Confidence Journal Prompts
I have an annoying, nagging little voice in my head that questions everything...literally everything I do. I bet you have it too. The one that replays every awkward thing you said three years ago? (idk, maybe that one is reserved for us Capricorns). The one that tells you you're not ready, not good enough, not qualified, not able to string sentences together to have a coherent conversation with strangers?
​
Yeah. That one.
​
That little annoying voice doesn't have to stand in the way of confidence, we just have to prevent it from running the show. We have to intentionally trust ourselves even when we're scared. Making decisions without needing everyone else's approval first. Taking up space without apologizing for it.
​
These prompts are for the days when you're tired of second-guessing yourself. When you want to remember who you are beneath all the doubt. When you're ready to stop shrinking to make everyone else comfortable.
​
You don't need to have it all figured out to be confident. You just need to start believing you're capable of figuring it out as you go.
​
Listen: Journaling is powerful, but it's not therapy. These prompts are here to help you process and reflect, but if you're really struggling, please talk to a therapist or mental health professional. There's no shame in needing more support than a journal can give you—that's actually wisdom.
​
Where Confidence Lives
​
1. When was the last time I felt truly confident? What were you doing? Who were you with? What made you feel that way?
​
2. What does confidence feel like in my body? Shoulders back? Head up? Steady breathing? Learn to recognize it so you can call it back.
​
3. In what area of my life do I feel most confident? There's at least one place where you trust yourself. What is it?
​
4. What skill or ability am I most proud of? You're good at something. Own it.
​
5. What compliment do I have the hardest time accepting? Often the compliments we deflect are the truths we need to claim.
​
Understanding the Doubt
​
6. Where did I learn that I wasn't enough? Someone taught you to doubt yourself. Who was it?
​
7. Whose voice am I hearing when I doubt myself? Is it yours, or someone else's criticism you internalized?
​
8. What am I afraid will happen if I'm confident? Sometimes we're scared of taking up space. What's the fear underneath?
​
9. What story am I telling myself about why I can't be confident? "I'm too much." "I'm not smart enough." "People will think I'm arrogant." What's your version?
​
10. Is that story actually true, or just familiar? Just because you've believed it for years doesn't make it fact.
​
What's Holding You Back
​
11. Where am I waiting for permission that I don't actually need? Who are you waiting to tell you it's okay to be yourself?
​
12. What would I do if I stopped caring what people thought? Really sit with this one. What would change?
​
13. Where am I shrinking to make others comfortable? Your small doesn't serve anyone. Where are you doing this?
​
14. What am I apologizing for that doesn't need an apology? Count how many times you say "sorry" in a day. Then ask why.
​
15. What decision am I avoiding because I don't trust myself to make it? The one you keep overthinking. What is it?
​
Reclaiming Your Power
​
16. What do I know for sure about myself, even when I doubt everything else? Your anchor truth. The thing that doesn't waver.
​
17. What have I already survived that proves I'm stronger than I think? You've been through hard things and you're still here. That's evidence.
​
18. What would I tell my younger self about confidence? The wisdom you wish someone had given you—give it to yourself now.
​
19. What compliment do I need to hear from myself? Stop waiting for someone else to say it. What do you need to tell yourself?
​
20. What boundary would protect my confidence? Sometimes confidence requires saying no to people who diminish you.
​
Taking Up Space
​
21. Where am I playing small because I'm scared of being "too much"? Your "too much" is someone else's favorite thing about you.
​
22. What would I do if I knew I couldn't fail? Remove the fear. What's left?
​
23. What opinion do I have that I'm afraid to share? You're allowed to have thoughts. What are you holding back?
​
24. Where do I need to stop explaining myself? Not everything requires justification. Where are you over-explaining?
​
25. What does taking up space unapologetically look like for me? Define it on your terms. What does it mean to you?
​
Building Confidence Daily
​
26. What's one small thing I can do today to practice confidence? Start tiny. Speak up once. Make eye contact. Wear the thing.
​
27. How do I want to show up in the world? Not how you think you should—how you actually want to.
​
28. What does my confident self look like? Describe her. How does she walk, talk, make decisions?
​
29. What's stopping me from being her now? Usually it's just permission. What if you gave it to yourself?
​
30. What would I do differently if I trusted myself completely? Dream here. What changes?
​
Handling Criticism and Comparison
​
31. Whose opinion matters most to me, and why? Contrary to popular opinion, there is only one correct answer...yours.
​
32. What criticism am I still carrying that isn't mine to hold? Someone said something years ago and you're still believing it. What is it?
​
33. Who am I comparing myself to, and why is that unfair? You're seeing their highlight reel, not their behind-the-scenes struggle.
​
34. What would change if I stopped comparing myself to others? Comparison is confidence's enemy. What would you gain by letting it go?
​
35. How can I celebrate someone else's success without diminishing my own? Their win doesn't mean your loss. Both can be true.
​
Trusting Your Voice
​
36. What do I believe that I'm afraid to say out loud? Your voice matters. What needs to be said?
​
37. Where do I need to stop asking for validation? You already know the answer. Where are you seeking permission?
​
38. What would I say if I knew people would listen? They're listening. What do you want them to hear?
​
39. When have I spoken up and been glad I did? Remember that moment. You were brave. You can be brave again.
​
40. What does using my voice confidently look like? Not loud, just unapologetic. What does that sound like for you?
​
Redefining Confidence
​
41. What's the difference between confidence and arrogance? One of them scares you because you've been taught to stay small. Which one?
​
42. Can I be confident and still have doubts? Yes. Confidence isn't certainty—it's trusting you'll figure it out.
​
43. What does quiet confidence look like? You don't have to be loud to be sure of yourself.
​
44. How has my idea of confidence changed over the years? What did it mean when you were younger vs. now?
​
45. What does confidence feel like at this stage of my life? It doesn't look the same at 50 as it did at 25. What does it look like now?
​
Moving Forward
​
46. What's one promise I can make to myself about showing up confidently? Small, specific, doable.
​
47. What support do I need to build my confidence? Therapy? A hype friend? A new environment? What would help?
​
48. What old version of "confident me" am I trying to get back to? Maybe you're not going back. Maybe you're becoming someone new.
​
49. What would my life look like if I owned my worth? Let yourself imagine it.
​
50. What's the first step toward that version of me? Just one step. What is it?
​
How to Use These Prompts
​
Pick the prompt that makes your stomach flip a little, that's usually the one you need. Write messy, write honest, write without editing yourself. This is your space to figure out who you are when no one's watching.
​
You don't need to answer all 50 at once. You don't need perfect insights. You just need to keep showing up and asking the questions.
​
​
Keep Going
​
For more content for women over 40 navigating anxiety, life transitions, and finding themselves again, check out the freebies page and browse all blog posts.​​​
​
​
​
Want This Delivered?
​
Look, I get it—remembering to come back here every week is just another thing on the list. So if you want these prompts (plus helpful content and resources) sent straight to your inbox, join the Penned Pals. No pressure, just what you need when you need it.
​
Look, I get it—remembering to come back here every week is just another thing on the list. So if you want these prompts (plus helpful content and resources) sent straight to your inbox, join the Penned Pals. No pressure, just what you need when you need it.
​
​
​
​
