Monthly Planning for Entrepreneurs: 3 Days You Should Block Every Month
You've probably got a weekly rhythm — theme days, time blocks, some version of a plan. But if your admin pile never shrinks, your goals keep getting bumped, and you're constantly reacting instead of leading, the missing piece might be happening at the monthly level.
This episode covers three monthly planning days that work differently from your weekly structure: one for rest and recharge, one for clearing the admin and organizational backlog that's weighing on your brain, and one for stepping back to actually look at how your business is doing. Together, they break you out of the day-to-day grind and give your month a real shape before it runs away from you.
These lessons come straight from what I teach inside Chaos Detox — because getting out of reaction mode requires more than weekly planning. It requires building in the space to zoom out.
In this episode, you'll learn:
What theme days are and how they eliminate context switching and energy drain
Why a Hooky Day belongs on your work calendar — not just your wish list
How open loops from unfinished admin tasks drain your focus all week long
What to actually work on during your Back Office Day to move the needle
How to structure a Review and Planning Day so it's useful, not overwhelming
What to include in your monthly review: metrics, goals, ideal work week, journaling (00:07:19)
How to make sure all three days actually stay on the calendar (00:08:01)
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Want to read the original blog post that inspired this episode?
CLICK HERE → Creative Productivity: 3 Things Entrepreneurs Need To Do Every Month
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Full Episode Transcript
# (49) Monthly Planning for Entrepreneurs: 3 Days You Should Block Every Month
[00:00:00] What if the key to getting more done wasn't about squeezing more into your week, but about three specific days you can block off every single month? Welcome to Ditch The Chaos. I'm Cara Chace, and this is your space to figure out how to run your life in business without running yourself into the ground.
[00:00:17] Today I am walking you through three monthly theme days that I personally schedule every single month, and why they can do more for your productivity and creativity than almost anything else you could put in your calendar.
[00:00:29] So if you've been around here for a while, you know I'm a big fan of theme days.
[00:00:34] The idea is simple. You group similar tasks together so your brain can actually stay focused instead of bouncing between 20 different kinds of work. Context switching is one of the biggest creativity and energy drains out there. And theme days are one of the best antidotes I've ever found. Most of the time when people talk about theme days, they're talking about your week.
[00:00:55] Like Mondays are for client calls, Tuesdays are for content, that kind of thing. And [00:01:00] that's totally solid and actually what I teach as well. But today I want to zoom out and talk about three theme days that I schedule at the monthly level. These are not weekly recurring things. They happen once a month.
[00:01:13] They're intentional and they change the way your whole month can feel. These three days are a hooky day, a back office day, and a review and planning day. So let's go through each one. First up, the hooky day, and yes, I mean exactly what it sounds like a day off, not a sick day, not a day. You're wrangling kids schedules a day. You take off from work purely for yourself. And here's why this matters. As entrepreneurs, we are mentally on almost all the time. Even when we step away from the laptop, our brain is still running tabs in the background.
[00:01:51] The problem with never fully closing those tabs is that creativity starts to dry up. You lose perspective, you're constantly in [00:02:00] reaction mode. You start making decisions from a place of depletion instead of clarity. A full day off, not a few hours, but a real actual day gives your brain space to breathe.
[00:02:12] And when that happens you come back with ideas and solutions that you couldn't have accessed when you were deep in the grind. I also find that when I've had real time to myself, I'm genuinely more present with my family. Not just physically there, but more kind and engaged, and it's worth a lot. Now, practically speaking, your hooky day should fall on a day that you'd normally be working.
[00:02:36] That's the whole point. You're not just adding it to an already free day on the weekend. You're protecting time that would otherwise get swallowed up by just another workday. And what do you do with your hooky day when you do whatever fills your cup? For me, as an introvert, that often means doing something alone.
[00:02:55] My favorite is a spa day when the budget allows, but it could also be a long [00:03:00] drive, a matinee and lunch, getting outside for a hike, spending a whole day shopping without an agenda or a list. And I wanna be clear, shopping for yourself is not the same as running errands. This is not a pickup stuff for the house day.
[00:03:16] It's a lunch by yourself. Wander around, try things on day, or it could be nothing at all. Sometimes the most helpful and restorative thing you can do is stay in your pajamas. Read something you've been meaning to get, to take a nap without guilt. Watch a movie. A few things that actually make the hooky day work are to set your out of office autoresponder in your email so you're not anxiously wondering who's waiting on you.
[00:03:43] Give whoever's in your household a heads up and coordinate so logistics don't fall apart. And then truly commit to being off. No email, no social media. If you spend the whole day half present and thinking about B roll, you'll just come back as depleted as when you [00:04:00] left. Okay, on to day number two. Your second monthly theme day is your back office day.
[00:04:07] This is the day you set aside for all that admin and organizational work that lives in your business, not client work, not content creation, but the internal stuff that keeps piling up in the background. These could be things like reorganizing your Google Drive or Dropbox, cleaning up your project management system, archiving old client files, revisiting your marketing or PR plan, updating something on your website.
