Podcast #442

100 Journaling Prompts and Questions to Boost Your Self-Esteem and Confidence

The practice of journaling, when done correctly, can change your life. Most people journal haphazardly or sporadically, and therefore don’t get the mental breakthroughs and life-change that is possible. If you’ve ever struggled with knowing what to journal, how to do it, where to start or just feel burnt out on inspiration, this podcast episode with 100 journaling prompts for your self-esteem and confidence is for you. Get the full show notes at www.trishblackwell.com/442  


In this episode of The Confidence Podcast we’re coaching on:

  • How to journal and make it a disciplined part of your thought life
  • The difference between deciding and hoping, and how to use your journal to create winning thoughts
  • My best journaling prompts to inspire breakthroughs for your self-esteem and confidence



Just some special love and deep gratitude your way for how you support the show. You are a small and mighty group and each and every one of your contributions feels like a big, warm, wiggle hug. Thank you.

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Thank you for all your advice! 5-Stars, Lizz1689

I have been caught up in always trying to make others happy and people-pleasing. Always saying yes and having to over-explain my no’s. I came across your podcasts about 2 weeks ago after searching “confidence.” So far I have listened to podcasts #187, 189, 359, 261, 402,219, 421, 423, 433, 435, and 436. I am trying to learn that I do not have to have it all together and that I don’t owe anyone anything. It’s okay to not be liked by everyone. 

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Journaling has the power to change your thoughts, and therefore your self-esteem and your confidence. The act of journaling can change how you see yourself and how you see your life. So why doesn’t everyone do it? Because sometimes staring at a blank page of paper can leave you intimidated and not knowing what to write. Enter: journaling prompts. Specifically, journaling prompts for self-esteem and self-confidence.

When you journal, the act of taking a thought and putting it onto paper gives you the ability to really see it and examine it. This process neutralizes the thought from any extra emotions, or judgment it might be carrying and gives you the power to decide what to do with the thought. You can choose to keep the thought, to re-write, or rewire the thought to be similar, but more positive, or to push the thought away and uninvite it into your brain. 

The act of taking pen to paper is perhaps the most life-giving foundational strategy for anyone who wants to master their mindset.

Another way to think about the above described process of journaling is that the act of journaling is like breathing for your brain. What you put on paper is an exhale of what’s cluttering your mind, and what you write down in return, your compassionate responses and your guided new thoughts, is an act of inhalation. 

There is no need to ever feel intimidated by a blank paper, but it’s natural that there will be days when you just need a little inspirational boost to get your journaling juices started. (If you are looking for a daily journaling structure, click here to learn my 8-minute journaling method.) Journal prompts are like little superheroes to supercharge your mind to open up and explore the deeper level of your thoughts.

The more you can see your thoughts, the more you will be able to understand them. The more you understand them, the more you will be able to manage and direct them. The more you train your ability to direct your thoughts, the more you will master your mindset and have power in the way you think and approach every element of your life.

Use the journal prompts for self-esteem in this post to help you master your mindset and feel as unstoppable, as beautiful and as filled with purpose as you deserve to feel. 



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To inspire your journey of  self-acceptance, purpose and courage, here are my favorite confidence journal prompts: 



1. What does confidence mean to you?

2. When in your childhood did you feel the most confident? Describe that version of yourself in as much detail as possible. 

3. How would you describe the most confident person you know?

4. Why does that person inspire you and what are they able to do that you want to do?

5. What compliments about your personality do people often give you?

6. When is the last time you really celebrated your own success and gave yourself credit for what you are doing well?

7. What does your morning routine look like when you have your ideal day?

8. What is the ideal nighttime routine that makes you feel relaxed, fulfilled and peaceful at night as you lay your head down to sleep?

