Jillian McCloskey's Travel Agency Designed Just for Moms

Please share a brief introduction about yourself and your business:

Hi, I’m Jillian, the founder of Momcations.co, a travel agency designed exclusively for moms who need a break. After experiencing burnout myself, I took a solo trip that changed everything—I reconnected with who I was beyond motherhood. That trip inspired me to create Momcations.co, where I take care of all the planning so moms can take a guilt-free getaway to rest, recharge, and rediscover themselves. Whether it’s a solo escape, a small group getaway, or a hosted experience like my More Than Just a Mom Group Cruise, I help moms say yes to themselves for once.

Who are your customers?

My customers are moms who are exhausted from always being “on.” Whether they are working moms balancing careers, stay-at-home moms managing everything at home, or moms in a transition phase (like empty nesters), they all have one thing in common—they need a break. My goal is to make taking a Momcation easy, stress-free, and completely guilt-free.

What was your background prior to starting your own business?

I’ve always been passionate about travel—I’ve visited 17 countries, 4 continents, and 25 U.S. states—but I spent years doing all the research and getting certified to ensure Momcations.co was a legitimate, well-prepared business. Before launching, I took my time building the foundation so that moms could trust me to handle every detail of their trips.

What made you take the leap to start your own business?

After taking my first solo Momcation, I came home feeling like myself again—not just a mom, but Jillian. I realized how much moms need space to rest, recharge, and reconnect with themselves, but most don’t take the time because of guilt, stress, or the overwhelm of planning. I knew if I could remove the obstacles, I could help more moms say YES to themselves.

Did you always know you wanted to be an entrepreneur?

Not exactly, but looking back, it makes sense! I come from a family of entrepreneurs and have worked alongside my family in our business since I was a child, so starting a business of my own always felt natural. Over the years, I had ideas for different businesses, but none of them truly lit a fire in me. It wasn’t until I came up with the idea for Momcations.co that I felt an undeniable drive to make it a reality. I’ve always loved planning travel and helping others experience something meaningful, and Momcations.co combines all of that with my passion for supporting moms. This was the business I was meant to build.

Take us back to when you first launched your business; what was your marketing strategy to get the word out and did it go as planned?

At first, I thought that simply talking about Momcations would naturally lead to bookings. I quickly realized that while moms loved the idea, they needed more guidance to see how they could actually make a Momcation happen. I’ve since shifted my marketing to focus on education and empowerment, showing moms why they deserve this and how they can make it happen.

What is the biggest challenge you have encountered along the way so far and what have you learned from it?

My biggest challenge has been getting visible and putting myself out there. I was nervous about being on camera and felt like I had to be perfect to show up online. But I’ve learned that being real and relatable is what actually connects with my audience. Moms don’t need perfection—they need honesty, and I’m learning to embrace that.

What accomplishment are the most proud of to date in your business?

Honestly, my biggest accomplishment is simply starting.

I had the idea for Momcations.co for over five years before I finally took the leap. In that time, I would talk about it with other women, and every single one of them told me, “You need to do this!” But I kept saying, “One day.”

In my head, I came up with every excuse—I already had a full-time job, a husband, kids, was a Girl Scout leader, on the PTA board, involved in my community, all while managing some health challenges for both myself and my daughter. How could I possibly add starting a business to that list?

But the more I thought about it, the more I saw why it was needed. I had taken the time for myself and experienced firsthand the power of a Momcation, but so many other moms wouldn’t allow themselves the same break. That’s when I realized—if I don’t create this, who will?

So I stopped saying “one day” and made it happen. And that, more than anything, is what I’m most proud of.

Do you have any recent wins from the last year that you'd like to celebrate with our community?

Yes! I was recently interviewed on a podcast to share my story, and I’m starting to see more traction on my Instagram and Pinterest, which means more moms are finding Momcations.co. I also created a weekly newsletter, “Your Weekly Escape,” to build a stronger connection with my audience.

What's next for your business? What can we expect to see over the next few years?

I want to expand my group trip offerings beyond cruises to include small group tours, wellness retreats, and adventure getaways for moms. My goal is to make Momcations.co the go-to name for moms looking for a break—whether solo, with friends, or in a group.

