Writing the (Perfect) Holiday Letter

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Love it or hate it — not many people take the middle ground on the issue of the holiday letter. Those who hate it feel it’s just a chance for their acquaintances to brag. Those who defend it feel it’s a way to say, “I’m alive and well and I am remembering you at this time of year.”

I don’t send letters annually, but I have friends who do, and I really like newsy letters. When I occasionally send them, I agonize over every sentence. Should I talk about our last trip (travel is our extravagance) or will it sound boastful? Should I tell about Katie’s soccer award, or will it sound like I’m bragging? Does anyone care that my brother got his doctorate?

1989 was a memorable year for me: I left my long-term job with a large newspaper to join an entrepreneurial ex-boss in a new venture where I was the only employee. My husband and I built and moved into a new home. My niece and my father died within a day of each other. And, I got pregnant for the first time (with twins!) and miscarried. No, I’m not making this up! I felt I had to write a letter that year — if for no other reason than to give everyone my new address. Keeping it upbeat was the challenge.

Holiday letters tend to fall into four categories:

The Year in Review – Each family member’s activities and achievements are recounted in this version. It’s a good way for people to catch up with you, but it can seem boastful. Perhaps if one of the children writes it, bragging will be forgiven.

The Family Chronology – This format leads the reader through the year, highlighting dates of importance for family members. Chronologies can be plodding if nothing noteworthy has occurred in a particular year and, again, it’s a struggle to keep it interesting without appearing to brag.

The Philosophical Overview – Writers who’ve had a major life-changing event during the year (e.g., overcoming breast cancer), might tend to favor this one. It’s a chance to share feelings with many people in a format similar to that of a personal letter. If it’s too personal, however, you probably don’t want to send it to scores of people, as that would preclude the nature of “personal.”

The Entertaining Letter – Some people have a real flair for writing witty, dramatic or thought-provoking letters. You know, the ones that make you think, “Why can’t I write like that?” If this is you, try this version. It could playfully exaggerate the successes and failures of the family. Or you could go for the “10 stupidest things I did this year.” Or, the family cat or dog could write the letter — telling the news from his perspective.

To dress up your letter, simply add some holiday clip art or print it on holiday paper with a cheerful border. You also can incorporate photos and different fonts (and colors). However, remember that you don’t want your words to play second fiddle to the graphics!

If you’ve decided to take on the letter task this year, here are a few hints:
1. Begin the letter with a digital photo of the entire family. (Be sure to identify everyone.) One picture, you know, is worth a thousand words.
2. Write two letters — one for the people you see regularly, one for those you only contact once a year.
3. Include the letter with a hand-signed Christmas card (and hand-sign the letter).
4. Add a personal note whenever possible.
5. Think about what you want to know about the families with whom you’re sharing news, and give them that info about you. Let them know you’d be interested in learning what is happening in their lives, too.
6. Make it clear who’s writing the letter. It’s difficult and a bit weird to have everyone in the family referred to in the third person as if an outside writer were profiling your family. And it’s awkward to use “we” and then try to talk about things you did as individuals.
7. Tell them something they don’t know about your family. Not everyone knows you have four cats and a canary and much of your time is spent keeping them apart!
8. Be sure to add your phone number and e-mail address so friends who might have lost touch can catch up.
9. Be sensitive to friends and acquaintances who’ve experienced loss during the year. A simple card might be better than the usual letter.
10. Read it aloud. This is always a good way to evaluate what you write. Your letter should sound as if you’re speaking with friends, not running a business meeting.

I have almost 20 years of holiday letters from a friend in Ohio. Through them, I have a brief journal of his family’s lives: the schooling, the jobs, the college graduations, the weddings and the grandchildren. I feel special that he remembers me each December, and when he and his wife dropped by last summer, I had a “cheat sheet” so I didn’t call his children by the wrong name or forget that he got his pilot’s license. If that sort of thing is important to you, the holiday letter might be right up your alley.

Elaine Heitman is a Charlotte freelance writer and former executive editor of Charlotte Parent magazine.