6 Ways I’m Closing Out 2019 and Preparing for 2020

The quiet time between Christmas and New Year has been a special time for me to bring closure to the previous year and intentionally prepare for the next.  I often find that my days are so full throughout the year that I lose myself in the grind and neglect to recognize how much I have accomplished and grown in a given year and what major events and memories have helped shape who I am.

This tradition started five years ago when I went through some painful events that, frankly, I found difficult to process, bring closure to, and pick myself up from. It was during this time that I borrowed a workbook my father had purchased from the Michael Hyatt Company on bringing year-end closure.  While initially I was skeptical that this would help, I found that I loved the process that Michael had outlined, the clarity and perspective his questions provided, the way I was able to see the good and lessons learned in the midst of pain, and ultimately the way I was able to tangibly see and track my own personal growth.

Over the years, I have refined my annual review process and have experimented with additional methodologies/questions that I have added to the core list that Michael outlined.  I’m always tweaking to adapt to my needs in a particular year, but here’s a look at how I’m currently closing out 2019:

Start with the questions

Before I can look to a new beginning in the next calendar year, it’s important to bring closure to the previous year.  Every year I open a page in a OneNote notebook I’ve created to capture these notes and start with answering Michael’s “7 questions to ask about last year”.

  1. If the last year were a movie of your life, what would the genre be?
  2. What were the two or three major themes that kept recurring?
  3. What did you accomplish this past year that you are most proud of?
  4. What do you feel you should have been acknowledged for but weren’t?
  5. What disappointments or regrets did you experience this past year?
  6. What was missing from last year as you look back?
  7. What were the major life-lessons you learned this past year?

Review your growth

Of all of Michael’s questions, number seven is my favorite in that it helped me to see the good and important moments throughout the year. Essentially, I “pause time” to take a detailed look at who I am as an individual and what lessons I can take away from each situation.  As I’ve collected life lessons throughout the years, I’ve aggregated them into a single list batched by year that I then review annually.  This helps me to keep these lessons at the forefront of my mind, avoid repeated mistakes, and understand how I’m growing.  Here are four examples of lessons I’ve learned throughout the years:

  • I can diffuse a painful situation or confrontation by asking the other person to help me understand.
  • I love encouraging others.  I never want to be so focused on myself or my own pain that I miss an opportunity to reach out to someone else.
  • It feels wonderful to save for something big and finally buy it.  I would rather be patient and have fewer but nicer things.
  • Good and faithful friends have turned out to be the most unlikely of people.  Never disregard anyone.

Review areas where you have settled

When I first started this review process, I created a little table that outlined Michael’s questions for reviewing areas I’ve settled.  These questions were:

  1. In what areas of your life have you settled?
  2. When you think about those areas, how does that make you feel?
  3. What would it be like to feel a breakthrough in these areas?
  4. What are the internal barriers you need to overcome in order to experience a breakthrough?

I found that this was important to help me process the emotions surrounding these areas and causing blockers.  That said, over time I’ve increased my self-awareness and have not needed to answer every question annually.  In the past two years I’ve simply made lists of the areas I’ve settled and used it to inform and transition myself to looking to the future. 

Set SMART goals

I’ve never really liked the idea of setting New Year’s Resolutions as they are often vague.  That’s why the process of setting SMART Goals (Goals that are Specific, Measurable, Actionable, Realistic, and Time-Bound) resonated so much with me.  As a part of this process, I make a list of all of my SMART goals and my 4-7 “why’s” for why this goal is important to me.  I then outline both my key motivation for each goal and an overall push goal (a single goal that I can begin tackling or prioritizing that will make tackling the other goals on my list easier).

Set a “Word of the Year”

This past year, I was inspired by a tip on Gretchen Rubin’s podcast, Happier to set a one-word yearly theme. As I reflected on the SMART goals I had set for 2019, I noticed that many of them had a common theme:  Discipline.  As I made “discipline” my word of the year, I noticed that it became easier for me to remember the other goals that were tied to this word.  “Discipline” became my mantra as I made key decisions and I discovered that I became more aware of and interested in resources, discussions, articles, and podcasts on the topic throughout the day.

Setup a system to track your progress

If there was one thing I’m constantly tweaking in this system, it’s the best way to both regularly review my goals and allow them to inform daily tasks and decisions  I continue to experiment in this area, but here are some things I’ve tried that have been helpful.:

  1. Tape a printed copy of my goals to the bathroom mirror to review daily.  This proved to be more effective them keeping them in a digital format and reviewing them only weekly.
  2. Define habits I need to form to achieve my goals and track them.  I’ve tried a few processes for habit tracking but currently use the Productive app for iOS.
  3. Go with paper – While I’m a big fan of digital systems, this year I’m experimenting with a hybrid digital and paper productivity system to force myself to slow down, minimize distractions during planning, and better plan.  I’ll let you know how it goes in a future post!

Do you have a year-end ritual?  If so, I’d love to hear from you in the comments below:

Please note: I reserve the right to delete comments that are offensive or off-topic.

Leave a Reply

Your email address will not be published.

This site uses Akismet to reduce spam. Learn how your comment data is processed.

One thought on “6 Ways I’m Closing Out 2019 and Preparing for 2020

  1. I liked your recommendation of Michael Hyatt’s seven questions and the additional recommendations to turn them into next actions for the new year. I’m going to try it later today. I did do Tim Ferris’ recommendation to look through your calendar and find POSITIVE and NEGATIVE events or people interactions. I ended up with a lot more POSITIVE items than NEGATIVE ones.