Last December, I wrote a whole blog post called “Reflection: Whys and Hows,” where I broke down the practice of doing an end-of-year reflection and shared the journal prompts I use at the end of each year. For this year’s end-of-year reflection post, I’d like to revisit some of that instruction and share my revamped list of reflection questions in the form of a free Year’s End Journal Prompts guidebook.

On Reflection

The instruction to reflect holds strong across academia, business, and self development. Yet, regardless of its value, many of us fail to actually follow through on our intentions to reflect. 

This may be due in part to the complex double act of reviewing and planning: by definition, the verb “reflect” means both “to bend or fold back” and “to make manifest or apparent.” As it stands, we might simply not know how to do it, why it matters, or we don’t want to waste our thinly-spread-as-it-is time.

In what follows, I break down the whats and whys of reflection to show the benefits of the practice, how to make it work for you, and share with you the reflection practices and questions that are most helpful to me. What better time than the hinge between two years to resee reflection as both an act of “looking back” and a “looking forward”?

The Whats and the Whys

According to Tracy Kennedy, Lifehack’s Personal Development Expert, reflection offers multiple benefits. As detailed in her article, “How Self-Reflection Gives You a Happier and More Successful Life,” reflection can improve our lives in the following ways:

  • Improves self-awareness
  • Provides perspective
  • Allows you to respond, not react
  • Facilitates a deeper level of learning
  • Improves confidence
  • Challenges your assumptions

In addition to improving our self-knowing and presence, reflection can help us make better decisions when it comes to growth and change. Jennifer Porter, an executive coach, reports in her Harvard Business Review article “Why You Should Make Time for Self-Reflection (Even If You Hate Doing It)” that:

The most useful reflection involves the conscious consideration and analysis of beliefs and actions for the purpose of learning. Reflection gives the brain an opportunity to pause amidst the chaos, untangle and sort through observations and experiences, consider multiple possible interpretations, and create meaning. This meaning becomes learning, which can then inform future mindsets and actions.

Porter breaks down the purpose of reflection by connecting it to other important ideas and actions: learning, pause, untangle, consider, meaning, and, perhaps most importantly, future. She reports that many of the leaders she coaches actually put off doing reflection, sometimes because they lack an understanding of how to do it or other times because they have not prioritized it. So, let’s learn how to do it, shall we?


The Hows

Although reflection is greatly beneficial for decision making and planning, it still often ends up on the back burner. I think this is because reflection requires three things: time, energy, and focus.


I recommend that you set aside, and even schedule, time for intentional reflection. The goal is to view reflection as something that serves you, not as one more thing that you’re trying to squeeze in between meetings or forcing yourself to do before bed.


It’s no surprise that reflection pulls on our mental energy: we are remembering and considering and interpreting. But, I want to note that it may also require emotional labor. 

Reflection prompts ask us to think about both the highs and the lows. It is possible for us to get stuck in the quicksand of things we didn’t achieve, things or people we lost, disappointments or embarrassments, or other crummy memories. For that reason, I encourage you to pair questions such as “what didn’t work out well?” with others such as “what went well?” or “what did I feel proud of?”

Here’s a real life example of how this works. When I teach writing, I ask my students to reflect after each paper on two things: 1) something they struggled with and improved on, and 2) something that they continue to struggle with. I do this because I want my students to know that I do not expect them to become expert writers and researchers in one semester. In fact, I explicitly encourage them to see the acts of learning and practicing as a continual process.


You can reflect in multiple ways, including handwriting, typing, and/or sharing out loud with someone else. There’s no right or wrong way to “do” reflection, and while I like the slow rumination of handwriting, typing out my answers allows me to capture more ideas quickly. I’ve done all three, but admit that my favorite reflection process is sharing out loud with someone else. 

In one-on-one coaching, I ask my clients specific reflection questions about their progress and process and I hold space and attention for their answers, which I record for them in our session notes. In my personal life, I often ask my Sweetie to reflect with me (”what are you grateful for?” or “what are you most looking forward to about X and why?”) on car rides or on walks together, and I absolutely love learning about what makes her feel fulfilled, moved, and inspired. I enjoy sharing my answers with her, too, which often leads to what we call “air signing” AKA a Gemini and a Libra talking for hours about life. Feel free to mix it up and adjust your reflection process for your particular passions and preferences!


Today’s takeaway is a free 24-page Year’s End Journal Prompts guide! This guide will help you reflect on your personal and professional experiences in the last year (and in the last decade!) and will assist you in setting some specific goals for 2020. You can access it by clicking the following link. Enjoy!

Click here to access the free Year’s End Journal Prompts guide!

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