• Sending Out Holiday Cards and Letters: A Guide

    The holidays present a wonderful opportunity to reconnect with family and friends via snail mail. In this article, we’ll talk about how to send holiday cards (or letters) to everyone on your list!

    "Artistic Ornaments"-Themed DIY Christmas Card Tutorial | The Postman's Knock
    If you plan to hand-make all of your holiday cards (no judgment here if you don’t have time time, though!), this artistic ornaments card concept is fairly quick and easy.

    You probably have friends and family members whose company you enjoy, but it’s difficult to stay in touch. The grind and responsibilities of daily life can make it difficult to keep friends and family in the loop! Consider the holidays an excellent opportunity to catch up. Today, I’ll share my technique for sending out holiday cards (and/or letters) in a low-stress and efficient manner.

    Why Send Holiday Snail Mail?

    Holiday Calligraphy Printable Exemplar + Worksheet | The Postman's Knock
    You can learn how to make this flourished tree in the TPK Holiday Calligraphy Worksheet 2016 Edition. It looks stunning when calligraphed in gold ink on a simple black card (made from folded cardstock).

    Holiday snail mail — a pretty card or a letter — provides a way to connect with someone you might not get to talk to on a regular basis. Around the holidays, snail mail is more common than other times of year, so this is the perfect opportunity to send something. Your recipient will open your envelope, appreciate what’s inside, and likely not feel pressure to write back — which is good! The holidays are all about giving, and you’re providing your friends and family with the gift of knowing that they’re on your mind.

    1. Decide What to Send

    Assorted Goodies from Maureen Vickery
    This is the card that I received from artist/calligrapher Maureen Vickery in 2019. She sent a copy of the joyful pig card to all of her recipients, along with a thoughtful hand-written note. (Love Maureen’s pig? She’ll teach you how to make a reindeer in the same style!)

    Before you do anything, evaluate the amount of time you have and about how many people are on your holiday card list. If you have a fair chunk of free time and a small list, consider hand-making holiday cards (find a list of holiday card tutorials here). If you’re tech-savvy and pressed for time, you can design a card on your computer, then print off multiple copies.

    Holiday Card
    I used hand-illustration and Photoshop to design this card in 2012 for a former roommate. (You can learn the technique for making this chalkboard-style card in the Digitizing Artwork & Calligraphy eCourse.)

    The third option — and my favorite — is to write a general update letter for all of your recipients. Think of all the significant things that happened this year, and write them down. What do you want people to know? Did you start a new job? Have a baby/grandbaby? Move? For letter prompts and ideas (plus a letter layout planner), see The Letter Writer’s Complete Resource. You can either type your letter up and print out several copies; or you can hand-write the letter, scan it, and print multiple copies. The letter doesn’t have to be pretty … just informative and interesting.

    2. Gather Addresses

    The Letter Writer's Complete Resource: A Guide for Writing Letters | The Postman's Knock
    This address organization sheet is from The Letter Writer’s Complete Resource.

    Once you have decided what to send, make a list of recipients and their mailing addresses. If you’re not sure of a mailing address, find it with a Google search or by reaching out to someone who knows it (or the recipient themself, if necessary). After you complete this step, you’ll have an official count of how many holiday cards or letter you’ll actually need, so you can go ahead and create your cards/letters.

    3. Buy Envelopes

    Inspirational #10 Envelope Art Examples
    If you’re sending out holiday letters, consider using #10 envelopes. US letter size paper folds to fit perfectly inside!

    As you’re prepping your holiday paper goods, it’s a good idea to buy envelopes. You can either do that online (find a list of reliable retailers here), or you can do so locally, preferably at a place that specializes in good paper. Purchase ~25% more envelopes than you actually need, just in case you make address writing errors.

    4. Address Your Envelopes

    Six Calligraphy Envelopes, Two Hours

    Once you’ve got your envelopes and your recipients’ mailing information, you can write out addresses. I prefer to write addresses in pointed pen calligraphy, but of course hand-lettering or everyday handwriting gets the job done just as well! (If you have several envelopes to address, see this article for tips on how to tackle fairly large quantities of envelope calligraphy.)

    Beautiful Holiday Envelope | The Postman's Knock
    This is another variation of the flourished tree from the TPK Holiday Calligraphy Worksheet 2016 Edition.

    If you’re only sending out a couple of holiday cards, consider investing the time to make gorgeous holiday mail art. (This Christmas tree envelope art tutorial is one of my favorites on the site!) It’s not realistic to make mail art if you have a lot of mail to send and not a lot of time, but if you’re sending letters to ~5 people or less, mail art is a possibility.

    5. Apply Postage to Your Envelopes

    Once you’ve finished writing out the addresses on your envelopes, double-check that they are correct. Then, add postage to your envelopes! (If you want to get fancy, you can make a postage stamp collage.)

    It’s important to wait to apply postage to your envelopes until after you’ve written out the addresses. Otherwise, you might miswrite an address on an already-stamped envelope and waste a perfectly good stamp.

    6. Get Your Envelopes to the Post Office

    This might seem like an obvious step, but it’s worth discussing how to mail your holiday envelopes. If you only have a couple of envelopes prepared, you can put them on your mailbox for your mailperson to pick up. If you’ve got more envelopes, it’s best to take them directly to the post office or drop them into a mail collection box.

    Mailbox with Letters
    I usually send my envelopes just like this. Depending on the format of your mailbox, you can use a clothespin or a clamp to securely hold envelopes as they wait to be sent.

    You know your postal situation best, so do what most makes sense to get your letters safely in the post office’s possession. Crucially, remember that mail delivery times always get longer around this time of year … and the ongoing pandemic hasn’t helped that. If your recipient list includes people who live internationally, try to send your holiday mail by November 15th. If all of your holiday cards are destined for domestic delivery, shoot for December 1st. These dates will help ensure that your mail arrives before Christmas.

    Flourished Snowman
    Want to incorporate this snowman into your holiday paper goods? You can learn how to make him in the Not Your Average Calligraphy Drills: Holiday Edition (2021) packet.

    I hope that this article inspires you to send out holiday cards this year and/or helps you to streamline the process! If you have any tips or questions, please feel free to contribute to the comments. Happy holidays!


    Lindsey's Signature | The Postman's Knock