A monthly planning system that feels like a check-in with yourself, not a performance review.

TL;DR

This guide reimagines monthly planning as self-companionship, not self-surveillance.

Instead of asking "Did I hit every goal?" ask "How am I? How'd the month go?"

The 8-section template includes:

All sections are optional and modular—take what serves you, adapt what doesn't, skip what feels like too much.

This isn't about perfect planning; it's about creating just enough structure to notice when you need rest, when you're aligned, and when your creative energy wants to emerge.

Skip to the template walkthrough →

From Performance to Presence

Why This Kind of Planning is Different

I love the energy a new month brings. For me, a new month serves as a reset point, a sort of recalibration, if you will—a chance to orient myself again. And yes, this love of fresh starts is absolutely written in my star chart and woven into my personality: I am an avid planner through and through.

I'm a Virgo sun who loves systems, a Capricorn rising who craves structure, a Pisces moon who needs flow, a Human Design 2/4 Manifestor learning to honor my initiations, and an MBTI Logistician-Advocate split between order and meaning. I've been planning since I was 18, and I genuinely enjoy tracking the arc of my life through color-coded stickies, spreadsheets, thoughtful templates, and physical planners —all the planners, all the journals! I love them. It's a love language, honestly. [Check out my running list of recommendations]

You might assume that someone with a significant amount of earth and structure in their chart would have all their planning well in hand. However, as a recovering perfectionist, I’ve had to reimagine my approach to planning thoroughly. I regularly tweak my systems; for a time, I felt like I was flighty and couldn’t stick to anything (that’s what the overculture—and some internal voices, thanks to the overculture—want me to think). However, this evolution occurs naturally because I’m constantly growing.

The most significant change in my perspective that has helped me as a recovering perfectionist is understanding that the strategies that once helped my productivity-driven self no longer work for who I am today. I am now focused on learning how to support myself through the different cycles of life. While the basic components of planning systems remain the same, my approach to using them has shifted from causing feelings of frustration and low worth to becoming a more supportive practice. And I hope you can take away something from this guide.

Here's what mainstream productivity culture often overlooks: planning can become another aspect of performance rather than a helpful tool. By 'performing,' I mean the tendency to judge our worth or abilities based on our plans rather than using them to genuinely improve our lives. This might involve obsessively perfecting to-do lists, constantly comparing our productivity to that of others, or feeling guilty for missing self-imposed deadlines. It can easily become just another way to criticize ourselves.

One of the things I still struggle with is the constant feeling of having to be "on"—feeling behind, feeling like I'm not doing enough. I blame the burnout culture we live in and the hustle mythology we've all been taught. But it's something I'm actively relearning and reconditioning in myself. I'd love to meet others who relate to this struggle (bc bih, it’s real).

Let’s approach monthly planning as an ally rather than a tool for criticism. We don’t need another performance review that highlights our shortcomings or exercises that make us feel we have to prove our worth through achievements. Instead, let’s view it as a practice of reconnecting with ourselves—a gentle check-in, a way to recalibrate, and a supportive method for navigating the messy yet beautiful cycles of being human.

Are you ready? Let’s go..

A Note Before We Begin

Challenging What Planning "Should" Be

Somewhere along the way, many of us absorbed the idea that planning exists to maximize productivity—to extract more output, hit more goals, prove our worth through accomplishment. We learned to treat our monthly reviews like performance evaluations, measuring ourselves against rigid standards and feeling inadequate when life didn't cooperate with our perfect plans. But recovering perfectionist, what if we've been asking the wrong question?

Let's shift the inner (and outer monologue, yeah?)

Not "Did I hit every goal?" (and then spiral into self-criticism when we didn't meet our own rigid standards).

But "How am I? What am I actually up to? How'd the month really go?"

This is the shift this template invites you into: planning as a practice of self-companionship, not self-surveillance.

This monthly planning template focuses not on maximizing your productivity, but on fostering a natural rhythm of reflection and intention-setting. It recognizes a fundamental truth: your energy fluctuates throughout the month, and that's not a flaw—it’s a vital aspect of how organisms operate.

External forces shift us. Internal forces shift us. For those of us who menstruate, hormonal phases dramatically change our energy and mood. The seasons change. Life happens. A planning system that doesn't account for this isn't realistic—it's just another way to gaslight yourself into thinking you should be a machine. News flash, you are not a machine. And this template won't treat you like one.

This System is Modular and Flexible

Important: Not every section will be relevant for everyone, and that's by design.

