Ever felt like planning your day was a prison rather than a support system? In this episode I chat with day planning expert Jess Massey to uncover how to shift from panic-led planning to intentional, peaceful productivity.
Jess shares her personal journey and tangible steps to make day planning a flexible support system tailored to you. We delve into her Hustle Sanely framework, designed to help you prioritize without sacrificing your well-being. If you’ve ever felt overwhelmed, directionless, or constantly dropping the ball, this episode is your guide to reclaiming control. Don’t miss out on turning chaos into calm!
DSL Workshop, Peacefully Productive Planner, previous episode with Jess
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TRANSCRIPT
Monica Packer: Hi, I’m Monica Packer, and you’re listening to About Progress, where we are about progress made practical. During the winter holiday break, I took a break from a few habits. It was mostly a shift, like I didn’t have to wake up at the same early hour or exercise in the same way, because my kids were getting up later, but other habits totally went on the back burner.
I simply needed a break from them, like meal planning, day planning, some personal journaling. And that was all well and good. we have ebbs and flows with our habits, if they’re there to support us, then it’s okay
if we don’t do them the same way day in and day out, But near the break, in a span of just 24 hours, I forgot about two important things. One, a church activity for one of my kids who was really excited to attend. And then second, a piano lesson. And both of these things were totally on my online calendar on my iPhone, but they weren’t on my day planner because I wasn’t day planning.
Forgetting about those two events reminded me why I day plan. When we think of day planning, I think a lot of us envision someone who is super regimented and disciplined and type A. I am none of those things. And yet I love to day plan.
I day plan, not because I am naturally good at, or even like the process. I day plan because I appreciate the results. . I haven’t always been a day planner. I’ve had a volatile relationship with day planning in the past from when I was an overachieving perfectionist who was time blocking every second of my time lived and died by my planner to being someone who didn’t plan at all for years and years.
Day planning was a habit I gradually picked up over the last few years. And while I took a break from it in 2023, I reprioritized it in 2024, after I was out of my survival year of having a newborn.
And how did I know that day planning needed to be one of the top on my list to bring back? Well, my brain was always spinning. I was dropping balls right and left. I constantly felt both overwhelmed and directionless. It was time. If you’re feeling it’s time for you too, to consider day planning, this episode is for you.
I interviewed Jess Massey, who has been on the show before to talk about peaceful productivity. But today we are talking about how to shift day planning from being something that is panic led to more intentional and peaceful driven. And it, we talk about her own history with planning and practical ways that you can take on day planning in ways that work for you.
There’s going to be levels of day planning. There’s so many different forms of day planning, regardless of where you lie in any of that.
She has some good practical takeaways that I believe apply to anyone in any season and to any degree in which they wish to day plan or have the capacity to do so.
So if you’re nervous about an episode on day planning, don’t be. Jess Massey is the host of the hustle sanely podcast, a planner, creator, and founder of the community centered productivity brand hustle singly. She uses her framework, the hustle sanely planning system to teach ambitious women, how to live peacefully, productive lives by creating harmony between their work well being and relationships, no matter what season they’re in.
That interview is coming up after a quick break for our sponsors.
Jess Massey, welcome back to About Progress.
Jess Massey: I am so excited to be here again. Thank you, Monica, for inviting me back. What an honor.
Monica Packer: I love learning from you. I also feel like everyone who follows you online probably thinks, oh, you feel like a friend and that’s who you are. You’re like the internet’s friend. And you’re also the internet’s like, hey, let’s get you to be more productive without losing your mind
Jess Massey: Yes, that is my goal. so I appreciate you saying that. I always, uh, when I first started Hustle Sanely, you know, on Instagram, how like next to your name, you can put like your title or, you know,
whatever. Mine says Jess Massey dash Hustle Sanely now. But before Hustle Sanely was the name of my business, it was Jess Massey, your online BFF.
So I
appreciate that. Yeah.
Monica Packer: Okay. I didn’t even know that. So like, there you go. Now you just got proof that you’re doing your job really, really well. I love it when that happens. Well, we’re going to be talking about day planning today. Last time we talked about, specific habits to form that help you be productive in ways that you are peacefully productive, what you’re not sacrificing your mental health for.
Uh, but today I wanted to dive into day planning, which actually is not my favorite topic. If I’m going to be
Jess Massey: I love the honesty, I do.
Monica Packer: it’s not my favorite topic, but I have to tell you, it is so helpful. It is so supportive. So while it’s not my favorite thing, it’s one of my favorite results
Jess Massey: There
Monica Packer: all the habits, yeah, that I have.
