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How to Do an Annual Reflection (With Templates!)

It's important to slow down and reflect from time-to-time. This blog and the templates included will get you started!
Ben Winn
December 16, 2020

Since 2017, I’ve been doing an annual reflection exercise and an annual gratitude exercise.

I’ve never been able to stick to daily or even weekly journaling, but I have been able to stick to this one yearly habit thus far, and the truth is I really enjoy it which is why I want to pass it along to all of you. 

First I’ll share the most important reasons WHY reflection is so critical, and then I’ll share my custom templates and frameworks that will help you reflect effectively and have a fun time doing it.

Why should you reflect annually

1. It’s healthy for your mind and body

Our society has moved to being so focused on competition and high achievement, that it’s become uncomfortable for us to feel proud of our accomplishments or even to simply stop rushing forward so that we can take a moment to feel good about where we are and what we’re doing. 

This is not healthy. It is already in our nature to compare ourselves to each other constantly, so the last thing we need is additional societal pressure to do so. It’s easy for us to focus on the things we haven’t done yet, or the things that we still need or want to do, but while being focused on the future and what we want to do is a great way to become a high achiever, it can foster a feeling of permanent inadequacy. As anyone who has accomplished a major goal before knows, by the time that goal is achieved, the focus is already on the next goal. There is always more to do, there is always that next promotion or that next step in life. 

Doing a guided reflection on your year is a great way to calm your mind, alleviate some stress and anxiety, and feel good about what you’ve accomplished, which in turn has numerous positive effects on your body.

2. It leads you to significant learnings and realizations

Ironically, in our efforts to continue the charge forward through life, we ignore or quickly pass by learning opportunities that could have a significant impact on our ability to achieve even more. It has been shown time and time again that in many cases, slowing down allows you to move even faster, and the end of a year is an excellent time to do so.

When you reflect on your highs and lows of the year, and you really think them through, writing out your thoughts and feelings about them, you start to see key ideas emerge. You connect dots you never connected before, you notice trends and patterns of behaviour that you never noticed before, and you gain a better understanding of who you are and how you function. By gaining a better understanding of yourself, you are then able to determine what strengths you have that you should be leaning further into, or which behavioral patterns you have that might be causing you anxiety or inhibiting your productivity. 

3. It’s something you’ll always be able to look back on.

This is probably the most personal reason, but it honestly is one of the most important motivations for me, which is why I feel compelled to share it. When I’m old, I want to have these annual reflections to look back on. When I’m 80 (knock on wood), I want to be able to read what I wrote at age 23 and see what I was grateful for that year, what I was worried about, what I was looking forward to, etc. 

Life is a collection of experiences, and we forget a lot of those experiences as we move through our lives. Having a solid record (daily or weekly journaling), or at least a highlight reel (an annual reflection), is the best way to make sure that you will never forget what you’ve gone through in your life. 

Even now, I can look back on my reflections from 2017 and think about how different a person I was, how much I’ve changed since then, and how far I’ve come. This in turn inspires me because it shows how much more I can grow over the next 3 years and beyond. It’s cathartic, it’s nostalgic, and I hope you’ll take the time this year to give it a try.

Ben’s Simple Annual Reflection & One-Page Gratitude Exercise

I do these exercises every year between December 26 - 31, and it usually takes me around 90 minutes to complete.

  1. Click here to download the template for the annual reflection.
  2. Click here to download the template for the one-page gratitude exercise.
  3. Pour yourself a drink (if you drink). I find an Old Fashioned is ideal for this exercise.
  4. Put on music, make sure you’re somewhere you won’t be disturbed, and take your time to complete it.
  5. Once complete, store the documents on a hard drive and a cloud drive so that you can be sure you’ll never lose them (just make sure you’ll know where to find them next year).

Deloitte’s Professional Reflection & Planning Exercise

I was discussing this initiative in a recent conversation with Deloitte, and they mentioned that they also have some simple yet powerful reflection and planning templates that they recommend people use for work and with their team/manager. They were kind enough to supply me with those templates to share with all of you.

To access, click here.

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