Writing Holiday Letters

Your only competition is with yourself.

A writer has the duty
to be good, not lousy;
true, not false;
lively, not dull;
accurate, not full of error.
—E.B. White

At the end of 2020, I followed the national trend of retiring from my job earlier than planned. I was also in the trenches of a years-long writer’s block that I’d tried to ignore by being employed. Now that I wasn’t, my empty future stared balefully out at me. So, I did what I do when some real-world thing needs dealing with: I curled up with a book. And another. And another.

At some point, I learned about an online organization that reviews self-published books. It paid crap, but it paid me to read, which I’d been doing anyway. It gave me deadlines and purpose. And it forced me to write. Sure, I wrote for an industry that both encouraged and profited from writers unable or unwilling to publish with the depressingly few remaining “legitimate” book publishers. But they got me off the couch and occasionally even out of my pajamas.

I fussed over those reviews as if I were writing Wolf Hall or The Night Watchman or Little Women or The Weight of Ink or People of the Book or, I dunno, Hamlet. “Drop that passive verb,” the editor in me would scold as I banged the delete key. “Too much about the plot,” I’d mumble, trying to cut my chatter down to the maximum word count. I’d finish, write the hardest bits—the one-sentence summary and that odious 1-to-5 rating, as if a book could be summed up like a math formula. I’d sleep on it and then send it off, and a few weeks later, there it was, online for me to relish.

Sometimes I’d laugh at myself for making such a big deal over the polishing I did on these trifles, mere crumbs in the business that was only one in a broad racket: there are lots of sites like it. And while I believe that, given the absurd state of book publishing today, these entities have genuine value, I’m also perfectly aware that they are bottom-line businesses that have figured out how to get eager writers to part with their money as skillfully as has done the Writer’s Digest franchise phenom of the past century.

One day, I was contacted out of the blue by the editor of one of those entities. She’d followed my reviews and liked what she read, so she asked me to write for her. Her standards are higher, the system is more professional, and the pay is better. Still low, but double that of the other site. And it isn’t so much about the pay as it is about how it made me feel about myself as a writer—and a person.

I’ve taken far too long to make my point, but I hope that point is clear: Aim to do your best. Whether it’s a memo introducing a new company procedure, a recipe for your grandson, or—here we are!—your annual holiday letter, make it the very best you can.

You should have fun writing your holiday letter, of course, or what’s the point? But take the time to find one more place you can brighten the story, sharpen the description, shorten the trip to the punchline, thank your loved ones more distinctly.

Here are some tips on how to go about doing that.

The Harvard Business Review offers great advice in a very simply nugget: the “one idea” rule. The advice is general but works for how you think about your holiday letter or card.

Every component of a successful piece of writing should express only one idea. For instance, let’s say you’re writing an essay. There are three components you will be working with throughout your piece: the title, the paragraphs, and the sentences. Each of these parts should be dedicated to just one idea. The ideas are not identical, of course, but they’re all related. If done correctly, the smaller ideas (in sentences) all build (in paragraphs) to support the main point (suggested in the title).

Unfortunately, the full article is only available with a subscription, but the author has written a book expounding on the notion. In a nutshell, the key is focus. You need to know the main message you want to convey, and you need to care about it. Keep focussed on those two things—your message and why it’s important—and your writing will be sharper.

I came at this from another angle in last year’s column on holiday letters when I explained the motive behind my first-ever holiday letter, written the year my then-home state’s Minnesota Twins won the World Series.

I didn’t talk much about what my family had done that year, or what achievements we’d accomplished. I mostly talked about what it had been like to watch a World-Series-winning team in my adopted hometown. I freely admitted I was a fair-weather baseball fan. I’d never paid any attention to the Twins. I didn’t even consistently follow baseball. But just as everybody is Irish on March 17, for those golden years in the late 1980s (the Twins won the following year, too), I was a Fan.

I cared about that pennant—and, as I hoped my letters showed, about my adopted hometown, still relatively new to me—and that’s what I wrote about. I got such positive responses to that letter than I kept writing one each year since.

You can find lots of online resources that offer general advice for improving as a writer, including Rockcontent, which, according to its site, “invests in professional growth and development through continuous learning, knowledge sharing, and mentoring programs.” A very long do list includes these specifics:

• be clear and concise
• vary sentence structure
• avoid overused words
• don’t overuse exclamation marks
• avoid qualifiers
• use anecdotes

Do you recognize that last one? Anecdotes? Aka nattering on about something that happened? Have you noticed it in any of the issues of Well Worded—or, more specifically, every single one of them?

At Coursera, an online educational portal that collaborates with universities, general advice for overall writing improvement suggests writing regularly, just as you practice piano every day to get better at it. Make it fun. One suggestion might be familiar if you’ve ever dipped your toe into the self-help world: start a journal or a blog.

In these troubled times, I highly recommend another offered suggestion: Put together an opinion piece for your local newspaper or a publication that you like. (Two points for this: writing practice and civic duty.)

Another feeds specifically into making your holiday letter better: Write letters to friends or family. Just imagine how tickled they’ll be to get actual mail that isn’t asking for money or shilling yard services! The youngins will wonder what these are and why you sent them, so you’ll be serving posterity, too. (Teach them cursive while you’re at it.)

Other suggestions:

• Choose strong verbs (for example, “sprinted,” “dashed,” or “bolted” instead of “ran”).
• Avoid passive voice.
• Vary sentence length.
• Cut unnecessary words.
• Replace cliches with original phrasing.

Over at Wordstream, another very long list includes these recommendations:

• Write like it’s your job and practice regularly.
• Accept that first drafts are often bad and revise.
• Don’t be afraid to say what you mean in what you write.
• Don’t delay writing. Get it done now.

Worstream’s “don’t delay” and my “make it better” might seem like too much to ask. But really, they’re not.

“Make it better” means futzing around with a handful of words, enjoying the flagrant waste of an hour by seeking the perfect synonym or smushing a few gerunds into active verbs—as opposed to, say, spending that hour doom-scrolling or tweeting.

“Don’t delay “is relative. It’s early-ish November now. Depending on how you define “the holidays” (one friend wrote a Groundhog’s Day letter), you have plenty of time. Start between now and a couple weeks from now for a satisfying experience sharpening your letter for arrival before the end of the year.

Don’t agonize over your holiday letter, but give it the effort your friends and family deserve. Because in the end, the one who will most enjoy what you produce will be you.

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Lagniappe: As everybody knows, the dictator Julius Caesar was stabbed to his bloody death by a circle of his feckless senators on what became known as the Ides of March, in 44 BCE. “Et tu, Brute?” were his dying words, spoken to his erstwhile closest friend.

Except he didn’t say them. Shakespeare made them up.