This sounds like the difference between a tourist and a traveler that one of my college profs taught me a long time ago.

A tourist sees what they have come to see - a waterfall, mountain, or a park. They come expecting to be given an experience, or to have something happen to them. They are essentially passive consumers of the experience.

A traveler goes and experiences what it around them. They don't enter with a lot of preconceived notions, but hopefully with as few as possible, in order to view a place or experience on its own terms (not their expectations). They are active consumers of the experience - participating in it regardless of what it ends up being.

There are a lot of people that go to WDW expected to be entertained... and they aren't disappointed. If you think the point is seeing the castle from main street, or riding BTMRR with your kid the way you did with your dad, you are likely to get that experience. But if you allow yourself to be taken down the interesting sidepaths, down the byways you didn't know about before you went... you will sometimes (often!) end up with an experience you never dreamed of... and that will fill your dreams forever after. That doesn't mean you don't plan (travelers often do far more planning, because they don't know exactly what will happen), but it does mean you can start to feel like your plan is in control, and not you or the experience.

We plan a lot. Often ADR's, targeting parks due to morning EMH and then skipping to a different park that didn't have morning EMH later. In about a week, we'll be going down to run three different races with five individuals, and will be meeting up with three different families (that have never met each other), we have numerous ADR's, a special pirate cruise during Wishes, etc., etc. It is a trip that is planned to the hilt, in deep detail...
...and I guarantee that there will be times that we simply don't know about, and hadn't planned, that will make the trip amazing and magical. Remembering that those will happen whenever, wherever, and not on the schedule I laid out in advance - that's an important part for me.

Most recent best time? Literally stomping and splashing in a flooded EPCOT during torrential rains. Not because it was in our schedule... but because it added to our day

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Brian Davis