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.




How We Knew We Were Ready for Another Baby

The Gilroy Family

Our reasons for feeling ready for Baby #1 were much different than what they were the second time around, so for other parents who are curious about making the leap from 1 to 2 babies, we’re sharing how we knew we were ready for another baby.

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When Courtney was 6-months postpartum with our first child, people were already asking us when Baby #2 was coming along. At the time, we couldn’t fathom adding another baby because we still didn’t feel adjusted to having one baby yet.

We were still nursing all the time! We would simply mentally shut down the idea of adding another child as we politely blew past the question.

At the suggestion of our midwife, we had promised ourselves to not even consider having another baby until we approached our first’s 2nd birthday.

Note: Did you know that it takes the female body 2 years to fully recover from birth?

So, with a promise of a full recovery for Courtney, we put the idea on the shelf until then.

And time flew! In a blink of an eye, our first baby turned 2 years old. Sure enough, it was at her 22-month mark when we felt like we needed to truly start talking about having another child. 

We found ourselves wondering “how do we know when we’re ready to have a baby?” And we think that wondering in itself is an indicator that we were getting close to feeling ready.

We had a positive pregnancy test in-hand by the time Kensington blew out her 2nd birthday candles. 

Our reasons for feeling ready for Baby #1 were much different than what they were the second time around, so for other parents who are curious about making the leap from 1 to 2 babies, we’re sharing how we knew we were ready for another baby.

No. 1 — We knew Courtney’s body had physically recovered from the previous birth.

Our midwife had told us that our confidence in Courtney’s physical recovery was huge + our new midwives (since we moved out of state) + health team confirmed that it was, in fact, an indicator of readiness for another pregnancy. 

Our home birth taught us that Courtney’s body had everything it needed to grow + birth a baby the first time + we knew that when we were “back in position,” we could + would attempt a second home birth again.

We had a handle on our sleeping arrangement. We bedshared + at 2 years + 1 month, Kensie still did not “sleep through the night” consistently (+ that’s biologically normal!). 

[Related: Bedsharing Safety Guidelines]

So we wanted to make sure we at least had the rhythm of bedtime in a good place + that Courtney was getting solid stretches of sleep, even with Kensie’s continued night wakings.

Our bedtime routine wasn’t perfect — but workable — + something we could still have in a good place 40-weeks from then. 

Kensie nursed down to sleep, would wake in the middle of the night — depending on her needs — for a snuggle or nursing, then would nurse upon waking in the morning. 

We felt like we were getting enough decent sleep to sustain a healthy pregnancy if we coupled this sleep routine with napping with Kensie during the day — a happy bonus for a stay-at-home mom of 1! 

No. 2 — Kensie asked for a lot more interactive play.

Early babyhood was a lot of exploring + independent learning for Kensie, but as she got into toddlerhood, the excitement of any experience — old or new — was amplified when she shared the excitement with someone. 

We found ourselves having these mini moments of “aww, she needs a friend”.

Kensie was often asking to call her grandparents on the phone or to go visit Courtney’s aunt + her dog “cousin”. 

We would meet new friends at a playgroup + Kensie would ask about playing with them again soon. She would always ask “play me!” to us even after a full day of being with us. 

Kensie’s craving for engagement was huge!

No. 3 — We had successfully carved out a pocket of time just for us as a couple + individually.

Admittedly, we didn’t hold to this as much as we probably should have — our “me time” is always the first to go when our schedule needs to be changed — but we know that with a commitment, we can always tuck away for some quiet time everyday.

To our family in this particular season, this looks like Kevin + Kensie putting dinner together while Courtney meditates + journals during the week. 

On the weekends, Kevin + Kensie go grocery shopping on Saturday + have an outside daddy-daughter date on Sundays before nap time while Courtney gets a longer stretch of time to herself.

During Kensie’s weekend naps + on Kevin’s work-from-home days, we have a little intimate lunch date to reconnect as husband + wife. 

Kev gets up early before all of us, walks the dogs + goes on a run or meditates before getting ready for work. He keeps that set appointment with himself everyday religiously.

So, us adults were getting our independent + marriage needs met. When practicing attachment-style parenting, having a healthy marriage can be so challenging + requires intentional planning.

Keeping a schedule means little time for other social events, but our young family thrives on this consistency (+ most toddlers do, too!).

We felt like we had a plan that could honor all of our priorities well.

The Gilroy Family

No. 4 — We felt financially literate — again.

