How in the ‘World’ did I get here?

For seven months in 2000, I was a Walt Disney World Cast Member. And I’m still not quite sure how it happened

Tim Hammill
40 Days to 40
6 min readOct 1, 2020

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You ever do anything on a total whim, and it actually ends up going well? I did. Once. And only once.

It went so well, in fact, that it resulted in me getting offered a job. But not just any job, the kind of job people dream about — a Cast Member at Walt Disney World.

Full disclosure: I am not one of those people.

Sorry. We never went to Disney World as kids. Mostly because my parents pretty much never took vacations. And when they did, it was to get some rest and relaxation. I don’t even remember ever asking my parents about a potential Disney vacation. We never rushed to the movie theaters to watch the latest Disney movie. We just weren’t a Disney house.

So how in the world did I end up working at Walt Disney World? Good question.

As I wrote about on Monday, I went to Northeastern University, a co-op school that required us to work internships for half of the school year starting sophomore year. In 2000, I was a sophomore and very much in need of my first co-op job. I had gone on a few interviews but with the clock ticking, I had yet to land a job.

Walking to class one morning near the end of spring semester, I spotted several flyers around campus that prominently featured Mickey Mouse. Just a reminder, this was 2000, when our cell phones were just phones so if it wasn’t ringing we weren’t looking at it. And so you can put up flyers around campus and students would definitely notice them.

I checked out Mickey’s flyer, which read:

WALT DISNEY WORLD COLLEGE PROGRAM INFORMATION SESSION AND INTERVIEWS — TODAY. BUSINESS ATTIRE REQUIRED. AND ALSO IN LIKE TWO HOURS, TIM.

Weird, that that flyer knew my name and knew what time I’d be looking at it.

Okay, it didn’t say that last part. But that was about right. I had like two hours from the time I saw the flyer to the time of the information session.

Business attire was going to be tough to pull off in two hours though. After my last job interview a couple weeks prior, I just threw my one and only suit in the back of my closet. Fortunately, Northeastern is just down the street from the Prudential Center mall. So I ran down there and went to some men’s store and bought a shirt and tie that I had no plans on ever wearing again.

I threw on my new shirt, my new tie, left the tag on the tie (it was a $45 tie!) and ran into a room in the library with about a minute to spare before the info session kicked off. The room was packed. Guess all these people saw the flyer too. I look around and notice that about half of the people in this room are brand new faces to me.

They were new faces because they didn’t go to Northeastern. It took me a bit to realize this but our campus was the only stop in Boston that the recruiters for Disney were making. Students from just about every school nearby and some even further away had made their way over here for this information session. The very same information session that I just found out about.

For them, this was a really big deal. For me, it was also a big deal but not because I always wanted to work at Disney World. It was a big deal because I needed an internship, any internship to fulfill my co-op requirement.

Following the information session were group interviews, with four candidates and two recruiters in the room together. I don’t remember much about my interview other than thinking I didn’t do very well. I walked out of there feeling like I needed to keep on looking for an internship because the chances are pretty high that I did not get that one.

The first thing I wanted to do after that interview was walk back to the mall to return this $45 tie and then go back to my dorm and keep on looking for an internship.

I would go on to make a huge mistake trying to return that tie.

When the salesperson asked me why I was returning it, I said “I wore it to a job interview and won’t be needing it anymore.”

Apparently, that was too honest.

“You wore the tie and you want to return it?” he said. “Yes, I had it on for like a total of thirty minutes,” I said, being less honest than my previous answer. I definitely had that tie on for at least three hours.

“I’m sorry we can’t take back clothes that have been worn,” he angrily said as if he was personally offended by my attempt to get my money back.

“But it’s not clothes, it’s a tie,” I said with my final attempt at getting back my $45.

He wasn’t having it and so I walked out of there with a tie that I didn’t really want.

About six weeks later, I’d be wearing that tie again. This time in Florida, sweating in a suit for my first day of a seven-month stint in the Walt Disney World College Program. Yeah, I got the job!

I was participating in an eight-hour orientation that the folks at Disney call, “Traditions.” That’s where they teach you to point with two fingers (the Disney point), and so much more. So. Much. More.

Just a few days after that orientation, I found myself on my first day at my new job standing on the roof of one of the nightclubs on Pleasure Island (now known as The Landing at Disney Springs) firing a confetti canon as the clock struck midnight on a random Tuesday in early June. In case you’re wondering about the confetti at midnight, Pleasure Island’s gimmick was that every night was New Year’s Eve. Every. Single. Night.

As the confetti fell, it felt like an ending to a movie. It was euphoric, even. I couldn’t help but think, “How in the world did I get here?”

The euphoria wore off eventually.

I was getting paid $6.50 an hour to check IDs and pretend like it’s New Year’s Eve every night. Was I happy? Definitely, I’m working in the happiest place in the world (well, second happiest behind Finland). But euphoric, not so much.

I may not have been as passionate about the college program going into it as the people who came from all over the Boston area to attend an information session on my campus. But by the end of it, I was thrilled with my experience.

Exactly 20 years later, I keep Disney World on my LinkedIn profile and my resume. It’s a great conversation starter. When it comes up in conversation that I worked at Disney World, the questions just start flying. And to answer some of the questions you probably have right now:

No, I was not a Goofy or any other character.
No, I didn’t work in one of the parks.
Yes, we do get into the parks for free.
Epcot is my favorite.
Yes, guests really do ask what time the 3 p.m. parade starts.

Shout out to all the WDWCP’s, especially the Summer and Fall Classes of 2000, and even more special shout out to my Vista Way Building 32 and/or 34 (sorry, I can’t remember which one I lived in)!

Tim Hammill is a communications professional in the nonprofit sector. He’s turning 40 on October 20, 2020. He’s writing about the final stretch to this milestone age in 40 Days to 40, a collection of stories, thoughts, reflections and whatever else comes to mind each day. In addition to writing a blog, Tim has also decided to donate his birthday to This Is My Brave, an organization he very recently learned about that brings stories of mental illness and addiction out of the shadows and into the spotlight. If you’d like to support Tim’s birthday fundraiser, go here.

Additionally, there are three other organizations that are close to Tim’s heart: Save the Children, Stand Up To Cancer and the Bridgeport YMCA. Click on each to learn more and to support their work.

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