25 Journal Prompts for Insecurity

journal prompts for insecurity

Let’s face it, insecurities are a pain in the butt. Some go waaaaay back and are deeply rooted in our belief system. They are like underground roots, entangling themselves in anything that gets too close. But they don’t have to be like that. At least not in a way that is holding you back or impacting your life. Remember, the insecurity likely thinks it’s helping you. Saving you from heartache, being seen, or putting yourself out there and getting judged. When the insecurity is hindering, instead of helping, that’s when we need to make a decision. Live with the insecurity, or shift it.

The first step in crushing, or working with, an insecurity, is to first identify it. You will notice I will never say, “your insecurity.” The insecurity doesn’t belong to you. It isn’t yours. Thinking it is you, or yours, is why we cling to them in the first place. But not anymore, you deserve a different story. First, you need to be open and honest. Less holding back, less worrying about being judged, and less beating yourself up. Here, it’s just you and your journal.

Awareness is everything. We’re going to get to the bottom of the insecurity and release the hold with nothing but love.

While you're here please feel free to check out our prompted self-care journals!


Journal prompts are guided questions to encourage exploring new topics and reflection of oneself. Guided questions sometimes vary by specific topics such as healing, self-love or self-discovery, and there are also questions that are unrelated. So, whether you're pursuing personal growth or development in a specific area, or would simply enjoy writing suggestions, then journal prompts are for you!


Guided journal prompts are beneficial to those who want to write in a journal but aren't sure what to write about. And, they're also a great way for daily journal writers to switch it up and add something new to their journal. Maybe you're getting bored of always writing the same things in your journal and want to get creative! Here are a few benefits of journal prompts:

  • Helps guide what to write about
  • Self reflection
  • Takes the guess work out of writing
  • Builds confidence
  • New and creative entries in your journal
  • Faster! If you're in a time crunch but want to write, you can simple answer one question a day


  • Self-discovery and reflection
  • Encourages creativity, positivity and mindfulness
  • Provides clarity of thoughts and feelings
  • Reduces stress and anxiety


How you decide to use journal prompts is ultimately up to you! Whether you'd like to sit and answer 20 questions all at once, or prefer to answer one question a day, it's at your discretion. For myself I enjoy answering one question a day because it allows more time for reflection in-between. To me, journaling is all about reflecting.

I hope you enjoy the 25 Days of Journal Prompts for Insecurity!

Let's get started!

journal prompts for insecurity


1. What do you think the insecurity is?

2. When are you most triggered by the insecurity?

3. Do you notice any patterns?

4. How do you feel when you're triggered?

5. How does the insecurity impact your life and relationships?

6. What would your life and relationships look like without the insecurity?

7. Can you pinpoint when the insecurity began? Describe.

8. Have you ever gotten to the root case of the insecurity? If not, try the "why" game. (Here's an example: I need to always be in a relationship. Why? Because I need the validation of a partner. Why? Because I don't feel enough on my own. Why? Because I have no idea who I am or what I have to offer.) Boom. Working with the insecurity is easier once you know where it originated.

9. Make three columns on a page. Title them: Where I am | Where I Want To Be | Adjustment

10. Under "Where I Am", be honest. List how you feel on a daily basis.

11. Under "Where I Want To Be", list how you want to feel on a daily basis.

12. Under "Adjustment", transform how you feel, and how you want to feel, by creating affirmations. (Example: Where I Am: I feel unlovable. Where I Want To Be: I want to feel loved. Adjustment: I am deserving of giving and receiving the highest love.)

13. On a separate page, write each affirmation out seven times. Tape one, or all, to your mirror or dashboard. Write them in your journal when you wake up or before bed. Say them while you're walking or working out. Say them while you're falling asleep. Say them while you're showering or brushing your teeth. Engrain them into your daily routine until you wholeheartedly believe them. It may not happen over night, but don't quit. Any lifestyle change takes time.

14. Is there someone impacted by the insecurity, like a partner, friend, or family member? If so, write out a few points to talk to them about. Communicate the insecurity, and that you're working on moving past it, but that in the meantime some patience may be required. Feeling understood will help.

15. How would you soothe a friend with the same insecurity? Write it to yourself.

16. Reflect on a time you felt powerful and unstoppable.

17. How did this make you feel? How did you harness the energy and where did you apply it?

18. How can you tap into that energy when you feel the insecurity creeping back in? (You may not be able to dissolve it immediately, which is why it's important to be aware and work with it).

19. If you could talk to the insecurity, what would you say to it? (Feel free to be as gentle or harsh as you'd like, shadow work isn't all love and light).

20. Are you surrounding yourself with people who are empowered and self-aware? If yes, what do you enjoy about their company and energy?

21. If not, how can you surround yourself with people who are confident, energies, and aware? (Remember, we are greatly influenced by who we spend the most time with, choose wisely. Choose people you admire, those who inspire you).

22. Is there a way to prepare yourself, or talk to yourself, when you start to feel triggered? (Example, I recognize that I feel ________________ . I feel like this because in the past __________________ . I trust that ________________ , and would prefer to let this feeling pass and instead, feel _________________ . )

23. Focus on your positive characteristics. Describe how you lift others up, what you're passionate about, what you're confident of, what you know, what you believe in, what you're grateful for. You don't need to be "fixed", but you do deserve to be celebrated.

24. Write out: I am not defined by ________________ (the insecurity). I love myself as I am. I love what I contribute to the world. I love how I show up in the world. I trust that all is well. All is well.

25. Name the insecurity. Fred, Chanel, Linda, Karen, Tom, anything. Then, next time it creeps in, challenge it. Talk openly to it, in your mind, in your journal, or out loud in front of total strangers. When you do this, you create a boundary and remember YOU are not the insecurity. Say, "Hi Karen! You're back again I see. Thanks for coming, but I've got it covered this time. I know you're trying to keep me safe, but I'm going to trust myself this time. I'll let you know if I need you, thanks! Have a good day, bye!" It's liberating, I promise.

Thank you!
Don't forget to pin these for later!

guided journals for self-care 

*Please remember these journal prompts do not replace therapy or professional help. Self-discovery and growth doesn’t necessarily have an over night quick fix. If you feel like you need additional help, do not hesitate to reach out to someone qualified.