So we’re going to be talking to the people who were like me, but maybe they haven’t gotten into the actual habit yet of being like, Oh, you know, it just feels like too much. I don’t want to do it. But I also. I know I need to, I know it’s time,
so let’s start with your own history of day planning. and if that’s been just part of your personality or not.
Jess Massey: I love this question because it took me back mentally when I was looking over it. I’m an eldest daughter I am very very type a like I’m pretty sure that I came out of the womb ready to take control and Plan
my little heart out Growing up. I planned from a place of panic to
Whereas now, I plan from a place of peace. So, I used to plan every little detail, like, down to a T. Like, it was definitely from a place of control and panic. And I would freak out, like, freak out internally, externally, like, all of it. If everything didn’t go just like perfectly according to my plan, I would beat myself up. I would push myself so far past my limits in the name of getting my mile and a half long to do list done every single day. Now I know that our schedules and routines are tools, not chains. That’s something that I say all the time and I plan so that I can steward my time well. So my mindset Has really shifted when it comes to day planning I plan now so that I can be intentional with my time so that I can show up for my days in a way that Aligns with my priorities So i’ve always been a planner But my heart posture toward planning has gone from an unhealthy place to a healthy place if that makes sense
Monica Packer: It does. And it’s actually helping me understand why I said it’s not my favorite topic. And it’s because I had such a panic filled relationship with planning in the past, especially when I was an aspiring perfectionist. And just like you said, like planning to the minute detail, and then your whole day gets thrown off if you don’t get one thing right.
And then just the level of expectation was so unrealistic. So let’s just tell people that’s not this.
Jess Massey: Absolutely not no
Monica Packer: That’s not this. But how, how would someone know if it is time to consider day planning? Like, what are some signs that, oh, maybe I should revisit this topic, even though, and this habit, even though I thought it wasn’t for me?
Jess Massey: I think when I’ve worked with clients and students, I think the number one sign is you go to bed feeling unaccomplished and kind of bummed out and stressed out about how that day went, and then you’re also going to bed and waking up anxious about the day ahead. So, that’s like the number one sign, is if you feel like you’re just in this thing. Kind of, uh, unescapable. Is that a word? I don’t know. We’re gonna
go with it.
Monica Packer: Yeah.
Jess Massey: Unescapable
cycle of, like, going to bed stressed and waking up anxious. Just about the day behind you and the day ahead. Like, you can’t
find any peace. Whether it’s how the day went or how the day’s gonna go. Mm. Mm.
Monica Packer: I basically put it on the back burner after I had my baby in 2023, which I know you and I have babies really close together. That was a back burner habit, but I knew I had to bring it back to the foreground when I was filling those things.
And also when I was dropping major balls, like forgetting piano lessons or major things in my life, and just feeling kind of that brain on constant. Running mode. Like I couldn’t get it to stop. So it helps. It helps that mental load piece. , so with this, why does it help so much? I mean, you talked about that posture, your heart posture that you changed.
Why does day planning even matter? And why should people consider to have this in their lives?
Jess Massey: I feel like I kind of alluded to it a little bit already, but I truly believe, and I’ve seen it in myself and in others, when we plan our days, we get to decide what matters and how we’re going to show up for what matters to us. Planning your days with intention. I feel like it’s taking ownership of your life, right?
It means you’re not watching from the sidelines. You’re you’re a player in the game, right? And so when I think of day planning and I think i’ve heard you say this before too Day planning to me it truly is an investment in yourself Because a little bit of time to plan up front saves you so much brain power and squandered time the next day When we don’t plan and we go into the day just kind of I say flying by the seat of our pants, it can feel like Life is happening to us instead of for us like we’re kind of running around putting out fires all day But we don’t really have anything to show for it at the end of the day other than feeling spread too thin Feeling plagued by a never ending to do list when we don’t plan our days We we just don’t have a metric to look at to help us say okay cool today What well like I feel good about today At the end of the day, instead, we just constantly feel like we didn’t do enough, we didn’t measure up and, like I said earlier, we go to bed already stressed out about how much we have to do tomorrow because we didn’t get it done today.
Monica Packer: So what does wise day planning look like? And I say that because you talked about, you know, we’re recovering perfectionists in this community. So we talk about the spectrum of perfectionism, the all or nothing, and how they’re often feeling the same. Like when you plan too much, you can feel really scattered.
And when you don’t plan at all, you can feel really scattered. But sometimes we don’t do something because we think there’s only one kind of way to do something like that minute, panicked kind of way. So what does wise day planning look like?
