4 Year-End Reflection Questions for a More Fulfilling New Year

Grace Ho
December 30, 2020

In modern life, we don’t have as many occasions where we consciously mark time and transitions.  This is especially true this year, when being home more has warped our sense of time and meaning, and when we’ve had to reimagine how we celebrate holidays and long held traditions.  

This is why I think it’s especially powerful to carve out time this New Year period to reflect on the last 12 months, and set intentions for 2021.  For several years now, I’ve used the questions from YearCompass as a starting point for my exploration.  

Holly, Anjani and I came together recently to design a few of-our-times reflection questions that you are unlikely to find from other resources.  We hope these prompters allow you to see yourself and the world from less familiar vantage points, and that this leads to unexpected insights which help you live more fully and authentically in 2021.   

Year end reflection

  1. In 2020, what did I learn about myself and my relationship to uncertainty and complexity?  How can these lessons help me be more resilient in 2021? 

This year, you’ve likely experienced sustained uncertainty and complexity in almost every domain of your life.  You’ll have plenty of data points showing how you respond to the unexpected and messy - enough to see behavior patterns and habitual mindsets, and to notice how different conditions and contexts affect your response.  

If you pay attention, you can uncover powerful lessons and insights about the qualities and conditions that enable you to be more flexible, creative and resilient in the face of inevitable uncertainty.  

Here are some additional questions that can help you deeper and more specific in your reflections: 

  • What emotions were predominant?  Which emotions did I find the hardest to be with? 
  • In which parts of my life did I find it hardest to navigate uncertainty? Why?
  • How much did I try to (re)gain a sense of control? What did I do?  
  • What kind of support did I most need?  What did I do to get that support?

  1.  What changes forced by the circumstances of this year do you want to keep in the new year/the “new normal”?  What would it take to prioritize these? 

As vaccine adoption goes up in the new year, it’s possible that some elements of life which were upturned in 2020 will go back to the “old normal”.  When the office expects you back, when social obligations pile in, when you have fewer reasons to chat with your neighbors etc, what habits and obligations do you not want to slip back into?  Perhaps you’ve relished becoming a more present friend or family member, or you’ve loved taking up a new hobby instead of feeling obliged to go out every Saturday night.  

How will you protect space for the things which you’ve discovered are important and valuable to you? Are there some bigger, longer term changes (like moving to a new city or switching careers) that you want to work towards next year? 

  1. Recalling all the major things I did this year – which were in the “wanted to” bucket and which were in the “should” bucket? Were there any “wants” that didn’t end up being done or got traded for a “should”?

This is another question that helps to clarify what really matters to you, and what may be getting in the way of you pursuing those things.  

“Should” is a word that’s loaded with self-judgement and other people’s expectations.  As long as we’re prioritizing “shoulds”, we’re acting out of guilt and a sense that we’re not good-enough.  This isn’t conducive to us being at our best.  

As you read through your lists, notice whose expectations/needs might you be carrying unconsciously.  Also, consider whether some of your “shoulds” are actually “wants” - sometimes, all it takes is a reframing of mindset or motivation to transform a heavy obligation to a heart-felt wish. 

  1. What is one guiding question for 2021 that can help me stay focused on what matters most?

Unlike a resolution or goal which is static and focused, a guiding question is alive and can help you take wiser decisions and actions anywhere and any time in your life.  An example of a guiding question you’re likely to be familiar with is Marie Kondo’s “does this spark joy?”.  

As you design your guiding question, think about the qualities you want to embody, the values you want to live, or the people/systems/causes you want to serve.  For example, if your intention is to spend more outside your comfort zone in 2021, you might ask, “What would I do if I was 5% more courageous in this moment?”.

Here are a few examples of guiding questions we’ve seen other people adopt:

  • What is my gut/body telling me?
  • What is the opportunity cost of doing (or not doing) this and am I ok with that? 
  • Who am I really doing this for?
  • Will I be proud of this on my deathbed?


We encourage you to capture your reflections somewhere so you can revisit them in the future.  Not only will it solidify your insights and intent, it is also a precious resource to look back on to see how you’ve grown and evolved.  

We hope you enjoy spending time with these questions.  We would love to hear what you chose as your guiding question for 2021! 

Have a peaceful, healthy and joyful end to 2020, and Happy New Year! 

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