What is your top productivity tip? 

Batch content. I set aside time to create multiple posts, emails, or videos at once so I don’t have to scramble every day.

On the flip side, how do you avoid burnout?

I remind myself that rest is productive. If I try to do everything at once, I won’t do anything well. Taking a break actually helps me come back stronger.

What is your approach to work-life balance / integration?

I set realistic expectations and accept that balance won’t look perfect. Some days, my business needs me more; other days, my family does. I give myself permission to adjust as needed instead of chasing an unrealistic “balance.”

What is one thing you wish you had known when you started your Entreprenista journey?

That visibility is everything. I was hesitant to put myself out there at first, but people connect with people. The more I share my story, the more my audience grows.

When hiring, what is your go-to interview question?

I’m not hiring yet, but when I do, my priority will be hiring moms. Moms understand firsthand what other mothers go through when trying to take a break—the guilt, the logistics, the mental load, and most importantly, what they truly want from their time away.

As for my go-to interview question, I’ll ask: “How do you problem-solve when things don’t go as planned?” Travel planning requires flexibility, patience, and creativity, and I want a team that can think on their feet while always keeping a mom’s needs in mind.

Are you a Mamaprenista? If so, please share your best advice for simultaneously managing a business and a family:

Yes! And for me, the key to balancing family and business is routines.

In our house, we operate on a Week A / Week B system. Each week has a set menu, assigned chores, and clear expectations. This means:

Everyone knows what’s for dinner (if it’s Monday of Week B, we’re having meatballs—sometimes with pasta, sometimes as a sandwich, but no one has to ask).

Grocery shopping is streamlined because I know exactly what to buy.

Household chores rotate every other week, so no one feels like they’re “always” the one taking out the trash or feeding the dog.

By structuring our home life this way, I’ve removed decision fatigue, reduced the mental load that so often falls on moms, and made it easier to focus on my business without feeling like I’m constantly juggling a million things. Routines give us freedom!

What's the one app on your phone you absolutely cannot live without and why?

Google Calendar—hands down. If it’s not on the calendar, it doesn’t exist.

I have my personal, work, and business calendars all synced to my phone, color-coded for different events and who needs to attend. If it’s a new place, I add hyperlinks with maps so that if I’m not the one taking my kids, my husband isn’t texting me last-minute asking where to go. All the necessary information is in there.

As my girls got older and started using tablets, I added them to the calendar so they could check it themselves before asking if they could make plans. Same with my husband—everyone knows to check the calendar first. And just in case someone still “forgets,” I also have a Skylight digital calendar in the kitchen that displays everything from Google Calendar in real time, so it’s visible to the whole family.

And the best part? No one can say, “But you didn’t tell me we had to do X!” Oh yes, I did—and it’s on the calendar!

What is your favorite business tool or solution and why?

Right now, it’s Tailwind—even though I wasn’t sure about it at first!

I was feeling overwhelmed trying to post on Instagram, Facebook, and Pinterest separately, and a fellow Entreprenista recommended Tailwind. Once I got it set up and realized I could use the same graphic to schedule posts across all three platforms at the same time, it was a game changer.

The best part? I batched my content for two weeks in one sitting, which saved me so much time and stress. Now I can focus more on engaging with my audience instead of scrambling to post every day.

What advice do you have for aspiring Entreprenistas?

Don’t wait for perfection—just start. Clarity comes from taking action, not from waiting until you feel 100% ready. If you’re passionate about what you’re creating, trust that it will evolve over time, and give yourself permission to learn as you go.

Also, listen to all the advice people give you—but don’t try to do it all. I made that mistake in the beginning. So many people had well-meaning suggestions, and I felt like I had to implement everything at once to be successful. I quickly learned that it was impossible to keep up, and within a month, I was completely overwhelmed.

So I took a step back, chose a few things to focus on first, and started keeping a notebook of all the other ideas that seemed good but weren’t priorities at the moment. Now, instead of feeling like I’m failing because I can’t do everything, I have a list of ideas I can come back to when the time is right.

Success isn’t about doing everything at once—it’s about doing the right things at the right time.

Learn more about the Entreprenista League and join today!