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Meet Holley Long of Winter Garden

Today we’d like to introduce you to Holley Long.

Hi Holley, thanks for joining us today. We’d love for you to start by introducing yourself.
Growing up, I visited Orlando as much as possible. Disney World was the biggest draw, then Universal became a favorite destination, but when I became an adult and ventured outside of the theme park bubble, I knew I wanted more out of the city than I could get with a five-day vacation. So, in the summer of 2021, my husband and I moved to Orlando, settling in Winter Garden, and I started The Orlando Dreamer, a social media presence that has become my digital diary to document all of the wonderful things I’ve gotten to enjoy around the city. Of course, I’ve created a LOT of theme park content, but I’ve also had the opportunity to share my experiences at local restaurants, fun attractions, and so much more.

We all face challenges, but looking back would you describe it as a relatively smooth road?
So, I moved to Orlando in 2021—but the idea of living here had been a constant nudge in my brain since 2018, when my husband and I went on our first Disney World trip together. After that trip, we talked and dreamed about moving to the city a lot, but work and family obligations kept us rooted in our hometown for a while. Then, in 2020 we felt ready to make the move but, well, a global pandemic happened. It was only after the world started opening back up that we both were able to land jobs in the city and make the leap. So, getting to Orlando was a long time coming, but the journey is half the fun, and I think we arrived right on time.

Appreciate you sharing that. What else should we know about what you do?
Content creation is something I never thought I’d get into. I’m always the last person to download a social media app, and I might post to my personal accounts once a month. But The Orlando Dreamer has been a fun platform to play with. Since I started it, I’ve shared DITLs, silly trends, skit-style videos, and more. I’ve posted reels and TikToks with my thoughts on restaurants throughout the city, documented my race days with runDisney, and taken followers along for nights at events like Halloween Horror Nights. I, of course, want to spread the word about these fun things happening in Orlando, but my main goal with the account is to just have fun. I love this city, and I’m sure I won’t live here forever, so I want to be able to look back at these photos and videos one day and smile at all the amazing times I had.

Do you have any advice for those just starting out?
In terms of moving to a new city—just do it. Of course, make a plan and handle any obligations that are keeping you rooted somewhere else, but I think too often our biggest roadblocks are the ones in our heads. Just know that if you make the move it doesn’t have to be permanent in order to be wonderful. In terms of content creation, make content that is authentic to you. I can’t tell you how many times I’ve tried to make a video with a trending sound or concept only to stop, take a step back, and realize that I’m not into it and it doesn’t feel like “me.” I think it’s easy to fall into the trap of making things for the algorithm, but if your online persona doesn’t feel like “you” then I think the point is lost.

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