When Jess Winns tells you she had about six weeks to prepare for an international move with four children, including a toddler, your first instinct might be to wonder how that’s even possible. But spend five minutes listening to her talk about it, and you start to understand: sometimes the most radical decisions aren’t the ones that take the longest to make. They’re the ones you’ve been quietly preparing for your whole life.
I had Jess back on the podcast when she was pregnant the last time she sat down with me, and now she’s calling in from Playa del Carmen, five months into a new life in Mexico. She moved there in October 2025 as a single mom, with no village waiting and no backup plan. Just her kids, her entrepreneurial spirit, and a deep knowing that it was time.
The moment that changed everything
Jess’s connection to Mexico goes back to 2016, when she visited the area for the first time and unexpectedly crossed paths with her father, a man she hadn’t seen since she was three years old. He’s Mexican and was living there. Something about the place moved her immediately. She came back. And again. By 2022, sitting on the beach at the end of a birthday trip she took with her brother, she genuinely didn’t want to leave. That feeling never went away.
When a planned family move fell through and her relationship ended, she made a decision: she was going anyway. Alone. She had six weeks to hand off her organic body care business, find housing through a Facebook connection, get the kids emotionally ready, and book the flights. “When we got here, it all hit me,” she told me. “I was like, ‘Oh my gosh. I did it.'”
Fear of staying, not leaving
One of the most powerful things Jess said in our conversation was that she didn’t really have fears about moving to Mexico. Her fears were about what would happen if she stayed. That reframe is everything. For so many mamis, the discomfort of the unknown feels bigger than the discomfort of where they already are. Jess flipped that. And she believes fear itself is a signal – not a stop sign, but a green light pointing you toward growth.
The kids are more than okay
Her 12-year-old wanted nothing to do with the move at first. There were meltdowns. There were hard conversations. Jess second-guessed herself. But she also did something brilliant; she intentionally chose a community where her daughter would have an immediate soft landing: twin girls, same age, same interests. Gymnastics. Baking. Sleepovers. “I couldn’t ask for anything more,” Jess said. Her 7-year-old is now on Duolingo every day and selling baked goods in the community, which means she’s learning Spanish out of necessity, the best teacher there is.
Claiming what’s hers: the dual citizenship journey
Because Jess’s Mexican father isn’t listed on her birth certificate, claiming her dual citizenship has required going through the courts to have his name added – a process that involves affidavits, a judge, vital records, and a lot of patience (especially when your father operates on his own timeline). It’s not easy. But Jess is doing it because she wants her kids to have what she didn’t: official access to their lineage, their heritage, their roots. “It’s their right,” she said. “Even if they choose differently as adults, I want to give them that door.”
Her best advice for the mami on the fence?
Two things. First: if the desire is in your spirit, it’s there for a reason. Go visit. Make a plan. Know that if it doesn’t work out, you can come back – you already know that life. Second, and maybe more importantly: stop telling people your plans before you’re ready. Their fears will become your fears. Their what-ifs will live in your head. Buy the ticket, then share the news.
Jess Winns is proof that you don’t need everything figured out to make a move that changes your life. You just need to be more afraid of staying than you are of going.
Show Notes
In this episode of the Mamis Abroad series, I’m sitting down with Jess Winns, a mom of four, published author, entrepreneur, Board-Certified Holistic Health Practitioner, and Transformational Leadership Coach, who made the bold decision to pack up her family and move to Playa del Carmen, Mexico as a single mom.
We talk about the moment she knew it was time, what it’s really like to build a life from scratch in a new country, and why she says the secret is to stop telling people your plans.
This episode is for every mami who has whispered “what if” to herself, and hasn’t given herself permission to find out.
What You’ll Hear:
- How to reframe fear as a signal that you’re moving in the right direction — not a reason to stop.
- Why protecting your dream from other people’s doubts might be the most important step before making a big move.
- A practical mindset shift for mamis worried about uprooting their children — and why kids adapt faster than we think.
- Key things to know before starting the journey, including why adding a foreign parent to a birth certificate matters more than most people realize.
- What it really takes to create income and community when you move abroad without a village waiting for you.
Resources Mentioned:
- Listen to Jess’s first interview on the VLM podcast! Episode 39
- Jess’s personal Instagram: @thejesswinns
- Family travel IG page: @thisfamilywinns
- Jess’s book: Beneath the Skin
- Jess’s skincare line: Ari Rose Body Care
About Our Guest
Jess Winns | Entrepreneur, Author, Speaker, World Traveler
Jess Winns is a mother of four, published author, entrepreneur, and dynamic speaker born and raised in Chicago. As a Board-Certified Holistic Health Practitioner, Functional Nutrition Counselor, and Transformational Leadership Coach, she has built a career at the intersection of wellness and leadership – founding businesses in leadership development, holistic wellness, and sustainable skincare, including her organic body care line, Ari Rose. She is also the author of Beneath the Skin, a powerful exploration of personal growth and transformation.
Today, Jess is writing a new chapter as a single mami abroad, raising her four children abroad and expanding her global youth leadership program.
