Connecting Dots: A Creative Postcard Challenge

Posted inCreative Prompts
© Amy Cowen, 2024

Welcome to Connecting Dots, a monthly column by writer Amy Cowen, inspired by her popular Substack, Illustrated Life. Each month, she’ll introduce a new creative postcard prompt. So, grab your supplies and update your mailing list! Play along and tag @printmag and #postcardprompts on social.


When was the last time you sent a postcard? When was the last time you carried up a stack of mail and found a small card, glossy photo on one side, handwritten note on the other, tucked in among the circulars and bills? Wish you were here!

There is something unique about a postcard. It is small and compact. It may be thin, bordering on flimsy, and yet with a corner stamp in place, it is designed to make it through the system.

How many words can you fit in the split panel on the back? Do you need words? What happens to the narrative if you send drawings? Portraits? A selfie? A sketch of your morning coffee, your pet, or from your favorite cafe? What happens if you swatch your palette (ink or paint or colored pencils) each month on a postcard and mail it to someone?

What if you record thumbnails of morning light every day for a week? What happens if you write how you really feel in that blank space and send it off?

If I look out my window and draw the shape of the tree and write the colors of the sky and, later, drop it in the mail, how will you reply? If I do it once a month for a year, what will I capture? What record will the postcards hold? What will it mean to the recipient?

Intimate and Exposed

A postcard feels intimate, a whisper in the wind, and yet its intimacy is undone by the fact that its contents are not hidden. It is not concealed. It is a message that is out there for anyone to read. Saying just enough is part of the allure, part of the puzzle, part of the dance. Maybe your words are cryptic or abbreviated or written in a shorthand that will only make sense to the recipient. Or, maybe you write plainly, hold nothing back. Maybe you have nothing to hide.

An Unassuming Substrate

As a surface, a postcard is a simple and beautiful container, a glorified index card, often with a photograph or art on one side, that we intentionally compose, address, stamp, and send on a journey to connect.

Other than the annual jury duty summons, very little real or important mail arrives as a postcard. Postcards, for the most part, are personal. They are from or to someone you know. They have been selected with specificity.

Maybe we are somewhere special, or on vacation, and are sending a note to someone to let them know that we are thinking of them. Maybe it’s a bit of a flex, a throwback to days before social media: “Look where I am.

Maybe we simply have to share that bridge or that view of sunset or that hillside in the mist. Maybe we are enjoying ourselves so much that the desire to send someone evidence of our adventure is irresistible. We don’t really mean to brag, but we want someone to know, someone to witness our journey.

Or maybe our postcards are more humble. Maybe we are sending words from home, a note carefully tucked into the small space and a favorite art series on the other side. Maybe we have the Pantone postcards. Maybe we’ve selected a specific color. Does it reflect our mood? The sky? The color we think of when we think of the recipient?

Will you send national monuments or falling leaves, paint brushes or sunsets or roosters or cats or photos of chairs or bridges or lighthouses or quilts or children’s book illustrations? Will you send photos of works by favorite artists (like Hopper, Matisse, Van Gogh)? Will you send photos of hot sauces or birds or rainbows, stacks of books or spine art, Studio Ghibli scenes, New Yorker covers, national parks, or coffee cups?

The art is part of the equation, and then there is the flip side. You only have a small space in which to write (or illustrate) your note. What will you say?

Postcard Prompts

In a series of monthly prompts, we will create a set of postcards, each one responding to a simple nudge. You can use existing postcards, focusing on filling the blank side. This is the easiest approach. Or, you can use blank cards, your responses filling both sides.

Month by month, you will develop a set of postcards, a series of epistolary art. You might choose to work in the same medium or style or palette each month or work with repeated elements that help tie the cards together. Or you may view each postcard as a standalone piece, disconnected from others, and let the prompt guide your choices.

Simple and Mindful

The prompts will not be difficult. 

These are prompts you may have done before. But we will do them in this monthly format together as the world changes over the next year, as our lives change, and as we process whatever we are going through, highs and lows, celebrations and milestones, personal journeys, and the quest for meaning.

Who will you have in mind as you create your postcards? Will you mail them?

A Postcard from Your Journal

One of the projects that I run and that I encourage others to consider is the keeping of an illustrated journal that documents life with a combination of art and words. I use a weekly format because I particularly enjoy the ways in which taking things a week at a time allows for fluidity across a span of days. There is no pressure to finish pages or drawings every day. Instead, I work on spreads that can be built and shaped and filled in over the course of a week. It’s mindful. It’s flexible. Every Sunday, I start a new week.

Many of the postcard series prompts could easily be done in an illustrated journal or sketchbook or in the margins of a bullet journal or planner, but I hope you will consider the postcard as a format. The postcard presupposes a recipient, a reader, a viewer.

