The Case for the Holiday Letter

AP: You mentioned that your holiday letters were your first foray into writing. Can you tell me more about that? 
NC: Well, that’s not entirely true. I either lied or was repressing my first real forays into writing which were 1) shockingly bad love poems in high school and 2) two blogs from 2011 and 2012. The poems did NOT launch my writing career to say the least. But I would say the blogs sparked the flame that burns today. That’s probably because I wrote them not to be writing, exactly, but to chronicle a time in my life that was both hard (my mom was dying) and hilarious (my mom and I lived together because she was dying, and I was a pregnant newlywed who’d taken leave from my business career to make healthy cookies and accompany my mom to New York City for a months-long clinical trial.) During those blogging years, my mom was the one who pushed me to write—and she always read the posts before I published them. Sometimes, she laughed so hard she snorted. She was dying—but we were laughing.

When my mom died in 2013, I didn’t plan to write anymore. What more was there to say? The blogs were about her life, and that had ended. A couple years later, I was a mom of two toddlers, and I heard a writer who doubled as a busy young mom say she wanted to write but all she had time for was an annual holiday update letter. That sparked something in me—it felt like a nudge from my mom. So, in 2016, I wrote my first Holiday update letter. This year will be my 8th annual “Big Update Letter,” which is its official and unoriginal name.

AP: How do you prepare for writing your holiday letter? Do you collect stories throughout the year and jot them down in a file? Do you write them all in one shot near the end of the year? Do you ask family members for insight? Tell me what the actual writing looks like.
NC: I definitely collect stories all year. I keep a Google doc called “Big Update Letter 20XX Brainstorm.” Any time a kid says or does something memorable or hysterical, it goes there. Dialogue plays a big role in my updates, which may be not intuitive. I mean, do you want to hear that my kids “are funny and sometimes articulate children” or would you like to know that, when I asked my youngest how she described me to her teacher, she said, “You have very long and black eyebrows and sometimes you wake up with a sweater on”? Let’s just say the latter is more my speed.

The other way I get ideas is from my readers! Let me explain. Now that I have done this 7 years straight, friends and family who are part of our daily life often lob comments in, usually after I tell a verbal story, like, “That better make it into the letter this year!” So I add it to the document.

AP: Your letters are hysterical! How do you amp up the humor? Any tricks/tools there that other writers can emulate?
NC: Thank you. It’s comments like yours that both light me up with pride and also terrify me. Every year, I convince myself that I will never crest my last letter. But in terms of actionable advice, I would say lean into the mundane ridiculousness that you don’t think anyone cares about. Because for real, how many letters that start “This year, our family visited 4 countries, earned 7 gold medals in sports, and graduated with honors” do you finish reading? It feels like reading an Instagram reel and who needs more of those?

But if a letter tells me right out of the gate that the writer’s Kindergartner walked in on their middle-aged male neighbor while he was in the shower (not hypothetically), I climb on that train and read on. I suppose you could say, then, that I’m writing for the people who feel the same way. I’m 100% sure I disappoint many readers (sorry, Uncle Phil) who would prefer I stick to the grid, recite the family facts, and provide reasonably regular photos. I do none of those things. Last year, I used the absolute worst photo of my youngest child, but listen, it was taken as an actual school picture and it made for the best caption of her personality.

AP: What has writing your holiday letters taught you about writing in general? Have you stolen bits from these letters and transformed them into essays?
NC: You know, it’s an exercise in finding humor in the everyday. But it’s also a refresher in humor writing. Humor is an easy writing muscle to lose track of, and a tricky one to get back. So every year, in the last months of the year, I try to read (or listen to) as much humor as I can. Favorites include Elissa Bassist (whose thought-provoking and hilarious memoir, Hysterical, is also available as an audiobook in her voice), Jenny Lawson (same audiobook comment), Jen Hatmaker, who has books, a blog, and a podcast, and David Sedaris whose essay “Me Talk Pretty One Day” was one of the first things I remember reading and laughing so hard I cried. And yes, a time or two, a story I’ve written about in my letter turns into a publishable humor piece like one about ziplining and another about Zoom Kindergarten.

AP: What would you tell other writers who dream about writing a holiday letter that elicits phone calls, texts, and messages saying “Your letter is the best thing I’ve read all year!”
NC: I would say DO IT IMMEDIATELY. I think everyone should write updates! I love letters! But I would also say it’s tricky to balance providing an actual update (my letter is probably 10% actual information like how old the children are and what activities they enjoy, 80% silliness, and 10% sappy seriousness like how I’m counting the days left I have to sit in carpool lines and it’s kind of sad).

I do sometimes panic, usually after I’ve placed my FedEx order for 150 dual-sided color copies on recycled paper, that I’ve over-indexed on humor and failed to provide anyone useful information at all, or that I’ve stolen limelight from real news with my attempt to make someone laugh.

Last year, I panicked that I’d also offended my children. So before I sent the letters, I asked my then 8- and 10-year-olds to read the letters. I videoed my son, and I’m so glad I did. He laughed harder than I’ve ever seen him laugh, and it made me cry happy tears.

AP: Do you ever dread writing your holiday letter and how do you power through that?
NC: I wouldn’t say I dread it, but every year, usually around late November/early December, I convince myself I have nothing to say. I play out scenarios in my head where I write something dumb and no one likes it and no one sends feedback and my writing career is over.

AP: Anything you would like to add that we haven’t addressed yet?
NC: I kind of alluded to it above, but getting kids’ buy-in becomes important at a certain age. When they were toddlers, I made fun of them mercilessly. I still do, but with permission. This year, my 6-year-old is on the fence about a story I hope she’ll let me include. It’s by far our family’s most guffaw-y laugh all year, and maybe that’s why she’s hesitant. I want to both honor her wishes and privacy, and I will let her make the final call, but I also want to teach her that laughing at ourselves is a wonderful thing to do. (This story is 100% innocent and perfect and one day she’ll see that and laugh and that’s why I hope she says yes…)

I will also say that writing a holiday update, or an any-time of year update, for your close friends and family, provides a wonderful ongoing keepsake of sorts, corny as that sounds. Lately, my kids have been asking to hear prior years’ letters as bedtime stories, and I can think of nothing greater.