This template has 8 sections, but you don't need to use all of them. Think of this as a menu:

• Core sections that provide the most value: Header, Reflection, Focus, and Closing Ritual

• Optional/situational sections you can add as needed: Calendar & Milestones, Resources & Support, Rituals & Rhythms, Highlight Reel

  
  

Begin with what feels doable for you.

Add more as you master and adjust.

Omit what does not benefit you.

The aim is self-orientation and companionship, not filling every blank space.

What You'll Need

• A quiet 30-60 minutes at the end/beginning of each month

• Documentation tool (a notebook or your computer)

• The template (provided below—feel free to adapt it to your needs)

• Permission to be imperfect (this is non-negotiable)

• Optional: Your menstrual cycle tracker, planner, or calendar for reference

How to Plan Your Month: A Guide for Recovering Perfectionists

Let me walk you through each section and explain why it matters—not just what to write.

Header Section: Setting the Tone

1. Month & Theme:

2. Word of the Month:

3. Affirmation/Intention/Quote:

   
   

Why this matters: Themes ground us in the cyclical nature of life and earth. I align mine with the seasons—October brings the Autumn energy of balance and harvest, a time to reap what we've sown and restore equilibrium before winter's withering rest. You also don't need to use all three; all three might feel extra, so which one stands out? Which one do you like? Use it as an anchor for the month.

How to use it:

• Choose a Word of the Month that feels aligned with where you are (not where you think you should be). Examples: Rest. Courage. Play. Release. Build. Connect.

• Craft an Affirmation/Intention or find a quote that supports this word or the overall theme of the month.

Reflection (Previous Month): The Gentle Accounting

1. Top 3 Wins:

2. Lessons Learned:

3. Energy Audit:

   • Aligned:

   • Draining:

4. Carry Forward / Let Go / Change:

   
   

Why this matters: Reflection before planning is essential for learning. It's also how we practice self-acknowledgment instead of self-criticism.

How to use it:

• Top 3 Wins: These don't have to be "big." Did you rest when you needed to? Send that scary email? Make it through a hard week? Count it.

• Lessons Learned: What did the month teach you? Frame this with curiosity, not judgment. "I learned that I need more buffer time between commitments," instead of "I failed at time management again."

• Energy Audit (this is the game-changer):

  • Aligned: What gave you energy? What felt easiest? When did you feel most like yourself? (Projects, people, practices, times of day, phases of your cycle)

  • Draining: What depleted you? Moments or days when you felt most tired? This isn't about eliminating everything hard—it's about noticing patterns. Did you say yes when you meant no? Were you forcing something that wasn't ready?

  • Tracking your menstrual cycle can help you understand your energy levels. I note my phases in my planner since my initiation energy is highest during the follicular phase. Conversely, the luteal phase calls for slowing down and allowing personal space and rest. I often feel tender and critical during this time, so I avoid scheduling important tasks. After discovering I have PMDD in my 30s, tracking my cycle has helped me manage this experience more effectively.

• Carry Forward / Let Go:

  • What incomplete items actually still matter? (Carry forward)

  • What can you release without guilt? (Let go—this is permission)

I used to carry all my unfinished tasks with me constantly, which made my to-do list seem endless. It often felt like I’d never really be done. Over time, I've realized it's okay to let go of tasks and projects that no longer serve me or, frankly, that I no longer want to do. This was a tough change for my former perfectionist self, but it has made my life more manageable and joyful. When tasks swirl in my head like a hamster wheel, I write them down, unload them, and handle them at a better time. My old self would overthink task completion because I wanted to get everything done.

Focus (This Month): Strategic/High-level Overview/Clarity

1. [Your Priority Area 1]

2. [Your Priority Area 2]

3. [Your Priority Area 3]

4. [Your Priority Area 4]

5. [Your Priority Area 5]

   
   

Why this matters: You can't do everything every month. This section forces strategic choice. Before you dive into specific goals and weekly tasks, take a step back and consider the big picture. What's the overarching focus of this month? Is there a major event, trip, deadline, or project that shapes everything else? This section helps you identify your strategic focus, ensuring that you don't treat every task as equally urgent.

How to use it: Start by identifying your life domains or priority areas—these are the major categories that organize your energy and attention. These might include areas such as business growth, academic commitments, creative projects, financial stability, personal wellness, family obligations, or community involvement. Your categories should reflect your actual life, not an idealized version.

