Say Yes More Often: Jill Anderson on a Life Built on Travel, Connection, and Curiosity
- Jill Jakelis Anderson
- 1 hour ago
- 8 min read
What is your name and what do you want the world to call you?
My full name is Jill Jakelis Anderson, and everyone calls me Jill.
Where are you from and where do you call home now?
I grew up in Colts Neck, New Jersey, a beautiful town known for its horse farms. Ironically, I've only ridden a horse once, and it wasn't even there! Today I call Pompano Beach, Florida, home, where I've built both my business and a wonderful community.
If someone met you for the first time at a dinner party, how would you want them to describe you after the conversation ended?
I hope they'd say I made them feel comfortable right away, that I'm curious, a good listener, and fun to be around. I love great conversations, good food, a nice glass of wine or cocktail, and bringing people together.
I hope they'd say I made them feel comfortable right away, that I'm curious, a good listener, and fun to be around.
Take me back. What were you like as a little girl? What did you dream about becoming before the world told you what was realistic?
I was a curious, energetic, and slightly goofy little girl who was always laughing. As the youngest of three girls, I grew up with two older sisters to look up to and learn from. I honestly don’t remember having one big dream about what I wanted to be when I grew up. I was much more interested in enjoying whatever was happening at the moment, having fun, being around people, and making people laugh.
Was there a moment, a person, or an experience early in your life that shaped how you see yourself today?
By high school, my friends had nicknamed me "Julie, Your Cruise Director" after the character on The Love Boat. I was always organizing get-togethers, making sure everyone was included, and planning whatever adventure came next. I was class president, captain of the cheerleading squad, captain of the soccer team, and I genuinely loved bringing people together. Looking back, it's funny how that nickname ended up predicting my career.
What is something about your upbringing that explains who you are now, even if it does not seem obvious on the surface?
I grew up in a loving family where hard work wasn't just encouraged; it was simply part of who we were. My grandparents, parents, and sisters all led by example. We were taught to work hard, care about people, and always do the right thing, even when no one was watching. Those lessons still shape who I am today.
What was happening in your life right before you decided to build what you are building now?
Before starting my business, I was working in corporate event planning. I loved the people I worked with, but I had reached a point where I knew I was ready for something different. When COVID brought the world to a standstill, it also gave me the chance to pause and ask myself what I really wanted the next chapter of my life to look like. The answer brought me full circle. My very first career out of college was at a small, family-owned travel agency, where I spent about eight years. I realized that travel had been my first professional love, and it was time to come home to it.
Was there a breaking point? A moment you knew something had to change?
I wouldn't call it a breaking point as much as a quiet realization. I wasn't feeling the excitement and sense of purpose I once had. COVID gave me the space to slow down, reflect, and really listen to what my heart was telling me. I realized I wanted to spend my days helping people create meaningful experiences and lasting memories through travel.
What did you have to walk away from to become who you are today?
The biggest thing I had to leave behind was the security of a steady corporate career. Becoming an entrepreneur meant betting on myself, taking a leap of faith, and building something from the ground up. It was definitely a little scary, but it has also been one of the most rewarding decisions I've ever made.
If you could go back and tell yourself one thing in that moment, what would it be?
Trust yourself. You don't have to have every answer before you begin. Follow your intuition, take the leap, and don't be afraid to build a life that feels aligned with who you are. Looking back, everything I'd done up to that point had been preparing me for this, even if I couldn't see it at the time.
Trust yourself. You don't have to have every answer before you begin. Follow your intuition, take the leap, and don't be afraid to build a life that feels aligned with who you are.
How did you land in this specific field? Was it intentional or did it find you?
A little of both. Again, my first job out of college was with a small, family-owned travel agency after a family friend suggested I give it a try. I immediately fell in love with the industry. Although my career later took me into corporate event planning, travel was always a part of my life. I organized meetings and events that often involved travel, continued exploring the world personally, and never lost my curiosity about new places and cultures. When I reflected on what I truly wanted, I realized travel had always been the common thread. It felt less like finding a new career and more like coming home.
What is the real reason you do this work? Not the polished answer. The true one.
I genuinely love creating experiences that people remember long after the trip is over. One of my favorite moments is watching strangers become friends and seeing those friendships continue long after everyone returns home. That's when I know the trip was about so much more than the destination.
