Journaling is one of the most powerful tools for self-transformation. Research from the American Psychological Association shows that expressive writing can reduce stress, improve immune function, and enhance psychological well-being—making it a perfect complement to the 75 Medium Challenge.
Below you'll find 75 prompts—one for each day of your journey. Each prompt is designed to match where you are in the challenge, addressing the specific mental hurdles and growth opportunities at each stage.
How to Journal Effectively
Before diving into prompts, here's how to get the most from your practice:
Getting Started
- Choose your medium: Physical notebook, digital app, or voice recording
- Set a time: Morning for intention-setting, evening for reflection
- Start with 5-10 minutes: Consistency beats length
- Write freely: Don't edit, censor, or worry about grammar
Journaling Styles
- Free writing: Stream of consciousness, whatever comes to mind
- Prompt-based: Answer specific questions (like below)
- Gratitude journaling: List things you're grateful for
- Bullet journaling: Short, structured notes and lists
💡 Pro Tip
Re-read your entries every 2 weeks. You'll be amazed at your progress and gain insights you missed the first time.
Week 1-2: Foundation (Days 1-14)
The first two weeks are about establishing your why, setting intentions, and building initial momentum.
Day 1
Why am I starting the 75 Medium Challenge today? What do I hope to gain? What am I willing to sacrifice?
Day 2
Who do I want to become by Day 75? Describe the person in detail—habits, confidence, energy, relationships.
Day 3
What has stopped me from achieving my goals in the past? Be honest about patterns and excuses.
Day 4
What does discipline mean to me? How is it different from motivation?
Day 5
What am I grateful for today? List 5 things, big or small.
Day 6
What negative self-talk did I notice today? How can I reframe those thoughts?
Day 7
Week 1 complete! What worked? What needs adjustment? What surprised me?
Day 8
Who in my life supports this journey? How can I lean on them? Who might I need to distance from?
Day 9
What's my biggest fear about this challenge? What would I tell a friend with the same fear?
Day 10
Describe my ideal morning routine. How close am I to living it?
Day 11
What healthy habit am I most proud of so far? How did I build it?
Day 12
What excuse almost got me today? How did I overcome it (or not)?
Day 13
How is my body feeling after almost 2 weeks? Energy, soreness, sleep quality?
Day 14
Two weeks complete! Write a letter to your Day 1 self. What would you tell them?
Week 3-4: Building Momentum (Days 15-28)
The novelty is fading. This is where real discipline starts. According to habit research, these weeks are critical for identity formation.
Day 15
The excitement has worn off. What will keep me going when I don't feel like it?
Day 16
What does my inner critic say most often? Give that voice a name, then write a response.
Day 17
What small win can I celebrate today? We often overlook progress—acknowledge it.
Day 18
How has my relationship with food changed? Cravings, energy, mindfulness?
Day 19
What am I learning about myself through exercise? Physical capabilities, mental limits?
Day 20
Who am I becoming? Describe specific behaviors that show your growth.
Day 21
Three weeks complete! The average habit takes 21-66 days to form. What feels automatic now?
Day 22
What boundaries have I set during this challenge? With people, time, or situations?
Day 23
How do I handle stress differently now compared to Day 1?
Day 24
What have I given up that I don't miss? What have I gained instead?
Day 25
Write about a hard moment this week. How did you push through?
Day 26
What does self-care mean to me now? Has my definition changed?
Day 27
How am I showing up differently in relationships? Family, friends, coworkers?
Day 28
One month complete! List 10 things that are different from Day 1.
Week 5-6: Mid-Challenge (Days 29-42)
The "middle slog" is real. You're not new, but the finish line feels far. These prompts address the unique challenges of this phase.
Day 29
What unexpected benefits have I experienced? Physical, mental, relational?
Day 30
If I quit today, how would I feel in a week? In a year?
Day 31
What's the hardest part right now? How can I make it even 1% easier?
Day 32
Write about someone who inspires you. What qualities do they have that you're developing?
Day 33
What has this challenge taught me about commitment?
Day 34
How has my energy throughout the day changed? Morning, afternoon, evening?
Day 35
Halfway point! Write a progress report. Physical changes? Mental shifts? Habit strength?
Day 36
What would I tell someone starting Day 1 today? Your best advice.
Day 37
What's a limiting belief I've proven wrong? "I can't..." that became "I can."
Day 38
How do I feel about my body now? Strength, capability, appreciation?
Day 39
What's one thing I do now that would shock Day 1 me?
Day 40
Describe my ideal Day 76. How will I feel? What will be different?
Day 41
What relationships have improved during this challenge? Including relationship with self?
Day 42
Six weeks complete! What's easier than Week 1? What's still hard?
Week 7-8: Going Deeper (Days 43-56)
You've built momentum. Now explore the deeper changes happening in your mindset and identity.
Day 43
What does mental toughness mean to me now? How has my definition evolved?
Day 44
What negative habits outside the challenge have I naturally dropped?
Day 45
How do I handle discomfort differently now? Physical and emotional.
Day 46
What am I most proud of so far? Why does it matter to me?
Day 47
What fears have diminished since Day 1? What gave me that courage?
Day 48
How has my self-talk changed? Write an example conversation with yourself.
Day 49
Seven weeks complete! If you could only keep 3 habits after Day 75, which would they be?
Day 50
50 days! What's different about the person writing this vs. the person who started?
Day 51
What has 75 Medium taught me about my potential?
Day 52
How has my sleep quality changed? How does this affect everything else?
Day 53
What's a moment when discipline felt like freedom?
Day 54
How do I want to be remembered? What's this challenge teaching me about that vision?
Day 55
What would failure teach me that success won't? (You're not failing—but reflect.)
Day 56
Eight weeks complete! 80% done. How does it feel to be this close?
Week 9-10: Final Push (Days 57-70)
The finish line is visible. These prompts help you maintain focus and prepare for life after the challenge.
Day 57
What does finishing this challenge mean for my self-trust?
Day 58
What will I miss about the structure of 75 Medium? What won't I miss?
Day 59
How has my definition of success changed?
Day 60
60 days! Only 15 left. Write encouragement for your Day 70 self.
Day 61
What does discipline feel like in my body now? Describe the physical sensation.
Day 62
What advice would future-me give about this final stretch?
Day 63
Nine weeks complete! What's the biggest lesson of this entire journey so far?
Day 64
How will I celebrate Day 75? Plan something meaningful—you've earned it.
Day 65
What new goals are emerging? What's next after this foundation?
Day 66
Research shows 66 days is average for habit formation. Which habits feel permanent now?
Day 67
What's a challenge I want to tackle next? Professional, personal, physical?
Day 68
How has this challenge changed my relationship with discomfort?
Day 69
What would I do differently if I started again? Advice for future challengers.
Day 70
Ten weeks complete! 5 days remaining. How does your body feel? Your mind?
Week 11: Completion & Reflection (Days 71-75)
The home stretch. Time to reflect on transformation and set intentions for what's next.
Day 71
What's the most important thing I've learned about myself?
Day 72
Write a letter of gratitude to your body. Thank it for what it's done.
Day 73
What will I tell people who ask about this challenge? Your summary.
Day 74
Tomorrow is Day 75! What emotions am I feeling? Excitement? Nervousness? Relief?
Day 75
You did it. Write freely about this moment. What are you feeling? What does this mean? Who have you become?
?? Congratulations
These 75 journal entries are now a priceless record of your transformation. Keep them. Re-read them when you need motivation. Share them if they help others. You've proven that you can do hard things.