Productivity & Time Management

Episode #342 – The Calendar And To Do List System That Helps Me Stay On Top Of Everything

May 14, 2024

I’m Cherylanne.
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Today, Cherylanne is redefining what it means to manage life with a full plate. Are you juggling a demanding career, family duties, and personal goals?

Cherylanne shares her game-changing system that integrates digital calendars, a to-do list, and a paper planner to streamline your week from overwhelming to organized. Gain crucial insights and practical tools to balance your schedule, reduce mental clutter, and prioritize what truly matters.

Ready for an empowering session on mastering your time and elevating your daily productivity? Let’s get your life back on track, starting now.

Show Highlights:

  • The importance of maintaining a calendar and to-do lists. 00:42
  • Learn to balance work and life as a professional woman  01:42
  • How to handle the complexity of multiple calendars. 05:57
  • Do you want to conquer overwhelm and chaos in everyday life? 07:34
  • Are you feeling pulled in different directions? 10:27
  • How to choose the right planning tools. 14:25
  • Discover ways to deal with a lack of trust in yourself. 17:31
  • Do you ever feel like your calendar is going out of control? 23:32

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Today, we’re talking about a calendar and to-do list system that really helps me stay on top of everything, and y’all, this is a good one. So, thanks for tuning in today. Because as I was getting ready for this, I was thinking about how often over the last, I don’t know, let’s say 14 years or so since I started my entrepreneurial chapter, how often I have been asked about my personal productivity. And the answer is quite a lot. It comes up quite a lot, likely because, you know, a fair amount of the content that I have shared has been in the realm of work-life balance. And because of that, I think one of the core challenges people face when they’re trying to find better balance is, how am I still going to get all the things done, you know? Am I going to have to just fly by the seat of my pants if I want to have some downtime? Or am I going to have to become this little robot who does nothing but productive tasks on the schedule in order to create any kind of space or leisure, you know, and even like service work if we want to have time for that. Sometimes we’re wondering how my productivity cycle is going to enable me to do the things that I want to do. And I think this has been a journey that has unfolded over my whole adult life.

And as we get this episode started, I want to admit that my natural set point for productivity is probably objectively pretty high. Okay, people who know me in my real life, not as a podcaster but who know me in my everyday life, would say, “Yeah, you get a lot done.” I have pretty high executive function in terms of my planning skills. I have a good sense of maybe time or how long things might take. So, there’s a bit of natural aptitude at play here for sure. But the real inflection point for me came when I had to move from running on instinct, you know, I was able to just sort of get everything done on instinct, to something that had more of a systemic approach. That happened when I had children. And I think this is probably true for a lot of you listening today, that up until that point, I was essentially just responsible for me, myself, and I, you know. Even when I had a lot going on, like at school when I was at college or in my first jobs before I was married and had kids, there was enough of me to go around. I was able to fit the things in without too much trepidation. And honestly, even when I got married and I was running a household and keeping things afloat for two people, that wasn’t really that much of a challenge. But when I got into the era of raising children, and I have three of them, if you’re newer to the show, you might not know, and they’re teenagers now. But when I started raising children is really when I pressure tested my way of doing things.

Things that I had done for years that had always worked started to just not work. And I can remember thinking things, in crazy thoughts like, “I don’t know how I am going to get this letter into the mailbox.” Like, when I had my first child nineteen years ago, I was trying to just get the basic things done. You know, cook a meal while I was holding this newborn, go to the grocery store, and it just felt like there was so much new pressure on my ability to get things done that I started realizing I would need to make some kind of adjustments or improvements to the system that I used for how I was going to do them right? How I was going to plan the things that needed to be done, how I was actually going to get them done hour by hour. And that got progressively worse when I added a second child and a third child to the mix. You know, there was a point where I was doing multiple jobs, and I had my entrepreneurial job, I was doing a full-time job in marketing for a skincare company, I had three children already, I was running my household. So, just the complexity was ramped to full tilt, and the more pressure there was on the system, the more this complexity was causing pressure, the more challenging it became. Now, I’m using that word “complexity” really choicefully here because I think that when we reach the point where we have to integrate multiple people’s schedules along with multiple schedules of our own, that creates one of the real pivot points. So, for example, if I had an entire calendar of activity that was associated with work, this is my work calendar, and a whole calendar of activities associated with what’s happening at home, and then I multiply that home calendar times, you know, at least three more children, and I multiply it by three children’s school calendars, right? By the time I had kids in school, the complexity that starts to get there with three school calendars, three kids’ activities calendars outside of school, my work calendar, our family’s social calendar, and then my husband who we’re trying to plug into all of this who’s running his own calendars, that’s a lot of complexity. And you may be in the same boat going, “Oh my goodness.” That’s what happened, you know, that’s the insight of what really shifted. Why did I used to be able to do this with a level of grace, a level of ease, and you know, now I feel edgy? And it feels perilous, like at any moment I might not be able to get these things actually done. Maybe things are even starting to fall through the cracks for you? Maybe you’re missing deadlines? And I vividly remember the day that I forgot about preschool pictures. My son was four; he was in the four-year-old class. I went to work, I sent him to school, and I got this call from the preschool office like, “Hey, we don’t have his picture form.” And I thought, “Oh my God. Not only do you not have his picture form, he isn’t even wearing anything that I want captured with permanent photographic evidence,” you know? And it felt like such a mom failed. And of course, with the benefit of retrospect, he’s now almost seventeen. We’ve survived the preschool picture debacle, but it really felt to me at the time like evidence that I was starting to miss things. And that was really the impetus to put a little bit of a more adaptive and robust system in place, but one that had to be simple, because I had to be able to keep up with it in the middle of all that complexity. You know, I had to feel confident that this would actually work, that I could prevent some of those moments of things falling through the cracks, where you know you’re slapping your hand on your forehead going, “I cannot believe this just happened.” So, if you are in that place now where you’re feeling overwhelmed by a packed schedule or multiple packed schedules for that matter that you’re managing, and if you’re constantly playing catch-up and wishing that you had your arms around things a little bit more, then this episode really is for you.