As I've gotten older, I've also realized that travel can be about so much more than checking places off a list. I want the trips I create to be joyful and meaningful while encouraging us to appreciate the communities we visit. Whether that's supporting local businesses, participating in a volunteer project, or simply traveling with gratitude and respect, I hope people come home feeling like they received something special and gave something back in return.
What is the transformation you are actually trying to create in the people you serve?
I want people to feel more connected than when they left. Connected to the world, to new friends, to different cultures, and sometimes even to themselves. Many people want to travel but don't have someone to go with, don't know where to start, or feel overwhelmed by the planning. I welcome solo travelers and love creating an environment where people feel welcomed, included, inspired, and excited to say yes to their next adventure.
If your business disappeared tomorrow, what is the one thing you would want people to remember it stood for?
I hope people would remember the friendships that were formed, the laughter that was shared, and the memories we created together. More than anything, I hope they would say they felt cared for, welcomed, and part of something bigger than just another vacation. I’d also love for giving back to be part of that, finding meaningful ways to support the places and communities we visit along the way. If I can help people experience the world with a little more gratitude, connection, and generosity, I’d feel incredibly happy about that.
When you are not working, who are you? What lights you up that has nothing to do with your business?
When I'm not working, you'll usually find me spending time with my husband, Derek, family, or friends. I love sharing meals, discovering new restaurants, getting outside for a walk, and riding roller coasters! One of my favorite memories is celebrating my 50th birthday at Disney World with my entire family. Watching my parents, sisters, and their partners and the little ones all on the Tea Cups laughing together is an image I go back to when I need a little lift. I think experiences are the best gifts we can give each other, whether they're halfway around the world or just an afternoon spent together.
What does a perfect ordinary Tuesday look like for you right now?
My perfect Tuesday starts early with gratitude and meditation, followed by a morning walk or fitness class with friends. Then it's a productive day helping clients and planning future adventures. In the evening, I'm happiest sharing a homemade dinner that my husband cooked (how lucky am I!!) or meeting friends for dinner, good conversation, and maybe a glass of wine or a cocktail. It's not fancy, but it's exactly the kind of life I love.
What is something most people do not know about you that you wish they did?
People often see me as outgoing, but what they don't always realize is that I also need quiet time to recharge. Every morning I spend time in meditation, expressing gratitude, and setting my intentions for the day. It helps me stay grounded, present, and focused on what really matters.
What are you most afraid of, and how has that fear shaped the way you move through the world?
I've always been afraid of letting people down. That fear has made me someone who tries to show up, keep my word, and be someone others can count on. As I've gotten older, I've also learned that I can't be everything to everyone, and that's okay. Doing my best with kindness and integrity is enough.
If you let yourself dream without limits, what does your life look like in five years?
In five years, I hope I’m still exploring the world and expanding my own travel adventures, but I also see myself giving back in a bigger way. I’d love to mentor new travel advisors, sharing what I’ve learned and helping them build businesses and lives they truly enjoy. Being of service to others has always been important to me, and I hope the next chapter of my life gives me even more opportunities to do that.
What is the legacy you want to leave behind, separate from money or titles?
I hope people remember me as someone who made them feel welcome, cared for, and included. Someone who encouraged people to make time for the relationships and experiences that matter most.If I helped create a little more joy, connection, and kindness in the world, that would be a legacy I'm incredibly proud of.
What is one thing you are still working to become, even now?
A better version of myself. I never want to stop learning. Whether it's through travel, new friendships, new experiences, or simply listening to different perspectives, I hope I continue to grow with curiosity, gratitude, and an open heart.
If a woman reading this is standing exactly where you stood before everything changed, what do you want her to know?
Trust yourself. It's never too late to choose a different path or rediscover something you've loved all along. Follow what brings you joy, work hard, and don't be afraid to take the leap.
What is the one sentence you want people to remember about you?
Say yes more often. To the adventure. To the conversation. To the opportunity that scares you just a little. To the dream that's been quietly waiting for you. You never know where one yes might lead.
Meet the expert:
Jill Anderson is the owner of Wahoo Travel by Dream Vacations and believes the best journeys are the ones shared with others. With a background in psychology, corporate event planning, and decades in the travel industry, she creates experiences that inspire connection, curiosity, and lasting memories. When she's not planning her next adventure, you'll likely find her on a roller coaster at Disney, enjoying great conversation over dinner, or encouraging someone to say yes to their next adventure.
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