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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.

It can also mean pursuing temporary opportunities that expose you to new people in areas where you would like to grow professionally. My first foray into the Entertainment world was on a temporary assignment working on The Candlelight Processional. Even though I wasn’t performing myself, I was helping young people realize their own performing dreams—and it was fulfilling in a completely different way!

Joining the 2011 Traditions team (a group of facilitators that welcome new Cast Members to the Company) was another opportunity to meet professionals from almost every department across property. It was also where I discovered my love for facilitation and passion for the people who make the magic.

If you work for a Company that offers multiple avenues of growth and development, it’s up to you to make the most of those opportunities. Ask how you can contribute, propose projects that will benefit your team, and apply for responsibilities that may be outside your comfort zone. If you don’t take any risks, you won’t reap any rewards.

Lesson: The world is your classroom! Provide value in your area any way you can. If your immediate role doesn’t offer developmental opportunities, create some or find ways to sharpen your passions during your free time.

Be like Hercules: You can go the distance in any role

At the conclusion of that busy first year (which also included my wedding at some point), I applied for the role of Walt Disney World Ambassador.

It was an honor to make it to the semi-finalist round (top 10 candidates) at such an early stage of my career. However, nerves and an intense desire for the role got the better of me and I didn’t move forward to the final interview.

While I was disappointed I hadn’t moved forward, I took the rejection as an opportunity to learn one of my greatest lessons of my Disney career.

I decided in that moment that I didn’t need a pin or a title. I was an ambassador for Disney and I would emulate the characteristics of an ambassador every day. I could be a positive influence for fellow Cast Members and a beacon of positivity on behalf of the Company no matter what role I was in.

We are all ambassadors for our companies or personal brand every day—and we have the choice of being a positive representation or a negative one. At Walt Disney World, we are ambassadors every day we have the honor of putting on our Disney nametag.

And it was with this renewed vigor and knowledge that I received a call the very next day offering me a temporary role as an Entertainment Manager at Magic Kingdom Park.

Lesson: You can make the choice to be your personal best every day. At Walt Disney World, we are all brand ambassadors because the Disney nametag inspires hope and inspiration around the world—and we each bring that to life.

Follow Rafiki, he’ll show the way!--My time as a Disney Leader

Leaders can create a nurturing work culture, demonstrate true compassion for their employees as people, and ultimately determine whether a company is worth working for or leaving.

To be honest, when I accepted that first leadership position, I really had no idea what I was doing. My first leadership role was at the busiest park in the world, at the busiest time of year, during the grand opening of New Fantasyland. I had never worked within an operation before and I learned firsthand the meaning of “baptism by fire.”

But what I did know was people. Since my background was in organizational and interpersonal communication (a soft skill that I think is undervalued in the corporate world), I focused on listening and supporting those I led.

I started by asking Cast Members what it was they loved about their favorite leaders. I carried a notebook with me everywhere I went (because I have a memory like Dory) and took note of any questions or concerns my Cast Members ever had. And while I couldn’t solve every problem, I always tried to “solve for yes.” When you listen to people, they feel valued and they take notice. This is the difference between being a leader and being a manager.

In fact, I wrote an entire article about servant leadership lessons I learned while working at Walt Disney World that you can read here:

While my leadership role at Magic Kingdom Park was short, I went on to a long-term management position shortly thereafter with the Costuming team at Disney’s Hollywood Studios, before I made my second attempt for the role of Walt Disney World Ambassador.

Lesson: The best leaders care about the people who work with them and can communicate effectively in all situations.

The Ambassador Years

My time as a Walt Disney World Ambassador was a unique opportunity. The lessons I learned about representing a company 24/7, maintaining a personal brand, and truly serving others in a public capacity was invaluable.

In addition to professional growth, I grew as an individual—stretching myself in ways I never thought possible, learning from the stories of others, and meeting one of my closest friends through a unique work partnership.

My time as an ambassador may deserve its own article in the future. For now, if you are interested in learning about the role of ambassador, I wrote an entire article about the history, the process, and the responsibilities of the role here:

Be like Alice: Don’t be afraid to fall down the rabbit hole—I take the chance to explore new professional experiences

As we progress in our careers (or life), it can be easy to just stay the course simply because we’ve been on it for so long—even if it may not be leading somewhere we want to go.

Shortly after my ambassadorship, I returned to a role within operations, but I had come to the conclusion that while I loved working with my Cast, life as a theme park manager was not the road for me. I needed an off ramp.

Since I’ve always been a bit of a risk taker, and I was open to light bulb moments, a friend of mine made a novel suggestion. Maybe it was less of an off ramp and more of a crazy detour down a dirt road without a clear destination, but I took it. I moved to China to work for Disney English in Shanghai.

