Drawing Quiet: Susan Cain on Waking Up

Drawing her face felt less like a commission and more like writing a thank-you note with a dip pen.

If you’ve been reading this newsletter for a while, you’ll know I’ve been the portrait illustrator for Waking Up, Sam Harris’s meditation app, for years now.

Every guest who sits down for one of the app’s Conversations gets a hand-drawn portrait: real ink, real paper, real swearing when the nib catches. I wrote about the whole collaboration here, back when I called it the most fulfilling project of my career. I stand by that. It remains the only job I’ve ever had where the brief is essentially “please stare at interesting people’s faces for hours,” which is what I was doing on the subway for free anyway.

But this week’s portrait was different, because this week’s portrait was Susan Cain.

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Some books arrive at exactly the right moment in your life. Quiet: The Power of Introverts in a World That Can’t Stop Talking arrived at mine as a court summons. Here I was, a stand-up comedian who spends his evenings shouting into microphones in basements, reading a book that gently explained I was, in fact, an introvert: a person who finds other people enjoyable in roughly the way one with Irish skin finds the sun delightful. Wonderful. Essential. Best enjoyed in limited doses before retreating somewhere dark to recover.

It rearranged the furniture in my head. I stopped apologising for leaving parties early. I stopped treating the need for silence as a personality flaw to be managed and started treating it as the place the work actually comes from. Every cartoon I’ve ever sold was drawn alone, in a quiet room, by a man avoiding a social engagement.

So drawing her face felt less like a commission and more like writing a thank-you note with a dip pen.

She’s a great writer. Precise, completely unsentimental about sentiment, which is the hardest trick in the book. And her conversation with Sam on the Waking Up app is well worth your ears. If you’ve ever suspected the world was designed by and for people who think out loud, she’ll confirm it, then explain what the rest of us are for.

She has a new #1 New York Times bestseller called “Bittersweet: How Sorrow And Longing Make Us Whole”, which is another brain-changer. You can find her talk in the Conversations section of the Waking Up app. Tell her portrait I said hello.

‘til next time!
Your pal,

PS. Look, if this actually did something for your brain (or at least distracted you from the creeping dread of your own inbox for six minutes), please consider restacking this and sharing it with your people. It’s the only way the word spreads.