I tend to approach things analytically (helps me conquer those irrational fears, though it has not yet gotten me on Splash Mountain!)
I'd break down what aspects of being alone on the trip intimidate you the most
For some people it might be flying alone. It may help to imagine how you'd feel if you were flying with other people as usual and your seats were split up (either because of availability or because you were asked to move so a mom could be with her small child, etc.) Chances are, it wouldn't affect you all that much -- you'd read your magazine, watch the movie, close your eyes... maybe wave hello and exchange a word or two with the rest of your party on the way to the bathroom, but otherwise... you wouldn't think much about it, I assume.
For some people it's dining alone. Fortunately at WDW there are various ways of dealing with it (unlike traveling to business hotels where sometimes you're stuck with the hotel restaurant or room service, with no outside options).
You can simply eat fast food, especially at "off" times -- those places are so chaotic that people aren't likely to notice anybody else, period. You can time your meals so that you eat breakfast in your room, grab lunch at the hotel food court on the way back for your afternoon siesta, then eat it in your room, and eat candy and popcorn and icecream for dinner
You can grab a hot dog and sit on a bench and people watch. If you're worried about what people might think, they probably will be thinking you're killing time eating a hot dog while your family rides something you don't want to ride.
As for the rides... even with a group, don't you sometimes ride alone? Or do other members of your family? Either alone in your own car (even though you waited in line together) or alone because the rest of your party isn't brave enough, or THEY"RE brave enough and off riding something more challenging while you're killing time taking one more loop on It's a Small World?
Chances are you've run across the street to look in a gift shop or to get snacks for the group while others waited for the parade... and you were alone then and you probably didn't feel like The Center of Attention. You were just going about your business, as everybody was, and never gave it a second thought.
As somebody said --- alone at Disney or mad at home... easy call.
Props that might help - sometimes busywork takes your mind off wondering if people are looking at you: A notebook to jot down impressions, a camera to snap random images, a book to kill time while waiting for a show to start... these can all help make you feel like you're actively engaged in something as opposed to just... being alone.
My first partially solo trip to WDW is this November, but I've traveled alone extensively elsewhere, and it really is a relaxing and liberating feeling to be independent of ANY needs and desires but your own. If that means a Mickey Bar for breakfast, a slice of pizza for lunch and a first class meal at California Grille that evening, so be it. If it means 21 straight meals of chicken fingers... that's okay, too, though I wouldn't recommend it.
The best part, though, as people have said, is that if at 10 am your feet just hurt or you feel a headache coming on -- take your break THEN! You won't be hurting anybody else's good time. You can plan out every single minute then ignore your entire itinerary because the drink you had at the pool bar the first night was so fantastic you just want to go back and relax and end your second day the same way.
It will be YOUR vacation in a way you never imagined. Enjoy!
I'd break down what aspects of being alone on the trip intimidate you the most
For some people it might be flying alone. It may help to imagine how you'd feel if you were flying with other people as usual and your seats were split up (either because of availability or because you were asked to move so a mom could be with her small child, etc.) Chances are, it wouldn't affect you all that much -- you'd read your magazine, watch the movie, close your eyes... maybe wave hello and exchange a word or two with the rest of your party on the way to the bathroom, but otherwise... you wouldn't think much about it, I assume.
For some people it's dining alone. Fortunately at WDW there are various ways of dealing with it (unlike traveling to business hotels where sometimes you're stuck with the hotel restaurant or room service, with no outside options).
You can simply eat fast food, especially at "off" times -- those places are so chaotic that people aren't likely to notice anybody else, period. You can time your meals so that you eat breakfast in your room, grab lunch at the hotel food court on the way back for your afternoon siesta, then eat it in your room, and eat candy and popcorn and icecream for dinner

You can grab a hot dog and sit on a bench and people watch. If you're worried about what people might think, they probably will be thinking you're killing time eating a hot dog while your family rides something you don't want to ride.
As for the rides... even with a group, don't you sometimes ride alone? Or do other members of your family? Either alone in your own car (even though you waited in line together) or alone because the rest of your party isn't brave enough, or THEY"RE brave enough and off riding something more challenging while you're killing time taking one more loop on It's a Small World?
Chances are you've run across the street to look in a gift shop or to get snacks for the group while others waited for the parade... and you were alone then and you probably didn't feel like The Center of Attention. You were just going about your business, as everybody was, and never gave it a second thought.
As somebody said --- alone at Disney or mad at home... easy call.
Props that might help - sometimes busywork takes your mind off wondering if people are looking at you: A notebook to jot down impressions, a camera to snap random images, a book to kill time while waiting for a show to start... these can all help make you feel like you're actively engaged in something as opposed to just... being alone.
My first partially solo trip to WDW is this November, but I've traveled alone extensively elsewhere, and it really is a relaxing and liberating feeling to be independent of ANY needs and desires but your own. If that means a Mickey Bar for breakfast, a slice of pizza for lunch and a first class meal at California Grille that evening, so be it. If it means 21 straight meals of chicken fingers... that's okay, too, though I wouldn't recommend it.
The best part, though, as people have said, is that if at 10 am your feet just hurt or you feel a headache coming on -- take your break THEN! You won't be hurting anybody else's good time. You can plan out every single minute then ignore your entire itinerary because the drink you had at the pool bar the first night was so fantastic you just want to go back and relax and end your second day the same way.
It will be YOUR vacation in a way you never imagined. Enjoy!