Well Hello Magic: A Disney Planning & Experience Podcast
Jessica Mickelson is the voice behind Well Hello Magic, a Disney-loving mom of four, former therapist, podcast host, content creator, and trusted expert in Disney vacation planning for families, moms, and first-time travelers. She is also part of a proud military family, bringing an added layer of understanding to planning trips around real-life schedules, budgets, and seasons of change.
A lifelong Disney fan raised on Main Street magic and Mickey-shaped memories, Jessica helps families confidently plan trips to Walt Disney World, Disneyland, and Disney Cruise Line without overwhelm, burnout, or blowing the budget. Her approach to Disney trip planning focuses on realistic expectations, thoughtful strategies, and creating meaningful experiences that work for real families.
As a mom who has done Disney with toddlers, teens, grandparents, large groups, and multigenerational families, Jessica shares real-world Disney planning advice rooted in emotional insight and hands-on experience. From stroller-friendly itineraries to thrill-ride strategies, from solo trips to girls’ weekends and group vacations of 14 or more, she gives listeners the tools to plan Disney vacations that feel magical and manageable.
On the Well Hello Magic podcast, Jessica shares Disney vacation tips, park planning strategies, Lightning Lane guidance, event guides like Mickey’s Not-So-Scary Halloween Party and Mickey’s Very Merry Christmas Party, and honest reflections on the emotional side of Disney travel. Episodes feature expert guests and fellow Disney-loving moms who understand the balance between preparation, flexibility, and enjoying the moment.
Beyond the podcast, Jessica creates daily Disney and family travel content on Instagram and YouTube, blending humor, helpful hacks, and heartfelt storytelling into practical videos for Disney travelers at every stage of life.
Well Hello Magic: A Disney Planning & Experience Podcast
108: Behind the Magic – Guest Creator Brianna from Expedition Watson
I’m thrilled to welcome Brianna Watson of Expedition Watson to the podcast! Brianna is a dedicated mom blogger, lifestyle and travel creator based in Orlando, where she shares her family’s real-life adventures through motherhood, Disney, travel, and everyday magic. Her brand is all about keeping it real and inviting families to find joy in the beautiful chaos of life.
Brianna has built an incredible platform filled with warmth, authenticity, and creativity. Over the years, she’s partnered with a wide range of brands, hotels, and family destinations, all while staying true to her mission of helping families make meaningful memories. Her collaborations reflect the trust she’s built with her community and her talent for creating content that feels genuine and inspiring.
What makes Brianna’s story even more special is her leap into full-time content creation. After years of growing Expedition Watson while raising her family, she made the bold decision to turn her passion into her profession. She’s now sharing not just her adventures, but the lessons, courage, and heart it takes to build a business rooted in storytelling and family connection.
In this episode, we talk about:
- How she approaches partnerships and stays authentic in sponsored content
- What it really looks like to transition from side hustle to full-time creator
- Her favorite family travel moments and how she plans content around her kids’ interests
- How she continues to grow Expedition Watson while staying grounded in motherhood
You can find Brianna on Instagram at @expeditionwatson and on her website expeditionwatson.com, where she shares family travel guides, lifestyle tips, and stories from their life in Orlando.
This conversation is such a good one—honest, uplifting, and full of heart. I can’t wait for you to hear it!
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