Jay Michaelson talks about the holidays as a time of joy, and also as a difficult time for many people. Much of that difficulty results from cultural expectations of what it means to be happy during the holidays, and trying to make it happen. He has found that he is much more likely to be happy if he drops the effort to be happy, similar to the experience of learning to relax by letting go of the striving to relax, in meditation or in daily life. You can find his discussion here: Actually Having a Happy Holiday
There’s an interesting article in Tricycle about the practice of starting over and it’s connection to the Winter Solstice, and also to New Years Day. The article connects starting over in life to starting over in meditation. You can find the article at this page: Starting Over, Again