Why Do I Feel Like I’m Gambling Every Time I Go to Disney World (And Is It on Purpose?)

I’ll be in Disney World in less than a month, and while I’m so excited I can hardly think about anything else (good thing I work here, huh?), I also need to brush up on my gambling skills.

No, I’ve never actually gambled a day in my life, nor can I juggle, but when I’m in Disney World, it feels like I’m doing both to accomplish everything I want to do. Do I know when characters are meeting? Yes. Do I know what Lightning Lane I want to book first with Genie+ and make sure I know to stay on the lookout for them all day so they don’t sell out? I have two portable chargers and yes, I’m ready to go. But WHY does it have to feel like this?

The sad truth is that if you’re someone who doesn’t like to plan, like, at all, Disney World probably isn’t the best place for a vacation. Because with how crowded it is and how long those lines get, plus add in the fact that some attractions aren’t open all day/characters don’t meet all day, you HAVE to plan before you get to the parks.

Now, I’m a Type A person and plans, lists, and schedules are part of my everyday life (I literally have a To-Do list book where all my lists go, it’s glorious), so planning a Disney World trip and all the ins and outs are exciting for me. But even then, finding that balance between having a plan and being able to go with the flow when things inevitably go sideways is HARD.

Let’s say you’ve splurged for Genie+ on your vacation. That’s great! Now you have to make sure that:

• You research what ride in that park sell out the fastest and book that first
• You make a list (mental or physical) on which rides are your top priority to book, preferably in order of how fast they can sell out
• Set reminders and timers each time you can book a new Lightning Lane after your 2 hour cool down, or after you use your existing Lightning Lane
• Have a Plan B, C, and D for when rides go down, are fully booked up, etc.
• Continue to check back at what Lightning Lanes are available and see if you can modify for an earlier time

Oh, did you say you’re park hopping, so you’re getting Lightning Lanes for two parks? Double all of what I just said.

Did you read on AllEars.net that there’s new merchandise in the park you want to check out, or maybe it’s the first day of an EPCOT festival and you’re prepared for that merchandise to sell out? Yeah, you might want to make sure that’s your first stop of the day so you don’t miss out on the item you want. Trust us, it’s happened SO. MANY. TIMES.

And don’t even get me started on Advance Dining Reservations. While I’m a planner, I’m also a massively picky eater, so most dining reservations (especially prix-fixe ones) aren’t my style. However, on my very first adult trip to Disney back in 2021 to celebrate my 20th birthday, I wanted to dine at Chef Mickey’s for those iconic Mickey shaped pancakes. I failed to realize how popular that reservation was, and was too late grabbing it 60 days in advance. Yes, 60 DAYS in advance I was already gambling with the concept of time to try and grab a reservation for two months later. (Side note: I did end up grabbing a same-day reservation for the Plaza Restaurant and that was amazing — shoutout to the Cast Members for making some birthday magic for me. ?)

So much of Disney World requires pre-planning that even a planning aficionado like myself was overwhelmed a few times. So why does Disney do this? Is it on purpose? Some of this stuff COULD be easier…right?

Yes, I’m sure Disney could make some of these aspects easier on us, such as making Genie+ more user-friendly, making Advance Dining Reservations more accessible — the list goes on and on. But, I don’t think Disney is necessarily making things difficult for us on purpose, I think it’s just a caveat of having parks that see tens of thousands of visitors every day.

Hear me out, okay. I think Disney is trying to make things easier for us — they ARE listening, even if it’s going at a slower pace than we’d like. You can now cancel most Advance Dining Reservations up to 2 hours before they take place (MUCH better than the 24 hours before many of them were), changes are frequently being made to Genie+ in attempt improve its performance (it doesn’t always work though), and in January, park pass reservations finally went away and the Disney Dining Plan came back — something many guests had been asking about for years.

However, Disney has also made lots of decisions that seem to just be in the market of making more money — price increases on anything and everything, surge pricing on Genie+ and park tickets, and I’m REALLY not a fan of that. While I don’t think Disney is purposefully making this more DIFFICULT for the consumer…I do personally think they’re working towards becoming a vacation destination for those who can afford it, not necessarily for all families. 

And unfortunately, that’s turned into a lot of us feeling more stressed than we should as we gamble with what we want/can spend our time on during our Disney vacations.

Ultimately, Disney vacations are not what they were 10 years ago (from what I hear, at least, I was 12), and while that sucks in many regards, the best thing we can do if you still choose to vacation at the parks is know what you’re getting into. Understand that you have to do research and plan accordingly — sometimes when things go wrong, it’s easy to blame Disney and point fingers, but we also have to take responsibility for our own lack of preparation sometimes. Like me with Chef Mickey’s! I KNEW better, I KNEW I needed to be on my game, and I wasn’t — at the end of the day, that’s my fault!

The whole AllEars team — the writers, editors, YouTube team, everyone — has been in your shoes. Actually, we ARE in your shoes, every day. We know the frustrations you deal with because we face them too! Even when we do everything we should, sometimes things still go wrong, and that’s why we tell you all about them — so that way you don’t make the same mistakes we do. So stay tuned to AllEars for all your latest good, bad, and ugly Disney news!

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What’s the hardest part about planning a Disney vacation for you? Tell us in the comments!