10 simple steps for creating an annual holiday letter

It’s that time of year again when mailboxes are clogged filled with holiday letters from various friends and family, updating everyone on the various accomplishments of the past year. I seem to received a lot of these letters (I post my own online, for instance here and here) and having read many thousands of such letters, I have come to recognize certain patterns. Since it is still fairly early in December, I thought I would share my insights with you all and give you 10 simple steps for creating a holiday letter that will be the envy of all your friends.

1. Salutation

Most of these letters start off in one of two ways. The decision on which way you start off the letter is crucial because it sets the tone for the rest of your message. In the salutation, you are addressing your audience and in letters like these, your audience is often broad and varied. The two most common variants are as follows:

  1. Dear Friends and Family,
  2. Dear Family and Friends,

I’ve listed these two salutations in order of popularity. This is a tough decision for those afraid of offending anyone. By listing “friends” before “family” you risk offending family members by relegating them to second place in the salutation. However, by listing “family” before “friends” you risk the same with your friends. One could argue that “friends and family” has a more sonorous ring to it, and feels more natural rolling off the tongue, but in these tough diplomatic situations, how something sounds is less important than the meaning it conveys.

A reasoned approach is necessary which is why I recommend addressing your letter to “Friends and Family.” Friends you can lose by offending them. Family is family no matter what. They are stuck with you and you them. In consideration of the fact that friends can be lost when family cannot, in the same sense, be lost, going with “Dear Friends and Family” is the obvious choice.

A more ambiguous (and if you ask me, somewhat cowardly) approach is to leave off the salutation all together and jump right into item #2. In this instance you single no one out so the chances of offending any one group is far less. The chance of offending all groups seems greater, however. As far as anyone can tell, with this approach, you might be addressing the dog or the pet goldfish.

2. A reminder of the passage of time

Once you have decided on an appropriate salutation, it is customary to make an obvious statement of fact regarding the passage of time. Some samples of these are listed below for you to choose from in creating your own holiday letter:

  • “Well, another year has come and gone.”
  • “It is hard to believe another year has past.”
  • “It’s that time once again when the holidays remind us of the importance of friends and family.” (Substitute “family and friends” if you went with that particular salutation.)

I’m not certain where the tradition of starting a holiday letter by reminding everyone of something obvious got started. It is not clear from the literature, but what is clear is that virtually every holiday letter ever written starts in a manner similar to this. Some are more creative in their approaches, reminding us that “winter is once again upon us, and with the falling snow, we cast our gaze back over the year, each falling snowflake a memory of the cheer the season brings.” Others are more to the point: “Holy [expletive removed]! Has it been a year already?”

If you are to composing a winning annual holiday letter, you must start your letter with a reminder of the passage of time.  Doing otherwise will only confuse your readers.

3. Remind your audience who everyone is

Once you have established that a year has indeed passed, in whatsoever manner you have chosen, the next step is to remind your audience of everyone you will be mentioning in the letter. Think of this as a kind of dramatis personae for your holiday missive. This section should be brief, but inclusive and should make clear all of the various relationships in a sentence or two. For example:

It has been a busy year for Bill and myself, to say nothing of our kids, Ronnie, Bobbie, Ricky and Mike. Our newest addition, Alfalfa, our pet hamster, has helped see to it that our year has been full of surprises.

Obviously, this section will vary in length based on the size of your family, but there are a few basic rules to follow to avoid annoying your audience:

  1. List only immediate family members and pets. UNLESS,
  2. You are a grandparent, in which case it is permitted to discuss your grandchildren

This is not just for brevity but for avoiding awkward situations. I have seen, for instance, holiday letters in which the letter writer has written more about her son’s best friend so that the best friend outshined her son and cast him in a poor light:

Billy’s friend Dominic made Eagle Scout this year. He has something like 24 badges. It is a truly remarkable accomplishment, especially considering the handicap he worked under. Namely being Billy’s friend.

Keep your list of cast members as short and to the point as possible. Introduce any new arrivals briefly and proudly. Then move on.

4. Your achievements unlocked

Once you’ve established your cast of characters, it is traditional to begin listing various accomplishments of that cast over the course of the last year and most holiday letters begin with the accomplishments of the letter writer and his or her spouse.  There are often two places that people run into difficulty here: trying to list too many achievements, or having no achievements to speak of whatsoever.

In the former case, please try not to list everything here, but pick one or two representative achievements and list them briefly before transitioning to the achievements of your kids. What is a good representative achievement? That is a question that carries with it much debate. New jobs, promotions, buying a house, adding a child or a pet are often the most common achievements listed in a holiday letter. Less frequently you see things like your favorite sports team winning some crowing event–something that is their achievement, not yours, but gets listed anyway.

