About Retrospectives
As part of my commitment to growth and belief in the importance of self-reflection, I added a new element to my year.
The purpose of the retrospective is pulled directly from Agile Methodology. As stated in the Principles from the Agile Manifesto:
At regular intervals, the team reflects on how to become more effective, then tunes and adjusts its behavior accordingly.
I’m adopting the retrospective to look back on what worked, what didn’t, and collect some thoughts on future actions.
While this post is primarily an exercise for me, I’m also committed to working in public and I hope that seeing the process will inspire you to reflect on who you were this year, and get you thinking about who you want to be next year.
Every year my first post will be My Three Words and my last post of the year will be the Retrospective.
This is the last blog post of 2020 for me.
Cooling down is an easy exercise, done after a more intense activity, to allow the body to gradually transition to a resting or near-resting state. Wikipedia
Revision literally means to “see again,” to look at something from a fresh, critical perspective.
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I love the end of the year almost as much as I love the start of a new one.
The beginning of the year is where I hit the ground running with renewed energy and passion. I’ll have charted a course for a new destination and I’m loaded with excitement, curiosity, and determination.
None of this can happen, without a critical examination of the year that’s coming to an end.
The end of the year is where I take the opportunity to reflect upon the previous 12 months. It’s a chance to think about what went well and what didn’t. It’s a chance to look at everything unexpected that came up and better prepare myself in the future. It’s the best time to plan for the coming year because everything has slowed down.
It always feels like everyone is taking the time to catch their breath before starting again and that makes it the ideal time to cool down.
The Cool Down
I recognize that not everyone can do this, especially those who work in retail. For those that can, the first thing I would encourage you to do, is to consciously and deliberately make the time at the end of the year for this cool down exercise. That means you have to set expectations with others about your availability, block off time on your calendar, and commit to using this time in a way that best serves you.
Since 2014, I have been taking the last 2 weeks of the year “off” in order to create the space for reflection. While I still occasionally have a client obligation in the final 2 weeks of the year, I tend to set expectations early enough with my clients that it’s generally not an issue. In most cases, with very little actually getting done during the holidays, clients have been receptive to it, especially since many of their clients are out of the office as well.
This creates uninterrupted space for deep thinking.
If you are able to make this time it’s important to understand that once you have it, YOU get to decide what you do with it.
For me, I choose to reflect and catch-up. The following is an outline of my annual cool down process, including some reflections of my own.
How To Review & Reflect On The Year
1. Accomplishments
I think the best place to start your reflections is by thinking about accomplishments.
My process is to look back and make a list of at least 5 things that I am proud of accomplishing since January 1st. Now is no time for humility. For once, let yourself relish in what you’ve done.
This year I am proud of…
- Starting a brand new phase of my career that was very profitable in my first year. I finally feel 100% aligned in what I do, why I do it, who I help, and I’m able to do it at a price that is fair for both me, and my clients.
- Completing the first draft of my book, The Lovable Leader, and started to work with an extraordinary publisher (Page Two) to bring it to life. Expected publish date: January 2022.
- Publishing 42 posts on this blog including an unbroken twice-a-week streak that began on July 14. I also feel as though this year represented some of the best writing in my career.
- Starting to work out with a trainer late in the year, and maintaining a consistent schedule of subjecting myself to worthwhile physical activity.
- Becoming much more intentional about my habits and even starting to track them. I’ve been practicing Mandarin on Duolingo for around 130 straight days and have missed less than a handful. I’ve made it a point to read for at least 15 minutes each day and reached a streak of 82 straight days. This lead to the year of my largest book consumption (30).
I have some other things on my list that I’m proud of both personally and professionally, but I’ll leave it at these 5 for the sake of this post.
2. Gratitude
During a recent Superhero Hangout, we discussed end-of-year routines, and Grant Crowell, author of Grantasms, mentioned that he goes through his gratitude journal and takes some time to re-live all of the things he felt grateful for throughout this current year. While I’ve only just adopted the habit of gratitude journaling, I thoroughly support this idea and have officially added it to my end-of-year routine this year. Thanks, Grant.
Once I finished acknowledging my accomplishments, I turned to looking at my life and identifying things I’m grateful for. Again, I recommend making a list of at least 5 things you are grateful for but add as many things to the list as you can.
I’ll limit mine to three for this post.
- I’m grateful for my incredible wife, who encouraged me to take some time off in 2019 to think about what I wanted to do next. She carried the full financial load for our family, while pregnant, so that I could have the time to think, talk to people, and figure out what came next. Without her, I wouldn’t be the person I am today. I could fill 100 pages listing all of the reasons I’m grateful for her.
- I’m grateful for my daughter being born healthy and happy. She has made 2020 an incredible year for me despite the pandemic and all of the other craziness—like the election and murder hornets.
- I’m grateful for my friends, family and my network, all of whom have been so supportive of me as I transitioned into a new phase of my career.
If there are any people you are particularly grateful for, be sure to tell them in person. Maybe they can then add it to their own list of accomplishments.
3. Critique

