I’ve spent a lot of time at Walt Disney World.
I’ve studied the marketing. I’ve studied the customer experience. I’ve watched Cast Members. I’ve paid attention to the queues, transportation, storytelling, signage, merchandise, restaurants, resorts, and all the little details most people simply walk past.
I’ve even written books about the lessons entrepreneurs can learn from Disney.
So naturally, the question eventually came up:
Would I make a good Disney Cast Member?
The answer is…
Absolutely.
And absolutely not.
There are certain jobs at Walt Disney World where I think I’d excel.
There are others where I’m fairly confident Disney Security would have my picture before my first shift ended.
After 31 years as an entrepreneur, I’m accustomed to looking at something that isn’t working and changing it.
That’s wonderful when you own the business.
It gets a little more complicated when your name tag says “Rob” and somebody half your age says:
“Rob, that’s not how we do it.”
So, purely for entertainment purposes, here are five Disney jobs I think I’d be pretty damn good at…and five where I might not survive orientation.
5 Disney Jobs I’d Absolutely Excel At
1. Guest Relations
This might be my best frontline Disney job.
Before becoming a marketing consultant, author, and publisher, I owned a carpet-cleaning company for almost 20 years.
You want to learn customer service?
Spend two decades walking into people’s homes.
I’ve dealt with angry customers. Confused customers. Unreasonable customers. Wonderful customers. Customers who forgot their appointment. Customers who wanted miracles performed on carpet their dog had been destroying since the Clinton administration.
Eventually, you learn how to listen to someone, figure out what the actual problem is, and find a solution.
That’s Guest Relations.
A guest walks in screaming:
“YOU RUINED OUR ENTIRE VACATION!”
My response would probably be:
“Okay. Tell me what happened.”
Then we solve the problem.
Where I might struggle is after I’ve solved the problem and they still want to argue.
That’s when Entrepreneur Rob and Cast Member Rob would need to have a private conversation.
2. VIP Tour Guide
Now we’re talking.
This combines Disney, storytelling, customer service, knowledge, and creating experiences.
I’d love this.
Someone paying for a VIP experience isn’t just paying to get from attraction to attraction.
They’re paying for the experience surrounding it.
I’d want to know who they are.
What do they love?
Is this their first trip?
Is Grandma finally riding Haunted Mansion with the grandkids?
Is someone celebrating a birthday?
What can we do today that they’ll still be talking about five years from now?
That’s the stuff I enjoy.
The only potential problem?
At some point I’d probably start explaining why Disney positioned something exactly where they did and how it influences guest behavior.
The family would just want a churro.
And I’d be giving them a 20-minute marketing lesson about the churro cart.
3. Disney Business Training or Facilitation
This is probably the closest match to what I already do.
For years, I’ve studied Disney from the perspective of an entrepreneur.
Not simply:
“Wow, Disney is magical.”
I want to know:
Why does it feel magical?
How does storytelling affect buying behavior?
How does consistency create loyalty?
Why do tiny details matter?
How does an experience become part of the product?
How do you get people to willingly spend thousands of dollars, leave exhausted, and immediately start planning when they’re coming back?
Those are fascinating business questions.
Give me a room full of entrepreneurs and let me translate Disney principles into things they can use in their own companies.
I could do that all day.
In fact, I already do.
4. An Interactive Attraction
Jungle Cruise would be dangerous.
For Disney.
Give me a microphone, a captive audience, sarcasm, and permission to entertain people?
What could possibly go wrong?
Actually, I think I’d be pretty good at it because I understand something that’s easy to forget in repetitive customer-service jobs:
Your 500th interaction might be someone else’s first.
You might have delivered the same joke 47 times today.
That family hasn’t heard it.
You might have seen Haunted Mansion 5,000 times.
That six-year-old walking through the doors hasn’t.
You’re always on stage.
The potential problem would come when Disney told me:
“Rob, please stick to the approved material.”
“But my joke got a bigger laugh.”
“Rob…”
And here we go.
5. Guest Experience and Operational Improvement
Give me a notebook and tell me to walk around Walt Disney World looking for things that could work better.
I’d be in heaven.
Why are guests confused here?
Why does this queue bottleneck?
Why is that sign over there?
Why are Cast Members answering the same question 300 times every day?
Could the app explain this better?
Could that process eliminate three unnecessary steps?
Why are people walking past this without noticing it?
