How I’m winding down for the year [PMP #195]

The end of the year is fast approaching and when you look back and think about everything that’s happened this year, it’s crazy how fast the time has gone by!

As the end of the year approaches, I’m starting to think about how I want to finish off the year and prepare for 2021.

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This is what I’ve got planned so far…

Decide what dates to scheduled time off

Firstly, I’ve planned the dates I’m going to be taking off over Christmas and New Year. I see that in the US and UK, most people keep working right up to Christmas and during the week before New Year. In New Zealand, most people stop working a few days before Christmas, take a few weeks off and return to work in early January. As it’s our summer, we like to take advantage of the hot weather.

Personally, I can’t imagine working on Christmas Eve. I find I’m usually pretty checked out by that stage there’s no point working.

Taking this 2-week break each year is the perfect way to close out the year and reset ready to hit the ground running in January.

Updated Calendly settings

So, I’ve decided what dates I’m going to take off. The next thing I do is to block this out on my calendar so that I can’t be booked for consulting calls during this time.

Sending Christmas cards to clients

Each year I enjoy sending a few Christmas cards to clients I’ve worked with.

To do this, I use a service called TouchNote. With their iPhone app, I can create a nice, personalised card with a family photo and custom message. I simply enter the address and TouchNote takes care of the rest.

If you want an easy way to send holiday cards to your friends, family or clients, check it out!


Set aside time for reflection and analysis

As part of my annual close down, I budget some time to reflect on the year and analyse how I worked.

  • I’ll usually look back at Timing (affiliate link) to analyse how I spent my time across different areas of my business.
  • I’ll also export data from Asana and Pipedrive to analyse my time vs. income working on different types of client work. I like to see how much time vs. income can be attributed to big client projects compared to course sales and other forms of income so I can identify what worked well and where I can improve.
  • A few years ago, I listened to an episode of the Tim Ferriss podcast where Tim describes an exercise whereby he asks himself “What 20% of things resulted in 80% or more of my stress and anxiety this year?” and “What 20% of things caused 80% of my happiness this year?”. This type of reflection is a great way of getting clarity on the things you should be doing more or less of.
  • I’ll look back at my goals for the year and work out what I did or didn’t achieve.

This reflection and analysis helps me to prepare for the next step, goal planning.

Set aside time for goal planning

Next, I like to write down some specific goals for the following year. I do this in Asana (where else?).

I usually write down a number of personal goals related to health, fitness, family and travel.

I’ll also write some business goals related to time, income and projects I’d like to complete or changes I’d like to make within my business.

In previous years, I’ve tried to give myself a keyword or theme for the year. Something that guides my decision-making and gives me a sense of focus. For example, one of my keywords for 2016 was ‘essential’. I’d just read the book Essentialism and felt that this really resonated with me at the time as I was focussing on growing my side-business.

I’ve been doing this in Asana since 2016 and each year I enjoy going back and reflecting on my goals over the years to remind myself of the progress I’ve made and how far I’ve come.

Working out initial priorities for 2021

Before I wind down for the year, I try to get clarity on what the first few weeks of January are going to look like when I return. Both in terms of client work and internal projects I want to work on.

Rather than starting work in January after 2 weeks off and trying to set my priorities, I prefer to plan this all while I’m in the right headspace in December.

At this time I’l also communicate my availability to clients so they know how much access to me they’ll have over the holiday period.

Scheduling social events with friends and family

And finally, in late November and early December, I will plan social events and day trips with friends and family.

The Christmas – New Year break is the perfect time to catch up with friends you haven’t seen for a while and do the things you said you’d do during the year.

Literally, as I was writing this post I remembered that my friend Chuck previously said we should go on a hike sometime. As is often the case, we haven't made time to do this yet. So I just messaged him and we’ve planned some time for a day trip before Christmas.

As well as spending Christmas with family, this is the perfect time for sunny afternoon BBQs and day trips to the beach. I make sure to get all this kind of thing on the calendar nice and early before people get too busy (as you can see, I’m as disciplined with scheduling my time in my personal life as much as I am with work).

So, what does your end of year routine look like? How do you wind down or prepare for the new year? Let me know in the comments below!