Hello, my fine drawing-oriented friends!
It’s Sunday, March 16, 2025. Guess what??
TODAY WE ARE FIVE!
How the heck did that happen?!
Back in March 2020, as the world adjusted to sheltering in place and we prepared to stay home and isolate for a few days (ha!), I paused my work drawing stories to teach kids to draw. I thought it would be a week or two. It’s been five years.
❤️✏️❤️ Drawing is looking, and looking is loving ❤️✏️❤️
Long before DrawTogether, all the way back to twenty years ago when I was drawing and talking to strangers on the subway, I understood a simple truth: Drawing connects us to the world and each other. That truth is the thread that runs through every chapter of the DrawTogether story.
Today, let’s take a look back at all we’ve done in DrawTogether over the past five years. I am certain you’ll see bits of yourself in this story. This is one big collaboration, and it would not exist without YOU.
I’m taking down the paywall this week and opening up our assignment: we’re creating a collaborative quilt of all things DrawTogether, day one till now. We want to know, what do DrawTogether and the Grown-Ups Table mean to you? Hope you join in.
Alright, DT Peeps. Buckle up. Let’s take a look back at what continues to be a hella joyful ride.
From the Beginning: “Pencils Up!”
DrawTogether LIVE
DrawTogether was born at 10am on March 16, 2020. It was the first day of pandemic school closures in the San Francisco Bay Area. It was scary, and we were all afraid, and we all did our best. For us that meant taking a deep breath, making a pencil mustache, and broadcasting a live interactive drawing show via Instagram from our home studio in San Francisco.
My then-wife Caroline — AKA Art Assistant Caroline as she quickly became known to kids around the world — handled the cinematography. Suso watched over from the chair nearby (we miss you Suso!) And I led 12,000 kids through drawing a dog. What was supposed to be 5 minutes for 5 days ended up being a 30-minute live drawing class every day for months. With the help of special guests including illustrator Christoph Niemann, builder Emily Pilloton-Lam, and color wizard Jason Logan, we practiced drawing, laughing, deep talks and deep breaths, checked in with our inside weather, and grew an unexpected worldwide community of artists, all drawing our way through the toughest times together. The live classes were featured in newspapers like the SF Chronicle, the New York Times and even the TODAY Show.




DrawTogether Art Kits for kids!
While we could offer the art classes for free, many kids didn’t have basic art supplies at home to participate. Partnering with the amazing Michelle Morrison at Dropbox, we created a run of emergency art kits for kids, then launched a public fundraiser to make many, many more, eventually distributing over 3500 art kits to kids and classrooms across the USA. By forming a partnership with local art supply shop Arch in San Francisco & national distributor MacPherson, local art-focused businesses survived a tough time, and helped get supplies into the hands of kids who needed them. Blackwing donated pencils, and Waymo volunteered delivery service. SO MANY people kicked in funding, and Vinny Eng helped make it go!
DrawTogether Evolves… into a Newsletter, Show, and Podcast!
The Set & The Show
What do you do after making a live show on Instagram? You build a whole world out of cardboard and paper mâché by hand and shoot an entire TV show, of course!
Seeing the impact of DrawTogether on kids’ hearts and creativity made me double down on the power of drawing and the possibilities of creative, interactive, slower-paced educational media. With the help designer/builder Bryan Burkhart, Art Assistant Caroline, and incredible SF community members (including kids!), we built an entire TV set by hand inside The Marsh Theater in SF. The stage was lit by Little Giant Lighting, and we shot 12 full episodes on iPhones donated by Apple.