And I think the evidence that you want to make a shift is if you feel like you’re rushing all the time and there’s not a lot of peace and calm in your day, you feel like you’re constantly fighting fires and you’re always a step behind, and if that’s true, then we’ve got to make some changes. And for me, a major part of making those changes was the adoption of what I now call “the unified calendar system.” So, what is the unified calendar system? Well, it’s not super sophisticated. It is really just a simple way of integrating all of the different activities that you have to manage into one single calendar. So, you’re no longer toggling between multiple different places to figure out what’s happening when. Now, if you’re feeling like, “Wait a second, my life’s not that complicated. I don’t need to do all that. I can remember things.” You’re absolutely right. You know, there are certainly plenty of people who are able to remember all of the different things happening across their life without having to do this. I’m just going to encourage you to consider that if you’re spending a fair amount of cognitive energy just trying to keep all the balls in the air, then you’re not actually as productive as you could be. You know, that cognitive energy that you’re spending on trying to remember the things and the angst that comes from the fear that you’re forgetting something important, that’s energy that you could be spending doing things that you actually enjoy or that move you forward in your goals.

So, here’s how the unified calendar system works. You’re going to start with one digital calendar. And yes, I’m saying digital intentionally here, because while there are certainly people who like paper calendars and if that’s your jam, you do you, I am a big fan of digital calendars for a few reasons. One, because you can share them across devices, right? So, whether you’re looking at your phone, whether you’re looking at your laptop, whether you’re on a tablet, you have access to the same information no matter where you are. And two, because they’re infinitely mutable, right? You can move things around, you can change things, and you don’t have to worry about scratching it out and making a mess. So, that’s why I prefer a digital calendar. You can choose whatever platform you like. I use Google Calendar; you might be a Mac user, so you’re using iCloud Calendar; you might be using Outlook Calendar. Whatever it is, they all work roughly the same way. So, you’re going to start with one calendar and you’re going to enter in all the commitments that you have across your life, okay? So, you’re going to put in the work meetings, you’re going to put in your children’s activities, your social commitments, your appointments, anything that you need to do, you’re going to put it all in there.

And then you’re going to color code it, and this is a key step because the color coding is what makes this all manageable. So, for example, in my Google Calendar, all of my work-related activities are in a particular color. All of my children’s activities are in another color. All of my appointments are in another color. All of my social commitments are in another color. You get the idea. You can decide what colors make sense to you, but that’s how I have it organized. And then, you’re going to be able to see at a glance everything that’s happening across all the different areas of your life. You’re not going to be wondering, “Okay, what’s happening on Friday? Let me check this calendar. What’s happening on Saturday? Let me check that calendar.” You’re going to be able to see all of it in one place. And here’s where the real magic happens. Once you have everything in there, you’re going to sit down on Sunday evening, or Monday morning, whatever suits your rhythm, and you’re going to take a look at the week ahead, and you’re going to make a plan. You’re going to say, “Okay, on Monday, I’ve got these work commitments. On Tuesday, I’ve got a meeting at the school. On Wednesday, I’ve got to get my haircut. On Thursday, I’ve got a social commitment. On Friday, I’ve got to get this report done.” Whatever it is, you’re going to make a plan for when you’re going to do all of those things. And the key to making it work is not just having it on the calendar but being really explicit about when it’s going to happen.

So, you’re not just saying, “Okay, Friday I’m going to get the report done.” You’re saying, “Okay, Friday morning from 8:00 a.m. to 10:00 a.m., I’m going to work on the report. Friday afternoon from 1:00 p.m. to 3:00 p.m., I’m going to finish the report. And Friday evening after the kids are in bed, I’m going to proofread the report.” You’re going to get really granular about when it’s going to happen. And what I have found is that by doing this, it gives me a sense of calm, you know, knowing that everything’s been captured, that nothing’s going to fall through the cracks, that I’m not going to get that email saying, “Hey, where’s that thing you were supposed to send me?” And it gives me a sense of control because I know what’s happening when, and I know that I’ve made time for the things that are important to me. And I think that that’s really the key, is that when we’re not intentional about how we spend our time, it’s very easy to get to the end of the week and go, “Oh man, I didn’t do any of the things that I wanted to do. I didn’t spend any time on the things that are really important to me.” And by having this system in place, it helps me make sure that that doesn’t happen.

So, that’s the unified calendar system in a nutshell. It’s really simple. It’s really straightforward. But I think it can be incredibly powerful if you give it a try. So, I would encourage you, if you’re feeling like you’re drowning in a sea of commitments, if you’re constantly feeling like you’re fighting fires and playing catch-up, give it a try. Set up a digital calendar, put all your commitments in there, color-code it, and then sit down at the beginning of the week and make a plan. And see if it doesn’t make a difference for you. I think you’ll be pleasantly surprised. So, that’s it for today. I hope you found this helpful. And as always, I’d love to hear from you. So, if you have any questions or comments, please don’t hesitate to reach out. Thanks for tuning in.

Go to and you can buy my complete toolkit to get immediate access. You can start implementing it right away and experiencing those results. By the time things really ramp back up again at the end of the summer, and as we head into the school year, you’ll be experienced in this system. Don’t forget to message me and tell me how it goes! I know it’s going to be just brilliant.

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