Jess Massey: To me, wise day planning involves a lot of margin and a lot of flexibility. So, okay, I’m a productivity coach and I will be the first person to tell you, The chances of your day ever going, like, perfectly according to plan, like, that you have in your little planner, or on your little notepad, or on your Google calendar, whatever you choose to use to plan, the chances of your day going according to that ever? Very slim. I won’t say impossible, because nothing is impossible, but very, very slim, right? But having that plan in place as a guide for your day is going to give you just so much more peace, because you’re not in react mode all day. And you’re not going to have that decision making fatigue. And I feel like wise day planning means that you’re giving yourself the margin to be flexible because life happens, right? No matter who you are, you have different roles that you’re responsible for in your life. Right? And so the key to not. Feeling like you’re kind of running on that hamster wheel and how to make day planning support you Well is to do it in a way that you can pivot within your days
Monica Packer: And this is why I love talking to you because even now, as I put this back in my life, I still have that part of me that thinks, Oh, day planning is like, you know, very, very specific and very detailed and like no margin. And you’re, it’s. It’s exact opposite. It’s building in the margin. It’s creating the ability to be flexible.
Let’s talk more about the practical ways they can do how. We’re, we’re going to talk maybe about, uh, like mediums, um, they can use in a bit, but let’s start with like, no matter what you use, here is what peaceful, mindful day planning looks like.
Jess Massey: Yeah, so It sounds kind of silly when you say it out loud but to me In order to plan your day well You have to have a plan to plan, okay? So
it’s, it’s so daunting to just sit down and stare at whatever medium you’re using and try to plan if it’s not something that you’re used to doing. If it’s not a habit that’s already woven into your life, right?
Like. Even if you’ve planned in the past, if your season of life is different, if the roles that you’re showing up for are different, the way that you’re going to have to plan is going to look different. So I think you have to go into planning with a plan. Okay.
And so I, when I create a plan, my first step is always to set the intention because I learned this about myself in therapy. I need to know why I’m doing something or I’m not going to want to do it. That, that’s what creates motivation in me is knowing why something matters, why I’m showing up to do it. And so to me, I teach what’s called the Hustle Stanley Planning System to my students and my online community, and part of that is having a daily planning meeting.
And so, the purpose of a daily planning meeting is to prep for the day so that you can take ownership of your time and energy so that you can show up with intention. So, that’s the first thing. Like, know why you’re doing it. Like, what does this matter? Why am I showing up to spend like 5, 10, 15 minutes prepping for the next day?
So that’s why. That’s my why. But you have to come
up with your own why, okay?
Monica Packer: So quick question on that, Jess. Is this like an overarching why for planning in general, or is it every day when you plan, you’re like, what’s my intention for planning today?
Jess Massey: Usually for me, it’s just like my overarching, like this is why I do it.
And then some of my action steps, because I’m a, I’m a, I’m a list girly. Like I need a plan to follow. I need a framework because I’m a mom. I’m a business owner. I’m a wife. Like I don’t have a lot of spare brain power. Right? So I like to be able to take a framework and kind of plug myself into it. And let it do the work for me. So i’m gonna share with you if you’re okay with that like the framework that I use to
plan my days. Okay, great
Um, yes Yay, perfect. Um, so it’s a five step framework and again It might sound daunting if you’ve never done it before, but I would encourage your listeners to just listen with an open mind and open heart.
Don’t go into it thinking that you have to start doing all of these things tomorrow or that you have to do them all perfect the first time you try it, right? Um, this is just like kind of a launch pad, right? Something for you to get yourself going. So, the action steps that I follow, um, step number one, make note of any time bound tasks.
So, you mentioned, Monica, that things are slipping through the cracks, like piano lessons. So, I’m assuming things like that, you know, they have a time attached to them that we’re not necessarily in control of, like, yes but like it is what it is we need to be somewhere a So that’s always my first step that I recommend people do is make note of any time bound tasks. Things that aren’t super flexible and that you’re like, okay, we’ve got to be at XYZ place at XYZ time. So make a note of those first. And then my second step is to check in with yourself to assess your energy.
So this kind of gets into my intention setting on a daily basis. So, and it’s more so kind of tuning into like, okay. How am I feeling what’s going on in my life? And how can I make my plan for either today or tomorrow depending on when you do your day planning support me where i’m at Um, so I am currently walking through a season of pretty heavy grief And so the way that i’ve planned out my days the past couple of weeks has looked vastly different because i’ve had to check in with myself
and Set the expectation of okay.
