family + business operations for parent entrepreneurs


We're Kevin + Courtney Gilroy: married best friends turned parent entrepreneurs. is the resource hub + like-minded community we were missing in our first days of new parenthood + business ownership.

Becoming a profitable stay-at-home family changed our life. Now, we help other current + soon-to-be parents have a healthy start to parenthood + entrepreneurship.

Learn more about our systems for running the business of family alongside the family business here or ask us questions here.




The Value of the Digital Family Calendar

happy man in front of computer

Today, we’re looking into the priceless value of using a digital family calendar.

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Are you a born planner?

Today, we’re looking into the priceless value of using a digital family calendar. Even if you’re a pen-and-paper type of person, stick around: you might just find that there’s a healthy opportunity to consider integrating some digital into your life.

If you want to know exactly what we use to go digital in our family-centered business, go to to get our must-have tech tools. We’ve listed them all there for you!

While we love our more digital setup for family + business now, we definitely didn’t start there

Courtney got her first official paper planner in elementary school. She was in 4th grade, in this brand new middle school + every student got a shiny black-and-orange planner with the weekly + monthly layouts.

This planner was the most beautiful product Courtney had ever seen + that became her gateway to color-coordination + scheduling. So no one was more turned off to digital than Courtney when the obvious time came to really consider if growing an active family + building an online business with a paper planner was the smartest move moving forward.

Our Reasons for Going Digital

No. 1 — We couldn’t operate well between 2 mediums.

Our family has a myriad of activities to keep track of such as our individual personal activities as adults, our marriage, our kids’ activities, our dogs, our housekeeping, our finances, our vacations, our shared family events, etc.

Simultaneously, we’re running a business with its own set of projects (our personal leadership activities, our team’s activities, our office-keeping, our finances, our shared events, etc.). We also went on to own multiple businesses where these needs are then multiplied.

With all this given, there is no possible way Courtney could delegate all of those moving parts well by keeping some of that information contained digitally (as required by the nature of an online-based business) + then some off to the side on paper where only she was accessing that in-person in real-time.

As Bethenny Frankel says, you can’t straddle 2 horses. We quickly learned that’s the truth for us.

No. 2 — We needed to have a clear way to make quick decisions. 

One of the greatest pleasures in paper planners, we find, is the journaling-type experience. We had to reconcile that paper planning was becoming less about the journaling experience + more about making sure the daily priorities were being executed towards the bigger picture.

We also had to reconcile that as parent CEOs, we couldn’t possibly fit writing every essential task into the particular day + do it well + on time. That was HARD to admit as a perfectionist go-getter. 

There’s no grace or scalability when you’re using a system built for a single person.

A paper planner simply isn’t meant to be shared or edited often.

When we could see the full operating system — all ongoing + one-time tasks — in one place, then we could start to create more flex + more white space in our days by delegating to others: both at home + in our virtual workspace. 

We could start seeing what wasn’t getting done, then give ourselves an opportunity to easily shift to another time, day or person, or delete the task altogether + learn the discipline of quality self-assignment in the first place.

From our years of coaching clients, we have clearly observed that sometimes as both parents + CEOs, adults tend to put more on their plates than is required to get a certain job done. 

We’re telling ourselves that we have to do more in order to qualify our job as a worthy pursuit or for us to be worthy of the results. And there’s something clarifying + humbling about noticing where you’re making your days harder for yourself + withholding the enjoyment that comes from honest work — however easy or hard it was to accomplish. 

The good news is that when you’re in a super simple one-click system that helps you see those misassignments + misalignments clearly, you can quickly recalibrate + reset. You don’t spend your time erasing, re-writing + feeling the shame of an imperfectly marked-up planner page

The digital calendar moves on immediately without giving you an opportunity for the judgment or additional obstacles you’re prone to. (Ahem, fellow doers + perfectionists!)

The Benefits of a Digital Planner

No. 1 — We have saved THOUSANDS of planning hours by going digital. 

Courtney here for this one:

I still have a paper notebook journal for sitting with intentionally to brainstorm, work through personal development, or check-in on our goal setting or my own mental wellness. 

I will always love writing + value putting pen to paper, but we value our TIMEthat non-renewable resourcemore

As a result, the way I once used paper to achieve mental clarity as a young woman without a marriage, kids + businesses ultimately required a change to meet this new + expanded version of me as a wife, mom + business owner. This is a change I am now SO grateful to have made. And Kev is, too.

Kev stepping in now:

I, on the other hand, wasn’t a natural planner. My schedule prior to starting a family had always been fairly simple + repetitive. In high school, that was school, training + practice or games, then repeat. Later on, I had work 9-to-5, workout, dinner, bed, then repeat.

All of my activities happened at the same time every day, so a planner at those times only seemed to put a wrinkle into something that I was already very mechanical at doing.