wrote and performed our theme song. Jon Mooallem helped with ideas, editor and animator Megan McShane made the show shine, and animator Edlyn Capulong made our stop motion intro. And Katie McShane and Leo Hardman-Hill composed an original score for every episode. Episodes featured special guests like chef and writer Samin Nosrat, and artist and illustrator LoveIs Wise.Launching on Substack: Show, Podcast & More
After some bonkers conversations with Netflix and PBS, a then up-and-coming company called “Substack” (maybe you’ve heard of it) and my wonderful friend/Head of Culture and Music there,
, enticed us to launch on their platform. Kate Levitt, Patrick Hruby and Ishita Jain helped build a newsletter for kids and exactly one year after DrawTogether began, we launched DrawTogether with WendyMac on Substack. Huzzah!!Soon after, I started making the DrawTogether Podcast, an interactive drawing podcast featuring special guests like musician
of The Decemberists, and illustrators Yuyi Morales and . (Super fun, and WAY less expensive to make than a show!)All this fun stuff caught people’s attention, and DrawTogether was profiled in publications like the Los Angeles Times and New York Magazine, and I gave a TED talk about drawing and how it connects us to each other.

DrawTogether Enters the Classroom
One of the most impactful applications of DrawTogether was in the classroom. We were astounded to learn how many educators were using DrawTogether lessons to teach art and social-emotional skills (and how little high-quality supportive programming there was for kids and educators in those areas!).
Working with Kate Levitt, PhD, we established DrawTogether Classrooms, a non-profit supporting educators to enhance social-emotional learning and art. Building on DrawTogether videos, podcasts, and activities, and funded by generous philanthropic supporters, we created a best-practices based curriculum for educators, ran a national pilot program to test its impact, and in March of 2021, made the whole thing public and free for all.
PBS Newshour did a wonderful piece on the program. You can watch it here.
Other DrawTogether Classrooms highlights included:
Partnering with NASA to send the first kids drawings into space (for real!)
Installing an interactive DrawTogether Classroom exhibition in the Indianapolis Museum of Art at Newfields.
Translating episodes and lessons into Spanish and Mandarin!
Thanks to the hard work of Kate Levitt with support from Kyle Ranson-Walsh and Molly Pilloton Lam, DrawTogether Classrooms reached over 300,000 learners in 10,000 classrooms around the world. Wow.
DrawTogether Grows Up (The GUT!!)
In the midst of all this, in August 2022, I started the DrawTogether Grown-Ups Table, affectionately called “The GUT” to jumpstart my own drawing habit. Every Sunday I gave myself an art lesson and a drawing assignment, shared my drawing in a group chat, and invited other people to join the journey. And wow, did they (you!) ever.
As of this post, DrawTogether with WendyMac has 97,000 subscribers! Every week, hundreds (even thousands!) of members post their drawings in the chat and support one another. The community is what makes the GUT so special. With visiting artists like Maira Kalman, Austin Kleon (who also has a Substack), Amy Tan, Gretchen Rubin, and Alexander Chee (who ALSO has a Substack!) our practice continues to grow. If art had a battle cry, ours would be “No rules in art!” “You do you!!” And of course, “Drawing is looking, and looking is loving.”
Two of the most well-known things to have been born of the GUT are DrawTogether Strangers, and The Drawing Habit - aka 30 Days of Drawing.
DrawTogether Strangers
DrawTogether Strangers began as a “GUT” response to increasing isolation in the world, and people’s avoidance of strangers on the street. As a simple social practice art intervention, I set up a table and two chairs in public places in cities around the USA with a sign that said “DrawTogether, it just takes 1 minute.” I asked strangers to sit across from one another and draw each other for 60 seconds without looking down. This pushed people to draw — a leap many are afraid to take — but more it invited them to look at someone without looking away for a full minute — and allow themselves to be looked at too.
After traveling to multiple states with a sign and a table, we created a free public toolkit and invited everyone to host their own DrawTogether Strangers experience. People around the world (including many GUT members) set up drawing stations and invited strangers to sit down and see (and draw!) one another.
I created a New York Times visual Op-Ed about the project, and it was the subject of a NYT Opinion podcast. The National Gallery of Art invited me to bring DTS to Washington DC, and Aspen Ideas Health invited me to bring it there, and this Spring we’ll be doing it at a major museum in SF. (Stay tuned for deets!)
