Applying for the Disney College Program is a lot like auditioning to be a human embodiment of pixie dust. They don’t just ask what you’ve done—they ask who you are, how you react, how you sparkle under pressure.
The first time I applied, I didn’t get in.
Not because I wasn’t capable.
Not because I wasn’t qualified.
But because—let’s be honest—I wasn’t what they were looking for.
I wasn’t their definition of happy.
And Disney can smell forced optimism from a mile away.
The same thing happened to my sister, Jessie. Rejection letters for both of us. A quiet, collective “welp.”
The second time around, though? We cracked the code. We understood the questions weren’t really questions—they were vibe checks. We answered the way Disney wanted, and surprise: we both got in.
But life had other plans.
I had just signed a lease. I was interviewing for what I thought was a “once-in-a-lifetime” career position with the State of Michigan. Practicality won. I stayed.
Jessie went.
And that decision? That one echoes.
🌴 Spring 2016: The First Program (aka Proud Grandparent Energy) 🌴
Jessie’s first Disney College Program was Spring 2016. My ex-husband and I flew her down for check-in somewhere around January/February—Florida air, fresh beginnings, and exactly zero chill on my end.
At check-in, I asked for a “Proud Sister” pin.
They didn’t have one.
They did have a “Proud Grandparent” button, which felt silly but correct, so I wore it proudly.
We stayed at Disney’s Caribbean Beach Resort, and I remember one very specific moment from that stay: laying in a hammock on the beach at night, the resort quieting down, warm air, water nearby, nothing expected of me. It was so incredibly relaxing—the kind of calm that sneaks up on you when you’re not even trying to rest.
We took her to her apartment at Chatham Square—first ones there, which felt very on-brand for us. She ended up with two roommates:
- A from Pennsylvania—still in her life to this day and even part of her wedding party
- J from Colorado—a walking red flag with a name I still remember for all the wrong reasons
One roommate became family.
The other became lore.
We didn’t do much that trip. We were hoarding PTO for our wedding like emotional dragons guarding time-off treasure. I remember a Walmart run for essentials and maybe an evening at Disney Springs.
Jessie worked Quick Service Food & Beverage at Hollywood Studios, specifically the Sunset/Dockside Complex—which, for the uninitiated, means fast-paced food service where you’re feeding hundreds of guests an hour while maintaining Disney-level cheer.
She absolutely hated it.
Like…deeply.
🎢 Fall 2017: Disney Confidence Is Contagious 🎢
Jessie has always been quiet. Timid. Observant.
She came back from her first program with what I lovingly call “Disney Confidence”—that subtle shift where you suddenly know you can exist in big spaces and not apologize for it.
We didn’t expect her to apply again.
She did.
Cue drama with her then-boyfriend (now husband), because of course there was. But she went anyway—Fall 2017. Once again, my ex-husband and I flew her down. This time, Ryan came along.
She worked Attractions at Animation Courtyard in Hollywood Studios—and loved the job. Hated the living situation.
Patterson Court this time. Her two roommates had already extended their programs, meaning she was moving into their established space instead of building something together like before. No bonding. No magic. Just existing around each other.
Check-in itself was quieter. Less sparkle, more routine.
We stayed mostly at the hotel. I remember Jessie and I sitting poolside while the boys played Nintendo Switch in the room. My legs got absolutely torched by the Florida sun. There was a solar eclipse happening, so we watched it from the pool area—which honestly felt very on-theme for that era of life.
The pool itself? Gorgeous. Inflatable movie screen. Poolside bar. One of those places where time feels suspended.
We probably did another essentials run. I don’t remember much beyond that—just the emotional undercurrent. Some stories aren’t mine to tell.
🎓 January 2018: Disney College Program Homecoming ✨
In January 2018, Jessie took me down for the Disney College Program Homecoming/Alumni Event.
Ryan wasn’t thrilled—but he understood. Disney was our thing. He’d go next time.
(He didn’t. Jessie was nine months pregnant by the next one. Life has a sense of humor.)
We flew in, checked into our hotel, then headed to check-in at the Contemporary Resort—already a serotonin hit. That night, we went to “The Magical World of Disney” dinner.
Characters everywhere.
Genie.
Merlin.
The Magic Mirror.
Jafar.
Hades.
We signed the DCP Homecoming banner. Took photos. Used a photobooth that made actual flipbooks—tiny moving memories you could hold.
The next day was Character Palooza, which might still be one of my favorite Disney events ever.
Mike and Sully.
Judy and Nick.
Jessie and Bullseye.
Joy and Sadness.
Balloon animals. Balloons everywhere. Pure chaos joy.
We had a break before the next event, so Jessie and I hopped over to the Polynesian for Dole Whip—because obviously. There was also a Pokémon Go event happening, so I remember briefly turning into my truest self.
Then came Epcot.
They’d given us Twilight tickets, and Festival of the Arts was happening, so it felt like the right choice. Wandering. Laughing. Existing without urgency.
I got to meet Baymax.
That was the highlight. No notes.
That night was the Hollywood Wrap Party—after-hours access to Hollywood Studios with music, food, performers, and more characters than my nervous system knew what to do with.
Pluto.
Donald and Daisy.
Goofy.
Minnie and Mickey.
Chip and Dale.
It felt like Disney saying goodbye with fireworks.
🛍️ The Extra Day (aka Budget Reality Check) 🛍️
We’d booked an extra day, wildly optimistic about our finances.
We did not, in fact, have park money.
So we went to the mall.
Got Dragon’s Breath—Fruit Loops dipped in liquid nitrogen. Window shopped. Went back to the hotel. Jessie did homework. We just…hung out.
Honestly? It was perfect in a quiet way.
🎭 Do I Regret Not Going?
Yes.
One hundred percent.
I thought that State of Michigan interview was my only shot. Turns out, student turnover is frequent. I could’ve gone later. I could’ve made it work.
But then again—if I had gone, I might not have climbed the ladder the way I did. I might not be who I am now.
Disney teaches you that timing matters. So does life.
I don’t know which version of me is better.
I just know one of them wore a “Proud Grandparent” button in Florida and meant it with her whole heart. 💫
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