This is where i’m at You What is realistic? What actually needs to be done, and what can I let go of in this season? So that’s why step two, it sounds fluffy, and it sounds, and I’m putting this in air quotes, extra, like, oh, I don’t really need to do that step, but doing that step, checking in with yourself to assess your own energy, is That’s where we kind of get out of that mindset of perfectionism and feeling like every day has to look the same.
Every day your
to do list has to be slammed, your calendar has to be kind of like bursting at the seams. Um, so that’s step two. Just check in with yourself to assess your energy and it’s truly as simple as asking, Okay, what’s going on in my life? How am I feeling? Is there anything I can let go of that I just don’t have the capacity for tomorrow or today depending on when you’re doing it So that’s step two Step three, and this one is pretty specific to hustling sanely, is determine and schedule your Hustle Sanely 5 habits. So, we talked about this on the last episode that I was on with you, and Hustle Sanely 5, it’s just a daily routine that I do and that I teach. To help people get the most important things done every day while prioritizing their mental health and the important relationships in their life. If you want a recap, I’m happy to like, read over the five steps really quick, just so we’re
all on the same
Monica Packer: Yeah, definitely share them again. We’ll definitely link to the old episode, but it would be helpful to get a
Jess Massey: Okay, perfect.
So, yeah.
Monica Packer: that’s cause I’m like part of your community, so.
Jess Massey: Okay, so the Hustle Saintly 5 Habits, we also call it HS5, is, the first one is Complete Your Focus 3. So, that one is the only one that people might be like, Huh? What is that? So, Your Focus 3, those are your three most important tasks to get done that day. So, whether it’s a deadline that needs To be met for work, whether it’s, helping your kid with a project that’s due later that week.
It’s kind of things that like you don’t have a lot of wiggle room on. You’re like, okay, this has got to be a priority today. Um, so that is the first one is complete your focus three. Second habit is move for 30 minutes. So I say move instead of exercise because this can look like whatever Movement feels good for you.
Like you that’s up to you. Okay, so move for 30 minutes Number three is tidy for 15 minutes. So I’m talking about your physical space here The fourth one is say or do one kind thing for yourself And the fifth one kind of goes along with that one and that is say or do one kind thing for someone else So that is my third You action step in my day planning routine is determine and schedule your hustle saintly five habits. So, uh, the fourth step after that kind of piggybacks off of it. So the fourth step is make a note of any other tasks that you’d like to complete once your focus three tasks are done. And I think it is so, so, so crucial. I don’t care what type of planner or system or anything. If you’re using a blank piece of paper, it does not matter. I think there is so much power in. Prioritization, but like actually setting aside the most important tasks in a different area on your task list, whether it’s just creating a different heading, whether it is highlighting them in a different color. I just think our brains are so visual, right? And so I think it’s, it makes our to do list so much. Less overwhelming if you look at it and you’re like, okay These are the top three right here and then all the rest of the stuff This is if the top three get done, right? It just for me. That was the
biggest mental. Yeah, exactly And that was the biggest mental shift when I started going from like panic planning to peaceful planning was knowing that like It’s okay if everything on my to do list doesn’t get done for the day, as long as the things that absolutely need to get done, get done.
Like,
everything else, like you said, it’s like, yay, good, I love the extra sprinkles on top, but like, life is gonna go on if these things don’t get done today. So that’s step number four, is make a note of any other tasks that you’d like to complete once those focus three tasks are done. And then the last action step for day planning is create your schedule using what I like to call energy aligned time blocking when possible. Um, and this, it’s a lot of words, but it’s basically just saying create a schedule that feels good for you and makes sense for how you operate. So if you’re a night owl, Do your creative work at night, right? Like if you’re a morning person like me if I try to do any work at nighttime like creative work It would take me three times as long.
I would have to, I would have to overcome so much internal resistance because I am a sleepy head at night. I am a morning person. I have my mental clarity, my mental energy in the morning. So I try to create my schedule in a way where those kinds of tasks are in the morning. So that’s what I mean when I say energy aligned time blocking, make your schedule make sense for how you’re wired.
I feel like so often We see, you know, especially on like social media, the, you know, productivity gurus, they’re saying like, okay, you have to wake up at 5am, you have to do like your most
important work in the morning, like this, that, and the other. And if you’re a morning person and that works for you, great, amazing, like ride with that. But what if you’re an evening person? What if you’re a night owl? Like that doesn’t work for you. So instead of just kind of trying to plug yourself into something that doesn’t make sense for how you’re wired, lean into how you’re wired and create your schedule accordingly where you can. I know some of us, we don’t get to set our work hours.
