy the holiday!
Happy Holidays everyone!
Footnotes
“OneNote as my Work Management System” section of External Brain
Dead Poets Society (3-rd lesson, look at things in a different way)
I *always* took advantage of the ghost town period when everything shut down. I didnt so as much planning as you outline here, some, but mostly super productive time, cleaned the office of clutter, got organized. Your suggested intentionality is definitely worth implementing!