In Judaism, the big fall "holiday season" is the month of Elul leading up to the Days of Awe, then Sukkot and the cluster of festivals which come at its close. In mainstream American culture, the big fall "holiday season" is the shopping season which begins with great fanfare on the day after Thanksgiving and culminates at Christmas.
This can be a challenging season. Here in the northern hemisphere the days are darkening (and at the latitude of northern Berkshire, the days feel short indeed!) Thanksgiving is an opportunity for gathering with loved ones, feasting, and cultivating gratitude...though for those who are alone, the family feast day may feel even more isolating. And even for those who are blessed to gather with family, a holiday like Thanksgiving may raise or exacerbate old tensions and old hurts. On top of that, of course, some of us are introverts -- which means that concentrated togetherness-time, even if it's something we anticipate and savor, can be draining.
Over Thanksgiving weekend we entered a new month on the Jewish calendar, the lunar month of Kislev which will hold within it this year both Chanukah (which is always on the 25th of Kislev) and Christmas (which is always on the 25th of December -- except in those Christian traditions where it is on January 6 or 7 -- but regardless, it doesn't always fall during this lunar month; this year 12/25 will.) Chanukah and Christmas too offer opportunities for gathering and togetherness as well as loneliness and alienation, for celebration as well as sorrow.
For some Jews, the approach of Christmas is an enjoyable opportunity to respectfully appreciate someone else's religious traditions. For others among us, it awakens childhood memories of feeling "Other," or of yearning for the glitz and sparkle the Christian kids got to enjoy but feeling guilty for that yearning. For some of us who were reared Christian but have chosen Judaism, this month raises anxiety about how much it's "okay" to still enjoy old family traditions. For some of us who were reared Jewish but have chosen Christian spouses, the season can raise similar fears and tensions.
Here is what I have to offer: be kind to yourself during these days.
Pay attention to what your body is saying, to what your heart is saying, to the places where your mind gets tied in knots. What are the stories you tell yourself about this time of year? What are the old hurts to which you can't help returning, what are the old joys which you can't help anticipating? Listen to your body, which is your oldest and dearest companion, and be gentle to it. For me that means getting enough sleep, drinking enough water, the ritual of my little iron teapot; it means making sure I'm eating vegetables, and it also means giving myself permission to enjoy holiday sweets.
Listen to your heart. Discern what awakens joy in you, as you anticipate the month of Kislev unfolding, and what awakens sadness or fear. Tell your emotions that you understand, you hear them, they don't have to clamor for your attention. Gentle them as you would gentle a spooked horse or an overwrought child. You deserve the same attention and comfort as any beloved animal or child. GIve yourself permission to feel whatever you're feeling.
Pay attention to your social barometer. For some of us, the approach of winter's dark and cold days brings out a yearning for people, for gathering and hosting and feasting. For others, this same moment in the year wakens the desire to curl up in comfortable solitude with a book and a glass of wine or favorite episodes of a familiar tv show. (For me, both of these things are true at once! This is why I always test as both an introvert and an extrovert when I've taken the Myers-Briggs type indicator test.) Wherever you fall on that spectrum, notice it, and make the decisions which will cradle and support you.
Try not to get caught up in expectations. "What if he doesn't like his gift?" "What if I'm not spending enough?" "What if I'm spending too much?" Oy -- it's enough to tangle one's emotional and spiritual life into knots (not to mention one's neck and back muscles.) Tell yourself that whatever you bring: to the potluck, to the Chanukah or Christmas party, to your friends and family -- whatever you bring is enough. You are enough. Not just this month, but the whole year long.