We received first family holiday letter about 10 years ago from my graduate school professor. As I understand that family holiday letter is an American tradition that people use to reconnect and get back in touch with friends and family. I thought that it was a very good idea, and we started our family holiday letter the next year, and have been practicing it ever since.
Though family holiday letter has been a staple of December holiday activities in America, it is still relatively rare in my circle of friends. So we are teased from time to time: some friends call our holiday letter an annual report of our family, or annual summary.....sort of, it is. Our family holiday letter typically highlights major events in our family for the year - mostly positive things, occasionally with reflections .
Writing a good family holiday letter actually takes more efforts than sending out a Christmas card. When Christmas is approaching, Lily and I will talk about writing family holiday letter. I will then recollect what happened during the year, checking our calendar, photo albums, and in recent two years our blog, to see what events are worth sharing in the letter. Each year I try to identify a major theme, and draft the letter around the theme - one year it was about very interesting or funny events, another year it was about the reunion with our friends from graduate school, last year the theme was travel and this year it is about change. What ever the theme is, I will always have a section on our travel and outdoor activities in the spirit of "explore nature have fun". When my draft is completed, I will send it to Lily for polishing. She is a good editor, improves my writing, deletes or adds some contents. I will then go through the final draft, always take her version as the final, making changes only to typos :). So it usually takes about two days to come up a decent family holiday letter for us!
Over the years, the format of the letter also evolves - initially it was in the format of a letter with a family picture on top, then I changed the format, making it more like a composite news story with 3 or 4 pictures accompanying the text. In recent years, I used this format with the addition of a row of 5 selected pictures at the bottom of the letter highlighting some events mentioned or not mentioned in the main text.
I feel that holiday letter can make a special personal connection with family and friends that social media cannot. The accumulated family holiday letters have become a chronicle of our family life, fond memory of good times. So we continue our tradition of family holiday letter in the era of online social media.