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 5 Essential Gifts We Give Each Other Every Year as Married Business Partners

Kevin + Courtney

We’re sharing our 5 essential gifts we give each other every year as married business partners: gifts that make our life simpler, sweeter + help create more of the space for what matters most to us.

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They don’t call Q4 “the most wonderful time of the year” for nothing. The last few months of the year can bring some of the most purposeful + profitable highlights for entrepreneurial families. We love watching our clients celebrate their holiday season success + start setting them up for a productive new year ahead.

There’s something so magical about feeling fulfilled doing the work you get paid for (sometimes passively!) + then getting to spend that time + money on what matters most to you during this festive time.

In this post, we’re sharing our 5 essential gifts we give each other every year as married business partners: gifts that make our life simpler, sweeter + help create more of the space for what matters most to us.

Let’s get listing!

We’ve found that well-rounded holiday season success begins with an intentional Q4 strategy for both home + business. We love keeping the presence in the holiday season just as much as the presents — + as parent entrepreneurs, we need to choose this strategy with a plan in-advance.

One strategy we use for our intentional Q4 planning — along with our Family Activities Templates — is templating traditions like the 5 essential gifts that we give each other every year as married business partners. 

We take the guesswork out of “what do I get my partner this year?” by having a go-to handful of evergreen gift ideas that both free up physical space just as much as the mental space for us as parent CEOs.

The Family Activities Template

With these strategies in-hand, we’re able to save time shopping + make smart investments with what we do spend year-over-year. We’re also able to coordinate gifts way ahead of the holiday rush, often finishing our holiday shopping before Black Friday when most people are just getting started. 

We love choosing to go shopping in the December holiday chaos without the pressure + getting to people watch the scenes the eye-rolling dads hauling shopping bags, kids with the “gimme-gimmes” elongating their Santa Wish Lists + moms trying to keep the peace while making the trips worth it. 

The stereotypical holiday chaos is so much more entertaining when you’re NOT the one reenacting National Lampoon’s Christmas Vacation in real-time. (And if this is you right now + you’d rather skip that chaos this year, we’ve got you covered here!)

No. 1 — Extra Mortgage Payment

We know, we know… this is not a glamorous gift in a box. However, we promise the return on investment of this gift is way better than anything tied with a bow.

Let’s start with emotional ROI: As parent entrepreneurs, we assume a big risk by being our own employers, which makes paying off any debt + being a cash-positive family critically important to us. 

Just like with having your own online-based business, having ownership of your own home creates a different level of confidence. We simply find that we show up to the dinner table differently when we know we own it outright. 

Now, financial ROI: Let’s say you have a $220,000, 30-year mortgage with a 4% interest rate. Making an extra house payment ($1,050) every year will get your mortgage paid off 4+ years early + save you more than $25,000 in interest.

Want to be exceptionally smart? Giving yourself this extra mortgage payment gift every quarter will get your mortgage paid off 11 years early + save you more than $65,000 in interest—cha-ching!

We make at least a full extra mortgage payment every January. Additionally, we round up every mortgage payment to an eye-appealing whole number for the year. For example, instead of $1234.56/Month, we would pay $1235.00/Month + have the little extra applied to the principal amount due. It’s like our own keep-the-change program.

Making an extra mortgage payment each year could reduce the term of your mortgage loan significantly. The most budget-friendly way to do this is to pay 1/12th extra each month, for example if your mortgage payment is that $1235/month, then adding an extra $103 to each month’s payment for the calendar year would have a similar impact.

Before you start making extra payments, here are 2 important key points to consider:

  1. Check with your mortgage company first. Some mortgage companies only accept extra payments at specific times or may charge prepayment penalties.
  2. Make sure your extra payment (+ that monthly little overage payment amount) gets applied to the loan’s principal balance — not to the following month’s payment. You may need to put that administrative request in an old-fashioned written letter if your current online banking setup doesn’t allow you to choose that setting on your own.

With those all set, you’re setting your entire family up for smart financial security that you can be proud of + retirement could come earlier!

No. 2 — Classic Luxury Item

Now, this one IS more fun! Think: Burberry trench coat, Gucci loafers, Hermes belt, Louis Vuitton purse, diamond earrings, etc… something material that feels indulgently good.

When we were first starting out, our definition of “luxury” was a lot different than those brand names. Our starting luxury was more like getting a real Yeti water bottle instead of the knock-offs or buying a real Moleskine notebook to start a personal journal library that we’d leave as a learning legacy for our kids. 

Choose for yourself what is a high goal to afford price-wise for your current circumstances, but the key here: please do not go into debt

Name what’s luxury for you right now + what could be the best high-quality product that will last a while for you. Let this purchase be within a stretch-reach financially. This purchase isn’t your everyday Target run + it’s also not so much of a spending stretch that you may max out the credit card or end up saying prayers for an “approved” beep at the grocery store checkout line.