Once you have your categories listed, ask yourself:

• What's the big picture for this month? Is there a launch, a major deadline, an important trip, a significant life event, or a seasonal shift that defines this period?

• Where does my active focus need to be? Which 2-3 areas require strategic attention and creative energy right now?

• What's in maintenance mode? Which areas are you simply sustaining rather than actively building?

• What can genuinely rest? Which priorities can take a backseat this month without causing problems?

Strategic layer: This isn't your to-do list—it's your attention map. When you know your strategic priorities up front, every decision becomes clearer. When an opportunity arises or a request comes in, you can ask: "Does this serve my active priorities this month?" If not, it's easier to say no or defer.

Think of this as setting the frame before you paint the picture. Without this high-level clarity, you'll end up reactive, scattered, and wondering why you're busy but not making progress on what actually matters.

Calendar & Milestones: The Weekly Pulse

Week 1: [ ]

Week 2: [ ]

Week 3: [ ]

Week 4: [ ]

Significant Dates: [ ]

This is where you plug things in.

Why this matters: This section bridges the gap between your big-picture strategic focus and the daily reality of living your life. It's where you get real about when things need to happen—but without the rigidity that turns planning into a pressure cooker.

How to use it: This step is optional. If fixating on dates and deadlines stresses you out or triggers perfectionism, you can skip the weekly breakdown and just note your major non-negotiables. The goal here is orientation, not obsession.

Here's what to capture:

• Fixed commitments you can't move: This is your anchor. Mark the appointments, events, and obligations that are set in stone—birthdays, health appointments, social events you've committed to, work deadlines, class schedules, travel dates.

• Your Body's Calendar: If you track your menstrual cycle, mark which weeks align with each phase. Knowing you'll be in your luteal phase during week 3, or that you're launching something during your menstrual week, is valuable information. You can plan with your energy instead of fighting against it.

• Recurring rhythms: Do you have weekly commitments that repeat? Maybe you have a writing deadline every Friday, a coaching call every Tuesday, or a financial review on the first of the month. Plugging these in prevents "surprise" stress when they roll around.

• Loosely set weekly intentions: For each week, jot down 1-2 focus areas or milestones if it helps you feel more oriented. Not a rigid checklist—more like "Week 1: focus on content planning" or "Week 3: client deliverables."

• The permission slip: You don't need to know exactly what you're doing every single day. You don't need perfect time-blocking. This section is about creating just enough structure to avoid being caught off guard by your own life—while leaving space for the unexpected, the spontaneous, and the human moments that can't be calendared.

If weekly breakdowns feel too overwhelming, simply note your major dates and move on. Done is better than perfect here.

Resources & Support: You Don't Have to Do This Alone

Tools/Systems: [ ]

Delegate/Automate: [ ]

Accountability/Support: [ ]

Why this matters: This section is a reality check—what support structures, tools, or people could make this month more sustainable? It's easy to default to "I'll just figure it out myself," but that's often how we end up overwhelmed and burned out.

How to use it: This step is optional, and it's not about having all the resources you wish you had. It's about naming what could help and being honest about what's actually available to you right now.

Things to consider:

• Tools/Systems: What's already in your toolkit that you can lean on this month? Maybe it's a project management system, a template you've already built, scheduling software, a budgeting app, or even just a simple spreadsheet. This isn't about buying new things or creating elaborate systems—it's about remembering what you already have access to that could lighten the load.

• Delegate/Automate: What could you hand off, streamline, or stop doing manually? This doesn't require a big budget or a team. It could be as simple as using AI to draft an outline, setting up an email template, automating bill payments, ordering groceries online, or asking a friend to co-work with you so tasks feel less heavy. Even tiny acts of delegation count.

• Accountability/Support: Who's in your corner this month? This could be a friend you check in with, a co-working date, an online community, a mentor, a coach, or just someone you text your weekly wins to. Sometimes support isn't formal—it's just not doing everything in isolation.

• The permission slip: You don't need to fill out every line here. You don't need a whole support system in place before you start. This section is simply an invitation to notice: Where am I trying to do everything alone when I don't have to? And What small shift could make this month feel less like pushing a boulder uphill by myself?

If nothing comes to mind right now, that's okay. Just asking the question is the first step.

Real talk: As someone on a tight budget building a business, I know delegation isn't always accessible. However, note what could be automated or what support already exists in your environment; naming it might help you manifest it.

