10 Questions to Capture the Year in Your Journal

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Day One

6 min readDec 8, 2016

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There’s always a certain degree of anticipation — an excitement in the air — for the turn of the calendar at the end of the year. It’s impossible to look at January 1st and not think about the chance for a fresh start.

By the same token, December 31st offers a tremendous opportunity to reflect. Undertaking a level of introspection — reflecting on the prior year’s accomplishments, failures, surprises, and expectations and how they are currently affecting you — is tremendously powerful. No matter who you are, it’s hard to know where you’re going if you don’t know where you’ve come from.

There’s no better way to undergo this year-end personal review than by recording it in a journal.

Year-end journaling is a gigantic work-in-progress. I began keeping a journal in 2011 and have kept fairly solid records of my life experiences ever since. But in the grand scheme of things, it takes far longer than five years to look back on your recordings and find appreciation in your own growth. Some people may appreciate self reflections mere months later, but I’ve found that a lifelong learning process is easier to witness in lengthier segments.

A good way to start is a half-hour session in the last few weeks of December. Sit down, brew a cup of coffee, open Day One, and just write. If you can just sit down, you’ve already overcome the most difficult part of this process.

What should you write about? What questions should you ask yourself? Here is a list of 10 questions to contemplate and answer at the end of the year.

(Remember: It doesn’t matter how detailed your answer or how specific your thoughts. The most important part is opening yourself up and writing a letter to your older, wiser, smarter self. Just get started.)

1. What was your favorite single day/event of the year?

Close your eyes and think about all that’s happened in the last 12 months. What’s the first thing that pops into your head that puts a smile on your face? Whatever the event, start off this introspection with a dose of positivity. It’s a great way to get the creative juices flowing.

2. What was the best thing you built/created?

More often than not, building and creating is a lengthy process. It starts with an idea and grows from there. But finishing a project is the most rewarding part. It takes guts to complete what you started, and the reward is usually worth the process.

We’re all builders in some way. What did you create this year?

3. What was the most impactful decision you made for you and your family’s future?

This might be a more difficult question to answer. It could also be worded as “Did I/we do something that will have a lasting effect on our family’s lives?” Things like moving to a new neighbourhood, going on a family vacation and experiencing a new culture, or investing in your or your child’s education might be potential answers.

By answering this question, you can bridge the prior year’s events with future year’s experiences. And, down the road, this answer will be interesting to look at to measure the impact of past decisions.

4. What was your best financial achievement?

Although success and achievement are often measured in non-monetary terms, it’s helpful to look back at the last year and reflect on your financial decisions as well. Did you buy your first home? Did you take the plunge and enter retirement? Did you pay off a loan hanging over your head? Or did you reach your savings goal and go on a vacation in the middle of winter?

We all have different financials goals, success, and struggles. Reflecting on them is fundamental to fulfilling future goals.

5. Did you achieve any lifelong goals?

Crossing items off your bucket list is incredibly rewarding. Perhaps you bought your dream vehicle, or drummed up the nerve to skydive out the back of an airplane. Maybe you visited a new country or met your favorite athlete. Or maybe you graduated from an education program.

This question is particularly fun. Bucket lists can feel endless, but checking off an item or two each year usually means you’re not just *existing* but *living*.

6. What was the hardest lesson you learned over the past year?

Making mistakes is easy. Admitting them and learning from them is incredibly hard. Which is why reflecting on your mistakes a few months later can often help in the overall learning process.

Experts say the best way to learn something is to teach it to someone else. So, if you’ve learned a hard lesson this year, perhaps consider helping someone else overcome what you struggled with.

7. Did you develop any new hobbies or passions? Are there any new hobbies or passions you want to develop in the New Year?

The daily grind can take its toll, so having hobbies is a perfectly healthy way to turn your mind off. Some people collect stamps or coins. Others shoot photographs. Others like to go skiing, snowboarding, or surfing. Still others like to craft, scrapbook, or play the piano.

If you don’t have any specific hobbies, perhaps you want to jump into one for the coming year. Write down what you’d like to do in the new year.

8. What was the most humbling experience of the past year?

This can be related to question #6 above, but it can also be taken a step further. Sometimes the worst happens and it serves to remind you of your humanity. Maybe you lost your job, or you got into a fight with someone you care about, or maybe you lost a loved one. These are hard conversations to have, but clarifying your thoughts on these events over time can have a lasting impact on how well you know yourself.

Perhaps more importantly, what did you learn from this humbling experience?

9. What is the one thing you are most grateful for from this past year?

This is my favorite question on this list. It’s difficult to show your gratefulness to others when life flies by at top speed, so these quieter moments of reflection offer a chance to recognize the gifts around you. I’m particularly grateful for my wife, for a fulfilling career, for hobbies that let my mind be creative, and for the opportunity to learn from friends.

Your list will surely be unique to you and your life. Take the time to make it. The people and gifts around us deserve proper reflection at the end of the year.

10. What are your personal goals for the coming year? Family goals? Religious goals? Health goals? Financial or career goals?

Finally, if you’re tired of reflecting on the year that was, then it’s time to dream about the year that will be. Of all the goals on this list, this might be the easiest to measure on an annual basis. Do you want to check another item off your bucket list? Do you want to attend your child’s high school graduation? Do you want to start a family? Perhaps get married?

No dream is too big or too small. Set one goal. Five goals. Ten goals. Make some that are easily achievable, others that are harder, and still others that may seem impossible today.

This isn’t meant to be an exhaustive list of year-end journal questions. Rather, I’m hoping this gets your introspective juices flowing.

There’s a lot of value in returning to these questions midway through the year. See your progress on current year goals. See if decisions from the prior year had a lasting impact on you or your family. Take time to appreciate personal achievements a second (or third) time.

At the conclusion of this year, I hope these questions give you a chance to reflect upon and appreciate the past, and look forward to the new year ahead.