Since having Kensie, we had the added expense of her growing needs (diapers, clothes, toys, activities, etc.) but we also had moved from Kansas to Boston + made some career changes.

To account for this, we budgeted our new household finances for a few months, which gave us a baseline of our recurring expenses + helped us ensure they were always less than our income.

We made plans for paying off Courtney’s last student loan. We made financial decisions ahead of them “coming up” for us, like what we’d do to maximize our current small house when adding another baby instead of figuring that logistic out after the fact.

We set career goals + created space for opportunity — like a time when we could look into new jobs without disrupting our financial footprint. This way, as opportunities came up, we had a game plan for saving, spending + unexpected change.

We also amped up contributions to our Health Savings Account to ensure we’d all have what we’d need through pregnancy + postpartum — extra chiropractor visits, paying for the home birth out-of-pocket, an emergency reserve for unexpected circumstances, etc. 

This is one less set of logistics to have to do (or stress about) during pregnancy.

No. 5 — Kensie’s interest in “going potty” peaked.

Kensie was interested in watching how we went to the bathroom as adults. 

She happily ordered a frog potty off Amazon + happily sat on it for 4-seconds at a time before saying she just wanted to play with the frog potty instead.

But there was an interest + also an avoidance of people whenever she started soiling diapers + she could feel the mess.

Note: People who have cloth diapered their children (or who have practiced elimination communication) have had this happen at like 18-months or even earlier, but for disposable diaper kids, this happens later because there’s more absorbency + cushioning. When kids don’t feel the discomfort of wetness or stickiness, they’re not likely to want to change.

Kensie would hide in another room to squeeze out a poop or you’d see her facial expression change when she realized she peed in her diaper. 

We knew from these cues that she’d be ready to try going to the potty on her own + a few months later, just letting her natural curiosity take the lead, she “potty trained” herself in 2 days! We were FLOORED! 

Reducing the cost + effort of having one baby in diapers for a few months during pregnancy was nice before we picked that back up again.

No. 6 — We had a solid support system — independent of family.

When we were first pregnant with Kensie, we lived in Kansas where the rest of our family was living in Boston + New York. 

We actually weren’t in connection with most of one side of the family for that time. When we moved back to Boston, we reconnected with one side + had some blips in the relationship with the other side of the family before all returned to normal — eventually.

All that is to say that even what appears to be the strongest familial relationships + friendships can + do have times of weakness. 

Change happens. Learning this the hard way + missing the support that we had always assumed we’d have in starting a family, we prioritized building a support team that wouldn’t waiver the second time around. 

We picked out our midwives in-advance + found therapists who could coach us through unbiased decision-making. 

We found our chiropractor, acupuncturist + laundry delivery service. 

What we didn’t have to do, we outsourced. That way, we could find more time to do what we did have to do if we were going to have to fly solo.

Any help we got from friends + family was a bonus, not something we relied on to function. 

We set our family life up like a business + built a team around us that we could depend on outside of family because we were paid + contracted to each other. This setup was an invaluable insurance policy, + again, one less item to worry about during pregnancy.

No. 7 — We had a gut feeling that our family would have more than one child.

We loved being pregnant the first time around. We felt incredible, the pregnancy was easy + Courtney + baby were so healthy. 

Kevin was a man on a mission to make Courtney’s life easier, while Courtney had the enormous job of growing a baby in her body.

Pregnancy is an experience that we’d honestly go through a thousand times over if we had the bandwidth to truly support that many children! 

Courtney grew up with 2 siblings + Kevin is 1 of 10 kids, so we’ve both enjoyed having + being siblings. 

After getting to know Kensie’s personality + feeling like we were at least playing man-to-man by going from 1 to 2 children (+ each of us could “take one” if we needed to divide + conquer at an event), we felt like we could handle the responsibility + enjoy parenting.

But above all, we simply had an internal instinct that this is what we were supposed to do for our family. 

We couldn’t stop shaking the idea + feeling genuinely excited about welcoming another baby (even with our pockets of wondering how we could love anyone as much as we love Kensie — we knew that’d work itself out in due time).

Baby #2 couldn’t be more welcome + prepared for. ????

How about you: are you considering adding a child to your family? 

What are your thoughts on going from 1 to 2 babies + beyond? Any tips to share with parents who are growing their families?

Share your story or tips with other parent entrepreneurs growing their young families in the comments below. We’d love to hear from you!