Rituals & Rhythms: The Living Structure

[Your Rhythm Category 1]: [ ]

[Your Rhythm Category 2]: [ ]

[Your Rhythm Category 3]: [ ]

[Your Rhythm Category 4]: [ ]

Why this matters: Rituals and rhythms are different from goals. Goals are about accomplishment—rhythms are about maintenance. They're the recurring practices and commitments that hold your life together, the steady beats that keep you grounded even when everything else feels chaotic. These are not optional, because without them, it's a sure way to burnout.

How to use it:

Start by identifying the recurring patterns in your life—the things that happen regularly, whether you plan them or not. These aren't aspirational; they're the actual rhythms that structure your days, weeks, and months.

Ask yourself:

• What commitments repeat? Do you have regular work obligations, class schedules, content deadlines, team meetings, or family responsibilities that happen on a predictable cadence?

• What practices keep you functional? What are the non-negotiable maintenance activities that keep your mental, physical, emotional, or financial health intact? This could be movement, therapy appointments, creative time, spiritual practices, or rest rituals.

• What would fall apart if you didn't tend to it regularly? Bills? Email inbox? Relationships? Your nervous system? Physical space? These often reveal your essential rhythms.

• What cycles do you want to honor? If you menstruate, maybe you build in rest during certain phases. If you're seasonal, maybe you adjust your rhythms as daylight changes. If you're neurodivergent, maybe certain routines help with regulation.

  
  

Create categories that match your life: Your rhythm categories should reflect what's actually present in your world. Some examples might include:

• Content/creative output cadence

• Academic or work commitments

• Physical and mental wellness practices

• Financial maintenance (budget reviews, invoice tracking, money dates)

• Relational rhythms (family calls, friend check-ins, community participation)

• Household/life admin tasks

  
  

Permission slip: These don't have to be daily. They don't have to be elaborate. A rhythm can be as simple as "financial check-in on the 1st of each month," or "therapy every other Tuesday," or "rest day on Sundays." The point is to name them so they're visible and intentional rather than invisible burdens you're constantly scrambling to maintain.

And if a rhythm isn't serving you anymore? You can change it. Rhythms are living structures—they're allowed to evolve.

Closing Ritual (End of Month): Honoring the Cycle

1. Celebrations:

2. Surprises:

3. Carry into Next Month:

Why this matters: We're conditioned to immediately look ahead without acknowledging what just happened. This ritual interrupts that pattern. In hustle culture, we're taught to chase the next milestone before we've even processed the current one. This section is your permission to pause, witness, and honor the month that just passed—not as a performance review, but as an act of completion.

How to use it: This closing ritual is designed to create intentional endings. Without them, months blur together, accomplishments go unacknowledged, and lessons fade before they can land. This is where you practice presence with your own life.

Think of this as the exhale after a long breath. You've moved through a full cycle—28 to 31 days of living, working, resting, struggling, succeeding, surviving. That deserves acknowledgment.

Celebrations: What deserves to be honored? This isn't about only celebrating "big wins." Small moments count. Quiet victories matter.

Ask yourself:

• What did I do this month that took courage?

• What brought me joy or made me smile?

• What did I complete, even if it wasn't perfect?

• What boundary did I hold? What risk did I take?

• Did I rest when I needed to? Did I ask for help? Did I show up for myself?

  
  

Examples of celebration-worthy moments:

• You made it through the month (especially if it was hard—that counts)

• You said no to something that would have drained you

• You tried something new, even if it didn't work out perfectly

• You had a meaningful conversation or deepened a relationship

• You created something—art, writing, a meal, a moment of beauty

• You kept a commitment to yourself, even a small one

  
  

Permission slip: If this month was about survival, and your celebration is "I'm still here," that is enough. There's no minimum threshold for what "counts" as worth celebrating.

Surprises: What unexpected thing happened? Good or challenging—name it.

Life rarely goes exactly according to plan, and this section helps you name the plot twists without judgment. Surprises can be delightful or challenging—both are worth experiencing.

Ask yourself:

• What caught me off guard this month?

• What opportunity or challenge arose that I hadn't anticipated?

• What changed—internally or externally?

• What did I learn about myself that I didn't expect?

• What assumption got challenged or proven wrong?

