We’re looking forward to introducing you to Jessica Winters. Check out our conversation below.
Jessica, so good to connect and we’re excited to share your story and insights with our audience. There’s a ton to learn from your story, but let’s start with a warm up before we get into the heart of the interview. What is a normal day like for you right now?
A normal day for me is a mix of mom life, homeschool, and running our family media business — all woven together in a way that somehow works. We start our mornings slowly with breakfast and homeschool lessons, and once the kids settle into their independent work, I shift into content-creator mode. That usually means editing videos, writing blog posts, managing social media, or planning our next trip.
My husband and I work together on the business, so throughout the day we bounce ideas back and forth — everything from YouTube edits to upcoming collaborations. And because our brand is focused on family travel, a big part of our routine includes reviewing footage, organizing photos, and outlining future adventures.
Afternoons are usually reserved for getting outside, errands, or more hands-on homeschool projects, and evenings are when we regroup, spend time together, and sometimes squeeze in extra editing or planning once the kids are asleep.
It’s a full, beautifully chaotic rhythm, but it allows us to build something meaningful as a family. I love that my “normal day” is never the same — and that every piece of it, from parenting to content creation, supports the bigger vision we’re building together.
Can you briefly introduce yourself and share what makes you or your brand unique?
Hi! I’m Jessica Winters, co-owner and content creator of Family Traveling USA, a family-focused travel media brand that I run alongside my husband and our three kids. We share family-friendly destinations across the United States — from theme parks and aquariums to state parks, seasonal events, and small-town gems — offering honest, kid-tested experiences to help other families plan fun, memorable adventures.
What makes our brand unique is that it’s a true family project. My husband and I work together on planning, filming, and producing our videos, and our children are right there with us — giving genuine reactions, adding personality, and helping us show what travel really looks like with kids. It’s the magical moments, the learning opportunities, and the beautiful chaos that make each adventure meaningful.
Alongside our travel content, we’ve recently expanded into another creative project under our LLC called Read Along Adventures Club — a kids’ read-along YouTube channel where we create original stories with word-by-word highlighting and mixed-media artwork made by our children. It’s been a fun way to blend literacy, creativity, and family connection.
Right now, we’re focused on growing our YouTube channel, expanding helpful trip-planning resources on FamilyTravelingUSA.com, and continuing to build a brand that encourages families to explore more, learn more, and create meaningful memories together. At the heart of everything we do is the belief that you don’t need perfect circumstances to have unforgettable adventures — just curiosity and the willingness to go.
Thanks for sharing that. Would love to go back in time and hear about how your past might have impacted who you are today. Who were you before the world told you who you had to be?
Before the world told me who I had to be, I was a curious kid who loved being outside, exploring whatever was around me, and creating little adventures with my closest friends. I wasn’t thinking about achievements or expectations — I was just fully present in the moment, always cherishing friendship, fun, and a reason to laugh.
As I got older, life naturally shifted toward being more structured and “practical,” and I started to follow the path I thought I was supposed to take. But becoming a mom — and later building Family Traveling USA — helped me reconnect with that original version of myself. The part of me that loves exploring new places, creating memorable experiences, and sharing things that bring people joy.
In many ways, what I’m doing now looks a lot like who I was before the world stepped in: someone who loves adventure, positivity, and making moments feel special. And it means a lot to me that I get to model for my kids that they can choose joy, kindness, and their own unique path — even if it doesn’t fit the traditional mold.
What did suffering teach you that success never could?
Suffering taught me the kind of strength, perspective, and gratitude that success alone never could. The challenging seasons of my life — the moments that felt overwhelming, uncertain, or disappointing — stripped away everything superficial and forced me to get really clear about what actually matters. They taught me patience, resilience, and the importance of trusting myself even when the path forward wasn’t obvious.
Those harder moments also made me softer in a way — more empathetic, more intentional, and more committed to choosing joy and kindness whenever I can. When you’ve walked through seasons that test you, it changes how you show up for others. You listen differently. You appreciate small things more deeply. You stop taking good days for granted.
And honestly, those experiences are a big part of why our family brand looks the way it does today. They shaped my desire to create something positive, uplifting, and centered on meaningful memories. They taught me that joy isn’t something you find only in perfect circumstances — it’s something you choose, nurture, and create, even after life hands you challenges.
Success can be exciting and motivating, but suffering is what taught me resilience, gratitude, and the importance of building a life — and a business — that’s grounded in love, purpose, and presence.
I think our readers would appreciate hearing more about your values and what you think matters in life and career, etc. So our next question is along those lines. What would your closest friends say really matters to you?
My closest friends would say that what matters most to me is creating a life filled with love, laughter, and meaningful memories — especially with my family. They know how much I value being present with my kids, making everyday moments feel special, and choosing positivity even when life gets messy.
Okay, we’ve made it essentially to the end. One last question before you go. Could you give everything your best, even if no one ever praised you for it?
Yes — absolutely. So much of what I do, both as a mom and as a creator, comes from a place of purpose rather than praise. Whether it’s planning a family adventure, creating content that helps other families, or building something meaningful for my kids’ future, I’m motivated by the impact and the intention behind it, not the recognition.
Motherhood taught me this more than anything. There are countless moments where you pour your whole heart into something — teaching, comforting, supporting, creating memories — and no one sees the work but you. But it still matters. It still shapes lives. And that makes it worth doing well.
The same goes for our travel content and the projects we build under our brand. Even if no one ever said “great job,” I’d still want to give it my best because I know it brings value, positivity, and joy into the world. I’ve learned that the real reward is in the growth, the connection, and the memories we create along the way.
Praise is nice, but purpose is what keeps me going.
Contact Info:
- Website: https://www.familytravelingusa.com/
- Instagram: https://www.instagram.com/familytravelingusa/
- Facebook: https://www.facebook.com/familytravelingusa/
- Youtube: https://www.youtube.com/@familytravelingusa
