Our daughter has always had a slow-to-warm temperament, needing extra time to transition into new environments. The newer the place, person or activity the longer it takes her to warm up (and down). I am also the same way. It has been very fascinating to learn more about this at parenting classes, because it has helped me to be much more effective at dealing with my own behavior as well as hers.
While my husband and I are keenly attuned to our daughter's needs, we try very hard not to baby her. We value independence and make a concerted effort to help her help herself. Little by little she has learned to reach out and make these transitions on her own. It has helped to talk with her about a new (or not so new) place ahead of time, but not too much. She can get anxious hearing too much information. Sometimes doing something to prepare ahead of time is comforting, like choosing clothes a few days before or making cards to give to special friends, etc. It doesn't matter if she ends up using them or not--it's just the act that gets her motivated and gives her some control.
We've also learned it helps if she can make a connection with something in her new environment--a familiar toy, a child her size, a kind and patient adult. This can be just the thing to encourage her to participate. At first we had to identify these things for her, but as she grows she's doing it more herself. Now she feels more comfortable expressing herself; she's actually very demonstrative, and loves to dance, sing, and play-act.
In fact, over the past few months she has actually started bounding away from us to go play in unfamiliar large group settings with little or no encouragement. To parents of a child with an easy temperament this may be an everyday thing; to us it was astonishing!
Despite her progress in adapting, we are still having problems with separation anxiety at school. She started Montessori two years ago and loved it. Last year we switched her to a new Montessori and they moved her up to preK/Kindergarten. Most of the kids were 1-2 years older. There were 30 kids with 4 teachers. She liked the work but had a hard time adjusting socially & emotionally. Next year we're moving her to a preK/K class there that has fewer kids, more laid-back teachers, and eases into academics more slowly. We're also trying to keep a more simple, consistent routine. However, it's hard since none of us are really that routine-oriented.
The last year has also been tough because I was hospitalized for a manic episode (I have bipolar disorder). Recently, I went out of town to help my mother get settled into an assisted living facility and it didn't go well. She also has bipolar. Our daughter seems to really pick up on my stress and hangs on me just when I need space. When she's anxious (which is quite often)she wants to stay home and says her tummy hurts. What about taking her to a child psychologist for more insight about her anxiety and the bipolar factor?
It is certainly a reasonable option to seek professional help, but to be frank with you I'm not enthusiastic about guiding you in that direction. Why? Because your daughter actually seems to be adapting well. You are clearly quite empathic and understanding with her, and you don't permit her to derive secondary gains from her reticence. While you'll have to monitor her as the years go on because of the genetic vulnerability she might have to developing bipolar disorder, there's no indication at this point that she is displaying symptoms of such. In your role as parent you can help her to see the connection between her somatic symptoms and her worry, while at the same time not allowing those same symptoms to interrupt her mastery of the daily demands of a four-year-old. If you discern that your daughter's anxiety is an impediment to managing her day-to-day situations at home, in school or with peers, therapy might be useful, but at this point my sense is that it is premature to seek therapy.
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