person holding pen with coffee on table
My next step is to review my year more critically. The first thing I do in this part of the process is related to something I have been doing every year since 2013: My Three Words ←click that for an explanation of my three words
This year, my three words were Embrace, Outspoken, and Disciplined.
I am exceptionally happy with how I lived these three words this year.
- I thoroughly embraced my new situations including: starting a new solo consulting practice for large companies, as well as a personal and professional development platform with coaching for small businesses, freelancers, and entrepreneurs. I embraced being a new dad. I embraced and felt grateful for all of the aspects of my life. I even embraced the opportunity to work from home when the pandemic hit. Embrace was about taking things as they came and pulling it close rather than turning away.
- I was more outspoken this year than ever before and I’m just getting started. In the wake of extreme civil unrest due to the 2020 election, as well as the 400 year history of racism in this country, I became very aware of my responsibility to speak up and never let injustice or discrimination get comfortable. Outspoken was part of the next step in the process for me, after listening and learning, which will be ongoing for the rest of my lifetime. I am proudly outspoken.
- Perhaps of all of my words, disciplined was my greatest success this year. I adopted more habits than ever before. I was more organized and planned my time and activities better than ever. I was disciplined in a way that I never have been before.
After I review my three words, I ask myself some more questions. Questions like:
- What lessons did I learn this year?
- What important project did I fail to complete?
- What knowledge gaps do I have that need to be addressed?
- Who could I have helped, but didn’t?
- How could I have been a better husband, father, son, friend, mentor, or vendor?
- What areas do I need to improve upon to keep me moving toward my life goals?
- What do I want to accomplish next year?
4. Plan

sticky notes on paper document beside pens and box
After I’ve gone through a full review and reflect period, I do a little planning for next year.
I try to determine what my priorities will be for the coming year, establish my “must-complete” projects, and a plan for my personal and professional growth.
Doing all of this work also helps me to narrow down my list of words to select my three words for the next year.
5. Catch Up

man in black nike hoodie wearing black headphones
The final step in my end of year cool down process comes only after I’ve completed the requisite reflecting and planning. Once I’ve done that and I’m clear on how the past year went and what I want out of next year, I catch up on things I didn’t have the chance to do throughout the year.
This can include going through Online Courses, reading Books, listening to Podcasts, reading Articles I’d bookmarked, or doing those stubborn Maintenance tasks (Digital or Household).
This catch up is not to be confused with catching up on work. This is not about work, it’s about growth and organization.
Are you cooled down?
What’s your process look like? Is it this formal? Does it change year to year? Do you just work right through until the end? Do you just take time off to watch Netflix and play video games?
I’d love to hear what you do, so sound off in the comments if you’d like. Otherwise, I’ll see you in 2021.
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