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  • Writer's pictureJon D'Alessandro

14 Journal Prompts for Special Occasions (New Years, Birthdays, Holidays)

Give this special occasion new significance by reflecting on your year, goals, and growth.

Holidays and other occasions can lose significance as we get older. But they're special days, and a powerful opportunity not only to celebrate life, but to reflect on your year, experiences, goals, and growth.

These milestones are opportunities to revisit resolutions (with varied success), write a bucket list, choose a "word of the year," or conduct a Pareto-inspired Past Year Review.

But deep reflective journaling is possibly the most powerful tactic to make sense of your past 12 months, and muster the clarity to attack next year with enthusiasm, energy, and massive action.

Maybe it will even help bring a new significance to your occasion of choice, and mark the beginning of a your most fulfilling chapter yet.

A note on 2020

This article is being published at the close of 2020, "The Year That Never Was," a real S.O.B. of a year that challenged and changed the world and everyone in it. While we're not out of the woods yet, it's an especially powerful time to reflect on the peaks, the many valleys, the lessons learned, and the path forward.

You can't control what 2021 has in store, but you can control what you do. Remember this quote:


Whatever the occasion - the New Year, a birthday, anniversary, holiday, or other special day - use the prompts below for journaling, discussion, or quiet reflection. You can answer them all, choose just a few, or use them for inspiration in creating your own list. There are only a few real rules:

  • Be thoughtful.

  • Be honest.

  • Set a timer for each prompt - you choose how much time - and don't stop writing, talking, or thinking until the time is up.

  • Finally, don't just answer the questions. Follow up by thinking about how to implement your ideas, and then take action.

Ready? Keep your beverage of choice close by (I'll be using this), and enjoy...


14 Deep Reflection Prompts for Special Occasions (Birthdays, New Years, Anniversaries, Holidays, etc.)

1. How are you celebrating (your birthday / New Years / another holiday) this year?

Whether it's a birthday, New Years, an anniversary, or another special day — in as much detail as you'd like, write about the day, weekend, or full week. What will you do? Who will you celebrate with? Why is it worth celebrating, to you personally?

2. When you think about the last 12 months, what immediately comes to mind?

Share whatever comes to mind (this is purposefully open-ended). Is it an event? A person? An idea? Something else? Why is it significant?

3. What are you grateful for?

Think of 5-10 events, people, surprises, or other things from the year, however big or small.  List them in no particular order. For bonus points, try to really embody the gratitude as you write.

4. What surprising change(s) took place in the last year?

John Lennon once wrote in a song:"Life is what happens to you while you're busy making other plans." [1] What unexpected things happened in your life this year? For better or worse, how did your plans change?

5. What goals have you achieved in the last 12 months? Have you made progress on your Bucket List?

Whatever you accomplished, however big or small, take a moment to congratulate yourself. Didn't set any concrete goals? Now is the time to jot a few down for the next 12 months!

6. What goals were you unsuccessful in reaching this year?

Why do you think that might have been the case? Is there an obvious answer (e.g. Covid) or is it less distinct (e.g. a sudden loss of enthusiasm, competing priorities, an unexpected obstacle, etc.)?

7. Where have you stepped out of your comfort zone in the last year?

8. What was challenging about the last year?

What did you do about these challenges? How did you overcome them? How have they made you stronger?

9. What was fun about the last year?

Especially this year, it might feel easy to focus on the negative. But challenge yourself to remember the joy you experienced this year. What are some mishaps, trips, or adventures you've had in the last year? What are some highlights and stories that you'll share for years to come?

10. What difficult problem or challenging situation is top of mind?

You can focus on just one challenging problem or repeat this prompt as many times as needed.

11. If you could speak to yourself 10 years ago, what would Younger You think about the problem above?

Would "Past You" be proud to hear you're in such a situation? Would your "Past Self" be proud to have come so far in the first place?

12. If you could speak to yourself 10 years from now, what would Older You say about the situation or problem?

Would "Future You" even consider it significant? Does it matter in the grand scheme of things? You're likely to find some surprising wisdom in your response as you channel this "Future Self."

13. What do you want your life to look like this time next year?

What will be different? What will be the same? What will you have? What will be gone? If you need help, focus on one or more of these themes:

  • Health

  • Career

  • Business

  • Financial

  • Home life and/or family

  • Romantic relationships

  • Friends

  • Hobbies

  • Lifestyle

  • Spiritual

  • Personal development

14. What could you do right away to make that vision a reality?

Set an intention, make a plan, and take action!


Answering these questions thoughtfully and honestly can offer unexpected healing, insight, growth, and hope. Do you have a favorite prompt that isn't in this list? I'd love to hear about it — comment below, email at, or DM on Instagram or Twitter!

P.S. — If you enjoyed these journal prompts, share them with a friend. Subscribe to the Bring Ambition Newsletter for more content to help you reflect deeply, overcome personal and professional challenges, and orient yourself for growth and gratitude.


[1] Lennon did say this, but it was borrowed from a 1957 Reader's Digest quote by Allen Saunders. The internet is notorious for misattributing quotes to John Lennon (examples: 1, 2, 3, etc.).


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