Lessons I've Learned from Writing an Annual Christmas Letter

The muse

It began a long time ago. I'm not sure what the first year was, but probably around 2000, we started sending out an annual holiday letter. Ok, so it's starting to turn into a "New Year Letter".

Now, I'm sure you get all sorts of Christmas letters from people. "Here is what the family did this year, in chronological and alphabetic order." "Little Bobby and Big Joey are now Physicists." One thing I can not stand is being boring. So, I was determined, if I was going to write a Christmas letter it was going to be entertaining. I think there are some great lessons in here, and then I think there are some things that are just about my personal dysfunctions.

Step 1: Create a list of notable events for the year#

This lesson was learned early on. I spent some time writing the letter with what I thought was important. Then I made it funny. Then I turned it over for review. The result was some version of "What about this? Why didn't you include that?" Evolution is a great teacher, so the next year, I didn't start until I had a list of what my spousal better half thought was interesting in the year.

Step 2: Write without inhibitions#

The goal of this is to just create content. Lots of content. You will throw a lot of it out, but if you censor yourself early on, you'll have a terrible product at the end.

The real question is "How do you remove inhibitions?" That answer is simple and as old as civilization: Alcohol.

I take my list and a laptop and I go with my wife down to the Tempe Festival of the Arts. We wander around for a bit until I'm tired of wandering around. Then I go to a brewery while she wanders around and I write pages of material. I will generally have 100% more content than will appear in the final product.6

Step 3: Edit mercilessly#

There are going to be parts of your (non-sober) content that you're going to love. They were hysterical. But, they have to go. Try to make it so that your words really have impact. Recognize, if you're doing this with someone else, there are going to be parts they don't think are funny/important. Unless it is just amazing, realize it may just not be spot on.

Step 4: Publish#

The letter that doesn't go out, doesn't matter.

Other lessons#

Have a plan#

For the first 10 years or so we were able to get away with simple text and pictures. But after a while, there is only so much variety you can have there. So now, we tend to have "themed" letters. Examples are:

  • Travel Agency
  • NFL Draft
  • Dungeons & Dragons
  • Pokemon

But, I've written a ton of content, and then we've decided on a theme, and a lot of that content was simply wasted.

If you do it right, you'll be a victim of your own success#

I'm tired of writing the letter (just like I'm tired out Out of Office messages, but that's a different post), but every year we get the feedback that people consider it part of their holiday ritual now. They'll keep it sealed until they can sit down with the family and go through it. This is not our parents and siblings, but neighors and acquantainces. I feel like we can't take a year off.

This pattern is true for a lot of life and work#

  • Create content without inhibitions
  • Edit merciliessly
  • If it's important, make sure that every word/sentence/slide/photo/video has a purpose. Not that it's there just because you didn't have the time or the discipline to make it better. (See: Blaise Pascal)

Samples#

Ok, I should provide some samples here, but it would be a lot of work to pull the PII data from them, so I'm sure I'll do it at some time, just not sure when.