We don’t get to bring our kid to piano lessons at 10 PM. If that works best for us, you know
what I mean? So when you can just make your schedule work for you. So those are the five steps that I follow to plan my day. And like I said, I know. that it can sound a little bit daunting or overwhelming if you’ve never done it. But now, as somebody who’s been a day planner my entire life, someone who uses this system, this takes me five minutes a day. I typically do it the evening before and then I kind of hammer in the morning of, like, I’m like, okay, let me check in, see if anything shifted, anything changed, if I feel different, if something popped up in life. Um, and So I think it might take a little bit longer at first, but just know that with practice you’ll get quicker at it and it won’t feel as daunting. And it, again, we talked about this earlier. It’s an investment in yourself, right? So investments take a little bit more work up front to pay off in the long run.
Monica Packer: Yeah, but that payoff is there, and that goes back to what the intention is behind this habit in the first place, which I think can also guide the how, in terms of how people do it. So if you’re at the beginning of this, I think you can, you know, take one piece of this framework that’s going to help you even get into a habit of day planning and then gradually add on the rest of the steps.
I want to talk about baseline in just a moment, like a baseline version, but I do want to just, as you were talking, Speaking, I was imagining like this visual in my mind, since we are visual people. But since this is a podcast, I have to like paint the visual. I was thinking like the way we used to look at planning was more like bars, like very, like iron metal bars.
Like this is the way we do things. And even down to like how people would do their framework. Like it’s about getting as much done as you possibly can every day. And instead what I see. your framework as is more of like a net. So it’s there to support you, but there’s flexibility there, both seasonally and day by day, um, to match your season, to match your preferences, to match what you even want to do or not do that day.
Um, and you spoke to your season of grief, your grandmother died recently, which we’re so sorry about. And I am so appreciative of how you’ve showed that flexibility for yourself and also the structure. So that’s what we’re looking at. This is a net. This is Annette.
Jess Massey: Absolutely. That is such a beautiful visual and it just makes so much sense. And I know that you sharing that just had light bulbs going off in
people’s heads because I’ve never heard that before. And so a light bulb was going off in my head. So I love that.
Monica Packer: well feel free to use it when you, when you share more about it in the future because that’s what it feels like.
Uh, so you know what baselines are because I’ve been able to talk to your community about habits,
is if there’s a good, Baseline way for someone to start. What do you think that would be? And I know that’s still going to be so individual for so many people, very subjective, but in general, where would you say, like, if this is all you can do, not just for a day, but even for a week, this, this is what I would recommend.
Jess Massey: I think, and of course I’m biased, using Hustle Sanely 5. So, planning out your Hustle Sanely 5 for that day or the next day. I will tell you, in my season of grief, walking through this with my grandmother, it’s been a very, um, So, um, I think it’s a really strange season because she was diagnosed with stage four pancreatic cancer in mid October and she passed away at the tail end of November.
So everything happened in the Very quickly, very quickly. And I’m in my full season at work. You know, it happened in the middle of Black Friday. I have a physical product that we sell. So it’s like, this is the time that we’re, I’m supposed to be like, leaning into work. Um, and so, by using Hustle Sanely 5 to plan each day, I was able to get the essentials done. While still honoring the season that I’m in which is grief and making sure that I’m Moving my body in a way that feels good every day My workouts looked very different than they did pre grief season if that makes sense
Um, you know my my work to do list they shrank An incredible amount over the last month and a half How I showed up for work Four people, the people in my life like saying or doing one kind thing for someone else.
A lot of that was time spent at the hospital with my grandmother.
Um, so I think using Hustle Sanely five, it’s meets you where you’re at. It doesn’t matter what you’re going through. It
doesn’t matter what season you’re in. I clung to hustle Sanely five when I was postpartum too.
Um, so I, that’s why I really love Hustle Stanley five is because it really does meet you where you’re at.
And it’s kind of an all encompassing. Routine that will hit the basics that you need to hit to protect your well being on a daily basis. So I think if any of this you’re gonna just You know grab on to one step and kind of try it out I would say to plan out your hs5 for that day or the following day depending on when you’re doing it Um, and if that feels too daunting if you’re just like, um, i’m not even there yet like four weeks Planning five things, like, that feels like a lot.
I would say just start with step one. Like, a lot of people feel like things are falling through the cracks. So, start making a note of your time bound tasks the day before or the morning of. And then, maybe once that becomes like, Okay, this feels good, this doesn’t feel like I’m having to grind to get through that, Then maybe add in your focus three.
