Ask Yourself These Questions & Build Your Year Retrospective

[Updated, December 2015] Every year many of us have the practice of doing a retrospective and learning from the year that is now coming to an end. While it seems a fairly simple exercise, it’s rather seldom done appropriately or i a deep and meaningful way.

Since many years ago, I’ve come to develop and keep evolving meaningful questions that can lead to a better understanding of oneself, and get ready for a better new year. Since 2013 I’ve shared the questions with everyone in my network. Hope it guides you in debriefing better the year and getting yourself all set for a great 2016. Now, let’s get started:

1. What have I discovered about myself?

Every year is unique and leads to different insights about ourselves. Probably you have experienced something new or particular this year that can tell more about your habits, strengths, learning points, or more.

The best way to get started is to get an overview of the key experiences and stories you’ve lived throughout 2015. You can either draw those stories or journal about them, and capture the essence of it in a way that reflects the highlights (both positive and negative) of such experiences. Once that is done, you can dig deeper and think about what those experience have told about yourself.

2. When was I at my very best?

Our journey is made of ups and downs. There is a tendency to let frustrations and pain points overcome the very best moments of the year. Remembering the moments where we felt at our very best (both personally and professionally) is the best way to understand what we do really well and preserve such insights when getting back to work in 2016.

3. Who contributed the most to my growth as an individual?

Conversations, interactions, advice, guidance. There are many ways of being influenced, but take a moment to think of the people and/or organisations that contributed the most for your personal growth. The ones that challenged you, inspired you and where present in the good and bad times. Also do not forget to take the time and thank them. And for once, don’t use social media to thank them. Do give a call, write a message or write a compelling email on why these people were important to your growth — it’s about them being a positive influencer to you — no need to tell the world about it.

4. What have I positively contributed for?

This is an important question and many times the positive contribution is highly connected to the moments where you felt at your very best. However it’s important to get out of your own ‘ bubble’ and think about the surroundings.

Who did you positively impacted? Which problem did you help solving? What did you left in a better place than a year ago?

This question should definitely not be overlooked, as many people confuse a having a job with having a career or a purpose. Knowing what you contributed for is a great way to understand your personal impact and if you’re on the right track.

5. What were this year’s financial takeaways?

It might seem a strange question and only recently I asked myself the same question. In a world driven majorly by financial metrics, it’s hard to escape thinking about it, either we like it or not.

Doing a retrospective of your year from a financial perspective can be highly insightful and tell a lot about the way you spend, invest and even increase your purchase power. Think about yourself as a company that has to generate revenues to cover its expenses, as well as invest in things that lead to bigger ROI in the long-run. How was your year from that angle? Are you sustaining the lifestyle you wished for?

6. What was my lowest moment? What did I learn about it?

We learn a lot from our lowest and toughest moments. Failing is part of our life journey. Take the time to think about the year that is now coming to an end, and what were those low moments that affected you, how did you overcome them, and what you’ve learned from them.

This question might lead to similar answers as in the first question, yet might not have been as deep as at the beginning of this exercise.

7. What did I miss to explore?

It’s not a bucket list. It’s more than just wishes. Thinking about what we miss to explore is also looking at missed opportunities throughout the year. We probably missed chances to do something different, meet someone new or even challenge our own beliefs through new cultural experiences.

What matters here is that you look at what you miss to explore from a physical, personal, professional and even spiritual point of view. Exploring something new many times requires us to move out of our comfort zone, so perhaps think about those moments you missed to explore due to fearing getting out of it.

8. What is worth continuing fighting for and what do I have to let go?

A final, yet crucial question. This questions combines a lot of smaller questions, such as: Are you happy with your work? Career path? Group of friends? Love life? Country of residence?

If you have gone through the other questions and answered them, take a moment to re-capture them and then ask yourself what is still worth fighting for. And by fighting for means that you will invest your time and dedicate yourself to the decisions you make.

Sometimes, in order to continue fighting for worthy things, you have to let go of other ones. Learning how to say “No” is also important. Let go things that are holding you back. Independently of how painful it could be.

These questions cannot be answered by just reading this article. Note them down, do the exercise and let me know if it helped you or not. Share your thoughts below and perhaps next year will come up with even more powerful questions.

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