  
  

Examples of surprises to note:

• An unexpected project or opportunity emerged

• Someone reached out and it led somewhere meaningful

• You discovered a new capacity or skill in yourself

• An old pattern showed up again (and you handled it differently this time)

• Plans fell through, and something better happened instead

• You felt something you didn't expect to feel

• A relationship shifted—deepened, ended, or transformed

• Your energy or health changed in ways you didn't predict

  
  

Why naming surprises matters: When we acknowledge what we didn't see coming, we stay humble and curious about life's unfolding. We remember that we're not in total control, and that's okay. Surprises—even hard ones—are data about how life actually works, not how we thought it would work.

Carry into Next Month: What thread wants to continue? Not everything wraps up neatly at the end of a month, and this section honors that some things are meant to keep unfolding.

This isn't just about incomplete tasks (though you might note one or two if they genuinely matter). This is about the living questions, emerging themes, and threads of attention that should continue into the next cycle [month].

Ask yourself:

• What question am I still sitting with?

• What theme or pattern kept showing up this month?

• What conversation or idea feels unfinished—in a good way?

• What seed did I plant that needs more time to grow?

• What creative impulse or curiosity is still pulling at me?

• What relationship or project wants my continued attention?

• What practice or rhythm did I start that I want to sustain?

  
  

Examples of threads to carry forward:

• "I'm still exploring what 'rest' actually means for me"

• "The question of how to price my work is still evolving"

• "I want to keep building my morning ritual—it's working"

• "The tension between structure and flow keeps coming up; I'm learning something here"

• "That creative project I started still has energy—carry forward"

• "I noticed I feel most alive when teaching—explore this more"

  
  

Permission slip: You don't have to "solve" everything or wrap it up with a bow. Some of the richest parts of life are the questions we live into over time. Carrying something forward isn't failure to finish—it's honoring what's still alive in you.

Bringing it all together:

This closing ritual is an act of self-witnessing. You're not rating yourself or scoring the month. You're simply saying: I see what happened. I honor what I experienced. I acknowledge what I want to continue.

In a culture that constantly pushes us toward the next thing, this practice says: What just happened matters. I matter. My experience deserves to be seen—by me.

And that, more than any productivity hack, is what sustainable living looks like.

Highlight Reel (Optional)

📸 Add photos, wins, screenshots, or quotes from the month.

Why this matters:  Your life is more than a list of completed tasks. This section invites you to capture the texture of your month—the moments, images, words, or wins that you want to remember. Not for social media. Not for performance. Just for you.

How to think through this: This is entirely optional, and there's no right way to do it. Some months, you might add nothing. Other months, you might paste in a photo that made you smile, a screenshot of an encouraging message, a quote that landed at the right time, or a simple note about something that felt significant.

Think of this as your personal archive—a way to see your life as more than productivity metrics. When you look back months or years from now, these small artifacts will tell the story of who you were and what mattered during this season.

Permission slip: You don't need to curate this beautifully. You don't need to add something every month. This isn't another thing to perfect—it's just an invitation to pause and notice: What do I want to remember about this time?

There You Have It: Monthly Planning for Recovering Perfectionists

If you're brand new to planning, please don't let this overwhelm you. Start small. Pick one or two sections that feel most relevant right now. Master those. Then layer in what resonates. Leave out what doesn't serve you. Most of all, make it fun. If you're not having fun, you won't stick with it. This template isn't meant to be followed perfectly—it's meant to be adapted, broken down, rebuilt, and made your own.

Some months you'll use every section. Other months, you'll skip half of it. Some seasons you'll be in creative flow, initiating projects with ease. Other seasons you'll be in survival mode, just trying to keep the basics intact. Both are valid. Both are part of being human.

This planning system isn't about forcing your energy into capitalist timelines or proving your worth through productivity. It's about creating just enough structure that you can notice what's actually happening—when your real creative impulses want to emerge, when you need rest, when you're aligned, and when you're pushing too hard.

Planning as Self-Companionship

The most radical shift isn't about finding the perfect template or the right app.

It's changing the question from "What do I need to accomplish?" to "How do I want to accompany myself through this month?"

That's what this practice offers: a way to accompany yourself.

You don't need to be more productive.

You need to be more present with yourself.

And that, dear human, is what sustainable planning actually looks like.

Your Turn: Let's Continue This Conversation

I'd love to hear from you:

• Which section of this template resonates most with you?

• What feels hardest or most challenging?

• How are you reimagining planning in your own life?

P.S. If you try this system and it doesn't work for you—that's data, not failure. Adapt it. Break it. Rebuild it. Take what serves you and leave the rest. The point is finding what actually supports YOUR life, not replicating mine.