Postcard Logistics

To qualify for the postcard stamp, a postcard needs to be roughly 4×6 or smaller. The USPS lists the following specifications:

  • Rectangular in shape (not square)
  • At least 3-1/2 x 5 inches and at least 0.007 inch thick
  • No more than 4-1/4 x 6 inches and no more than 0.016 inches thick

If using traditional, preprinted postcards, you will want to make sure the cards meet the size requirements (or plan to use a letter stamp for oversized postcards). If you are going to DIY your postcards, you can buy readymade blank postcards (plain or watercolor), use heavyweight index cards, or cut your cards from heavy cardstock, Bristol board, or watercolor paper.

Using preprinted cards minimizes the work. You’ll be sharing a photograph or piece of art you like and your own art and/or writing on the other. This is also a great way to use up postcards you may already have.

If it’s been a really long time since you saw a postcard in person, remember that on one side, you’ll need to put the address on the right and the stamp in the upper right corner. Also, be aware that the postal bar code will be added along the bottom edge. If you write or draw in that space, just know it will most likely be obscured during the mailing process.

Postcard stamps are slightly less expensive than letter stamps, but there aren’t a lot of options. Currently, postcard stamps feature sailboat art by illustrator Libby VanderPloeg. If you have old stamps floating around that aren’t enough for current first-class mail (and aren’t Forever stamps), using them on your postcards can be a good option. Just make sure they meet or exceed the postcard stamp in value.

Slowing Down

A postcard series almost sounds quaint, other than the fact that there are thousands of people writing postcards these days to encourage people to vote. Beyond that, sending almost anything with a stamp might feel just a bit old-fashioned.

As a creative project, thinking about a postcard series is exciting. I imagine postcards filled with lists, or data visualization (a la the Dear Data project), with drawings, portraits, quotes, poems, and more. I am hoping that we can push the envelope on this envelopeless space to create personal series that are unique, bold, quiet, honest, authentic, and visually awesome.

I hope we create postcards that, through their line and composition, through their art as much as their words, have something to say. I hope we send our postcards and reach someone.

An October Postcard

Not every postcard (or every piece of art) has to be deep or soul-baring or complicated. A lot of postcards just say something like “Wish you were here!” or “Wanted to let you know you’re on my mind.”

To kick off this postcard series, let’s focus on something that is relatively simple and can be tied to memory or not. It’s October, and Halloween will be coming around.

Your challenge for this month is to create a postcard (with a recipient in mind) and document a costume.

Maybe it is a costume that you remember from when you were a kid. Maybe it is a costume from your children’s Halloween years. Or maybe Halloween isn’t something that was ever a big deal for you, and you think about what kind of costume you might choose now or wish you had chosen then.

You don’t have to particularly like Halloween or be a dress-up person to do this prompt. I don’t, and I’m not. But I still find it interesting to think about my history with Halloween, most of which I don’t remember, and some of the characters that stand out for me from my parenting years, from comic books, and the world of cosplay.

You may want to separate the prompt from Halloween and think about the whole concept of dressing up (whether you do or don’t), the performative aspect of that, and even the ways in which dressing up can be used to flaunt or conceal. Maybe you are a fan of Chappell Roan and sometimes think about what it might be like to wear costumes like that. Maybe you loved Joaquin Phoenix’s version of the Joker. Maybe you love theater or anime. Or maybe you just have a soft spot for clever costumes, sewn at home or made from cardboard boxes.

So what will you put on a postcard?

I don’t dress up, but one of my favorite costumes that I’ve seen in the last few years, something that seems really “doable,” is Waldo (from Where’s Waldo), with his round glasses, red and white striped shirt, and striped hat with a red pompom. It’s an incredibly simple costume. It’s cute and clever. It looks like it would be fun. (The corresponding Wenda costume tends to involve a very short blue skirt. I would opt for Waldo. No question.)

I am also a fan of the Pantone color swatch costume. I love this idea even though it’s potentially an overthinker’s nightmare. What color would you choose?

Crayon. Alice. Rabbit. Harry Potter. Obi-Wan. Dorothy. The Tin Man. Banana. No. 2 Pencil.

Commemorate a costume on a postcard. You can draw your costume, or diagram it, or make a collage, or write it out in words. You might write the memory of a specific costume, a specific Halloween, or turn it into a poem. What does the costume say? Why this costume?

Have fun!

Notes: links to Amazon in this post are affiliate links. You can find postcards at your local souvenir stands, museums, and other shops. You can find postcard-making materials at your favorite art store or by scavenging paper products you already have.


Amy Cowen is a San Francisco-based writer. A version of this was originally posted on her Substack, Illustrated Life, where she writes about illustrated journals, diary comics/graphic novels, memory, gratitude, loss, and the balancing force of creative habit.

Header image: Assorted postcards. A. Cowen 2024