In The Trenches

A time for reflection

Published on December 16, 2019 Back to blog
sunset reflected in car side mirror

As we approach the holidays and end of the year, we often ask one another about resolutions for the New Year. However, at least for me, it seems difficult to consider the year ahead without reflecting on the year behind us. It’s the experiences and lessons of our past that can most effectively guide our future. Additionally, we often get so caught up on “what’s next” that we don’t truly take the time to celebrate and acknowledged “what was.” 

So today, as you prepare for the holidays and year ahead, I encourage you to consider the following questions to reflect on 2019 and consider how it can inform a happier year ahead.  

  1. What are you most proud of? I’m sure you’ve done many amazing things this year. Take a moment to acknowledge them and congratulate yourself accordingly. You deserve it. While you’re at, consider how that may guide some new goals for 2020.
  2. What do you wish you did differently? Sometimes, we look back on some situations and think, “I wish I approached that differently.” Until and unless you can honestly acknowledge those mistakes, you probably won’t change them.   
  3. What did you most/least enjoy doing? This is a big one. Perhaps even create a 2-column list of what you enjoyed doing and what you didn’t. For those that you did enjoy, consider how you can do more next year. For those you didn’t, consider how you may delegate them, automate them or eliminate them. (NOTE: This is a trick I recently learned from a great business speaker, Bill Flynn.)
  4. What relationships do you most/least appreciate? Similar to the above, consider applying the approach to people. For those you most appreciate, consider how you may want to enhance your relationship with them in 2020 (and consider sending them a note of thanks while you’re at it). For those you appreciate less (and those not yet on the list at all), consider how (and if) you want to build the relationship in the year ahead – and how to get them moved into the more positive column. 
  5. What were your greatest lessons learned? We tend to learn something new every day – and in the course of a year, some of those lessons combine to become much larger life lessons. Take a moment to reflect upon what you learned this year, take note and be sure to apply them (and share them) in the year ahead. 

While there are many other questions I’m sure we could be asking ourselves (I appreciate any thoughts/suggestions), I believe that these five will not only help you appreciate all that has happened in the last 12 months, but can also guide happier months ahead. And, with each question, be sure to ask “why” to get to the real heart of the answer.

As always, please feel free to share your thoughts with me by replying to this email or commenting on my blog. And, if there are other people you believe may enjoy this post, please pass it along.

With that, I wish you, your family and your friends/colleagues all the best for the holidays and the year ahead. I hope that, in some way, I am able to help you make it a great one.

Until next year,


PS. If you haven’t already checked it out, be sure to check out the Small Army Holiday PSA