Draw Your World

Draw Your World

‘My February’ Drawing Challenge

A 28 Day Self Portrait of Everything That’s Yours

Samantha Dion Baker's avatar
Samantha Dion Baker
Jan 19, 2026
∙ Paid

Hi everyone,

What inspired a whole 28-day drawing challenge? It came to me in a yoga class, as my mind was wandering right after the new year. I am calling it “My February.”

We didn’t travel during the holidays, and it felt so good to stay home and feel grateful for where we live. We didn’t need to go anywhere. We lack space, but in return we have so much more—New York City is our playground. I get to call this amazing city mine, and I get to return each day to a quirky old apartment building that holds my home. It’s not big enough for all of us when everyone is in Brooklyn to visit, but it’s cozy and full of memories.

My view when walking home from Montague Street in Brooklyn Heights.

When we get caught up in what’s missing—say, more space—we forget about what’s already ours, such as a long-lived-in apartment. And it goes beyond physical things, to the intangibles. My anxiety, for example, is also mine. What if I tried drawing it? My patience on good days and my overwhelm on harder ones. These quirks belong to me, and they deserve acknowledgment too.

As an added perk, I’ve noticed that when I pause and notice what’s mine—the useful, the imperfect, the deeply personal—the craving for more, whether physical or nonphysical, drifts away a little.

My hand with red nails

Inspired by all of this, I’m starting a drawing challenge on February 1st, and I’d love for you to join me. Every day in February, let’s draw something that’s ours. Maybe it’s a favorite mug. Maybe it’s your messy bun. Maybe it’s the knot in your stomach before a big day.

By the end of the month, we’ll have a self-portrait made from the things that shape our days, both visible and invisible, in this particular season of life, when the outside world feels so unpredictable.

I’ve listed prompts below if you’d like to follow along. But feel free to wander on any day if there is something of yours that you want to honor.

My beach bag that holds our essentials

I invite you to make organize this self portrait in whatever way feels special and inspiring to you. Here are a few ideas:

  • Draw in your sketchbooks, designating each page to be your one thing

  • Create small thumb nails in your sketchbook—all 28 on 2 pages

  • Cut out 28 small pieces of watercolor paper and put them in a box

  • Make a special saddle-stitch book that is 28 pages (plus a cover) to create a dedicated “My February” book.

  • 28 small little paintings and hang on your wall

  • Use your creativity and do whatever you want!

There are so many ways of putting this project together. I want this challenge to be a special exercise in self-reflection and appreciation, leaving you with a keepsake self portrait at the end.

If you want to join us for daily accountability and to share your work in the chat and meetups throughout the month, you can upgrade your subscription here. And if you want to do this challenge on your own, scroll down for the list of prompts and be sure tag me when you share your favorite drawings!

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My February Prompts:

  1. My hand(s)

  2. My favorite pair of shoes

  3. My oldest sweater

  4. My bathroom sink

  5. My nervous feelings

  6. My favorite friend (a pet or a person?)

  7. My front door

  8. My bag that holds my stuff

  9. My favorite place to drink coffee or tea in the morning

  10. My favorite pen or pencil or paintbrush

  11. My favorite song

  12. My forehead (or another small part of your body)

  13. My allergies (or other ailment that shows up)

  14. My coffee table

  15. My favorite jeans

  16. My favorite book (or a few of them)

  17. My biggest accomplishment

  18. My morning hair

  19. My pillow where I lay down to sleep

  20. My desk

  21. My keys

  22. My favorite heirloom

  23. My eyes (and my glasses to help me see)

  24. My favorite piece of jewelry

  25. My refrigerator

  26. My vitamins (and/or medications)

  27. My vase next to my bowl set up to make my own still life

  28. My finished project (draw your sketchbook or the box holding your drawings or the stack of papers)

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