Well Hello Magic: A Disney Planning & Experience Podcast
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.
Episodes
128 episodes
128: Disney Dream Cruise Recap: Embarkation, Food, Kids Clubs & Chaos
Planning your first Disney Cruise Line vacation? Wondering what embarkation day actually looks like with kids? Trying to decide if your family would rather cruise than do the Disney parks? This episode is for you.After sailing on the Dis...
127: Taking a Baby to Disney World for the First Time: What No One Tells You
Taking a baby to Walt Disney World for the first time is a completely different experience, especially if you are someone who has always known the parks inside and out. In this episode, we are talking about what it really looks like to bring a ...
126: Everything You Need to Know About Disney’s Value Resorts (Before You Book)
If you are planning a Walt Disney World vacation and trying to decide which Disney value resort is best, this episode breaks down everything you need to know about Disney’s value resorts, including price, transportation, room types, and which r...
125: Walt Disney World Solo Trip Recap: 3 Days, 3 Resorts, EPCOT Updates & Cruise Planning
I just got back from a whirlwind three-day solo trip to Walt Disney World, and this episode is a full, honest recap of everything I experienced. This trip was quick, but it was packed in the best way, and I’m walking you through it all from sta...
124: The Disney CEO Race: How Josh D’Amaro Won Disney’s Top Job with Amanda From Once Upon A Marathon
Disney has a new CEO, and if you’ve been following the leadership shifts at The Walt Disney Company over the past few years, you know this moment has been a long time coming. In this episode of the Well Hello Magic Podcast, I’m joined by Amanda...
123: Preparing for Our First Disney Cruise as a Family on the Disney Dream | What I Bought, Booked & Planned
In this episode, I’m sharing exactly how my family is preparing for our upcoming Disney Cruise on the Disney Dream and all the things we’ve booked, purchased, and planned to make this trip as smooth as possible. If you’re planning your <...
122: Disney Cruise Line for First Timers: Ships, Costs, Dining, Navigator App, and Mistakes to Avoid
Thinking about booking your first Disney Cruise Line vacation but not sure where to start? In this episode, I’m breaking down everything I’ve learned so far about Disney cruising for beginners as someone who still considers hersel...
121: Behind the Magic with Camille Dashana from Sparks of Magic
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 Jef...
120: Disney World Lightning Lane 2026: Pre-Booking Rules, Sell-Out Data & Best Time to Ride
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 tim...
119: The Magic of Friendship: A Galentine’s Celebration Inside the Disney Community
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 ...
118: Is the Disney Dining Plan Worth it in 2026??
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 y...
117: Behind the Magic with Kellie Krueger from We Don't Wear Ears
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...
116: Disney World Do’s and Don’ts: What Actually Makes or Breaks Your Trip
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 mar...
115: Behind the Magic with Guest Creator Matt Richardson
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...
114: Disney World 2026: What to Expect, What’s New, Closures, and Planning Changes
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 ...
113: Behind the Magic - Guest Creator Brittany from Travels by Brittanyb
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 ...
112: Fort Wilderness Tips, Jollywood Nights with Kids, and Why We Love Disney’s Hilton Head Island Resort
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 es...
111: Behind the Magic with Guest Creator Melissa from Happy Haunts Plan Magic
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 mag...
110: Behind the Magic – Guest Creator Shakira from Occasions by Shakira
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 sp...
109: Mickey’s Very Merry Christmas Party, Jollywood Nights, and Tips for Surviving the Holidays at Home
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...
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, ...
107: Mickey's Not So Scary Halloween Party Trip Report
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 ...
106: Behind the Magic – Guest Creator Amanda from Once Upon A Marathon
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 exper...
105: Best Places to Work at Walt Disney World + Last-Minute Halloween Tips
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: findin...