9. If you tend to overthink, what is the root fear that drives this spiral of second-guessing and over-analyzing?

10. How would your life be different if you saw failure as a good thing?

11. Are you more quick to notice what is going wrong or to notice what is going right?

12. How can you build up confidence in someone else today by complimenting them?

13. Create a list of 10 compliments to give yourself.

14. Write about how you can be more confident in being yourself.

15. When do you feel most yourself? 

16. What is one activity that cheers you up, no matter what?

17. What is your best physical quality?

18. What is one way you have failed recently?

19. Do you want to approach life with a “what if” mindset or with an “even if” mindset? 

20. Picture yourself completely confident. How does this version of you dress, speak and carry themselves?

21. What is the first thing you said to yourself this morning? What is the first thing you want to say to yourself tomorrow to have a more confident day? 

22. What is one new thing you would do if you knew you couldn’t fail or get hurt?

23. You are responsible for creating your own opportunities in life; what is one opportunity that you need to put yourself out there and go chase?

24. How would you feel if you really loved yourself without judgment, pressure, comparison or the self-critical voice?

25. Write out 10 positive affirmations to encourage yourself about God’s plan in creating you and His purpose for your life. 

26. Write a short note to thank your body for how it has carried you through life. 

27. List out 5 things you are grateful for about your body type and physical attributes.

28. List out 5 things you are grateful for about your inner beauty and personality.

29. How do your friends describe you?

30. How did your most encouraging teacher, mentor or coach describe you?

31. What negative things do you repeatedly say to yourself and why do you think you are still saying them? Are you willing to do the thought work and repetition it takes to change the way you think so that your conversation with yourself is more kind? 

32. Are you willing to start talking back to your inner bully? What will be the first bully phrases that you put an absolute stop to? 

33. What is your best inner quality? 

34. How can you be more kind to yourself about where you are in your life right now? 

35. What are your go-to stress-relief habits that are self-nurturing and allow you to recharge and feel good? 

36. How often do you compare yourself to others? When you compare, how do you feel?

37. Who do you know that radiates self-respect? How can you tell this person respects themselves and do you notice any habits they have that you wish to emulate?

38. What does being brave mean to you? How have you shown courage recently? 

39. In what ways do you wish you were more courageous? 

40. Who are your role models? What qualities do you have in common with them? What qualities do you want to practice emulating more in your life? 

41. Do you have any clothes that don’t feel good when you wear them, or that make you feel insecure, fidgety or uncertain of yourself? If so, throw them out or donate them today. 

42. What would you stop doing if you were more confident?

43. How does second-guessing yourself make you feel? How has it held you back in life?

44. What can you do today to nurture self-trust in your micro-decisions through the day?

45. Think about a challenge you have faced and how you became stronger because of it and through it.

46. What are 3 feel-good activities that make you forget any self-consciousness or insecurity you might have?

47. When is the last time you laughed so hard that you almost peed yourself? What were you laughing about? 

48. Have you complimented yourself today?If not, do it now!

49. What are three things you are proud of doing this month? 

50. Imagine that you are limitless; what difference would you want to make in the world and with your life?

51. Write out what phrase of encouragement you want to say to yourself when you face a challenge, a set-back or a new opportunity.

52. Write about a time you were really proud of yourself.

53. Make a list of 10 experiences in your life that make your story very unique. 

54. Make a list of 5 qualities you bring to your primary relationship in your life.

55. Make a list of 5 reasons you are a good neighbor.

56. Make a list of 5 good things you bring to your workplace. 

57. What are you doing to grow this month?

58. What habit do you need to stop?

59. What is the nicest thing you have ever done for yourself?

60. Investing in yourself builds confidence and worth. What is the best investment you have ever made in yourself? 

61. I am happiest when…

62. I am most at peace when…

63. What are things that you need to stop doing that are making you unhappy?

64. Our confidence gets most shaken up when our thoughts get cloudy and cluttered. What types of thoughts or thought patterns tend to make you feel distracted, self-doubting and insecure?

65. Awareness is the beginning of change. What new areas of growth are you now aware of for yourself?

66. Where your attention goes, neurons fire, and where neurons fire, they wire. Where are you putting your attention today? On things that are fear based or things that are faith based?

67. “Fine” is a “feeling in need of expression.” When is the last time you said “I’m fine,” or “it’s fine,” but you really needed to work out the feeling to it’s fullest expression?

68. You are more brave than you are afraid, and that makes your courage enough. List out some ways in which you have seen your inner bravery shine recently? 