This is how my brain works anyway.
I’d finally have someone paying me to be annoying.
Perfect.
And Now…The 5 Jobs Where I’d Probably Get Fired
1. Merchandise Cashier
I could certainly operate a register.
That wouldn’t be the problem.
The problem is that within approximately 37 minutes, I’d start analyzing everything around the register.
Why is this merchandise here?
Why isn’t that over there?
Why aren’t we upselling this?
Why does this transaction require three steps?
Why do we keep answering the same question?
Why don’t we—
“Rob, just ring up the Mickey ears.”
Oh.
Right.
Estimated employment: Four hours.
2. Quick-Service Food & Beverage
Nope.
Someone would eventually tell me there must be precisely a certain amount of fries in a container.
I’d ask why.
“Because that’s the procedure.”
Those are dangerous words around an entrepreneur.
I understand consistency.
I understand portion control.
I understand why massive organizations need procedures.
But after 31 years of making my own decisions, I’m not entirely convinced I’d flourish under intense French-fry supervision.
Estimated employment: Until lunch.
Ironically.
3. Parking Operations
Stand here.
Point cars over there.
Now point the next car over there.
Repeat.
For eight hours.
In Florida.
In August.
By my first break, I’d have developed an entirely new traffic-flow system just to prevent myself from going insane.
By my second break, I’d be explaining it to someone who absolutely did not ask.
Disney probably doesn’t need the brand-new Cast Member reinventing its parking operation.
Estimated employment: One full shift.
I’d finish the shift.
I just might not come back.
4. Character Attendant
At first glance, this seems like something I’d enjoy.
Families.
Kids.
Creating memories.
Helping people.
Then Mickey has to leave.
A parent gets angry.
Their child absolutely MUST see Mickey RIGHT NOW.
You politely explain that Mickey needs to go.
They continue arguing.
You explain again.
They demand a manager.
This is where my 31 years of entrepreneurship becomes a liability.
Because somewhere inside my head a voice would be screaming:
“The mouse has to leave. Your kid isn’t the only kid at Walt Disney World.”
Meanwhile, Cast Member Rob would be smiling:
“I completely understand your disappointment.”
I don’t know how long those two personalities could coexist.
5. Anything Requiring Me to Repeat a Script I Know Isn’t Working
This is the championship round.
My supervisor hands me a script.
I use it.
Nobody responds.
So I change it.
“Rob, you have to use the approved script.”
“But nobody responds to it.”
“It’s the approved script.”
“Then the approved script sucks.”
And…
I’m unemployed.
The Real Problem Isn’t Disney
Here’s the interesting part.
None of this means Disney does anything wrong by having procedures.
Quite the opposite.
Walt Disney World is an enormous operation.
Thousands upon thousands of Cast Members interact with millions of guests.
You cannot run something that complex by telling everyone:
“Eh, just do whatever feels right.”
Standards create consistency.
Consistency helps create the Disney experience.
I understand that completely.
The problem is me.
I’ve been an entrepreneur since 1995.
For more than three decades, when I’ve seen something that doesn’t work, my response has been:
Change it.
Try something else.
Fix the process.
Rewrite the copy.
Move the offer.
Raise the price.
Eliminate the unnecessary step.
Do something.
That entrepreneurial instinct has served me incredibly well.
But it might also make me a giant pain in the ass as an entry-level Cast Member.
And maybe that’s the larger lesson.
Being capable of doing a job doesn’t necessarily mean you’re suited for the job.
Some people thrive within systems.
Others thrive by building and improving systems.
Neither is inherently better.
They’re simply different.
So could I work at Walt Disney World?
Absolutely.
Just choose my role carefully.
Put me in Guest Relations, let me create experiences, teach business lessons, entertain guests, or figure out why something isn’t working.
But if you see me standing behind a popcorn cart staring thoughtfully at the queue…
Someone should probably warn management.
Because I’m not thinking about popcorn.
I’m redesigning the operation.
Rob Anspach is an Authority Architect, Legacy Builder, speaker, author, podcaster, and Founder of Anspach Media.
For more than 30 years, he has helped entrepreneurs build authority, create meaningful relationships, and leave a lasting legacy through books, speaking, trusted guidance, podcasting, and immersive experiences.
He is the host of the E-Heroes Podcast and the creator of Embracing The Magic and Exploring The Magic.
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