[00:04:32] These are all those tasks that you'll always mean to get to, but never quite do because they don't have deadlines attached to them and they don't feel urgent. But they just sit there half finished and they take up mental space and that's exactly the problem. Unfinished back office tasks are what I call open loops.
[00:04:51] Your brain knows they're not done, so it keeps pulling them up even when you're trying to focus on something else. They're are background hum of mental [00:05:00] weight that you carry all week without realizing it. It. When you schedule one dedicated day per month to tackle all of that open loop back office work, a couple of things will happen.
[00:05:11] Number one, you stop worrying about when you're gonna get to it because you know exactly when is happening, the day you've scheduled for it. And two, you actually finish things because you have a real block of time, an entire day. To work through something properly instead of pecking at it in stolen 15 minute windows when you're trying to distract yourself from deep work, the key here is picking the right thing to work on before your back office day.
[00:05:38] Think about what would make the biggest difference to how your business runs. That might not be the most satisfying task on your list. Cleaning out your inbox feels productive, but fixing a broken funnel or updating your onboarding process probably moves the needle more.
[00:05:54] Be honest with yourself about what matters most and when the day arrives, turn off [00:06:00] your desktop notifications. Put your phone in airplane mode for at least two hour stretches, and plan for things to take longer than you expect. Back office projects have a way of expanding. You go in to update one thing and discover three related things that also need attention.
[00:06:15] That's totally normal. Build buffer time in from the start instead of being surprised by it. And finally, your third day is your review and planning day. This is the one that ties everything together. This is where you zoom all the way out. You step out of the day to day and actually look at your business from the CEO chair instead of the worker.
[00:06:35] Be chair. Those two seats require really different kinds of thinking, and most of us spend almost, or all of our time in the worker bee seat. The structure I use is to split the day kind of in half. The first half is review, and the second half is planning. You might find one takes more time than the other depending on where you're at in your business, and that's totally fine.
[00:06:58] You'll figure it out as you go. [00:07:00] For the review side, you're looking at what actually happened this month. Pull out your key metrics, your website traffic, your sales numbers, whatever matters most in your business, go through your project management system or planner and flag anything that didn't get done so you can decide whether to carry it forward or let it go.
[00:07:19] Look at your ideal work week and ask whether it's still matching your reality or whether something needs to shift. Review where you are in your short and long-term goals. Are you on track? Did something change? And if this resonates with you the way it does with me, sometimes I'll spend 30 minutes at the end of the review block, just journaling about the month.
[00:07:40] Not analyzing, but just reflecting what came up, what was harder than expected, what surprised me, what kind of things do I wanna do more of? And less of that kind of unstructured thinking, often surfaces things that data alone won't show you. And then you wanna flip to planning. This is where the hooky day and the [00:08:00] back office day come back in.
[00:08:01] It is one of the first things I do when I'm planning my time is schedule all three monthly theme days into the upcoming month. Get them on the calendar before the month fills up because if you wait, it'll just get bumped every single time. Beyond that, use this planning block to schedule things that matter, important calls and meetings time set aside for your biggest priorities.
[00:08:24] Next steps on specific goals. You're not just filling your calendar with tasks, you're designing how you want the month to go before it runs away from you.
[00:08:32] And here's a really practical tip. Create a checklist or simple template for this day and review it every month. It doesn't have to be fancy. A Google Doc or a notion page you print out works perfectly. The point is that you're not starting from scratch every single time to try and remember what to review and what to plan.
[00:08:51] The structure and the scaffolding is already there, and you just move through it. So here's your reset and reclaim action step for the week. Open your calendar [00:09:00] right now and block those three days for next month, a hooky day, a back office day, and a review and planning day.
[00:09:06] Don't wait until the month starts because the month will fill up and these will just be the first things to go. Take 15 minutes right now to protect those days. That's the whole action step. Start there. If this episode resonated, I'd love to have you join the Productivity Rebellion.
[00:09:22] It's my free monthly guide for a woman who refused to choose between success and sanity. Once a month, you'll get one productivity strategy that actually fits your real chaotic life behind the scenes. Stories from my month, not Instagram. Perfect advice and the chance to ask me anything I answer subscriber questions right here on the show. Think of it as your monthly reset when you're tired of holding everything together with duct tape and coffee. You can sign up for free at carachace.com/productivity-rebellion.
[00:09:50] And PS. If you're ready to stop white knuckling your way through every week, check out Chaos Detox. It's my weekly planning method built for high capacity woman. [00:10:00] Learn more at carachace.com/chaos-detox.
[00:10:03] Thanks for listening. If this helped, please leave a review.
[00:10:07] It helps other woman entrepreneurs just like you find the show. I'm Cara Chace reminding you to keep questioning the rules and making your own.
