Chatfield X Waking Up: The Most Fulfilling Collaboration Project of my Career.
On Sam Harris, meditation, & its profound effects on the creative process.
Today, I’m really excited to finally share something with you that I’ve been working on for over a year.
Over these past 12 months, I’ve been scribbling away in my studio on an official collaboration with the team at Waking Up, which culminates in a series of shirt designs, wallpapers, and a personally curated playlist for app users to listen to. I’m really proud of how they’ve turned out, and you can jump in to take a look now at: wakingup.com/jasonchatfield
The best habit I ever started (and didn’t abandon after two weeks) is meditation.
After 12 years, it’s become hands-down the highest yield return on my time for creative work, stress management, and general mental health amid the chaos of life in New York City. With this ridiculous, bag-of-cats brain of mine, I’d be completely hopeless without it. The handful of minutes I spend meditating each day probably saves me hours of distracted thoughts and procrastination, which in this new attention economy is basically like printing money. Time is literally the only thing in Manhattan more valuable than square footage.
The Art of Paying Attention
Meditation might not immediately register as a creative skill, but I've discovered over the years that it works hand in glove with my artistic process. Not to get too woo-woo about it, but it honestly opened doors in my mind that I never even knew existed—like finding a secret room in an apartment you've lived in for a decade. I've woven the profound lessons from the app into my artistic practice, which mainly means I've stopped drawing while simultaneously texting, eating dinner, and watching three YouTube videos at once. (You’ve probably noticed it if you subscribe to Process Junkie.)
Conversation Portraits
As some of you may know, I’ve been fortunate enough to be the official portrait illustrator for Waking Up and have drawn over 100 portraits of the world's top meditation teachers, yogis, psychologists, and other experts in their field who feature on the app. I always listen to their voices while I’m drawing to make sure I’m letting that seep into the art.
Each is made by hand using a hybrid process of dip-pen ink line and wash supplemented with digital finishes, specifically
’s Photoshop brushes, which brilliantly mimic real-world tools. I approach each one individually, based on the personality and specialty of the person.
What even is Waking Up?
Waking Up isn't just a meditation app but a vast reservoir of wisdom. A brain's trust of knowledge from philosophers, therapists, Buddhist monks, yogis, and meditation teachers from across the globe.
In the stinking hot summer of 2014, I started reading “Waking Up” by
while waiting for the F train. About halfway through his story about his first experience on MDMA, I looked up to see the train doors closing; I didn’t even notice it had arrived. I was so compelled, I finished the book in a day. I don’t remember the last time that happened.
Do your own thing. Don’t be weird about it.
The overarching element that resonated with me most about the book (having initially practiced Transcendental Meditation, which is, sadly, laden with weird, culty elements) is that he sets the stage for a secular approach to spirituality, one that seeks to understand the nature of consciousness without resorting to religious dogma. Without being preachy or condescending, he asks you to consider that spiritual insight comes from examining the mind through practices like meditation, informed by scientific inquiry. It was the scientific inquiry that really appealed to me, and who better to delve into it than a bona fide neuroscientist?
For me, meditation was a really difficult thing ot learn. It’s not the ‘trying’ to make something happen— It’s the ‘not’ trying that’s my problem. For years, I’d been living in a constant state of ‘striving’ to get somewhere. Some far-off place where I’m zen / happy / content / organized, not realizing how futile that striving really was. It reframed a lot of my life.
An App Emerges…
As the years passed and the book gained popularity, he and his team developed it into an app of the same name. I immediately signed up for the first version, which was pretty boilerplate, but I was excited. Calm, Headspace, 10% Happier, Insight Timer, and a slew of other meditation apps had flooded the app store, but this one had something very different.
My favourite thing about the app is that there's nothing prescriptive about it; there's no one-size-fits-all approach, and there is no rigid doctrine to follow. You're encouraged to chart your own course through the mind. It's like being handed a subway map of your brain, where all the lines are running, and you get to decide where to exit. Trusted voices let me delve into anything from CBT to non-dual mindfulness, time and attention management, or Stoicism.
Unlike other meditation apps that feel like they're designed by wellness influencers who subsist on kale smoothies. It's refreshingly bullshit-free, which, as a New Yorker, I deeply appreciate. My tolerance for nonsense maxed out four meditation apps ago. Go figure.
Karaoke for the Mind: My Personally Curated Playlist.
Consider this playlist a small selection of my favourite Waking Up hits-- If I were in a Karaoke bar, these would be my go-to songs that I know by heart, and could belt out at a moment's notice without even glancing at the lyrics. I hope they sink into your mind the way they did mine. (Click on the phone to listen)
Easily the most creatively fulfilling project I’ve ever worked on.
I got free rein to experiment and dive into my own personal interpretation of what the app means to me and my process. It was like being a kid with unlimited art supplies and no adult supervision. I used everything from pencils to inks, washes, paints, and digital tools to work through the mess of ideas that fell out of my head.
My studio looked like a crime scene where the victim was a Michaels craft store. After weeks of manic creation followed by ruthless editing, the Creative Director and I managed to whittle down the chaos to the few designs you see on the official page. The cutting room floor of my studio is still littered with the corpses of rejected concepts that weren't quite weird or wonderful enough to make the final cut.
If you've never tried meditation before, I'd genuinely love to hear about your first experience with it. And if you're a seasoned meditator, drop me a note about your practice—what's worked, what hasn't, and how it's affected your creative process. I'm particularly curious about any unexpected ways it's crept into your art or writing.
In the meantime, I'll be here in my studio, trying not to overthink things while simultaneously overthinking the act of not overthinking. It's a special talent of mine. At least now I have some cool shirts and wallpapers to show for all that mental gymnastics.
‘til next time,
Your old pal,
PS - If you download the wallpapers, snap a screenshot of your home screen and tag me—I'd love to see them out in the wild. It's almost like being famous, but without the paparazzi following me to the bodega when I'm buying emergency 2am Ben & Jerry's in my pajamas.
RELATED READING:
A Decade of Zen: 10 Unexpected Lessons from Daily Meditation
November 9th marked a full decade of me sitting quietly in a chair. Hold your applause.
I very much enjoy seeing everyone of your new illustrations that pops up in the Waking Up app. But this is huge!
I followed your lead and started meditating after a crisis post surgery. It got me out of a real hole. And then, last year I used the app to help my dad.
He’s a technophobe, but I used an old iPhone and cleared everything off the home screen apart from the Waking Up app. I loaded up the introductory course and after a couple of days of doing it with him, I left him to it whilst I went off to Cornwall.
I came back a fortnight later and he had whizzed through the entire course. It was the thing that got him out of his head and back into the garden. Both are now transformed. He is happy and the garden is no longer the jungle it was.
Thank you again.
Congrats! I’m Day 3 of the Meditation App. Journaling as I go, and feeling positive.