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I posted earlier about social stories and how they help with trying something new. They are also helpful with transitions. Almost everyone has some extra anxiety or energy about transitioning from one state to the next. Getting up in the morning and going from bed at home to the bus to school and learning how to brush your teeth can be seen as transitions, from place to place and dependence to independence.
The trick once you have prepared your child for a transition with a calendar or social story is to prepare the adults involved. When transitioning SensiGirl from preschool to kindergarten, I helped arrange the appropriate placement for her and then it was time to prepare her new teacher for her. I wrote the Getting to Know letters to her new teacher, I also e-mailed and called ahead of time to talk with her.
When transitioning myself from home with the kids to an evening meeting, Grandma and Grandpa are prepared and are sure to know how to keep SensiGirl occupied or to distract her until I get home.
How well we adapt to transitions has to do with temperament. I am a slow to transition person. When someone suggests something new, I usually say no right away. I then think about it and if I like the idea after weighing it, I will agree to the plan. I think that kids who have trouble with transitions are a bit like me, it is hard to say yes and be open to change right away without thinking on it and envisioning what will happen.
Random Guy is always asks me in the morning "What are we doing today?" He usually knows since week to week things are pretty similar, but he checks to see if there is a change in plans so he knows ahead of time. He is a "no" person like me and he has found a way to be open to yes by checking to see if there is a change in plans. "No" people also like routines, it makes things manageable. If you know what you are going to have for breakfast each day then it makes choosing clothes easier. If you wear a uniform, then maybe you want to have a little variety in your breakfast. Less choice isn't always bad; lots of people like to have a routine or two to make sure things run smoothly.
If you can prepare for the change then your "No" child might just roll with things when you don't expect it. Our trip to the library has several steps; we have refined the visit to limit unexpected upsets. We get our reserved library materials from the shelf, check out our things and exit through the coffee shop. There we can get a treat if all goes well. SensiGirl likes to see what is there before she chooses her treat; Random Guy always is hoping there will be a yogurt parfait waiting for him. One time a book wouldn't clear the self check out and we had to wait while the librarian put a new scan sticker in the book. Since we all knew that the coffee shop was next, the wait was manageable.
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Even though Random Guy seems to handle transitions better, he is less likely to be a happy camper when the unexpected happens. If you ask him to do something new and different he will say "No." He might say yes in an hour or maybe next week. I try to ask him way ahead of time if I want him to try something new. SensiGirl can sometimes roll with it when things change, as long as she has had things go smoothly up to that point. If she is prepared for the next step after the change, all the better. Routines and the unexpected are part of life, recognize what kind of temperament you have, and your kids have and work with it. You may find that the transitions happen more easily as the routines are established in your calendar.When you are ready, throw a little surprise in from time to time. It helps make those no moments turn to yeses more easily.