Behind the Scenes: Creating My 2019 Holiday Letter

I spent last Friday making my 2019 holiday letter with pen and paper, like in 2018. The idea had been swirling around in my mind for a few weeks—to send out an unexpected letter mid-year, since I hadn’t sent anything out last December.

Like most creations, it began as some scribbles on scrap paper. I like to collect scrap paper (ie grab from recycling bins) for this exact purpose. It feels more accessible and easier to jump in with crap when the paper itself has already lived its first life, so I use this technique and keep scrap paper handy.

The content I wanted to share seemed to fall into two main categories:
1) a quick summary of the past year and a half

and 2) my present circumstances/reality:

Once I saw that structure take shape, I started on a more detailed draft-ish:

Unsurprising to me, I couldn’t fit everything I wanted onto two pages for a single front-and-back letter, so it quickly became four pages.

I really went with whatever came to me that afternoon/evening, and I didn’t overthink it. It was a one-time letter, not a zine that would be published over and over. I wrote with my nice pens directly onto the letter without knowing the exact phrasing that would appear.

Also, I knew I was going to be in a city with a photocopier the following day, and that time deadline really helped me to embrace “good enough,” keeping it a light project.

I made copies at a Staples self-serve photocopier on Saturday, then just needed to buy envelopes. I had this vision of bright teal or turquoise envelopes—how fun would that be to find in the mailbox? But all we were able to find, without making additional stops at the end of the shopping trip, were plain white business envelopes.

On Sunday morning, I thought about the quickest way to jazz up these white envelopes, using what I already had at home. Watercolor splatter!

I laid out all the envelopes on our table, and the splattering took all of four minutes.

When they were dry, I put on a TV series and addressed, stamped, and decorated all morning—while cooking and baking too.

By 3 p.m. I had a pile of outgoing mail to take to the post office!


Like my others, if you’d like to read (and print, to hold the letter in your hands!) my 2019 holiday letter, you can purchase a copy on Gumroad for $2+. It’s a 4-page PDF download.

If you’re interested in more holiday letters, here are my 2018, 2017 & 2016 creations:

Thanks so much for being here, and I wish you an excellent day!