DrawTogether with WendyMac

DrawTogether with WendyMac

DT Grown-Ups Table

Look Up! An Interview with Caroline Paul

The Art of Sky Gazing

Wendy MacNaughton's avatar
Wendy MacNaughton
Mar 08, 2026
∙ Paid

Hellooooo, DrawTogether GUT community.

We’re so glad you’re here. The series of symbols you all drew were powerful! We saw folks grappling with global and personal events, commenting on corporate brands, and advocating for peace. You all were so inspiring in your messages and so creative in how you adapted familiar icons to your own purposes. Bravo!

This week we’re spending some time up in the clouds, with author Caroline Paul. You may know her better as Art Assistant Caroline if you were here for DrawTogether’s early years. She is also Wendy’s lovely ex, whose last visit with the GUT was to talk about her book, Tough Broad.

Caroline has a brand new book, Why Fly, that just came out a couple weeks ago! From Wendy: “Why Fly is a book about two kinds of flight: the kind we do in the sky and the kind we do in our hearts. And all the lifts and lights and dips and drops both entail.”

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We’re excited to have her here with us today for a Q&A!

Q&A with Caroline Paul, author of Why Fly

The GUT: This book is about flight, and also about relationships. Tell us about the connection between the two and why you wrote it at this time in your life.

Caroline: I have been flying since I was twenty. I loved flying. But I wasn’t obsessed until, at 58, I began to fly a gyrocopter. It looks like a tiny helicopter, or maybe like a lawn mower dangling under a rotor blade. My newfound ardor was no surprise: I began my ascent in gyros during the descent of my marriage with Wendy.

We reach for control in difficult times, and what better thing to control than a funny-looking aircraft that soars me high above my troubles. As I say in the book, “It’s easier to learn a landing than a human heart.”

I didn’t want to write about my personal life, but I did want to write about flight, and the two had become inextricable. That said, writers are in control of the story. There is a world in which I could have excluded my relationship with Wendy from the book. But that book would have been inauthentic, and readers would have felt the gap. Inauthenticity, as GUT readers know, is a death knell to good work.

The GUT: What do you get from being in the sky that you don’t get down here?

Caroline: Flying small, lightweight, open-cockpit aircraft is an all-body kinetic experience. Mentally, you are totally absorbed in all the requirements of flight—staying straight and level, looking for other planes in the sky, watching the terrain. Physically, you feel the wind, you feel the temperature changes, you feel the turbulence. Emotionally, you can’t help but be awed at the view below your feet, which changes constantly as you gain or lose altitude. From the pilot seat it looks as if some cosmic sculptor has been languidly chipping and chiseling; it really is an artistic experience.

an aerial view of very long, narrow, undulating fields in rural Poland
George Steinmetz, Waldhufendorf, Suloszowa, Poland, 2022. Image via Colossal

This total absorption while in open cockpit flight is hard to match on the ground, except maybe when it comes to love. In the book I compare the two: Both are governed by tangibles—the laws of physics, and oxytocin, respectively—but both feel like magic when you’re in it.

Feeling inspired? Join us!

Caroline Paul “Wingwalking” AKA standing on the wing of a biplane as it does barrel rolls through the sky. GUTsters, DO NOT TRY THIS WITHOUT ADULT SUPERVISION/WHILE DRAWING

The GUT: How might our GUTsters capture some of what you get from flying (even if they can’t do it themselves)?

Caroline: The sky is mesmerizing from all angles. Even from the ground, it is like seeing a new painting every few minutes. There, a bird circling, now gone. Here, shifting cloud shapes. Over the course of the day the sky shades into the most amazing hues—it’s the richest color palette around. My favorite time is the half hour after sunset (also known by pilots as “civil twilight”) when the orange and yellows fade and only the deepest purples remain. Even at night, the constellations—those connections between stars that paint a picture and a story—represent the vivid imaginations of our ancestors. As an artist of any kind, you can’t help but be inspired by the sky.

This painting is divided into two broad sections. The lower two thirds of the painting are completely white. The top third of the painting is a gradient from blue to light green, with the blue at the top and the green meeting the white section.
Georgia O’Keeffe, Sky with Flat White Cloud, 1962. Image via National Gallery of Art

My advice is to take the window seat next time you fly commercially. Let yourself be awed by the beauty and the strangeness of being so high in the air; as I say in my Tough Broad interview with the GUT, awe is vital for our creativity. Now look at the geometries below—it’s like an abstract painting. Let that view spark what you create next. This is what Georgia O’Keefe, that master of the landscape, did when she began to fly in passenger planes in the 1970s. She was gobsmacked by the birds-eye view. She soon began her famous cloud paintings. Her first in the series featured an island from above, but quickly she abandoned the landscape altogether and just painted clouds and sky, so taken was she by this new vantage point.

Georgia O’Keeffe’s largest painting ever, Sky above Clouds IV, 1965. Image via Art Institute of Chicago

Thanks, Caroline! We have a giveaway of her book for GUT members in the assignment below, and we’re taking inspiration from Caroline’s time in the sky.

Let’s do this.

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