The latter case, in which you have no achievements of your own, is more difficult. Most often people try to make normal everyday events sound like big achievements, but I think this is a mistake. If you have no achievements to speak of, it is best just to skip this section entirely and focus on your kids achievements. You can even expand on them a bit more than you might otherwise have done because you have more space in your letter.

5. Your kids achievements unlocked

Similar rules apply to your kids achievements. Keep them brief. Johnny brought up straight A’s. Jenny had a perfect attendance record. Try to make sure the achievements are balanced, but remember that your kids are by far the smartest,  most amazing kids living on the face of the earth–possibly the most remarkable kids ever born into the human race. So while being brief and balanced, be sure to convey just how incredible your kids really are.

And if you don’t have kids? Pets are acceptable in the absence of kids, but the general rule is that dogs are granted more space than cats, and a list of achievements of your pet goldfish tends to be frowned upon by your audience. That said, just like with kids, be brief, be balanced, be sure to make them shine.

If you are a grandparent, you may skip the achievements of your own kids, which will likely be marginal, and focus instead on the achievements of your grandchildren. The exception to this rule is when your kids are also producing a holiday letter of their own. In that case, I suggest waiting to receive their letter, and then stealing most of what’s in it for your own. It will make your job a whole lot easier and save you a large chunk of your somewhat more limited supply of time.

6. Your big vacation

One trend I’ve noted in recent years is a description of some big vacation you took in the last year.  I’d recommend this not be more than a short paragraph. I’ve seen holiday letters in which 24-pages have been dedicated to a description of the family vacation to Mount Rushmore, and only 6 pages dedicates to the other 9-standard parts of the holiday letter. If I had my way, I’d recommend this part of your letter not exceed one sentence:

Early in the summer we took the family on a lovely vacation to Harriman State Park where we spent 6 nights camping illegally in a torrential rainstorm.

Having said that, however, I know most of you will not take this advice and will want to expand on your vacation in some detail. Do so if you must, but know that this greatly reduces the readability of your holiday letter.

7. An unfortunate loss or event

Just like in a  standard 5-paragraph essay where one paragraph is dedicated to a counterargument to your main thesis, so in a holiday letter can you dedicate one paragraph to some loss or unfortunate event you or your family experienced in the last year. Remember, however, that the general tone of this letter is supposed to be cheerful and you do not want to bring your audience down. Stating that a pet died or that someone lost a job is acceptable, but don’t go into too much detail, or you could end up with an awkward letter. I once saw this in one of the holiday letters I received:

But don’t let me give the impression that everyone was breaking my way this year. Two days ago, I came home early from work, and found Jolene in bed with the milk man. Even when I confronted them they pretended like I wasn’t even there, so eventually I left, headed over to 7-11 to get a coffee and some scratchers and went to a park for a few hours before returning home just in time for dinner.

8. A brief holiday message

The whole point of an annual holiday letter is really to express your good wishes to others and send a bit of holiday cheer. It is ironic, therefore, that in most holiday letters, this is not only the briefest part of the letter, it also comes near the very end. After struggling with salutations and introductions, after listing achievements and disappointments and describing in great detail your family vacation, you finally get to the heart of the message:

We hope this holiday season finds you well and is filled with cheer and joy. And best wishes in the new year.

When I get to this part of the letter, I often think a postcard would have been a better medium.

In any case, if you are to have a successful holiday letter, you must include some kind of brief holiday message before signing off. One of the big debates, of course, is do you say “Merry Christmas” or “Happy holidays.” Happy holidays is more all-encompassing, but can be seen as less personal to the victim reading your letter. This is something you will have to decide for yourself.

9. Signing off

In a perfect world, you’d simply sign, “Sincerely,” and be done with it, but “Sincerely” seems too impersonal to many people reading the letter. It has therefore become traditional to be more colorful with the signature. “With love and kisses and holiday cheer, yours,” or “Best wishes in the new year,” etc. So long as your are not quoting passages from the Twilight books here, you are probably fine, but once again, keep is as brief and simple as you can.

10. The enclosure

It has become de rigueur to include a photograph of the family in question with the letter. Whether this helps or harms the point of the letter is a matter of much debate. If you decide to include a letter, please see to it that no one has red eyes, that everyone is looking at the camera, that no one seems inebriated. A professional picture would be best, although no picture at all leaves it up to the imagination of your audience, which can make for a fun game. Better yet, have fun with your audience. Enclose a photograph you get from someone else’s holiday letter in your own and see what kind of reaction you get from people. It’s one sure-fire way of knowing whether or not people are actually reading your letter.

And there you have it, 10 simple steps for created a perfect holiday letter. Now go forth and write. And try and keep it to less than five pages, will you?


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