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Well Hello Magic: A Disney Planning & Experience Podcast
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Well Hello Magic: A Disney Planning & Experience Podcast

Author: Jessica Mickelson

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Jessica Mickelson is the voice behind Well Hello Magic, a top family-focused Disney World planning podcast and trusted resource for parents. She is a Disney-loving mom of four, former therapist, military spouse, content creator, and expert in realistic Walt Disney World vacation planning for families, moms, and first-time Disney travelers.


A lifelong Disney fan raised on Main Street magic and Mickey-shaped memories, Jessica helps families confidently plan Walt Disney World, Disneyland, and Disney Cruise Line vacations without overwhelm, burnout, or unrealistic expectations. Her approach centers on realistic Disney itineraries, Lightning Lane strategies for families, crowd planning, budgeting tips, Disney resort comparisons, and helping parents enjoy Disney without feeling pressure to do it all or spend it all.


As a mom who has experienced Disney with toddlers, tweens, 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 park days to Lightning Lane Multi Pass breakdowns, from solo trips and girls’ weekends to group vacations of 14 or more, she teaches parents how to plan Disney trips that feel both magical and manageable.


On the Well Hello Magic Podcast, Jessica shares practical Disney World planning tips, in-depth Lightning Lane strategy, rope drop guidance, Disney resort reviews, Disney Cruise Line advice, and event guides like Mickey’s Not-So-Scary Halloween Party and Mickey’s Very Merry Christmas Party. She also hosts honest conversations about the emotional and mental load of Disney travel, helping parents reduce stress while maximizing joy.


In addition to practical planning content, Jessica hosts Behind the Magic, a Disney podcast interview series featuring Disney content creators, bloggers, YouTubers, and Instagram influencers who share their love of Walt Disney World, Disneyland, and Disney Cruise Line. Through authentic conversations, she explores how creators build Disney-focused brands, grow engaged online communities, balance motherhood and entrepreneurship, and keep the joy of Disney alive in everyday life. Behind the Magic highlights the voices shaping today’s Disney creator community while offering inspiration and insight for aspiring Disney bloggers and content creators.


Beyond the podcast, Jessica creates daily Disney and family travel content on Instagram and YouTube, blending humor, therapist-informed insight, and actionable Disney vacation planning advice to help families plan Disney trips with confidence, clarity, and less stress.

