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7 Tips for Writing an Awesome Holiday Letter

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The holiday letter is a time-honored tradition for many families. The annual missive to friends and family, chronicling the ups and downs of the year, seems charmingly antiquated in a world of Facebook and Twitter. Social media may have rendered one aspect of the holiday letter irrelevant—after all, even your distant cousins and elderly great-aunts receive your status updates—but it still serves as a lovely way to connect with your loved ones.

Be Honest. Another consequence of social media is that people know when you, shall we say, embroider the truth. As Barb Valentin of mom.me points out, “These days, even toddlers have fact checking capability at their fingertips via the Internet.” By embellishing your or your children’s accomplishments, you run the risk of being found out. Is it really worth lying about a trip to Paris or your kid’s place on the honor roll?

Don’t Brag. Even if you’ve really had the best year ever, the truth is that most people are only willing to celebrate with you up to a certain point. Sharing your joys and sorrows with thoughtful insight or humor is a better choice than gushing about how wonderful everything is. Otherwise, the recipients of your letter may feel jealous or irritated by your excessive good cheer. Author Leslie Lehr writes, “Spreading good cheer is not about you, it’s about making your friends and family feel good about themselves.”

Keep it Short. Richard Nordquist of about.com advises, “A holiday newsletter doesn’t have to be silly or tedious. One that’s brief, thoughtfully composed, and marked by a sense of humor can be a charming way of staying in touch with distant friends.” Keep your letter to a page—three to four short paragraphs—and stay focused on the story you want to tell. It’s a good idea to outline your letter first, or at least jot down a few notes, before you start writing.

Be Creative. Holiday letters are usually printed out and folded up inside a card. Depending on the length of your list, you might consider handwriting the letters instead of typing them. If that’s not possible, you can express yourself creatively by including festive touches such as glitter or confetti. You might also consider writing a short poem or letting your kids contribute a message or drawing.

Consider Your Tone. Organizational expert Cynthia Ewer writes, “Like pantyhose, holiday letters aren't ‘one size fits all.’ Business associates won't be interested by a chatty, family newsletter, while distant cousins don't care about the ins and outs of workplace politics.” Try not to get over personal or give too many details—there is definitely such a thing as too much information. No one needs to know the exact total of your workplace raise or messy details about healthcare issues. Ideally, your letter will be upbeat, meaningful, and, if possible, funny. This may require several drafts.

Proofread. Many people keep holiday letters for years. Knowing that your letter might end up preserved for posterity in a scrapbook, don’t you want to make sure it doesn’t have any embarrassing errors in it? One of the best ways to check for awkward phrasing and basic mistakes is to read your writing out loud. You can also invest in web-based proofreading tools to catch your errors and improve your prose.

Pick a Good Photo. The photo is an integral part of the holiday letter, so it’s important to find a good one. This is the picture that’ll end up on corkboards and refrigerator doors for the next year. It should include all members of the household, so don’t forget the pets! Take multiple shots and let everyone in the photo sign off on the best one. Themes—goofy sweaters, reindeer noses, etc—can be fun, but the best photos are often the simplest ones.

Let us know what you love (or hate) about the tradition in the comments!

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