30-Day Planning & Journaling Challenge

Transform your planning and journaling habits with our 30-day challenge. Each day builds on the previous one to help you develop a consistent and effective practice.

Week 1: Building Your Foundation

Days 1-7 focus on setting up your planner and establishing basic habits.

Day 1: Set Up Your Planner

Take time to set up your 2026 Planner. Fill in your personal information, mark important dates on your yearly calendar, and familiarize yourself with all the spreads.

Journal Prompt: What do you hope to achieve with your planner this year? What planning challenges have you faced in the past?

Day 2: Define Your Goals

Use the Goal Breakdown spread to identify 3-5 major goals for the year. Break each one down into smaller milestones.

Journal Prompt: Why are these goals important to you? How will achieving them impact your life?

Day 3: Create Your First Monthly Spread

Set up your monthly spread for the current month. Include appointments, deadlines, and events.

Journal Prompt: What are your top 3 priorities for this month? What would make this month feel successful to you?

Day 4: Plan Your Week

Set up your weekly spread (vertical or horizontal). Transfer items from your monthly spread and break down your monthly goals into weekly tasks.

Journal Prompt: What's your biggest challenge when it comes to weekly planning? How might you overcome it?

Day 5: Daily Planning Ritual

Establish a daily planning ritual. Spend 5-10 minutes each morning or evening planning your day.

Journal Prompt: What time of day works best for your planning? What elements would make this ritual enjoyable and sustainable?

Day 6: Habit Tracker Setup

Choose 3-5 habits you want to track this month. Set up your habit tracker in your monthly or weekly spread.

Journal Prompt: Why did you choose these specific habits? How do they align with your goals and values? (You can find more prompts on our Journal Prompts page for inspiration!)

Day 7: Weekly Review

Conduct your first weekly review. Reflect on what went well, what didn't, and what you learned. Adjust your plans for the coming week.

Journal Prompt: What insights did you gain from your first week of intentional planning? What would you like to adjust for next week?

Week 2: Deepening Your Practice

Days 8-14 focus on refining your techniques and integrating journaling more deeply.

Day 8: Time Blocking

Experiment with time blocking in your weekly spread. Allocate specific blocks of time for your most important tasks.

Journal Prompt: How did time blocking affect your productivity and focus? What was challenging about it?

Day 9: Goal Check-in

Revisit your Goal Breakdown spread. Are you on track? Do any milestones need adjustment?

Journal Prompt: What's one small step you can take today towards one of your major goals?

Day 10: Mindful Morning Journaling

Start your day with 10 minutes of free-writing or use a prompt from the "Mindfulness & Presence" section of our Journal Prompts page.

Journal Prompt: How does starting your day with journaling impact your mood and mindset?

Day 11: Tackle Procrastination

Identify one task you've been putting off. Break it into tiny steps and schedule the first step into your planner.

Journal Prompt: What feelings or thoughts contribute to your procrastination on this task? How can you address them?

Day 12: Evening Reflection

End your day by journaling about 3 things that went well and 1 thing you learned.

Journal Prompt: How does this evening reflection practice help you process your day and prepare for tomorrow?

Day 13: Review Your Habits

Look at your habit tracker. What patterns are emerging? Celebrate consistency and identify areas needing more attention.

Journal Prompt: What's one adjustment you can make to better support a habit you're struggling with?

Day 14: Mid-Challenge Review

Reflect on the past two weeks. What's working well in your planning and journaling? What's been difficult?

Journal Prompt: What are you most proud of learning or implementing so far in this challenge?

Week 3: Expanding Your Horizons

Days 15-21 encourage you to explore new planning methods and journaling themes.

Day 15: Quarterly Vision

Use your Quarterly Spread to outline a mini-vision for the next 90 days. What key things do you want to achieve or experience?

Journal Prompt: How does thinking in 90-day cycles feel different from yearly or monthly planning?

Day 16: Creative Journaling

Try a different journaling style: mind mapping, bullet journaling, or sketching your thoughts. Use the blank pages in your planner.

Journal Prompt: Did exploring a new journaling style unlock any new insights or ideas?

Day 17: Batching Similar Tasks

Identify similar tasks you do regularly (e.g., emails, errands) and try batching them into dedicated time slots in your planner.

Journal Prompt: How did task batching impact your efficiency and mental energy?

Day 18: Gratitude Focus

Dedicate your journal entry today to gratitude. List 5 specific things you're thankful for and why. (See November prompts for more ideas!)

Journal Prompt: How does focusing on gratitude shift your perspective?

Day 19: Ideal Week Planning

Sketch out what your ideal week would look like, balancing work, personal life, rest, and fun. How can you move closer to this?

Journal Prompt: What's one small change you can make next week to align more with your ideal week?

Day 20: Problem Solving Journal

Use your journal to work through a current challenge. Write about the problem, brainstorm solutions, and identify next steps.

Journal Prompt: Did writing about the problem help you see it more clearly or find potential solutions?

Day 21: Three-Week Checkpoint

Review your progress over the last three weeks. What habits are sticking? What benefits are you noticing?

Journal Prompt: How has this challenge changed your relationship with planning and journaling?

Week 4: Sustaining Your Momentum

Days 22-30 focus on solidifying your habits and planning for continued success beyond the challenge.

Day 22: Future Self Journaling

Write a letter to your future self one year from now, describing what you hope to have achieved and learned, especially regarding your planning habits.

Journal Prompt: What advice would your current self give to your future self about maintaining these practices?

Day 23: Planner Customization

Think about how you can further customize your 2026 Planner to perfectly suit your needs. Any new sections or ways of using existing ones?

Journal Prompt: What's one unique way you've started using your planner during this challenge?

Day 24: Celebrate Small Wins

Look back through your planner and journal entries from the challenge. Identify and celebrate at least three small wins or positive changes.

Journal Prompt: How can you make celebrating small wins a regular part of your routine?

Day 25: Overcoming Obstacles Plan

Anticipate future challenges to your planning/journaling routine (e.g., busy periods, lack of motivation). Brainstorm strategies to overcome them.

Journal Prompt: What's your go-to strategy when you feel overwhelmed or unmotivated?

Day 26: Share Your Insights (Optional)

If you feel comfortable, share one key insight or benefit you've gained from this challenge with a friend or in an online community.

Journal Prompt: How might sharing your experience help solidify your own learning or inspire others?

Day 27: Plan Your Next Month

Using the skills you've honed, set up your monthly spread for the upcoming month with intention and clarity.

Journal Prompt: What feels different about planning your next month now compared to before the challenge?

Day 28: Create a "Continuation Plan"

How will you continue these planning and journaling habits? Decide on a minimum commitment (e.g., 10 mins daily planning, 2 journal entries per week).

Journal Prompt: What support systems can you put in place to help you continue?

Day 29: Review Your Yearly Goals

Revisit your yearly goals. How has this 30-day challenge better equipped you to achieve them?

Journal Prompt: Are there any adjustments you want to make to your yearly goals based on your recent insights?

Day 30: Challenge Reflection & Celebration!

You did it! Reflect on the entire 30-day journey. What are your biggest takeaways? How have you grown? Plan a small way to celebrate your commitment!

Journal Prompt: What are you most proud of accomplishing during this 30-day challenge? What will you carry forward?