Draw Me Anything Recap Post

Look, I know you've been waiting to catch up on these...

What I've Learned from 13 Conversations About Making Things

Welp! It's been two months since I started Draw Me Anything, and somehow I've managed to trick 13 genuinely brilliant people into sitting down with me to talk about the strange business of making things for a living. I realise not everyone can tune in during the live streams, so I always post the recaps a day or so later for you, and I also realise there are only so many hours in a day, so you can’t watch them all.

So! I’m putting together a bit of a recap below of all the episodes so far, so you can catch up if you’ve been meaning to. I put a lot of work into these, and I hope you like what I’ve been doing with them. I’ll still be sending you my regular written posts and drawings, but these are an extra little thing I’m adding to the selection of things you can get as a subscriber. (If you don’t like watching videos and prefer to read, I've written up the key takeaways for each conversation under each video.)

Someone was asking me when I got the idea for the “Draw Me Anything” live stream segment, and I had to scratch my head and confess I didn’t know. So I went back through my notes to find when I had drunkenly tapped the idea down in the Notes app on my phone…

…It was 11 years ago! If ever there were a record for “Time between having an idea and executing it.” I’d be the World Champ. Thanks, ADHD! You’re the gift that keeps on giving.

What began as a simple idea—"let's draw stuff on camera and see what happens"—has turned into something unexpectedly profound: a masterclass in creative survival, delivered by people who've figured out how to turn their particular brand of madness into actual careers.

Looking back through these conversations, I'm struck by how each guest has cracked the code in a unique way. There's Liana Finck, who can distil entire emotional universes into a few spare lines. Austin Kleon, arguing that 99% of people shouldn't quit their day jobs, but 100% should keep creating. Ann Telnaes, wielding her pen like a scalpel against political absurdity. And Matt Ruby, somehow turning meditation and mushrooms into comedy gold while railing against the algorithm overlords.

Each session has been its own mini-education in the art of not giving up. From Beth Spencer accidentally starting a global art movement from her introvert drawing club, or Chaz Hutton conquering the internet with what he modestly admits might just be "laziness," there's a common thread: these people have all found ways to stay curious, stay honest, and keep making things even when the world seems determined to crush that impulse.

And next Tuesday, Amy Kurzweil joins the conversation—along with a very special reveal from our favourite pencil company that I genuinely can't wait to share with you.

DMA#20: Amy Kurzweil: Tues 7/15 @ 5pm

Really excited about this one — we’re revealing a VERY special product from our favourite pencil company. Add it to your calendars now!

But first, let me take you through what we've learned so far...

Fellow New Yorker cartoonist Liana Finck shares insights on drawing inspiration from unexpected sources, including canine wisdom and children's creativity, while also touching on cultural references close to my heart… like fairy bread.

NYT Best-selling Author Austin Kleon shares his philosophy on creative survival, notably arguing that while 99% of people shouldn't try to make their creative work their primary job, nearly 100% of people should maintain some form of creative practice, offering guidance on balancing artistic pursuits with practical life considerations. He also happens to have the best ‘slide-into frame’ moment of any guest yet.

2025 Pulitzer Prize-winning political cartoonist Ann Telnaes joins the discussion to analyse current political tensions, particularly focusing on the Musk versus Trump dynamic and broader issues of freedom of expression, emphasising why it's crucial to stay engaged with current events rather than disconnecting from news cycles.

Extra Special Guest Mason Currey explored the creative process through the lens of creative rituals and priming techniques, discussing how procrastination can actually be a valuable part of the artistic process, with references to literary figures and their unconventional creative practices.

“Sneaky” Artist Nishant Jain recounts his journey from watching terrible stand-up comedy to finding his artistic voice, discussing how personal experiences and even heartbeats can influence drawing, along with advice on developing individual style and using drawing as a tool to overcome creative blocks.

I do a 30-minute creative competition against ChatGPT, exploring the capabilities and limitations of AI in artistic creation while examining what this means for human artists and the future of creative work. (Spoiler Alert: I win. Every time.)

This episode features artist Adam Ming in a comprehensive discussion about artistic subjects, such as dinosaurs knitting scarves, while also addressing the serious topic of time management and creative boundaries for working artists.

This episode features repeat-guest Jessie Kanelos Weiner in a wide-ranging conversation that spans from the challenges of stand-up comedy performance to unexpected topics like pigeons playing pickleball, offering insights into the creative process and her artistic journey in Paris across different mediums.

New York comedian Matt Ruby explores the intersection of comedy and mindfulness while discussing how algorithmic content distribution is negatively impacting creative expression, comparing comedic tension to the relationship between waves and surfers.

Beth Spencer discusses her transformation from leading an introvert drawing club to creating a global art movement, with the episode covering topics ranging from goats to creating art with human hands, and includes a special live cartoonist gift reveal during the recording. Also, she has the best accent of any guest yet.

Chaz Hutton discussed his unique artistic approach and creative process, with topics ranging from unexpected artistic materials to his distinctive illustration style and creative philosophy. We spoke from his office in London, by way of Berlin— He happens to also be an Aussie!

In my first episode of Draw Me Anything where I invited a guest, I teamed up with NY Times bestselling children’s book author-illustrator Claire Powell to draw dogs and talk shop about traditional tools, switching from digital media, and capturing canine personality. We shared sketches, studio habits, and a few laughs—plus a surprise snooker-themed doodle. I’m going to have Claire on again later this year.

Artist and author Samantha Dion Baker joined me for a therapeutic drawing session that evolved from casual pickleball chat into a masterclass on using art for presence and human connection. In this DMA, Sam shares her journey from graphic designer to adventure sketcher, discussing how her practice developed during constant interruptions, and how carrying a sketchbook transforms ordinary moments into meaningful observations.

If that doesn’t fill up your weekend while you’re doing your chores and running errands, I don’t know what will.

Thank you for reading, as always, and please feel free to leave comments. I love hearing from you.

‘til next time
Your pal,