So I think that would be a great starting point if you’ve never planned You just feel like completely you’re like this is brand new to me I want to start but I want it to be sustainable I would say make note of your time bound tasks and then choose the three tasks that are the most important for you to get done that day Yeah,
Monica Packer: there. You know, baselines, we, we talk about in our community, how baselines are for your worst of day. And you’ve been living that out, like your literal worst of days. And, um, oftentimes that’s proverbial, like it isn’t meant to be liberal. And in this case, it has been for you.
So it’s, it’s nice to hear not what you’ve been through, but how you’ve been able to support yourself,
even on your worst of days with the way that you’ve taken care of yourself via planning.
So. You talked about focus three and I just want to ask a quick question about that to clarify for people who are still in that pendulum swing of thinking like, like focus three, that means like they get my, they may get stuck in the weeds a bit.
They may put like three huge tasks that are impossible to do for a day. Or they may think like, well, do I need to put empty the dishwasher underway focus three? You know, it’s easy to get stuck in the weeds there with the both minute tasks or the bigger tasks like over planning. So just any suggestions you have for that focus three in particular, is there.
Yeah,
Jess Massey: Yeah,
I think it’s gonna depend on what season you’re in.
So, the season that I’m in with grief, things like unload the dishwasher might be on my focus three, right? Like, if I’m operating at my normal capacity, Something like that wouldn’t be on my Focus 3. like, I, yeah. exactly. Like, I don’t, I personally teach. Not to put habits on your focus three because they’re habits You’re going to
likely do them without having to think about it Anyway, focus three is more of a tool to hold you accountable to get things done that either have a looming deadline Or things that are gonna move you forward forward in the direction of a goal that you’re
working toward. And I’ll give you an example. So I just finished, it’s so wild to talk about. So I own a planner company, as you know, and I actually just wrapped up our 2026 designs and sent
them off, which I’m like, we’re not even in 2025 yet.
It’s yeah, it’s, it’s a wild time when you own a planner company. Don’t ever ask me what year it is.
Cause I can’t tell you.
Monica Packer: I bet,
Jess Massey: yeah.
So I just sent off our 2026 designs. And so I would never in my wildest dreams. Put on my Focus 3. Do 2026 designs because that is massive that is a huge task So instead complete the 2026 designs the way that I teach it in the hustle sanely planning system That would be my monthly focus goal and from my monthly focus goal.
I would then break it down into three three big action steps and then I would break those three big action steps into what we call nitty gritty action steps. So I would be using nitty gritty action steps as my focus, my daily focus three. So an example would be, um, instead of like on my focus three saying 2026 designs, like
do the 2026 designs, it would say write out all of the 2026 holidays.
Might be one of my focus three tasks for a day. Does that make
better sense?
Monica Packer: Oh, it totally does. I’m thinking about this even for my son’s room that I’ve been needing to redecorate all year. I keep saying, like, boy’s room, but until I finally was like, pick out the paint
Jess Massey: Yes.
Monica Packer: go get the paint for another one. Like, paint the room was a bigger task, but I did it.
And now it’s like, find a dresser, so.
That’s okay. Great examples there. So the way we’ve been talking about this, I think is so, it is for newbies because we’ve been talking about day planning, but you just mentioned, you know, your, your quarterly, your monthly, your weekly kind of planning too. So, so this is where I’m going to say that is. so helpful and that’s like the next kind of step.
But that is what will make your day planning easier too. So where I think you guide people to start and how I learned to start this both years ago when I finally picked up day planning and even just this past year as I picked up day planning again is just to start with the day and then gradually you can pick up the weekly version of the planning and the monthly and the quarterly.
I’m working on the quarterly right now. That’s what I’m trying to work on better doing those kinds of things. Um, so. Still, you know, don’t get too overwhelmed. But yeah, that’s, that’s the ideal we’re shooting towards.
Jess Massey: and like you said I did not start out You know planning my entire year now I’m at the point where like that I I do my yearly planning in November just because that’s what feels good for me and so I sit down and I plan out like my Business for the following year like my life goals for the following year and now it doesn’t feel daunting It feels supportive, but I had to build up to that.
So I’m glad that you mentioned that that it’s not It’s not just something that you should feel like you’re, you know, coming out of the gate ready to plan your year, every single quarter, every single month, every single week, every single day. Like, don’t let yourself go there mentally until you’re ready to go there mentally.
And that’s what I
always remind the women in my community. You’re in the driver’s seat. You’re the leading lady of your life. Like you’re the boss of these tools. They’re not the boss of you. You get to decide how they’re going to support you. They’re not there to stress you out.
Monica Packer: Beautiful. So this is where we could have another hour long discussion about different, like, mediums. Like, how do you do virtual? Or, like, do you do Google calendar? Your Apple calendar? And, and do you do, like, uh, I’m thinking of all the other product, productivity apps that I have totally lost.