So with planners nonexistent pretty much up until marriage, Court later suggested more intentional scheduling when life had more responsibility + more moving parts between marriage, a mortgage, an advancing corporate career, starting our own businesses + having kids. 

Planning had always felt more complicated than it really was to me. However, when I looked at planning from a family view, I could see that our shared calendar makes family life operations at-large easier. 

I feel like a better partner + parent + provider when I’m a part of the calendar effort, even though I was not a naturally-willing participant.

When we’re not working or parenting side-by-side together, Courtney can see what is going on for me + I can make decisions knowing what’s going on for her. We both know what’s happening with the kids when we’re away from them. 

We’re more connected via our calendar especially because it’s digital + updating in real-time. This is why we have embraced planning as family-centered entrepreneurs.

No. 2 — We have saved COUNTLESS conversation or conflict hours as a business-owning couple.

Save the few times Courtney broke the calendar sync by getting “too fancy” across multiple businesses, our virtual calendars have eradicated the non-essential conversations asking about both family commitments — like playdate schedules or chiropractor appointments or when the landscapers come next — + work commitments. 

This leaves room for more meaningful conversations as husband + wife, like talking about our dreams, our personal growth, or what new adventurous date activity or sex position we want to try. 

Those minutes matter because they’re what build + maintain intimacy over time time that gets otherwise prioritized by everyone + everything else if we don’t claim that time for ourselves

We hear so often that couples feel like 2 ships passing in the night or that they feel like volleying hand-offs of the human + business babies is the most supportive connection they have week-over-week. 

And, as we’re in the thick of raising young children + growing yet another business ourselves, we’re reminded of how sensitive this early growth season is in both the nuclear family + business family. We get it. 

No. 3 — Planning keeps the priorities of the family in-check. 

We can say with damn near certainty (granted, we don’t know your exact personal situation), that going all-in on a digital calendar hub is what keeps the priorities in-check.

We very rarely get pulled into the weeds of activities that we feel we should not be focusing on. This makes us successful CEOs. 

We are always looking at the bigger picture while knowing what the other characters in the story are doing. There’s no need to constantly ask what is on-deck, what the others are working on, or what is needed from us (even though Kevin still admittedly does at times! Old habits die hard!). 

And, in those times we do ask, we both already know the answer is simply to look on the calendar or in Asana. We can rely on the self-service tools we’ve made available 24/7 for ourselves + that takes the pressure off of any one person to be all-knowing. 

So if Kevin wants to make a decision on scheduling a catch-up with a buddy, he just looks at the calendar. If time is free, he puts it on there within the timeframe + we are good to go. The same goes for Court.

The schedules are sexy (Court’s turned on with the color-coding + naming conventions, but that’s another thing!) but also having all of those tedious details contained somewhere does allow us to not have to be so structured somewhere else

We’re constantly flirting, joking, having great conversations, great sex, making grand plans + as begrudgingly as Kevin was starting this type of calendar or planning at first, he knows that we can maintain the space for that goodness because of our digital operations. 

Kevin has come to love this system because he works best when things are simple. Keep the simple tasks simple. The more steps + barriers we can remove, the better. By being willing to put in a little initial startup effort, we’ve simplified life dramatically thereafter. 

We’re team digital calendar + challenge everyone to try it on, too.

Now, we’ve shared that Courtney was an immediate planner lover + Kevin most definitely was not. And we want to point out that if you are not the planner + your partner is, then starting that initial startup effort might feel more approachable if you focus on making YOUR PARTNER’S life easier for a moment + meeting them where they’re at. 

Being willing to try a system that your partner cares about because you care about them could, in turn, make YOUR life easier. That was certainly the case for us.

No. 4 — Planning keeps us present. 

When we are with the kids (which is ALL day… we’ve shared here that we choose to not have babysitters), we don’t catch up on business tasks. We’re very intentional about being present. 

When we play, we play. And we’re able to do this thanks to the digital family calendar because that tool keeps our plans queued up in real-time.

Conversely, when we work, we work. When we’re with our business babies, we step into “production mode” + we can stay focused in the moment there knowing that the work we are producing is what is going to push the needle forward + that our kids’ activities are queued up already + running smoothly behind-the-scenes.

We don’t have to wonder as we’ve removed the guesswork + simplified how to get the answers in real-time without relying on 1 person as the bottleneck. And we’ve found these systems work for any parent CEO who has the desire to be more present + on-purpose as a family-centered entrepreneur

So tell us: how do you organize your family’s activities?

Leave your tips + tricks in the comments below to help your fellow parent entrepreneurs.

And if you have been feeling tugged in a million directions (or you feel like in your upcoming season that you’re about to be), then please do yourself a favor + deeply consider the value having a digital family calendar could bring to your life.

Don’t know how to start? You can sign up for the Digital Family Calendar Masterclass or use one of our templates from the shop so that you can get your family-centered systems up + running quickly.

Cheering you on in reclaiming your invaluable time as a parent entrepreneur ASAP,

Kevin + Courtney