A Peek Inside a CEO Mom’s Digital Calendar
Proof that a Simple System can keep even the craziest life organized.
Now that we are a little bit down the road together, I thought I’d take a few minutes this week to give you a peek at my calendar, which is based on a series of Simple Systems I have developed over the years. And when it comes to needing survival tools, well…I have what you might call a wee bit of experience.
In my day job, I am CEO of a small company that imports products to the US for a very specialized market. I have a team of 10 people, give or take, depending on how hard the tariffs are hitting (and lately, they have been hitting HARD). For a number of years, I was a single mom raising a son under joint custody with his father. On weeks when he was with his dad, I was often on the road for work, sometimes abroad. When he was with me (or if I was home and he had something scheduled, like a sports game or school event), I was juggling work, his activities, homework, cooking, cleaning, and trying to stay above water.
Things are a lot calmer now that he is older and almost ready to head to college. I am remarried, so he has an awesome bonus dad, and I have a partner at home who is a unicorn in his ability to do housework without even being asked. But. BUT.
I am still the work-from-home parent. And the mom. And somehow in charge of all the family arrangements, keeping the schedules, making the meals, and keeping this whole enterprise moving forward. All while running my company and still having time for book club. (sometimes I even read the book!) Oh, and did I mention our aging parents who live in two different states and are very creative in coming up with ways to test my blood pressure? Mental load is my daily workout.
What I am trying to convey is not “I have this all figured out, ha ha”, or “I have piles of money so I hire other people to run my life” (I wish) but rather, I GET IT. I don’t have a personal assistant, or a secretary, or, to be honest, the salary you may assume comes with the title of CEO (money may not buy happiness, but if I could afford a house manager…man, those book club books would be in danger of being read every month!). What I DO have is a set of systems I have put together over the years that keeps my anxiety low, and reduces the chances I miss something important because I have taken the information out of my brain and into the systems that keep, organize, and communicate the information when I need it.
In the coming weeks, I will be sharing information on how to set up specific systems. Not all of them will apply to your life. You may already have a better way of doing some of these things (and I would love to hear about them! I am always looking for better ideas). But what you may see is something that hits a nerve and makes you say “ooh, that would be helpful!” I won’t be showing you how to set them up in this newsletter, but I promise, we will get there. So, let’s dive in with today’s show and tell session!
My digital calendar - the central command center of, well, everything
Once you start adulting, you pretty much need a calendar. Most people use a calendar for the obvious things - doctor appointments, family birthdays, school events, etc. But I have discovered first-hand that there is a HUGE difference between using a digital calendar to record all of the ways your commitments are running your life, and using it proactively to reduce mental load and create a system that works even under stress.
My preference for my central calendar is Google Calendar. It is linked to my personal Gmail account, which gives the calendar a few superpowers - most notably, it will automatically add calendar events from email to the calendar. Email invite to a birthday party? Added. Dinner plans canceled because the kids are sick on date night again? Removed. This fits with one of the basic rules of a Simple System - let the automation do as much of the work for you as possible.
Another feature you may already be using, or be completely unaware of, is adding multiple calendars to your main calendar view. My husband has his own Gmail calendar where he adds important dates, like when he will be in trial or out of town for work. My son also has HIS own calendar, which includes events like his part-time job schedule, his classes at the high school and community college, and his custody schedule, so he never has to wonder which house he will be at on a given day. By selecting or deselecting these calendars (which are linked to my main calendar view), I have a single overview of where everyone is scheduled to be on a given day. And they have the same view on their calendars, so I spend less time answering the question “what are we doing on…” (which is always answered with “what does your calendar say?").
The power of adding multiple calendars gets even more fun when you start adding in organization calendars. On my personal calendar, I have added links to volunteer organizations; my son’s classes (no more surprise assignments, so long as the teachers are keeping up!); and sports schedules (Gamechanger is a lifesaver, with practices and games added straight to my central calendar). I also have a calendar link to AnyList, where I plan our weekly meals. AnyList then adds an all-day event to my calendar, so I always know what I originally planned for dinner, even if it ends up being tossed aside for a pizza delivery night.
