How can I set myself up for an enjoyable holiday season?
1. Plan Guests and Dates. Ask friends and relatives what their plans are and if they would like to join us for a celebration on the day of the holiday or on a more convenient day. Write it on my calendar. Be gracious if plans have to change. If you’ll be having overnight guests, check guest bed linens and towels. Make sure there are warm blankets and pillows enough for everyone. Is the guest bath stocked with soap and toiletries?
2. Plan Table. Seasonal plates in correct quality, seasonal table linens, enough glasses and silverware, enough chairs, ideas for a centerpiece, serving pieces. If I’m short on anything, I have time to shop for deals beforehand. I have my eye on some sweet animal salad plates just the right size for serving meals to children with a festive, fun look. Pier1.com 
3. Plan Menu. Start saving recipes that sound good. Try them out at my leisure beforehand. Freeze now any seasonal ingredients necessary for planned dishes. Make sure I have large enough pans for the number of guests invited. Adding these recipes to that cold weather recipe notebook I mentioned in this post will make the recipes easy to find when you need them.
4. Plan an activity for all the guests while at the table. I want to be intentional about stimulating worthwhile conversation. This can be done by planning a few questions to ask the guests after the meal or by playing a game that stimulates conversations. It may help to prepare photos of family members from years past.
I may ask young guests to use their talents to entertain by playing musical instruments, reading aloud, or to make an art project to display on the sideboard, or make name cards, or DIY napkin rings, or a centerpiece made of collected things from outdoors or seasonal fruits and vegetables.
5. Plan Christmas gifts now. Figure out now what I want to purchase and watch for deals. I want to spread out the purchases, so I will buy several each month until early December. This year I’m going to make a folder on my computer of who I need to gift and what. Sure wish I had done that last year. But now is a great time to start. I try to think of something each family member enjoys and is good at. Then I try to buy items that will encourage their pursuit. A magazine subscription is a gift that keeps giving and kids love to get mail. I work on picking topic and age-appropriate subscriptions. Ordering gifts online and shipping direct saves me hassle for out-of-town family.
6. Plan outfits for the holidays. I always leave this until the day I need to wear something nice. This year I’m planning now what I’d like to wear that fits the occasions I’ll be attending. I’m on the look-out for something that is special, but versatile for later wear. I’m thinking a red sweater with a pretty scarf. If you have special events that you know you’ll be attending, plan your outfits for each one soon. A new piece of jewelry, scarf, belt, or shoes can rev up a tired outfit. Or this may be a good time to find an online deal on a new outfit! I recently found a good deal on booties at www.6pm.com and a jacket at www.hm.com.
Here are two helpful articles about planning for the holidays:
http://www.houzz.com/ideabooks/4914571/list/your-guide-to-stress-free-thanksgiving-prep
http://www.houzz.com/ideabooks/32361501/list/make-your-checklist-for-entertaining-season