20 Thought-Provoking Journal Prompts

Many people give up writing in diaries or journals because simply recapping the day to day happenings of their lives seems a bit dull. Whether you’re new to journaling or just beginning, this list is intended to encourage you to think about your life, identity, and perspectives in new ways. Don’t feel the need to stick exactly to the journal prompts, if reading one of these journal prompts inspires another topic let your mind (and pen) wander!

20 Thought Provoking Journal Prompts

By Jordyn Sifferman

20 Thought Provoking Journal Prompts

1. Is there a difference between happiness and fulfillment? What does it take for you to be happy? What does it take you to be fulfilled? Are the qualities the same?

2. Close your eyes and envision where you see yourself in five years. Don’t get hung up on the details you feel like you are “supposed to know” (i.e. career, savings, marital status) but instead focus on the aspects of your future that are important to you. Do you imagine yourself in a new city? With a different career? Learning a new hobby? Feeling a specific way? Open your eyes and spend 5-10 minutes writing about what you envisioned.

3. Defining our insecurities is one of the best ways to own them. List a few traits (physically, intellectually, emotionally, etc.) you are insecure about. Pick one or two traits to analyze. Why does this specific trait matter to you? Have you always been insecure about this trait? Has anyone else fed into these insecurities? Finally, write an affirmation helping you to own your insecurity and take control of it.

4. Create a thought map with the word identity in the center. Branch out and add aspects of life, ideas, and experiences you believe are crucial to your identity. Is having a family attached to your identity? What about a career? Creative expression? Continue to expand your thought map until you believe it paints an accurate representation of your identity.

5. Focus on a regret that haunts you. Spend 20 minutes writing a detailed account of the experience, the feelings it causes, you and what you wish you could have (or would have) done differently. Take a deep breath and release it. Write a sentence or two about what you have learned from this regret and how it can help you be better in the future.

nightstand styling

6. What does family mean to you? Describe your family dynamic and what you liked about it. What did you dislike? Do you believe your idea of family aligns with society’s?

7. Make a list of any 50 things that make you happy. List small things like fresh cut flowers and handwritten letters and big things like earning a promotion, etc. Be sure to consider all five senses!

8. What did you believe about love as a teenager? What do you believe about love now? Describe the similarities and differences. Why did your views change?

9. Describe a moment that drastically changed the course of your life. At the time did you know it was a moment you would remember forever? How did it impact you long term? Short term?

10. What is your relationship with sadness? Do you see it as a necessary component to life or try to avoid it at all costs? Do you find sadness beautiful or as a moment of happiness you’ll never get back?

shelf styling

11. Think of someone you admire, write the name at the top of your page and spend a few minutes brainstorming the qualities that make this person admirable to you. Circle the qualities you want to work on, star the qualities you already possess. If you wish, spend a few minutes describing how and why this person inspires you.

12. Write a short letter to your future self: What is something you would like her to remember about who you are today?

13. Describe your three greatest accomplishments, why are these accomplishments so important to you?

14. The word “Eunoia” means “beautiful thinking;”what does beautiful thinking mean to you? How do you engage in this sort of thought?

15. Would you describe yourself as introverted or extroverted? Do you feel you are fully one or the other or do you fall somewhere on a spectrum? How do you feel this classification affects your day-to-day life and preferences?

16. What is the greatest life lesson you have learned over the past year?

17. Think about your friendships. What does it mean to be a good friend? What makes some friendships better than others? Describe strengths of your closest friends and why you are drawn to them as people. If you wish take additional time to write a quick note to a friend describing the strong qualities you see in her to her. Everyone loves compliments and your note just might make her day.

18. Describe your personal style and aesthetic. Do you lean toward bright colors, neutrals, shades of black and gray? Do you follow current trends, celebrities, or models? Has anyone in your life influenced what you wear? Do you use fashion as a mode of self expression or take a more practical approach? Do you have any friends or acquaintances whose style stands out to you? Why?