30 Days of Drawing: The Drawing Habit
The 30 Days of Drawing, AKA The Drawing Habit, is an annual, epic creative/heart growth adventure that happens here on the GUT. The premise is pretty simple: I give everyone a drawing/creative/life lesson and an assignment every day for 30 days. Every day we share our work in a community chat, and support and cheer each other on. And it changes people’s lives from the inside out.
With the community-facing help of
, handling the backend and gallery, and most recently joining to help with larger GUT stuff in general, we’ve done it three times now. Twice in the past two Januarys.And it’s a life changer. The past two times we did a little study around its impact, and its proven to increase people’s confidence, creativity, curiosity, ability to use drawing to monitor and manage feelings, and so much more. I’m so, so excited to continue to make the Drawing Habit more impactful and accessible to more people.
Make what you want to see in the world
Toni Morrison said, “If there's a book that you want to read, but it hasn't been written yet, then you must write it.” This thread runs through every DrawTogether projects. When we get that magical feeling that something MUST exist but it doesn’t, it is up to us to make it.
I would like to invite you, my fine GUT friends, to approach your creative life like this. When something catches your eye and you think "That could be a drawing,” DRAW IT. When you want a space to be in, CREATE IT. If you wish there was a community to be part of, BUILD IT.
DrawTogether is one ongoing, big-hearted evolving group art project. There are so many creative, crucial collaborators on this giant experimental art piece, including YOU. I’ve named many here today, but far from all. You know who you are. Thank you. Thank you for being part of this, and for trusting me with your creative hopes and heart, your kids, family, and best friends. Thanks for drawing together through some of the hardest and the happiest times of our lives.
Thanks for being part of DrawTogether.
I’m leaving the anniversary assignment open so we all can join in.
Pencils UP. ❤️✏️❤️
xoxo,
w
THE ANNIVERSARY ASSIGNMENT: DrawTogether Memory Quilt
Whether you’ve been here for five years or just joined us recently, this week’s assignment invites you to join us in reflecting on our time together! Like all art projects, we have no idea how this will turn out. But let’s drop our shoulders, point our pens towards curiosity and connection, and I have a hunch we’ll be pleasantly surprised.
Step 1. Think back… What assignments stand out in your mind? When did you feel really proud of what you drew? How did an assignment resonate with you at a particular moment in your life? I’d love to hear your memories of that assignment!
Step 2. Go back through your photos or sketchbook and share your favorite DrawTogether moment in the chat. Please say a little about what you remember and why that one stands out to you. Our chat will “stitch” them together to make a 5-year anniversary quilt, a community creation to keep us cozy in these challenging times: “Everything is better when we DrawTogether!”
Step 3. DO OVER!! If going back to look at that assignment is leaving you inspired, go ahead and draw it again. See how your drawing changes from then till now, and consider how/why it’s changed the way it has. (Can you say, “practice?”)
Share both your old and new drawings in the chat! I’m so curious whether you will find yourself creating something similar or coming up with something entirely different!
See you in the chat, Grown-Ups Table!! Let’s stitch together some creative memories.
❤️✏️❤️
GUT Gallery: Sounds of Silence
Last week we took inspiration from “One Square Inch” of silence, the art project about quiet in the middle of the Hoh Forest National Park, and listened deeply and draw what we heard - either literally or expressively. The results were astounding. Many of you said you heard things you’d never noticed before, and took leaps and risks in your drawn response. Below are a few selections from the GUT Gallery/group chat. (PS - Special thanks to
for curating this gallery every week!)


Yahoo! What a wonderful ride it’s been! Thank you Wendy, thank you mom Candy, thank you Caroline, thank you Suso, thank you to the cast of thousands helping out in so many ways behind the scenes, and thank you GUT members for your continuing inspiration.
We lost our home in the Palisades Fire, but I evacuated with my GUT sketchbook. My collection of decorated boxes was consumed in the flames, BUT because of the GUT prompt to draw one of your collections, and tell a bit of the story while you’re at it, I have these drawings and am grateful my beloved boxes continue to live on these pages. Congratulations on Five Years of Drawing Together and thank you Wendy for you doing you!