Grow: How Wendy MacNaughton builds community with her 30 Days of Drawing practice

The Grow interview series is designed to share the nuts and bolts of how writers have gone independent and grown their audience on Substack. It has been lightly edited for length and clarity.

We invited

Wendy MacNaughton

, who publishes

DrawTogether with WendyMac

, to discuss her insights into building a community-first Substack and finding success with 30 Days of Drawing.

What’s your Substack about in one sentence?

How drawing helps us become more curious, creative, and connected to one another, and changes us (and the world) from the inside out.

What features or strategies have you found most useful for growth?

I started the Grown-Ups Table to create what I wanted for myself: a weekly dose of creativity, art, and community. I believed that a consistent drawing practice would make my life better, especially if I could produce those pencil strokes alongside interesting, positive people. Wonderfully, the GUT has proved me right. And I’ve found that as long as I’m pursuing my own curiosity and going with my GUT (so to speak)—being generous with my ideas and questions and mistakes and successes—others are excited to join.

Major moments of community growth (which I consider either getting bigger or going deeper) include partnerships with the National Gallery of Art, guest artists and writers like Amy Tan, Gretchen Rubin,

Alexander Chee

, and Maira Kalman, and, of course, our 30 Days of Drawing, which we just launched again on January 1. It’s not too late to join!

Growth by the numbers

• Started on Substack: March 2021

• Total subscribers: 77,000

30 Days of Drawing

Can you share an overview of 30 Days of Drawing?

Every day for 30 days:

• I send a short, approachable drawing assignment. (Insider secret: These lessons are more about paying attention to ourselves/others/our worlds than about creating a drawing that is “good” or “right.”)

• Paying subscribers get (and do) a 10-minute drawing assignment every day.

• Community members post their drawings in the Substack Chat, where (this is my favorite part) everyone cheers and comments and supports one another. It’s such an amazing group. People make legit friends.

• By the end of the month, subscribers have learned to let go of their perfectionism, become more curious and focused on the wonders inside and all around us, and made some pretty cool drawings they can hang on their walls, for real! Not to mention they’ve become part of a creative community that continues on for the rest of the year.

Why did you originally host 30 Days of Drawing?

I had fallen out of my own daily drawing practice and wanted to get back in the habit. I wanted to stop looking at my phone as much and instead actually learn something and be creative every day. I have never been successful at changing my habits alone, so I knew I needed to do it in community. Turns out all the things I needed myself, for myself, a ton of others needed too.

I also got to test if daily drawing did, in fact, change people from the inside out. We put together a little study, got back over 500 pre- and post-completion surveys, and learned so much. Mostly: It works.

Among all these other benefits, 30 Days of Drawing was also the inflection point for significantly growing our audience! So naturally, we’re doing it again this January.

How did you segment offerings for free vs paid subscribers?

Free subscribers get the drawing lessons, which include stories about artists' lives and work and the science behind art and drawing. I want everyone to learn this stuff.

Paid subscribers get access to the daily drawing assignments, our daily Chat threads, and the larger DrawTogether community—that means they can engage in the art sharing and community and get access to IRL DrawTogether member meet-ups and occasional video check-ins.

What kinds of prompts, activities, or conversations sparked the best participation in Chat?

The consistency of the lessons was an excellent spark in itself. And I think some of the more joyful or surprising assignments generated extra participation, like the week on Visual Storytelling, where we created illustrated lists.

When someone surprises themselves, it’s so invigorating. It was a joy to see people take risks, succeed, and celebrate their effort and drawing, especially with a challenge they’d never try outside of the GUT. I love watching hundreds—even thousands—of people look at the world through fresh eyes. It’s a thrill to witness someone’s aha moment in real time.

What was your strategy to direct people to Chat from your posts, Notes, and social media?

I mention the Chat in every post and tell subscribers to go there and leave some encouragement for others. That consistency is important.

Early on, I noticed many subscribers were getting confused about how to use the Chat. So we created an FAQ that explained how to use it, which made all the difference. We’ve made things even simpler and clearer this year.

We also curated a selection of people’s drawings from the Chat every day and featured them as a gallery in the next day’s newsletter. Subscribers love seeing their artwork featured in that gallery. We’re doing this again now, but this year we are letting free subscribers see a selection of drawings periodically, too

Drawings created by the community during 30 Days of Drawing

What metrics or community feedback helped you gauge its success?

Oh, you usually know quickly if something hits. My community isn’t huge on comments. We are a visual bunch. We speak in pictures and text. So the Chat is where it’s at.

What surprised you most about how subscribers participated?

I was most surprised by the interaction between subscribers. Seeing people self-organize meet-ups and accountability groups (for people who didn’t want to use the Chat) was a joy to witness. I feel honored and lucky to lead the community—but it’s really become a self-sustaining group. It’s grown into something more than I ever imagined.

What are you keeping the same, and what are you doing differently?

Last year was too much. I didn’t plan at all. Did no work ahead of time. I was conceptualizing, researching, writing, editing, and illustrating everything every day, in real time, for all 30 days. It nearly killed me. Within 24 hours of launching 30 Days of Drawing, I had to hire a community manager (Art Auntie Kathleen!) and a community editor (Kyle Ranson-Walsh!). I worked 24/7. I couldn’t have done it without them. By the end, I was exhausted and I got terribly sick. No more of that in 2025.

This year I’m approaching it with a framework of a main theme: Paying Attention—and being/doing “Good Enough.” Also, my crew has grown, I have more help, and we are doing more planning and front-loading. What does this mean for paying subscribers? Clear, fun, totally achievable goals that will help ensure that none of us get overwhelmed, that we all stick with it for the whole 30 days. “Ease” is the other theme for 2025. There’s enough stress going on in the world today. And there’s no such thing as an art emergency. We’re keeping this space easy and fun.

How do you maintain momentum after 30 Days of Drawing ends?

The Grown-Ups Table community keeps itself motivated! I continue to offer weekly lessons and assignments throughout the year that build on what we’ve learned and created in those 30 days. I’ve heard from hundreds of people that the drawing practice they started on day 1 of the 30 days continues to this day and that it changed their life. People got back in touch with a creativity they felt disconnected from, and they got to fully step back into that important part of themselves. It’s hard to put that genie back in the bottle.

Did your relationship with your subscribers change after you hosted 30 Days of Drawing?

By subscribers, you mean community, and by community, you mean friends, right? Yes! We got to know each other through our drawings, or efforts, our successes and failures. During the 30 days, we supported one member through a difficult diagnosis and another through the loss of a family member. The whole point of drawing, to me, is to connect with ourselves, the world, and the people around us. When people put in the effort, 30 Days of Drawing did all that and then some. It changed people’s lives, including mine.

What questions do you have for Wendy MacNaughton that we didn’t ask? Leave them in the comments!

To read more from this series on growing your publication, see our interviews with Noah Smith, Carissa Potter, Jørgen Veisdal, Anne Byrn, Nishant Jain, Michael Fritzell, Glenn Loury, Erik Hoel, Jessica DeFino, Mike Sowden, Elizabeth Held, Jonathan Nunn, Polina Pompliano, Michael Williams, Judd Legum, and Caroline Chambers.