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Rising Stars: Meet Jessica Harrington of Windermere

Today we’d like to introduce you to Jessica Harrington.

Hi Jessica, can you start by introducing yourself? We’d love to learn more about how you got to where you are today?
I was a woman who became pregnant with twins in a new and loving marriage at the age of 29, excited and happy for the future, yet still feeling so lost. Lost from a life I gave up and sacrificed due to previous pregnancies and a past filled with traumatic experiences and constantly putting everyone else before my own dreams. I grew up feeling judged and criticized by almost every person I loved, and who loved me. However, I was always a creative soul. An artist. A dreamer…and even though those things aren’t always well received, I never truly lost sight of that. I came across quirky and unrealistic to many around me, so I began shifting my mindset and molding my future self to the aspirations and visions of how other people in my life saw my future, instead of my own. This lead me down a path of confusion, hurt and unfulfillment. I spent years fighting my dreams and goals for myself with the life I had lead myself down up until this point, due to others emotions, not mine.

One day, after many destructive romantic relationships, some hard lessons and truth along the way and having two children at a young age, I decided I was done. Laying there, thinking about the 2 new lives I was about to bring into the world and finally finding a love that did not judge, test or harm, I made a decision in that very moment to embrace what I have done for myself and my life, and finally trust myself to rekindle that creative spirit I always had, and had been missing for so long.

When I was younger, I dove into poetry as an escape, and, I also went on many Disney vacations with my family. If I am being 100% raw here, it was one of the only times during my childhood where I remember feeling truly happy and content with my family dynamic. I suppose looking back now, this too was also an escape in some ways. However, it was also the one place we could all come together and not be blinded by fears, distrust and judgement. I could be my true self and allow that quirky inner creative to shine. No fake smiles, no anger, just joy. Mix that with the beauty and magic of Disney, well, it was easy to fall in love.

I remember the very first time I felt truly at home there. I was eight. We were staying at Disney’s Yacht Club resort, and my father and I were walking the dock by the lighthouse at night, with the entire lagoon lit up. I remember me running in front of him a little bit, and I began spinning in a circle. I could see him watching me out of the corner of my eye, smiling. I stopped and stared out onto the lake, staring at all of the lights and listening to the sounds of the boats go by, and in that moment I said to myself, “I love it here. It’s so pretty and I never want to leave.” It was then and there I decided that Disney would become my home, at just eight years old. Even though that love and dream diminished over time, as I grew up and molded myself to the realities and people that entered my life over the years, that spark never really left. Denial, confusion and fear may have pushed it way down deep, but it was never truly gone.

Discovering throughout the years my ability to learn many things quickly, and my passions for movies, photography, and writing, I rekindled that joy for Disney I hid for so long. It was time to use it in my daily life, as much as I could, as a reminder, to never lose sight of who I truly am ever again, no matter my age, and to never be afraid of my dreams, no matter how big or crazy they may be.

I started off in Youtube in 2017, sharing my love for writing, creative arts and a lack of memory, haha, through paper planning, when my twins were just 6 months old. I quickly realized I had a natural talent for video editing and graphic design through this. As I continued to share my creativity, I began feeling the the urge to share more of my life as a mom of 4 with twins, and all the ways I was trying to juggle balancing that life with my drive to experience all the things I missed out on at such an early age, through daily adventures and travel, in order to keep that spark in me lit. As lifestyle vlogging became my main focus, I realized the one thing that was still missing…Disney. At this point in time, I was 32 years old. I was an avid Disney vlogger enthusiast, watching big Disney youtuber’s almost daily, and I loved it. After a while I realized I wanted to be a part of this amazing community too, but my age worried me. Am I too old to break into this? Is this area already too saturated and would I just get lost in the chaos? However, I wasn’t about to let my fear of failure or perception from others start dictating my aspirations again. “You can inspire anyone at any age, Jess”, I confirmed to myself.

Fast forward to today, 7 years later, age 39, and this decision has taken me on the most incredible journey. Not only have I become an active member in the Disney social media community as a millennial “Disney adult”, but I am also a licensed Disney Travel Planner, have had the opportunity to be a brand ambassador for some small businesses along the way as well, including the well known Passion Planner brand, and am now literally living my dream, as I just relocated to the Orlando area in July of 2025 to continue pursuing this dream, with the hope of making it bigger and better than ever!

I am now a Disney pass holder, visiting the Disney parks weekly to capture all of the magic in real time, including limited food, holiday entertainment, ongoing resort and park updates, and just daily Disney local living. I’m even pursuing poetry again. The fact that I am even writing this story to be presented and shared to even more like minded people, who may be able to relate or even to help someone else who may be feeling lost and is looking for inspiration, makes me so emotional and feels so surreal, especially at my age. To know that, that once carefree eight year old girl, spinning on a dock in Walt Disney World, dreaming for it to be her home, and now, 31 years later, can actually call it that, is pretty incredible, and I am so proud of how far that scared, unseen teenage girl has come.

So, in closing, it may seem like some silly dream. How could Disney be all of that for one person? The truth is though, Disney was always more than just movies and rides for me. It was the one place where I felt like I could be who I truly was. It was the one place where I truly felt seen. Disney is what kept hope alive inside me. Hope for true love, hope for understanding, hope for strength to believe in myself. It was the one place where I truly felt at home, and now, I get to share that with all of you. I wouldn’t trade any of the past trauma, hurt, unplanned experiences, or sadness for the world, because it’s what led me here. It led me to finding myself again, and now I get to spin on a dock in Walt Disney World any time I want too.