I, cause I don’t use them.
Jess Massey: click up Asana, like
all the things. Yeah, yeah,
Monica Packer: all of those things.
Okay, we’re not going to go there because I just think it’s too much, and this is where it’s like, start where you’re at, but if we’re going to talk about paper,
okay, and you know, I personally use my, my eCalendar, like my Apple Calendar for appointments, and then I, then I still write everything out on my planner.
That helps. Let’s talk about your planner specifically, okay, because I bought this with my own money, just so everybody knows, and I’m already planning, this is going to air in 2025, but I’m already planning my 2025, which is a big. Good thing for me to be moving back up towards the ideal. Um, and I’m loving it.
So I want to
Jess Massey: Oh, thank you.
Monica Packer: what specifically you think people would find in your planner, the peacefully productive planner, what could they find there?
Jess Massey: I think the biggest feedback that I get from users of the planner is that it is, it’s not just a planner, it’s a lifestyle and it helps people. I think because, what sets the Peacefully Productive Planner apart is the fact that Hustle Sanely 5, that kind of daily routine that I mentioned earlier, It’s woven throughout the planner in a way that makes it seamless for you to plan that out each day without using a lot of brain power. Um, and so I think that’s the biggest set apart in our planners and the way that I created our planners, I was just sharing this on my Instagram stories, um, earlier this morning because I use our planners too. Surprise,
right? Um, and it’s just in the season that I’m in the planner has been so supportive because I feel like A lot of people are looking for a lot of space for long to do lists and, you know, just jam packing their days. Our planner isn’t set up in a way that allows you to plan that way, it’s set up in a way that kind of, uh, kindly pushes you to prioritize and
to make decisions before you start just, like, writing these mile long to do lists.
Um, And so that is what I love so much about our planners is that it they lovingly prompt you to learn the skill of prioritization Um, of course, there’s a spot for like a weekly to do list for like if you know You’re like, I don’t know what day this needs to be done I just know that it needs to be done like
there’s a spot for that There’s a little blank box for each day and some people like to use that space for to do lists, which is totally fine But that’s what I love so much about our planners is that They’re set up so that you can easily plan out HS 5 every day so that you’re showing up for your life in a well rounded way that prioritizes you as a person and not you as a productive machine.
And Yeah.
it just, like I said, it really teaches you to kind of sharpen that skill of prioritization.
Monica Packer: That’s what I love about it too. It feels both more, uh, structured, but in a way that’s also doable, but also forces me to actually be realistic and choose, which is really important. Now you mentioned planners and that’s because there’s two layouts.
I love the weekly layout. That means you get one planner for the whole year and each, like, when you open it, the spread is your week,
right?
Um, other people like, what’s the other version? I don’t know the name.
How to describe
Jess Massey: Yeah, we call it a quarterly planner.
So, the one that you described, the weekly, that’s the one I use as well. Um, and that is our dated planner. So, like you said, you buy one, you’re set for the whole year. And then we have our quarterly, that’s still called the Peacefully Productive Planner, but it’s just like the quarterly versus the weekly. The quarterly, it is a, it’s undated, so you can start it and stop it whenever you want. And it’s, the way that they’re set up, um, it’s three months. It’s worth of planning space, but it’s more detailed. So you have a monthly spread, you have a weekly spread, and then you have a daily spread. So that way if
you’re in a season,
Monica Packer: the whole spread is,
or that page is that
Jess Massey: That day. Yep. Yep. But there is a weekly spread as well for each week.
So it’s just, if you’re in a fuller season of life, maybe every single day just looks so incredibly different. Maybe you’re wedding planning or you’re planning For, you know, a big move or something, that’s when a lot of people chime in and say that they’re really kind of clinging to that quarterly planner is that they just have like a to do list that is a little bit longer each day because it’s made up of a lot of little things.
And so they just need that space to kind of get it out of their brain. Um, that’s when the quarterly planner would come into, I feel like good use, but we also have the daily planning notepad. So I personally keep a daily planning notepad handy. For if I’m working on a big project for work and I just feel like I need a little bit more space to like brain dump and organize my day, um, I don’t use it super often because the way that I have my life and my business kind of structured, it’s I’m able to like do my weekly and daily planning kind of just more Like bird’s eye view and I don’t really get in the weeds with list making and things like that on paper anymore Um, but that’s the point of having the two different kinds just so that they can meet you where you’re at Whether it’s a different season of life that you’re in or maybe you’re just a different style of planner than the weekly planner Has to offer, you know
Monica Packer: Okay, yeah, and I’ve, I’ve, Jumped around with so many planners over the years. And I’ve had a lot of online friends who’ve had great planners and I really, really love this. And I love, I personally have the weekly, um, but I can see, and you don’t need both just so people
Jess Massey: Yeah, no, no,
Monica Packer: one or the other quarterly or the weekly layout.
