Well Hello Magic: A Disney Planning & Experience Podcast
Jessica Mickelson is the voice behind Well Hello Magic, the #1 family-focused Disney World planning resource for parents. She is a Disney-loving mom of four, former therapist, podcast host, content creator, and trusted expert in realistic Disney vacation planning for families, moms, and first-time travelers. As part of a proud military family, Jessica brings a deep understanding of planning Disney 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 Walt Disney World, Disneyland, and Disney Cruise Line vacations without overwhelm, burnout, or unrealistic expectations. Her approach centers on realistic Disney itineraries, thoughtful planning strategies, 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 strategies for families, 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, Lightning Lane breakdowns, park strategies for families, event guides like Mickey’s Not-So-Scary Halloween Party and Mickey’s Very Merry Christmas Party, and honest conversations about the emotional and mental load of Disney travel. Episodes feature expert guests and fellow Disney-loving moms who value preparation, flexibility, and realistic expectations.
Beyond the podcast, Jessica creates daily Disney and family travel content on Instagram and YouTube, blending humor, therapist-informed insight, and actionable planning advice to help families plan Disney vacations with confidence, clarity, and less stress.
Well Hello Magic: A Disney Planning & Experience Podcast
096: Lead Planner Life & Summer Disney Trip Catch-Up
this episode, we’re diving headfirst into the world of Disney trip planning — specifically, what it’s really like being the lead planner. You know…the person in charge of flights, G+ strategy, resort picks, dining reservations, and making sure your cousin doesn’t Venmo you two weeks after the trip is over. 😅
Whether you’re coordinating a multigenerational vacation, a besties’ weekend getaway, or just trying to keep your own family alive and joyful inside Magic Kingdom, I’m breaking down the mental load lead planners carry — and sharing some of my tried-and-true resources, systems, and tips to make it less stressful and way more magical.
Then, I’m catching you up on our wild summer Disney adventures. In July, we spent a full 10 days on property — tackling the parks in peak heat, trying every snack Twinkie the Kid put out in the name of research, pool hopping like professionals, squeezing in midday naps at the resort, and perfecting the art of getting our kids to watch fireworks without anyone having a total emotional breakdown.
And just to keep my stress levels high, I turned around and flew right back a few weeks later for a Disney creators’ weekend, which included:
- a Grand Floridian Spa day (yes, facials before fireworks are a thing),
- a VIP tour that made me never want to wait in a Seven Dwarfs line again, and
- one more surprise moment watching Disney Dreams That Soar from the train station balcony — pure magic.
Finally, we’re chatting about what’s new in the world of Disney planning right now and I’m giving you all of my favorite current tips and tricks — from handling Genie+ with grace (kinda) to keeping grandparents happy, to saving your sanity with one simple rule: remember who needs the stroller.
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