Illustrating Grief: the Five of Cups
The meaning of the Five of Cups
The Five of Cups is a tough one. It’s the card pointing to the complex emotions of grief, mourning, and loss.
As an indie tarot artist, I wanted to illustrate it the way I felt my own grief. That is, like something (or someone) was suddenly gone from the picture of my life.
HINT: Scroll to the end of this post to see the final card design!
Examples from other tarot artists
This card usually includes a person in a long black cloak, their gaze down at the ground. They are surrounded by spilled cups and darkness.
Here are some examples of the Five of Cups card from various tarot decks I use.
Five of Cups cards from my collection of tarot decks; see footnotes for artist credits.
The missing piece
My own interpretation of the Four of Cups is this: Grief and loss can feel like a piece of us is missing. It’s as if the picture of our life has a hole in it.
Two years ago, my dad passed away. He had been ill for two years before that, so his passing was not a surprise. However, his illness did not prepare me for the feeling of loss I experienced after he was gone.
When I meditated on the themes of the Five of Cups when creating this illustration, I closed my eyes and thought of my dad. I thought of the role he played in our family, and the profound sense of loss I felt without him. I imagined a puzzle, with one missing piece. That piece you keep looking for, but never appears, and the puzzle remains incomplete.
My dad was a big coffee drinker, and always had a mug of coffee nearby. So our family puzzle is five mugs, all representing a different member of my family. Dad’s is green, which was his favorite color. The green mug has the piece missing.
Within the space left by the missing piece is … space. Literally, space. Don’t get me wrong, I love space, which I declare in this post about my illustration of The Hermit card. The space left by his loss was different somehow.
With that in mind, here is my original sketch for the Five of Cups tarot card illustration:
My sketch of the Five of Cups tarot card.
Colored pencil and paint pen on paper.
How I made this card
This illustration includes lots hand-drawn linework I created in Procreate, based on my original sketch above. I printed the linework on watercolor paper, then used liquid watercolor paints and watercolor brush pens to create the paint layers.
Here are some of the layers included in this illustration. Note the rough edges of the watercolor layers, which I crop out after I scan the painting.
See more about my tarot art illustration process here.
The final illustration
What do you think? Leave me a comment below! I love to hear from you.
The Five of Cups card illustration from my forthcoming Tarot of These Times deck, anticipated 2026.
© Registered copyright Molly Chidsey, all rights reserved.
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Footnotes
Materials and technique notes from this post
Blick Hot Press 100% cotton watercolor paper; EcoLine liquid watercolor paint and brush pens; Winsor & Newton masking fluid. I use an Epson Workforce Pro printer to print my drawings onto watercolor paper, using their water-resistant Durabrite ink.
Linework is drawn by hand with Apple Pencil on iPad Pro using Procreate app, and added as image layers on top of scanned painting using Photoshop.
Roman numerals, hand-drawn linework, and all calligraphy were drawn by hand using Procreate, Apple Pencil and iPad Pro.
Artists of other tarot cards featured in this post
Clockwise from top left: Rider-Waite Tarot, illustrated by Pamela Coleman Smith; Modern Witch Tarot Deck by Lisa Sterle; The Wild Unknown Tarot by Kim Krans; The Gentle Tarot by Mari in the Sky; Rainbow Heart Tarot by Rachel Rosenkoetter; and The Reclaimed Tarot, ReClaim it! PDX, collage by various local artists.
Learn about tarot
(1) Want to learn more about tarot? I highly recommend the book Modern Tarot: Connecting with Your Higher Self through the Wisdom of the Cards by Michelle Tea.
A note about Ai and this project
I do not use Ai (artificial intelligence) to write any of the content for this blog or create any illustrations. All concepts, illustrations, and written content are written by the human Molly.