19. How do other people’s perceptions of you match who you actually are? Do you feel understood? Misunderstood? Is there anything you feel most people wouldn’t guess about you?

20. Can you ever be sure you are on the right path in life? Do you look for signs, external validation, or something else? Describe the path you see yourself on now. What would you change? Did you have to make sacrifices to get here?

A few of our favorite journals: 

Kate Spade Notebooks // Anthropologie Journals // Rifle Paper Co. Journals and Notebooks // Sloane Stationary Notebooks // Design Darling Notebooks

And a few journaling resources:

Start Where You Are: A Journal for Self-Exploration // The 52 Lists Project: A Year of Weekly Journaling Inspiration // 52 Lists for Happiness: Weekly Journaling Inspiration for Positivity, Balance, and Joy // The Five Minute Journal: A Happier You in 5 Minutes a Day // You Are a Badass: How to Stop Doubting Your Greatness and Start Living an Awesome Life

What are your favorite journal prompts? 

Jordyn Sifferman works at bridal boutique in the rainy city of Seattle. She believes in the power of great shoes, a daily mocha and above all else being true to yourself. She blogs at The Fairy Princess Diaries.  

Image via SS Life and Style

28 Responses to 20 Thought-Provoking Journal Prompts

  1. Sara Kate says:

    Whew girl, these are deep. I think #1 and #2 would be the hardest for me though. As a workaholic, fulfillment and happiness are often one in the same/are reliant on my career success. Definitely worth some continued thought. Thanks for sharing!

    Sara Kate Styling

  2. Anna says:

    I absolutely love this post! I’m trying to journal more often, and this definitely gives me some more inspiration. Thank you for sharing this! 🙂

  3. These are such great prompts! One of my goals for this month is too journal more so I will definitely be using these. xx Merisa | Monogrammed Magnolias

  4. Alix Maza says:

    Umm sorta stealing this! It’s brilliant!


  5. These are incredibly thought provoking questions not only to write about, but also just to think about. For one of my classes, we were asked to define family and it definitely made me appreciate not only my biological family, but those who have become family.

  6. Um, I need to do all of these! Like now! Great post.

    Xx Taylor

  7. Sockwun says:

    I don’t keep a journal, but these will be great to use with my foundation composition students! Thank you for sharing.

    Sockwun | ExtraExtravagant.com

  8. Brooke says:

    I’ve been trying to get back to journaling more and these prompts will definitely help.

  9. Molly says:

    WOW I love this. I’m already thinking about a ton of these I want to write about just as I’m reading them. I feel like some would make great blog posts too! It’s great to journal and let go of some of those deep emotions mentioned.


  10. Savannah says:

    I’m starting with these prompts tonight, thank you SO much for sharing these! I love journaling.


  11. Nafisa says:

    Awesome post. Love the deep thought provoking questions. For some time now I have been trying to be regular at journal writing.This post will definitely help me.Thanks a lot for sharing!!!

  12. Lauren says:

    Wow. These are amazing journal prompts. I definitely get stuck when writing in my journal but these are some amazing topics to write about.
    The Fashionista’s Diary

  13. Wow these are some seriously great journal prompts they even could be great blog post ideas 😉 I’ve never done journaling before but I’m considering giving it a try because I really like all these prompts. I’ll let you know how it goes!

  14. Ashley says:

    These are some awesome prompts!! Thank you for the inspo! Definitely going to be stealing a few of these for my journal!

    xo Ashley

  15. Chronicling Home says:

    This is genius and perfect and something I totally need. I feel like I’m going through a quarter life crisis so maybe this will help me hammer down my dreams. Thank you for taking the time to put these together.

  16. I LOVE these! And I’m so excited to see Jordyn featured again 🙂

    I have been wanting to get more into journaling, so this is perfect timing!

    XO, SS || Seersucker Sass

  17. Journaling is one of my favorite past times, so this is such a fantastic post. I love how thought provoking the ideas are.

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  21. Ruth Kuhn says:

    Really great ideas! Thanks for sharing!

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