Um, but I, I really love it. I’ve also become an affiliate, so I will put my affiliate link in the show notes. Um, Jess this has been fantastic. We always end with the final question, but before we do that, where should people go if they want to, , learn more from you?
Jess Massey: Everything that I do on the internet is at jessicamassie. com and if you’re a visual person, you like a concrete example, I hang out on Instagram stories Monday through Saturday and I do my best to kind of showcase my daily HS5 in action just so that people can see like what I’m saying, like actually lived out
in like a day to day life.
And so my Instagram handle is at jessmmassie.
Monica Packer: Wonderful. And that’s what you’ve changed so much about how I’m showing up to my own work, because I realized, I told you this in the message, I was teaching and not showing and showing is so much better.
So thank you for inspiring that shift for me too. And for all that you were doing with Hustle Sanely, it’s really beautiful.
We’ll link to your podcast as well.
Um, so the final question is, we’ve learned a lot today. We’ve talked a lot. If there was only one thing they could do to get started today, what would that be?
Jess Massey: I would say, Plan tomorrow. Plan out Hustle Sanely 5 for tomorrow, or if you’re like, that’s just too much for me, plan out tomorrow. Write down what appointments and things you have, like your time bound tasks. And your three most important tasks that you want to get done tomorrow, and see how that feels.
See how you feel at the end of tomorrow, if it feels supportive. Um, and I just think that doing those two things, I don’t think that they will be too daunting for anyone. And I feel like they will just meet people where they’re at and make them feel like they’re investing in themselves, you
know?
Monica Packer: okay. I love that. We’ll make sure we put that on our progress pointers for the week for everyone who’s on the newsletter. So, Jess, thank you again. It’s been such a joy to be able to have you back on the show.
Jess Massey: Thank
you.
so much, Monica. I always love chatting with you, and it’s even more fun when we get to do it with your community. Yeah.
Monica Packer: a few messages after our last meeting.
I hope this episode gave you the hug and kick in the pants you need to grow. I’ll now share the progress pointers. These are the notes I wrote, so you don’t have to. And those on my newsletter, get them in a graphic form each week. You can sign up at aboutprogress. com slash newsletter.
Number one, day planning is a good habit to consider. If you go to bed, feeling stressed, but unaccomplished, you wake up feeling overwhelmed. But directionless. You find yourself forgetting about major things and dropping balls right and left. Or your mind is constantly running on anxious fumes. Number two, day planning is more about creating support, intention, and margin for flexibility than it is about following a regimented routine that keeps you tethered to it.
This sentiment should also be applied to how you choose to day plan. Number three, to get back into day planning or start it for the first time, begin with your overall intention. Why does this habit matter to you? Number four, A framework to gradually follow as you pick up day planning includes, make note of time bound tasks, check in with yourself to assess your energy.
Determine and schedule your Hustle Sanely 5 habits. I’ll share the HS5 to follow. Make a note of other tasks you’d like to complete if your Focus 3 are done and create your schedule using energy aligned time blocking where possible. And number five, HS5, the Hustle Sanely 5.
They are complete your Focus 3, your three most important to do’s. Move for 30 minutes, tidy for 15 minutes, say, or do one kind thing for yourself and say, or do one kind thing for someone else. Your do something challenge this week is to plan out tomorrow. What are those time bound tasks and what are your focus three?
If you do the challenge, I would love to hear about it. You can message me on Instagram at about progress or email me at hello at about progress. com. This show is listener supported members of the supporters club, get access to more content and more time with me, both virtually and in person,
my favorite benefit is more personal, our private premium, always ad free podcasts, where I lean into the personal side of personal development. In January, each Friday, we are sharing a shortened preview of the more personal content. And as part of that, inviting you to take advantage Of your first month being free.
You can sign up as a supporter at the Bestie or Ride or Die level with your first month free using the code FREEMONTH if you sign up by February 1st, and when you do that, you get access to more personal. Go to aboutprogress. com slash support and use the code free month at checkout.
Thank you so much for listening. Now go and do something with what you learned today.
Monica Packer: And you know, it’s, um, oh gosh, hold on. I had a thought and I just lost it, but it’s going to come back in just a second.
Oh, okay. It came back.
Jess Massey: It’s back.
Monica Packer: Yay.
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