69. In what ways have you underestimated yourself?

70. In what ways have you overestimated potential problems or areas of life that intimidate you? 

71. Progress, no matter how small, brings fulfillment. Pick an area of life you are working on, and list out 5 ways in which you’ve recently made progress. 

72. Everyone is thinking something about themselves that they don’t have to. What thought have you had about yourself that you don’t need to hold onto anymore?

73. What is one thought you wish you could think about yourself and it could be true?

74. Describe your alter-ego. What does the superhero version of you look like, feel like, act like and do? 

75. If it’s meant to be, it’s up to me. What is one thing you can do today to make the world better? How about to make your community better? Your relationships better? Your relationship with yourself better?

76. How would you feel about your capability if you could remember that everyone thinks things are hard too (it’s not just you)? 

77. How do you make those around you feel seen, known and heard?

78. What clothes make you feel best? Do you have anything in your closet that makes you feel not totally confident when you wear it? Remember take any items and donate them. Keep only what makes you feel good.

79. Who do you admire? What 3 specific qualities about them do you want to emulate? 

80. What are 5 things that you know you are good at?

81. What are 5 unique things about your body that you are thankful for?

82. Let your answer flow from this: “I feel best about myself when…”

83. What are your most common automatic negative thoughts?

84. Who are the cheerleaders in your life? Who are the people you can rely on when you are feeling low or need a boost of encouragement?

85. Write your body a letter thanking it for all it does for you.

86. Write yourself a letter thanking yourself for how you have grown and changed over the last 10 years.

87. How would your best friend or best coach describe you?

88. I feel most alive when I’m learning about….

89. What’s the best compliment anyone has ever given me and why does it feel so significant and meaningful to me?

90. What is a compliment I would like to receive? How can I start nurturing that character trait or growth within myself to become what I want to be?

91. List out 5 reasons you are proud of who you were as a child.

92. List out 5 reasons you are proud of who you were as an adolescent / young adult.

93. List out 5 reasons you are proud of who you are right now as an adult. 

94. When is a memorable time you overcame fear and self-doubt? What did you tell yourself to encourage yourself to focus more on faith than on fear in that moment? 

95. What do you want to learn, improve or change in your life right now? What is the first step to starting the learning process?

96. What 3 daily events in your day are you most grateful for? 

97. How can you implement more positive self-talk? What 3 daily things can you do to infuse more positivity in your life? 

98. Picture yourself winning a prestigious award. What positive things about you would be said about you as you were given the award? 

99. What can you learn from your most recent failure or set-back?

100. What can you learn from your biggest win? 

Okay, there you have it. Pick your prompt and start going deeper into exploring who God made your to be. Remember, what God breathed into you at birth is God’s gift to you. What you bring to life into this world is your gift back to God and to the world.

Let these encourage you, inspiring creativity and breakthrough in your journaling practice. To go deeper into more effective journaling, come coach with me in the College of Confidence. We have weekly journaling prompts paired with extensive coaching and discussion about the journaling topic to help you best integrate it into your life. Click here to check out the College of Confidence; it comes with a money-back guarantee, so it’s a risk free next step for your personal development and growth. 

For more resources on journaling, be sure to check out these:

·       Journaling for Anxiety and Depression Relief 

·       How to Feel Happier through Effective Journaling

·       Christian Journaling Ideas 

·       How to Journal In a Way that Increases Your Happiness and Your Confidence 

·       https://www.trishblackwell.com/100-journal-prompts-for-self-esteem-and-self-confidence/




You are heaven sent. I’ve been listening to you daily on my commutes to work and you are just brilliant. I originally found you trying to cure my jealousy and insecurities, but you’ve taught me so much more beyond that. You have a way with words that just makes me feel better. You give me hope that everything is going to be okay. You’ve made me a better wife, better mother, and better me. I share you with everyone I know because I want others to change the way they think too and just have faith. I preach a little Trish to friends and family all the time to try to give a more positive light. We can all find our happiness. Thank you so much Trish for sharing your story and your wisdom with the world. You are a gem to me. Keep on shining girl! 

Your friend,

Clarissa Ball 

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