Yes, China.

A few factors contributed to the decision—there weren’t many opportunities at Disney at the time and I recognized that I had become a little too comfortable. I thrive when I’m a little off-balance, when I am pushed to adapt. If you want to grow, you need to stretch yourself a little outside of your comfort zone.

There were professional reasons, too. I love traveling and I have always wanted to work for the travel arm of The Walt Disney Company. Joining a role that fell under Consumer Products (a revenue generating business—something I had never been a part of before) and Disney International could feasibly help me move in my preferred professional direction.

Plus, I’d always really wanted to live abroad.

There may be new jobs or assignments that scare you. Or there may be times you can’t see exactly what your job or life might look like down the road. But that’s no reason to avoid new experiences. I thought the opportunity to live abroad had passed me by—that kind of risk taking was for young 20-somethings without a mortgage or career. (Take a Leap of Faith: Say Yes to Life) But I knew if I made the most of our time there, I could hopefully parlay the unique experience into something meaningful.

We moved to China for about a year and had an incredible experience. (You can read all of my articles about living in China here.) That’s when I started this blog and it’s also what led me to a dream job I never expected—working for a travel technology startup.

Lesson: Never stop pushing your boundaries. If you aren’t uncomfortable, you aren’t growing.

We keep moving forward, opening new doors, and doing new things, because we're curious and curiosity keeps leading us down new paths.

--Walt Disney

Be like Walt: Play to your strengths and follow your heart—Leaving the Company

I never intended to leave The Walt Disney Company—but life handed me an opportunity.

All of my previous experiences—working for Disney, living abroad, my extensive personal travel, even writing for my blog—had piqued the interest of a small travel technology startup. I was terrified at the prospect of joining a startup (which is obviously a risky venture), but I was excited by their enthusiasm and the chance to really do something different. Plus, wasn’t Walt the ultimate entrepreneur?

Pitching our product in Singapore

My year with Bacarai and The Air Travel Group was wonderful—I was finally part of the travel industry and I traveled extensively for business, forging relationships with other travel industry professionals along the way. I learned a completely new language (literally, I learned how to code a little bit!) and gained an understanding of business acumen while pitching to investors. It was a challenging and rewarding experience.

Meeting with potential clients in Munich, Germany

But at the end of the day, it wasn’t Disney.

Throughout your career, you will discover your skill set and your passions. After almost a decade of working, I had discovered a few things about myself. I learned my greatest strength was my communications background—my ability to connect with people, speak publicly, and convey my thoughts through writing. And I learned I felt most energized when I had people to lead and develop. When I realized I wasn’t necessarily sharpening those skills and that I truly missed the people and the culture of Disney, I knew that it was time to return home.

Quick two day trip to Prague for work

Lesson: Take the time to evaluate your goals, your strengths, and your overall life values. That will help guide your professional and personal decisions. It may not always be easy, but it is important for continued professional growth and personal happiness.

Happily Ever After—Coming home to Walt Disney World and looking to the future

And that, more or less, brings me to where I am today. It is with deepest pride and greatest pleasure that I have returned to The Walt Disney Company.

Fortunately, I was able to lean on my supportive network I had maintained during my time away from Walt Disney World. It was a fellow friend and Cast Member who knew of a position back with the Company that might suit my skill set—working on specialized itineraries in a new business arm of the Company. (Almost like a startup!)

My Disney journey is far from over and I know there are more lessons to learn. For now, I am incredibly grateful to work for a company with a product I believe in, a culture I thrive in, and with colleagues I admire.

And in the meantime, I hope I can provide even some of the guidance and encouragement that my initial leaders gave to me. I know we are all searching for our path in this world—at work or in our personal lives, and it is always humbling to assist in any way I can.

This journey has been a wild ride and I am grateful for every twist and turn. Being a part of the Disney brand means I am part of something bigger than myself, something that gives so many people hope and happiness.

Today, as I sit on my couch on my final day of employment before our company-wide furlough due to Covid-19, I am a mix of emotions. Incredulity that I have had almost a decade of magical memories with a global company. Gratitude to the leaders and Cast Members who have helped shape who I am today. Sadness as we face a world without a single Disney park open to welcome Guests. But ultimately hopeful, knowing that we will come back stronger, more compassionate, and ready to make a difference for millions.

Disney, thank you for the adventure!

Please feel free to pin for later and share with others who you think may benefit! If you would like to stay up to date on professional development, more Disney stories, and travel tips, feel free to follow along on Instagram @caitoutdoors ! See ya real soon!

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