Integrating work into your personal calendar
I don’t know about you, but I MAY roll my eyes every time I hear the phrase “work-life balance.” A phrase clearly invented by a man who has a support system at home that allows him to focus 100% on work while at work, and on family and leisure while at home. For moms, it is a whole different ballgame. Don’t believe me? Try getting the school nurse to call Dad when Junior is sick at school, instead of defaulting to calling Mom. (a call that will inevitably come right in the middle of preparing your next big presentation on a tight deadline)
And even if you don’t have kids, life still happens when it wants to happen. I work from home, so I am the default home caregiver. I have to figure out how to balance working hours with repair and maintenance appointments, installations, doctor and dentist appointments, and all of the real-life activities we all need to get done during the day. For me, I get overly stressed when I get overbooked - and this is more likely to happen when I try to manage work and personal life separately. My solution to this has been to add all of my work meetings, including dedicated work time (such as working on projects, developing strategy documents, etc.), directly to my personal calendar. If your IT group at work is more flexible than mine, you can sync your work and personal calendars so that work events auto-populate on your personal calendar. If you’re like me and your work firewall is insanely impenetrable, there are some easy workarounds I’ll show you down the road, that will allow you to quickly add work events to your personal calendar without spending all day setting it up.
Magical apps that help you manage your digital calendar
Back in the day, if you had a paper calendar, you would manually add all events to your calendar, then break out the white-out when things moved around. With a digital calendar, not only can you move events as needed, but there are now apps that allow you to quickly upload and add events. One of my favorites is Ohai, which I have used for over a year now. Ohai allows you to forward an email, say, the school holiday calendar for the year, and it will add events to your calendar very quickly. I love that it gives you the power to select which events you add, so you don’t end up with a lot of junk on your calendar that isn’t relevant to you.
You can also choose to put your entire digital calendar into a paid app that helps communicate with family members. I personally do not use any of these apps, as 1) Google is free and 2) I find that Google is the most flexible for integrating outside sources of information easily.
If you look at my Google calendar, you will see it has additional calendar overlays from external inputs that tell me:
School events and days off (Ohai)
Work events (also Ohai, although I will show you how to link directly when we get there)
Baseball practice and schedule (Gamechanger)
Meal plan (AnyList)
Volunteer commitments (links to organization calendar feeds)
My son’s school assignment due dates (links from the class online learning management system, or LMS)
It looks like a lot and, well, that is because it IS a lot. But it is set up to keep me updated with as little manual input as possible. And, most importantly, it shows WHEN events are scheduled to happen, so I can see at a glance when I have a scheduling conflict; when I might need to delegate or even cancel commitments; and when I have breaks where I can do something revolutionary, like chill with a good book.
But what about tasks?
Calendars are great for events and reminders. But what about all of the daily STUFF that needs to happen? Let’s be real - if you added a calendar event for every single task you need to get done each day, you’d spend all day recording the tasks, and your calendar would induce some serious anxiety (which is what we are trying to alleviate!).
The approach I find helpful is to 1) keep a list of tasks in Google tasks (which I can open as a sidebar inside of Gmail - everything all in one place!); 2) set up recurring tasks for repeating activities (for me, that is my cleaning schedule, and recurring activities like scheduling oil changes, house maintenance, etc.); and 3) at the end of each week, taking the time to look at my calendar for the next week, and block off time for completing tasks grouped into “buckets” (so, for example, setting aside time for cleaning + laundry, workouts, house maintenance, etc.).
One of the brilliant side effects of this approach is that it helps make the invisible work visible. You are not “failing” because you never finish your task list - you feel overwhelmed because you are trying to take on more than any human can get done in a day. (hello, motherhood!) Keeping a task list is also powerful because it can help you identify tasks where you might need outside help, such as a cleaning service, laundry service, a babysitter (or grandma time) for some time to actually focus and knock out tasks all at once, or even using a virtual assistant service to help reduce the workload. When they say it “takes a village to raise a child”, what they really mean is “it takes a village to help a family navigate all of the craziness of daily life.” And sometimes, you have to build your own village in order to make that work.
The task list, in whatever one single place you choose to keep it, is also a great dumping ground for that list that bounces around your head at 3 AM. We will talk more about how to use a task list as a Simple System in future discussions, but for now, just know that it will reduce mental load by getting those pesky tasks out of your head and captured in a single list, where the only thing you need to do is decide how to manage them. And I do mean ONE place - sticky notes, cute little notebooks, shopping lists on the fridge - each one takes up mental space. When you focus on just one master task list, things become much simpler and less stressful to deal with.
We will talk a lot more about different ways to get these tasks completed. But for now, know that I use a combination of repeating task lists to remind myself what needs to be done and when, with a heavy amount of outsourcing to my digital virtual assistant service Duckbill. We will talk about the pros and cons of using services like Duckbill down the road. For now, know that when I do my weekly calendar review to identify upcoming events and tasks, I will send to Duckbill any tasks I need help with that fit with their service. For example, I have used it to choose and buy birthday gifts; call restaurants to ask about my food allergies and wheelchair accessibility for my father-in-law, then book the reservation; track down and purchase a perfect Christmas gift I saw in a news article; and this past spring, I even used it to plan out a 3 day stopover in Paris on my way to a work meeting in another country, where it helped plan and purchase tickets for my shopping and museum itinerary. These are all tasks I was perfectly capable of doing myself; but having the extra help so I could focus on other things was such a stress relief.
