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20 End-Of-Year Reflection Questions You Need To Ask Yourself

The 1st of January is right around the corner and you know what that means – it’s New Year’s Resolution time!

For the next two weeks it’s going to be squatting room only at your local gym, self-help blogs will enjoy a spike in their traffic, and you’re going be wading through a flood of “New Year, New Me” captions on Instagram.

Amidst all of this exciting resolving, one thing that can be forgotten is reflecting on the year that has been. If New Year’s Resolutions are the Brad Pitt of the personal development world, End-of-Year Reflections are his less sexy younger brother, Doug.

This is especially true for a year like 2020, which many of us want to see disappear from the rear-view mirror as quickly as possible. But as my high school history teacher loved to repeat, “Those who don’t learn from the past are doomed to repeat it.”

Without a doubt, this year has had more than it’s fair share of challenges you overcame, achievements worth celebrating, and lessons you can learn.  It’s worth taking some time in the next few days to reflect on all of that. Here are 20 important questions to ask yourself:


1. How would you summarise this year?

A great way to get the ball rolling is to think about the biggest moments of 2020. If you had to give someone a 30-second summary of your year, what would you include?

2. What is the achievement you’re most proud of?

Just getting through a pandemic is worth 5 gold stars, but the craziness of this year has required unique things from each of us. What’s one thing you’ve done that you know you can hold your head high for?

3. What were your biggest disappointments?

The norm is to try to forget about our disappointments and suppress the negative feelings associated with them. However, at my end-of-year work retreat, we decided to go around and share the negative things from the year that we needed to let go of. It surprised me just how cathartic it was to recognise these things and speak them out loud.

4. How did you step outside of your comfort zone this year?

COVID pushed me out of my comfort zone before I even had the chance to step outside of it. I went from being someone who speaks at live events to someone who had to learn A LOT about video and digital resources very quickly. But in that uncomfortable space, a huge amount of professional growth occurred.

5. What are you grateful for?

As I’ve written previously, introducing a daily practice of thinking about what I’m grateful for has been a game-changer in my life. No matter how tough this year has been for you, there will be silver linings. The simple act of acknowledging them can powerfully change your perspective.


6. Has your relationship with God deepened?

Our relationship with God is never static – either we are drawing nearer, or we are drifting further away. This is the single most important question to ask at the end of each year. Take a few minutes to honestly answer it. Have your drawn closer to God or drifted? Why?

7. Who had the biggest influence on you?

Even as someone who educates teenagers on the importance of good friendships, I don’t think I fully appreciate just how much the people who we are close to shape the person we become. Most of the time, this takes place beneath our conscious awareness, so it’s important to intentionally consider who these people are and whether their influence is positive or negative.

8. Who needs to be acknowledged in my life?

It might be a friend who showed you generosity this year, a colleague who has done an amazing job, or just someone whose presence you’re grateful for. Generally, we suck at actually communicating these feelings to the person in question. Let this question be your prompt to do just that.

9. Is there anything you need to apologise for?

Don’t go into the New Year with past wrongs hanging over your relationships. The idea of apologising after the fact might feel a bit awkward, especially if it has been several months. Do it anyway. The other person will probably appreciate your courage, and it can only have a positive impact on your relationship.

10. Have you kept in touch with friends?

Adult friendships are hard. You move away, you get busy, and before you know it, it’s been 9 months since you last caught up. But one of the top regrets of people at the end of their life is that they didn’t keep in touch with their friends. Is this something you need to re-prioritise?



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11. What is a daily habit you’ve found super valuable this year?

Daily habits are the building blocks for achieving our goals and living a fulfilling life. This year, getting up early in the morning to write (and from late October, being woken up by a baby early in the morning, to eventually write) is the best thing I’ve made part of my day.

12. What was your single biggest time waster this year?

If you identify something that is wasting time that you so desperately need elsewhere, wage war against it. Seriously. Ironing shirts used to take up like 2 hours of my week, every week. So, I bought shirts that don’t need to be ironed so often. Best $200 I spent all year.

13. Was there anything you found yourself consistently looking forward to?

If there is something that is regularly the highlight of your day or your week, recognise it. Small thing, but I love going for a run after work. My evening is better after I’ve been for a run. As much as possible, I jealously protect this exercise from being bumped off my schedule.

14. What new thing did you spend a lot of time on in 2020?

COVID restrictions prompted all of us to use our time differently this year. For me, it was videography and video editing. This is a skill I’ve wanted to learn for a while now, and between needing to develop digital resources for work and spending a lot more time at home, 2020 was the ideal year for it.

15. Does the amount of time you spend working stop you from enjoying life?

I absolutely believe that there are times, especially while we are young adults, where if you want to set ourselves up for long-term success, we need to work hard. But it’s easy to take this too far. I missed out on some of the best parts of university life because I wasn’t in the habit of asking myself this question.


16. If you could travel back to the beginning of the year, what’s some advice you would give yourself?

 I know, I know, this year it would probably be “Stock up on toilet paper in February” or “Buy shares in Amazon.” but seriously, knowing what you know now, what would you tell the past version of you? Is any of that advice still relevant as you move into 2021?

17. Were the goals you had at the start of the year really that important?

This year has looked very different to what I was anticipating. But if there’s one thing COVID has given us, it’s perspective. It has shown us the parts of our lives that really matter and those others that really don’t.

18. What should you have said “no” to this year?

James Clear reminds us that “No is a decision, Yes is a responsibility. When you say no, you are only saying no to one option. When you say yes, you are saying no to every other option.” If you feel like you’re dragging yourself across the finish line of this year, it’s probably because you need to be saying “no” more often.

19. What were the most meaningful moments of the year?

Maybe it was pursuing a passion more seriously, spending time with your family or housemates at home, or re-connecting with your community when COVID restrictions lifted. The idea is to discern what these moments were so that you can actively seek out more of them in 2021.

20. If you continue down your current path, what will your life look like in 5 years’ time?

I was introduced to this question recently by productivity YouTuber Ali Abdaal and it really caught my attention.

Several times over the past few years, I’ve done the exercise where you write out what your ideal life looks like in 5 years’ time. It always feels a bit synthetic. In the back of my mind, there’s definitely a little voice saying, “this is a nice fantasy, but there’s no way life is actually going to look like that in 5 years’ time.”

This question, on the other hand, is very tangible. It’s a powerful reminder that unless I intentionally make some changes, the way I’m currently living is going to largely determine what my life looks like in 5 years’ time.

Ultimately, this is what makes an end-of-year reflection is so valuable. It enables you to celebrate what you’ve done well and put the necessary steps in place to sustain that pattern of success. It also helps you to recognising what wasn’t so good, so you can address these areas.

Before you slam the door on 2020, take some time to work through these questions. Pay attention to your answers and use them in preparation for the best possible year ahead.

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