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 your go-to expert for planning joyful, stress-free Disney vacations.
A lifelong Disney fan raised on Main Street magic and Mickey-shaped memories, Jessica now helps families, moms, and first-time travelers confidently plan trips to Walt Disney World, Disneyland, Disney Cruise Line, and beyond without losing their minds (or their budget).
As a mom who’s done it all from toddler meltdowns to teens chasing thrill rides, from multigenerational trips to magical girls' weekends. Jessica offers real-world advice rooted in emotional insight, practical planning, and a deep love of Disney storytelling. Whether you're traveling solo, with a stroller brigade, or booking for a party of 14, Jessica gives you the tools to make it magical your way.
On the Podcast she shares Disney vacation tips, park planning strategies, event guides (like Mickey’s Not-So-Scary Halloween Party), and emotional reflections from inside the parks alongside expert guests and fellow moms who love magic as much as she does.
In addition to blogging and podcasting, Jessica creates daily content on Instagram and YouTube, where she blends humor, hacks, and heartfelt moments into helpful videos and reels for Disney travelers of all kinds.
When she’s not answering DMs about Lighting Lane or testing out stroller nap strategies, you’ll find her:
- Baking Disney-themed sugar cookies for her brand Well Hello Cookie
- Running her sign rental business Sign Gypsies Lehigh Valley
- Writing her debut YA novel series, Foreign Parents Syndrome
- Planning her annual Disney mom retreat, The Enchanted Escape
With thousands of families already turning to her for first-time Disney planning help, budget-friendly vacation strategies, and military Disney discounts
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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