Using Simple Systems to manage your digital calendar
I know the title of this article is about getting a peek at my calendar. But I want to emphasize that the calendar alone won’t solve the chaos. The calendar is the central organizing tool - but it only works if it is a reflection of the systems that feed into it. For me, my systems are built on the basic principles of:
Automatic inputs reduce manual work
Shared access improves coordination
Connected calendars improve visibility
Tasks and events each have a centralized home
Quick capture makes the system usable in real life
Outsourcing keeps the system realistic and sustainable
Building your own Simple Systems that support YOUR calendar
Hopefully, this article has given you some insight and even a tiny bit of inspiration, that incorporating Simple Systems into your life can help calm the chaos, and bring a bit of peace (or at least make sure dinner is on the table without a 4 PM crisis). If you are ready to start building your own Simple Systems, I recommend starting with my free download, which helps you identify what parts of your life could use a Simple System. Also, please consider subscribing to my weekly newsletter on Substack - we are just getting started, and I can’t wait to share with you HOW to easily implement these systems into your life!
FAQs
1) What do you mean by a “digital calendar system”?
It’s not just “put appointments on a calendar.” It’s using your calendar as a central command center that pulls in events automatically (from email, school feeds, sports apps, etc.), shows everyone’s schedules in one view, and helps you spot conflicts before they become a 4 PM emergency.
2) Why do you use Google Calendar instead of a paper planner?
Because it updates fast when life changes (no white-out required), it can auto-add events from Gmail, and it plays nicely with other calendars and apps. It’s the lowest-effort way I’ve found to keep a lot of moving parts visible.
3) How do multiple calendars work in Google Calendar?
You can “overlay” calendars—yours, your partner’s, your teen’s, plus school/sports/volunteer calendars—so you can see everything together. You can also toggle them on/off so you’re not staring at a rainbow explosion when you just want your day.
4) Can my spouse/partner and kids see the same schedule?
Yes—if you share calendars (or everyone shares access appropriately), you can all see the same source of truth. Which cuts down on the classic “What are we doing on Thursday?” loop.
5) How do you add school events, sports schedules, and meal plans automatically?
Many schools, teams, and organizations offer calendar links (feeds) you can subscribe to. Some apps also push events into your calendar. In my setup, things like school dates, sports schedules, and meal plans show up as overlays so I’m not manually typing everything.
6) What’s the easiest way to get started if my calendar is currently a mess?
Start small:
Pick one calendar to be your “home base” (Google Calendar is mine).
Add the next two weeks of must-do events.
Then add one shared calendar (partner or kid).
Then add one external feed (school or sports).
Simple beats perfect.
7) Should I keep work and personal calendars separate?
You can, but if you’re the default home caregiver (or you work from home), separation can create accidental overbooking and stress. I prefer one view so I can see reality all at once—and make decisions before the week eats me alive.
8) What if my workplace won’t let me sync calendars?
You’re not alone. Some companies have firewalls that laugh in the face of convenience. You can still manually add key work blocks/meetings to your personal calendar (or use workarounds), so your “real life” schedule stays accurate.
9) What’s the difference between a calendar and a task list?
Calendar = time-specific events (appointments, meetings, games).
Task list = the “stuff” (call the dentist, order gifts, schedule the oil change).
Trying to cram every task into your calendar is a fast track to anxiety. I keep tasks in one place (Google Tasks) and use the calendar for time-blocking task buckets.
10) How do you do a weekly calendar review without it taking forever?
I do a quick scan of next week, look for conflicts, and block time for grouped tasks (cleaning/laundry, errands, admin, etc.). The goal isn’t to plan a fantasy life—it’s to reduce surprises and make the invisible work visible.
11) What if I still can’t keep up—even with a great system?
That’s not a personal failure; it’s often a capacity problem. A good system helps you see what’s actually on your plate so you can delegate, outsource, or cut back without the constant guilt spiral.
12) Do I need a paid family calendar app?
No. Some people love them, but I don’t use one because Google Calendar is free and flexible for integrating outside sources. If you want “one app to rule them all,” a paid option might be worth exploring—but it’s not required to build a Simple System.