Of course, I wouldn’t be here if it weren’t for the unconditional support from all of the amazing friendships i’ve made through this journey, and my husband, kids and followers. So thank you to those who still believed I could pursue my dreams, despite my life path and age. And if you’re reading this unsure like I was 7 years ago, and you’re needing the same support, I understand you. I believe in you, and yes, you deserve it too, because the people in your life can only be as happy as they see you are. Don’t let your age stop you, and don’t let fear control you. Choose your happiness. Choose your dreams. Choose you.

We all face challenges, but looking back would you describe it as a relatively smooth road?
It was not a smooth road. My struggles began when I was just 12 years old. But I suppose that’s life right? We are only as strong as our struggles, and It’s all about how you rise above them. No matter how long it takes.

I had a mom who I caught cheating on a father that seemed so perfect, but as I got much older, realized he wasn’t.

I was in 2 abusive relationships, one of which was extremely violent and detrimental to my growing up. The other, narcissism mixed with a sometimes to forgiving heart, had me caught up in a life I never wanted for myself for far too long.

I became a mom at just 19 years old. It was scary, and hard, and the father wasn’t really in the picture, as much as I had hoped he would be. In the beginning I struggled with being a single mom for him, but I’ll never forget the moment I REALLY saw him, and chose to be the best mom I could be for him, no matter how young I was or how hard my life was at that time.

I got married to the wrong man to try and make everyone else around me happy, except me. This came with big lessons and a lot of tough love, and because of this relationship I was diagnosed with high functioning anxiety and borderline PTSD. There are still days I wish I could have been braver for myself, and walked away despite the judgements I knew I would receive, but you can’t change the past, only learn from it.

My best friend since middle school and I had a huge falling out, and I still mourn our friendship to this day. And although we do talk and check in from time to time now that we are older, and I will always love her, sometimes you just cant change the fact that you outgrow people, even a best friend.

I also struggle with frequent migraines and chronic vertigo and other small health issues that have made it more difficult to go about daily living at times, but I push through the best I can, not just for my kids, but for me as well, because I deserve it, and I refuse to let myself down anymore.

Finally, my weight has been a setback for me for some time now. I wasn’t always plus size. I was your average teenager, no concerns for weight. But after I had my daughter, and being in so many negative relationships, it caused me to lose myself in so many ways, including my hormones and weight control. Mix that with multiple pregnancies and a difficulty to exercise due to my health, my self confidence physically is still a constant mindset struggle. Most days I am able to embrace my new body, because I truly believe in loving yourself in each season of your life, but there are days where I questioned if this holds me back in ways too.

Appreciate you sharing that. What else should we know about what you do?
Currently I have multiple passions I am working on.

First and foremost, I am a lifestyle vlogger on Youtube, specializing in Disney local living, planning and hobbies. I like to just be real in my content. I like to think my videos feel like your on facetime with me, and I really do pride myself on that because my main goal is to just connect to my viewers as family and just share my life. It helps me not feel alone. Through this, I found a natural talent for photography, photo editing, video editing and graphic design! Along with this comes social media marketing so I can continue to make a name for myself.

Secondly, I am a Disney Travel Planner. I currently book vacations mostly for Disney, Disney cruise line and Universal Studios. I also specialize in New England destinations, as this is where I grew up and still have a love for many places there.

Finally, I have recently gotten back into writing, specifically poetry. I wrote so much when I was younger, and in my early 20’s I even started writing a potential book based off my life and all of the things I had been through as a child/teen. Although that book never was able to be completed, I recently found my way back to writing poetry, and now perhaps a new book could be in my future!

Can you talk to us a bit about the role of luck?
Woof…I have had a lot of “luck”, if that’s what you want to call it. Bad luck to be exact. Lots of life lessons, poor decisions and bad experiences that seemed out of my control. My first instinct is to blame my knack for choosing to see the good in everyone and everything, but I know now that is a really special thing in a person, and I couldn’t stop being like that, even if I tried. I often questioned the universe, “why is it always me?”, or screamed, “AGAIN!?”. I mean, no one asks for a near death experience at 15 like in the movies, or an accidental pregnancy at 17, or parents who you could always sense that they were unhappy due to your extreme empathy. However, I like to think that I was always built stronger than the things that happened to me. And yes, maybe a part of me was conditioned like that BECAUSE of all the bad things that I went through, but, I also have to wonder, if I never lost myself in the midst of the mess, would I be where I am today, pursuing what I am pursuing now, experiencing life to the fullest, if I hadn’t?…probably not.

I will say though, out of everything that I have gone through in my life, as far as GOOD “luck” is concerned, I would have to say I wouldn’t be believing in myself the way that I am today, without the courage, faith and trust my husband rekindled inside of my when we met. We met online of all places, and we spent months talking before even meeting. He let me vent about all of the bad, and never judged for one ounce of it. Im still learning why the universe brought him to me some days, cuz marriage isn’t easy no matter how much you love someone, but I can say this…I have never been so supported by anyone like I have him.

So, luck? Maybe…but I also truly believe at the end of the day, it was me, my perseverance, my courage, and my determination to not allow myself to stay stuck for too long, that got me here. To not stay stuck in the negative, the sadness, the fear, the unknown. At the end of the day, its only you who can bring you to where you want to be, to where you want to take your life to. Its only you who can get yourself out of the bad, and pursuing all the good. Yes, outside experiences can help shape the course of your life, but, it’s really only when you believe you truly deserve something, once you truly believe in yourself, that’s when your dreams can come true.

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