We are intentional about our one big luxury gift + truly enjoy thinking about this investment during the year. Any clothing or accessory we purchase in this category replaces a worn out item in our capsule wardrobe + we aim for any other items to be legacy-worthy that we could hand-down to our children someday.

This gift is the idea of quality over quantity for us!

No. 3 — Family Vacation

For Mom, Dad + Babies! This is where we would do a school vacation week away — like Disney or another bucket-list-worthy trip. As our kids get older + schedules get more complex, we’ve talked about transitioning this gift to a more local vacation home rental in the summer + inviting extended family.

Again, when we first started out, vacation was visiting family who lived out-of-town + staying with them for free instead of a hotel. Meet yourself where you’re at + simply get out for some adventure!

We’ve found the family vacation is an important gift to give ourselves as parent entrepreneurs (even though it technically serves everyone) because we’re goal-setting together with a big family memory-maker here.

We often think about when we are old + reminiscing in our rocking chairs with grown children out + living their lives somewhere, what do we want to be looking at in our photo albums? 

The Gilroy family in Disney World

And maybe a little more self-serving: how can we further solidify how awesome we are as parents — parents worth visiting in those rocking chairs! — all those years later?

When we name the annual family vacation in-advance, there’s less stress + more opportunity to plan the details thoughtfully. We only get this life once + we want to max out our physical ability to adventure together to the hilt with those we love.

[[ P.S. ⟶ If you’re headed to Disney with little ones under 5, grab our Family Disney Guide, including curated travel planning, family packing + theme park ride checklists in the most productive order possible. Yes, we put our family vacation operations into project management systems + trust us, once you do, too — you won’t look back! Life changing!  ???????? What’s more: we hook you up with our personal Disney travel planner who will make all of your custom reservations for you for free.]]

No. 4 — Couples Getaway

Being in the business of life with your husband or wife is the single most important, intimate + influential partnership of your existence. (No pressure!). 

Then layering on a business partnership on top of that loving relationship means that we’re with each other often — + we like it that way! 

Even with our preferences for working together often, we’ve found stepping away just the two of us into a different, unbiased environment gives us a refreshing reset from the everyday routine. We often take these getaway times to recalibrate our dreams + set the goals that will help get us there.

Kevin + Courtney in Italy

[Related: Organic Goal Setting in the New Year]

Now, though, with young children in the toddler years, we’re in a season of staying close to home. It’s too emotionally hard for us as adults to steal away for even a dinner out, let alone an entire weekend!

However, when our youngest is old enough to be comfortable with an overnight family babysitter (+ we’re comfortable, too!), we’ll return to our “mandatory marriage trip” every year. 

For now, our couples getaway means that the kids come with us for a more local overnight — like Martha’s Vineyard — where we can have a familiar local family member or babysitter takeover for an hour or two in a fun-for-us-adults location, or where we can enjoy upgraded hotel suite amenities late at night with the kids asleep on an early bedtime.

No. 5 — A Simple December

Then, we keep our biggest holiday season — Christmas in December — simple. As natural entrepreneurs, choosing simple can feel especially complicated at this time of year. We love what we do for work + have a lot of temptation to lean into the naturally high-demand for new year goal-setting + implementation by expanding our 1:1 coaching availability + our agency offerings. 

This gift is more of a behavior across the season, not gifted on one particular day or in one wrapped box.

All throughout December, we take extra time to be mindful to keep our priorities top-of-mind. We give ourselves the slow-down of extra-long snuggly morning chats with warm drinks.

This season is led by choosing how we’ll prep well for the family holiday logistics which you can read more about here. We wind the day down with the early sunsets unapologetically. All the way through the slowed-down December days, we remind ourselves what a true gift this life + legacy is.

Yes, there’s money to be made + mountains to be moved, but only when we’re fulfilled first as family-centered entrepreneurs.

[Related: 5 Ways We Prep Well for the Holidays as Parent CEOs]

When we hold each other accountable to the slow-down, we’re gifted with more breathability in what could otherwise be a natural time for the traditional hustle. 

Whatever the simple slow-down feels like to you: gift that to yourself + your partner. 

Comment below: how do you stick to the most meaningful parts of holidays + gift-giving for you + your partner?

What’s on your wish list this year?

If you’re wanting more support + accountability with intentional family planning as a parent entrepreneur, then consider gifting yourself our Quarterly Family Activities Templates from the OrganicFamilyCEO Shop.

We’re sharing our full ready-to-use templates with you, so that you can stop spending so much time planning your intentional family time + start being present for it.

Wishing you + yours the most peaceful, purposeful (+ passively profitable!) holiday season,