121 Episodes
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Send a text Camille is my dear friend, and in this episode of Behind the Magic, you are getting the full Disneyland girl experience. Camille is an entrepreneur, writer, Southern California native, mom of five, and married to her wonderful husband Jeff. She is also our cruise buddy. We sailed on the Disney Wish together and already have the Disney Destiny on the calendar next year. Disney is not just something she visits. It is woven into her life story, her marriage, her motherhood, and even ...
Send a text f you’re planning a Walt Disney World vacation in 2026 and feeling overwhelmed by Lightning Lane pre-booking, this episode is for you. Lightning Lane is not random. Sell-outs are not random. Mini drops are not random. And standby wait times are definitely not random. In this episode, I break down Disney World Lightning Lane strategy using real data — including pre-booking rules, Multi Pass vs. Single Pass differences, and what actually sells out first in each park. We go park by p...
Send a text Friendship can look a lot like magic and in this special Galentine’s Day episode, we’re celebrating the kind of connections that feel like home. This week on Well Hello Magic, Jessica is joined by three women who have become far more than fellow Disney creators: Corina from The Magical Latina, Meg from Meg For It, and Lauren from Lauren Dreams of Magic. What started nearly two and a half years ago on a hosted Disney trip grew into real friendship, mutual support, and a sisterhood ...
Send a text Is the Disney Dining Plan worth it in 2026? Should your family add the Disney Dining Plan or pay out of pocket? How does the Disney Dining Plan actually work, and who is it really for? In this episode, we break down everything you need to know about the Disney Dining Plan at Walt Disney World so you can decide if it makes sense for your family’s vacation. We start by explaining how the Disney Dining Plan works, including how dining credits are calculated, how meals are redeemed, w...
Send a text Disneyland hits differently when you experience it like a local, and in this episode of Behind the Magic, we’re unpacking exactly why. I’m joined by Kellie Krueger, a Disneyland pass holder of over 20 years and the creator behind We Don’t Wear Ears. Kellie brings a perspective that only comes from decades of regular park visits, raising a family alongside Disneyland, and learning how to enjoy the parks without turning every visit into a checklist. In this conversation, we talk abo...
Send a text Planning a Walt Disney World vacation can feel magical… until it doesn’t. Between budgeting, park planning, Lightning Lane decisions, dining reservations, heat, crowds, and kids with very real limits, it’s easy for a Disney trip to miss the mark—especially for families. In this episode, I’m breaking down the real Disney World do’s and don’ts I actually follow as a mom of four and someone who plans Disney trips regularly. This isn’t about doing Disney perfectly or squeezing every r...
Send a text In this episode of Behind the Magic, Jessica sits down with Disney Parks content creator Matt Richardson for a conversation that goes far beyond a typical Disney vacation story. Matt shares how his career in tech has taken him around the world, teaching and working with teams on how to integrate technology into everyday life. Those global work opportunities have also opened the door for him to experience Disney parks internationally, allowing Disney to become a natural extension o...
Send a text Planning a Walt Disney World vacation in 2026 and wondering what’s new, what’s changing, and what you need to know before you book? This episode is your complete Disney World 2026 planning guide, breaking down everything coming to Disney World in 2026, park by park, so you can plan with confidence. In this episode, we cover what to expect at Magic Kingdom, EPCOT, Hollywood Studios, and Animal Kingdom in 2026, including ride reopenings, closures, new entertainment, character experi...
Send a text Today’s episode is extra special because we’re welcoming back one of the original Well Hello Disney family members—Brittany B! If you’ve been here since the early days (we’re talking 2022, under 1,000 followers), then you might remember when Brittany was planning her very first Walt Disney World trip with her two young kids. What started as a mom planning her first Disney vacation has turned into something truly magical. Fast forward three years, and Brittany has gone from first-t...
Send a text This week on The Well Hello Magic Podcast, we’re taking you on a full Disney journey that spans Fort Wilderness Resort & Campground at Walt Disney World, the Jollywood Nights holiday party at Hollywood Studios, and the peaceful, relaxing escape of Disney’s Hilton Head Island Resort. If you’ve been searching for real reviews, tips, and honest experiences on Fort Wilderness campsites, Disney RV camping, DVC beach resorts, or what Jollywood Nights is like for families, this episo...
Send a text Melissa from Happy Haunts Plan Magic on Instagram is joining me today, and you are going to love this conversation. She is the owner of Foolish Mortal Planning Co. and a travel expert who has helped hundreds of families plan intentional and magical Disney vacations. Recently, she had the incredible opportunity to be one of the very first people in the world to step onto the Disney Destiny. Through her partnership with the travel agency A Mouse in the Beach, she was invited on the ...
Send a text In this episode of Behind the Magic, we’re thrilled to welcome Shakira Patterson of Occasions by Shakira, a family-first creator who turns the everyday into something extraordinary. Shakira opens up about life as a military spouse, raising four children, and building a brand centered on intentional memory-making. She shares how she started her career, the unexpected path it took, and how she developed her product line (including The Occasions Bin®) to serve families looking to cel...
Send a text The holidays have officially arrived at Walt Disney World, and we’re talking about all things Mickey’s Very Merry Christmas Party and Disney Jollywood Nights in this festive episode of the Well Hello Magic Podcast. If you’ve ever wondered which of these two holiday parties is right for your family, I’m breaking it all down with honest insights, practical planning advice, and real parent perspective. We’ll start with Mickey’s Very Merry Christmas Party at Magic Kingdom, the classic...
Send a text 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 p...
Send a text In this week’s episode of the Well Hello Magic Podcast, I’m sharing our family’s recap of Mickey’s Not-So-Scary Halloween Party at Walt Disney World. This was one of those quick Disney trips that filled our cups completely, and we packed in so much magic. From driving to Disney with kids to candy trails and fireworks, this episode covers it all. We start by talking about what it’s really like to drive to Disney as a family. I share our best tips for long car rides with kids, how t...
Send a text I am so excited to welcome Amanda Kass from Once Upon a Marathon back to the podcast. Amanda is a certified running coach, an incredible content creator, and one of my favorite people to talk to about all things Disney. She is not only an expert in runDisney but also someone who pours her heart into helping others reach their running goals. Amanda began running in graduate school and has since completed countless Disney races, including the Dopey Challenge, which is one of the mos...
Send a text Planning a Disney trip is magical, but it is not always perfectly polished. Sometimes it is a little last minute, a little messy, and a whole lot of fun. In this episode of the Well Hello Magic Podcast, we are diving into two big topics: finding the best places to work remotely while at Walt Disney World Resort and tips for pulling off a last-minute Halloween trip like a pro. First up, let’s talk about remote work at Disney. Whether you are a content creator, a parent squeezing in...
Send a text I am so excited to welcome Paula, the creative force behind @practicallyperfectfamily and @chronicallyperfectpaula to the Well Hello Magic Podcast today. Paula was one of the very first “froggy friends” with Undercover Tourist, which is where my journey of following her incredible work began. Over the years, I have watched her grow from hitting her first 10,000 followers to inspiring more than 150,000 people across multiple platforms. Her mix of humor, honesty, and heart has made ...
Send a text On today’s episode of the Well Hello Magic Podcast, we’re talking all about one of the most popular Disney experiences for families — character dining at Walt Disney World Resort. ✨ We’ll go over every single character meal currently available, plus a few beloved experiences that are now part of Disney history (goodbye Bon Voyage Breakfast and Supercalifragilisticexpialidocious Breakfast). We’ll also talk about what sets a true character meal apart from signature dining experience...
Send a text This week’s episode is extra special because my sister, Nicolette, joins me for a heartfelt conversation about our family’s multigenerational love for Walt Disney World. We grew up as true “Disney kids,” with parents who made magical memories a family tradition — and that legacy still shapes who we are today. Together, we reminisce about our earliest park trips, the ways Disney has influenced our values, and how those experiences have carried into our adult lives. Nicolette shares...
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