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We’re running all over, getting things done, working toward a noble mission. We take the action, then check it off our list. We get the project done, then move onto the next one. When it comes time to have the annual performance review, we take a look up and see how we’ve been doing these past twelve months. We might arrive at this conclusion: we’re being productive! Good for us.  

But as we begin a new year, it’s time to think about what all of that productivity has given us. Do we know why some projects were successful and others failed? Have we had the chance to process how far we’ve come professionally, and how our team has overcome obstacles together? Probably not. 

There’s no better way to reflect than to embark on some silent and patient self-examination. So as we all dive into this new year together, here’s a guide to help you reflect. This will help you learn from mistakes, understand what makes you successful, and undertake what’s ahead with enthusiasm. And with some advance planning and your calendar handy, you can take these skills to make 2020 the year of intentional and purposeful self-reflection. 

Self-reflection as a tool for learning 

Executive coach Jennifer Porter explains that “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.” 

Through a reflection practice, you can rewrite old stories that don’t serve you, examine the “why” of what happened, and explore “what’s next.” Thinking about your past can help you find out what’s holding you back and get it out of the way, or find the insights you need to stay on target toward a big goal. To get started:  

  1. Instead of simply pondering these topics, write out your thoughts. “Therapeutic or expressive writing” can help reduce depression, up your creativity and even make you physically healthier.
  2. Reflect regularly for the greatest benefit. Set some calendar reminders to reflect on your birthday, at the end of each quarter, or on the day of the summer or winter solstice (my personal favorite). 
  3. Be open to using reflection spontaneously when you’re stuck, when you’ve failed miserably, or when your team just accomplished something major.   

5 guided self-reflection exercises 

To get you started, here are some prompts you can use the next time you sit down to do some careful reflection. Set aside at least 15 minutes for any one of these and afterward, take action based on what you’ve learned.  

To reflect on a project or process, ask yourself:

  • What have I learned about how my organization works?
  • What barriers did I overcome? 
  • What will I do differently next time?
  • What do I know now that I didn’t know then? How did I acquire that knowledge?
  • What do I need to do today in order to make this learning concrete?  

To reflect on “where you are,” ask yourself:

  • What’s important to me?
  • How has what’s important to me changed in the past year? Five years? 
  • How am I aligning my actions with what’s important to me?
  • What’s difficult about it?
  • What actions can I take today in order to find more alignment? 

To reflect on a mistake (a rash decision you made, an offensive thing you said, a clear oversight in your judgement), ask yourself:

  • From the perspective of three other people, what happened here? How might I have been perceived by those people?
  • What will I do differently next time? Whose help do I need to make that happen? 
  • What’s the new entry I’ll now add to my failure resume?
  • With whom do I need to share my learning in order to maintain strong relationships in the future? 

To reflect on an article you’ve read, a quote that speaks to you, or a talk you attended, ask yourself:

  • Why are the ideas I’ve learned here so compelling to me? 
  • How am I currently living out the ideas expressed here? 
  • What might I do differently? 
  • What might it feel like to make this my personal mantra? 
  • What actions do I want to take next? 

To reflect when you’re feeling disengaged, antsy, uninspired, or just “blah,” ask yourself:

  • What are all of the things I’m feeling right now?
  • What’s going on in life that might be creating these feelings?
  • How do these feelings impact me?
  • Do I want to let this continue? Why or why not?  
  • What kind of support do I need? 
  • What are the next three steps I’ll take to move through (not around) these feelings?  

Finally, if you’re engaging in a group reflection, you can schedule a productive “post mortem” activity or call up a few quick but powerful reflection questions to recap a completed project. 

The bottom line

You might ask “What’s the point of all of this omphaloskepsis?” (look it up). Here it is: If we want to become more productive, impactful, and fulfilled, we need to understand what makes us productive, impactful, and fulfilled in the first place, and do more of that and less of the other stuff. Pretty simple, really.  

Here’s to you and a new writing practice in 2020 that provides new insights and a fresh perspective! 


How do you reflect on the year past and set intention for what's to come? Let us know on Twitter.

Liz Peintner profile image

Liz Peintner

Liz S. Peintner is a leadership coach and consultant based in Denver, Colorado who has spent her entire career in the social impact field. She helps people to better understand what drives them so they can choose careers they love and ultimately make positive social impact in ways that speak to their talents and passions.

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