30 More Days of Journaling

messy thoughts

Emma is the editor & creator (and occasionally writer) for The Messy Heads. She enjoys yellow curry, print media, and singing to herself.

A follow up to the last post, 30 Days of Journaling. If you tackled those, time to delve even deeper into yourself. You can write right when you wake up, before you close your eyes for the night, or at your favorite coffee shop. Get your friends in on it to- text them the prompt everyday in the morning as a reminder for both of you to write today. Share a response as an Instagram caption or a photo & tag us @Themessyheads. Lets do this together & do it for yourself. Pick up your pencil & open your mind. Let’s get started, another month of self discovery.


Day 1: What is the nicest thing you have done for somebody else?

Day 2: Who do you really admire? Do you like them because you relate with them or you are very different and somebody you wish you could be?

Day 3: What do you think about when you picture the ocean? Happiness, fear, uncertainty, bliss? Pick an emotion that might not immediately come to you and try and work with it.

Day 4: What are some mean things you say to yourself and how can you flip it around to be a positive?

Day 5: Write about a relationship that failed.

Day 6: Write about living in a city you have never been to. Talk about your daily routine in your new foreign home, the coffee shops you walk to, the breakfast you have, the smell of the air and the way people are dressed. Send yourself across the globe.

Day 7: Write about somebody you miss.

Day 8: Write about a time you did something totally badass. How did it make you feel?

Day 9: What have you learned about yourself today? In the past month? In the past year?

Day 10: What color resonates with you the most? It might not be your favorite color, but what color could your soul be and why?

Day 11: Write about the most recent thing that made you sad. Is it something that you can control? Why does it make you feel the way that it does?

Day 12: Write about your favorite piece of art that you have seen today. It could be a picture, a painting, a pattern in your shirt, or something that you made yourself.

Day 13: What traits shine brightest in you?

Day 14: Would 10 year old you be proud of who you are today? Why or why not? What were your dreams when you were 10 years old?

Day 15: Make the perfect road trip playlist and doodle a map of all the cities you would go to.

Day 16: Reflect on your current situation in life. Are you in a place where you are happy? If not what can you do to change that?

Day 17: Try to compliment as many people as you can today. Write about their reactions and your experience. Reflect on how you usually reply to compliments. Do you take them with grace or deny them?

Day 18: Write a poem about being in love.

Day 19: Are you a trend follower or consistent with your style? Sketch some things in your closet that you absolutely love and if you would’ve loved them five years ago or if you think you will love them five years from now.

Day 20: What are you most afraid of?

Day 21: Write a thank you letter to your parents.

Day 22: What have you changed about yourself to make other people happy? What traits did you lose or gain while seeking for approval?

Day 23: Write about habits you want to break.

Day 24: Write out five simple goals for today, make them all ones that benefit only you. Meditation, taking a bath, reading a new book, getting work done on time.

Day 25: What do you think the future holds for you? Do you think you are in control of your own future or do you think it is out of your control?

Day 26: Why do you talk badly about certain people? Look at these people you may gossip about from the angle of their best friend or somebody else that loves them. Chances are they really aren’t as bad as you think they are. People make mistakes, forgive them, even if it is just on this piece of paper.

Day 27: Write about your favorite character as a child and what about them you loved so much.

Day 28: Write about your past crushes and if  you were truly yourself around them.

Day 29: Write about your best friends.

Day 30: What are things that you REALLY can’t live without. Don’t get all literal and say oxygen and water, I mean what things are essential to your purpose on this planet and who you are as a person?

Pick up a Messy Heads journal from our shop, they come with a fold in of 90 more journaling prompts to get you started and inspired. 



  1. Julia says

    This is the first time that I have read the journal entry ideas and it took me by surprise because it was way more reflective and raw than I had thought. I think it’s because we had to do a similar thing back in school for English but the prompts were always really bland and easy to answer in one word. Where as this mass you think, and be truly honest to yourself because it’s your journal so there can be no judgement which is scary and liberating. I think I have lost track of what I was saying. Anyway, I love the entries. Can’t wait to start! X

  2. I will most definetly do it & try to stick to it. Such lovely ideas that make you think and really get to know yourself a bit better by digging in to get some answers. Amazing!! xx

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  4. Is it sad that I’m afraid to try these “30 Days of Journalling” challenges? Literally afraid. Because I’m afraid to face my emotions once I get to certain prompts… I guess that means I NEED to take the challenge.

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