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  • Writer's pictureCait

From Hourly Cast Member to Walt Disney World Ambassador—My Disney Journey and the lessons I learned

I am a current employee of The Walt Disney Company. Any opinions or thoughts expressed here are my own and I do not speak on behalf of the Company.

One of the best parts about working for The Walt Disney Company is becoming part of a global, supportive family. During my time working at Walt Disney World, I have met with multiple leaders and Cast Members across property, hearing about their Disney journeys and learning from their experiences.

A career path at Walt Disney World is not straightforward—it’s full of surprises, new opportunities, and temporary assignments (leaving your full-time role to work on a special project or event).

I have had the honor of working for the Company for almost a decade in probably a dozen different roles. And I have had help and encouragement each step of the way.

During my tenure, I have also met with hundreds of Cast Members looking for guidance while navigating the thousands of career paths within the Company.

Since I can’t meet with every single Cast Member (though I’d love to!), I thought I might put together some of my career highlights here, in addition to the lessons they taught me.

If you are a current Cast Member looking for guidance, an aspiring future employee, or just a professional looking to gain some career insights, I hope you find this useful!

Adventure in the great wide somewhere: Getting my start at Walt Disney World

They can be called “lightbulb moments,” “lollipop moments,” or “ah-ha” moments—but they happen a few times in your life and can completely alter your course.

These moments are important, but they can be easy to miss. It was a lightbulb moment that completely altered the course of my life and led me to Disney World.

Disney had always held a special place in my heart. I grew up visiting Walt Disney World almost every year with my family. It never entered my mind it was an actual place with real people who made it work. To me, Cast Members only existed in the realm of the theme park and promptly turned to pixie dust as soon as I left.

Fast forward a number of years when my college boyfriend surprised me with a trip to Walt Disney World to celebrate our one-year anniversary.

(Spoiler alert: That boyfriend later became my husband, because you marry the person who brings you to Disney.)

While in the parks, I would enthusiastically wish random strangers happy birthday (designated by their birthday buttons, of course) and a Cast Member off-handedly said to me, “Wow, you should work here!”

And that was my lightbulb moment. I had never even considered working at the place that had brought me so much joy. It was a novel thought. At the time, I was living out my “dream” working in New York City—commuting five hours round trip each day and maintaining a long distance relationship. It wasn’t exactly what I had envisioned, even though I had secured a job at one of the most prestigious book publishing houses (during a recession, no less!).

But life-changing moments can happen at any second and can come from the most innocuous places. Sometimes it’s important to allow your “life plans” to be flexible, slow down, and listen to the voice of intuition inside of you.

It was literally in that moment that I decided to move to Florida and work at Walt Disney World.

Lesson: Don’t miss your lightbulb moment! Be flexible in your “5-year plan” and open to accepting life-altering moments.

Be Like Peter Pan: Prepare to fly--take calculated risks with prepared leaps of faith

My career has been punctuated by a number of risks. Quitting my steady NYC job to move to a theme park was just the first. However, it didn’t happen right away.

It’s important to acknowledge that I didn’t get back from our vacation and quit my job the next day. I did a lot of work to prepare for a successful move to Florida; taking a calculated risk with a prepared leap.

(I can’t take all the credit either, a lot was due to my mom’s advice and encouragement to first prepare financially. She really has some great advice—you can learn from some of her “momisms” here.)

At the time, I was working in New York City right after the 2008 recession. I had graduated with a significant amount of debt and I was doing everything I could to pay it off quickly.

Being unable to afford living in NYC, I woke up every day at 4:30am, drove to a park and ride where I could park for free, took a free shuttle bus to the train station, took the train into Grand Central, and then walked a mile to work every day (rain, shine, or snow) to save money on metro tickets (which were over $100/month for unlimited rides at the time). I would leave work promptly at 5:00pm, get home in time to warm up leftovers for dinner, go to sleep, and do it all over again the next day.

It was probably the most trying point of my life, but my mom was my Jiminy Cricket, telling me that once I had paid off my loans, I would be free to pursue my dreams.

It took about 15 months (and a lot of phone calls to Andrew complaining about my days), but when I paid that final student loan bill, I was ready to soar! I had the confidence to start my life over because I knew I would be able to make my situation work even if things didn’t go exactly the way I had planned (which they didn’t).

Lesson: Risk-taking is a practiced skill. You don’t need to make a big leap of faith right away, you can build confidence by taking little hops from one milestone to the next. Over time, taking risks won’t seem like you’re crossing chasms.

Be like Tiana: Work real hard each and every day and grow where you are planted

One of the many lessons I’ve learned since working for Disney is that the road to your dreams isn’t always what you expect, so you may need to find new paths. But no matter the path, dedication will take you far.

My original goal had been performing. While Broadway had always been my passion, I hoped I could at least ride down Main Street, smile, and wave in a parade. I was never selected to perform and though I was disappointed, I was undeterred.

I found an apartment and a job and moved to Florida. But my first actual job at Disney didn’t come about until months later. And I wasn’t walking down Main Street, USA in a parade…I was wearing waist-high polyester shorts conducting surveys.

Working as a Research Specialist had not been part of my plan. And taking this role also wasn’t without its own risk. It was only part-time, so I would be giving up a steady income and benefits to pursue my Disney dream.

But if you have a goal in mind, you make it work—and I knew I wanted to work at Walt Disney World. I decided that no matter what job I had, I was going to be the best I could be. My very first Disney leader called this “growing where you are planted.”

In my first two months with the Walt Disney Company, I definitely grew where I was planted. If I finished my work early, I didn’t hide in a break room—I grabbed stickers and made magical moments, or picked up garbage on Main Street, or took photos for Guests. I took advantage of every free course available to Cast Members to develop my professional skills. I joined Toast Masters to meet other Disney professionals and sharpen my public speaking skills. I approached every day with energy and positivity and found ways to be a team player—like completing extra surveys if we were falling behind on quotas.

And, luckily for me, I worked for a supportive leadership team, dedicated to developing Cast Members.

After only two months with the Company, I interviewed for an open full-time position! During that interview, my leaders took it upon themselves to ask a few additional questions which resulted in a full-time role and a promotion to a coordinator.

If you wait until a position opens up to start putting down roots, it may be too late. But if you nurture your career consistently, and bloom where you are planted, you will be ready to be picked when new opportunities present themselves.

Lesson: Hard work and strong professional advocates create incredible growth opportunities. There’s no such thing as good luck, professionals advance when preparedness meets opportunity.

Just Around the Riverbend: My road to Leadership in the first year

Within that first year with the Company, I continued to benefit from one of my most supportive leadership teams—they believed in me, advocated for me, and supported me in my pursuit of growth.

Growing where you are planted means adding value to your current area however you can. That year, we created a team of Cast Members to create the department’s first ever teambuilding activity day.