How to Write a Holiday Letter People Actually Want to Read

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Photo courtesy of Justin Russell via Flickr.

It’s almost officially the winter holiday season, and those of us who still send holiday greetings through the mail are prepping our lists and trying to figure out what to write.

I’m including this post on this blog, which so often touches on personal and family history, and I hope the connection is obvious. Holiday letters can act as the rough draft of a memoir or family story. They can be an intimate way to recount the meaningful moments of the year with those you are closest to. And they can be a fun way to entertain and update far-flung friends and business associates with news of your family or your personal life.

Holiday letters can act as the rough draft of a memoir or family story. They can be an intimate way to recount the meaningful moments of the year with those you are closest to. And they can be a fun way to entertain and update far-flung friends and business associates with news of your family or your personal life.

But none of this can happen if they don’t read it. Family holiday letters have a bad, although somewhat deserved, reputation as semi-fictional brag-fests, and all too often, they are gently placed in a decorated holiday basket with shiny holiday cards, appreciated (the thought, at least) but unread.

How can your missive avoid this fate? By creating a letter that is as much about your audience as it is about you. I’ve tapped my personal historian expertise, as well as my experiences as a third-generation holiday letter writer, to share a few tips on how to write a holiday letter that your recipients can’t wait to read.

 

  1. Think about your mailing list. Seriously, who are you sending this to? Close family members who know all of your personal stuff anyway? Friends, the in-real-life kind, or the ones you haven’t seen for decades but love because of your shared high school shenanigans? Business associates? If the group is exceptionally diverse, maybe consider designing two versions — the “privy council” version and the “safe for work/cocktail party conversation” version.
  2. Ask your family about what they want. Usually one or two people in a family unit volunteer to write a holiday letter. But that doesn’t mean you shouldn’t share your content with the people you’re writing about until you’ve mailed everything out. Discussing which highlights you want to share with your grade-school children could turn into a great learning experience in how to summarize and write about a long time period in a few sentences; if your tweeners and teens are sensitive about what you write about them, you might be able to get them to write your first draft of their updates.
  3. Include challenges and joys. This tip will probably not jive with some of the other guides on how to write a holiday letter, but since this site is all about writing about your life as a whole, I am going to suggest that you write about your entire year – good and bad – in your holiday letter. That doesn’t mean if you’ve had a crappy year that you should unload with paragraph after paragraph detailing the atrocities committed against you. It does mean you don’t necessarily have to sugar-coat challenges – after all, aren’t most novels and films filled with dramatic tension from a narrative featuring a protagonist who has to overcome all sorts of obstacles? (And it may even be good for your health, too.)
  4. Consider framing difficult news in terms of gratitude for support or lessons learned. Following up on the previous tip, if you’re trying to figure out how to write about the not-so-awesome stuff, one approach that seems to work and not come across as depressing or hostile is to focus on who has been helping you through your dark times, or the ways in which you’ve grown as a result of experiencing the yuck. Don’t take this approach if you’re not genuinely feeling gratitude, or don’t have any actual lessons learned, but if you do have those feelings about your challenges, this might be worth a try.
  5. Have a sense of humor about your life. I’m talking a gently self-deprecating sense of humor, not teasing or blistering sarcasm. Laughing at the follies of your own life is much safer (and kinder) than laughing at just about anyone else.
  6. Frame your annual story as an installment in an epic, continuing narrative. In the 1960s and 1970s, my grandmother sent out an annual missive, the title of which managed to play off of her first name and make reference to a popular early 20th century melodrama: The Perils of Pauline. My father continued the tradition in the 1980s (and I helped him with the writing toward the end of the decade) by imbuing our holiday letter in a sort of post-modernist medieval storyline. We were “the Masseys of Boggy Moor.” Our amateur musical adventures were referred to as “practicing the black art of music” and Dad always referred to them in a slightly scandalous tone – with himself as the chief scandal-maker. If you’re consistent with the story template you use year after year, this approach can have readers eagerly anticipating your next “episode.”
  7. Avoid inclusion of lengthy political or religious diatribes. Even if you are a clergy person or an elected official, trust me on this – the only way you’ll get a lot of people to read your polemic is if one of the recipients posts it on social media to be made fun of and it goes viral.
  8. It’s OK to play with different formats if you can successfully pull them off. It’s true that writing your family letter in a particular style – such as the melodramatic or medieval narratives mentioned above – takes more energy than just running through a list of the high points and challenges for each family member. But don’t you think your readers are more likely to remember the exploits of a family that posits itself as a band of pirates who write sensitive, rhyming love poetry compared to if you write everything up like a news brief in a Rotary Club newsletter?
  9. Consider how much ink you’re going to use. It’s tempting to include lots of photos in the family letter, now that almost all the photos we take these days are digital and entry-level page layout programs are readily available. However, as the recipient of my share of photo-heavy holiday letters, I can tell you that they almost always come out too dark to really identify distinct details. Plus, if you run your letters through your own printer, you’re guaranteed to run through at least one of those exorbitantly expensive photo ink cartridges, even if your mailing list is only 10 people.
  10. If you have a lot of multimedia to share, create a separate project with which to share it. This ties in with the previous tip. If you really just want to share a bunch of photos with captions, maybe you want to send out links to a Flickr photo gallery. Or, maybe instead of writing endlessly cute descriptions of your toddler and/or your new puppy, maybe you want to edit together the best mobile phone videos of them you captured this year, add the slo-mo filter, add dramatic royalty free music, and post it to Vimeo or YouTube? While a written text that’s mailed to recipients is the format you can count on (well maybe not the mailed part) to not go obsolete, really engaging personal/family multimedia is often too good not to be shared with friends.
  11. Think about what 1-3 things you’d like readers to take away from your letter. Many people struggle with feeling uninhibited enough to share something meaningful in a holiday letter, but others seem to unleash a torrent of TMI, and can’t figure out how to edit themselves. You might try putting topics for your letter on index cards or sticky notes and spend time arranging them on a wall or whiteboard until you’ve got the right “mix” of personal tidbits. Aiming for only a few main points keeps things concise and helps your letter stand out as remarkable.

The questions to you

  • Do you or your family produce an annual family letter? Why or why not?
  • If you receive family holiday letters, what are your favorite and least favorite types of these letters to receive?

 

 

 

 

 

 

 

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