Jessica Helfand|The Icarus Diaries
April 6, 2026
12: Scout
Read the introduction to this series.

Oil on canvas
24 x 24 inches
2025
Sometimes when I slow down, strange things start to happen. Random associations. Curious deviations. I start to make mistakes, and (I think) the paintings become more interesting.
Honor thy error as a hidden intention. (Brian Eno in Oblique Strategies.)
I consider gravity—as in the graveness of the situation, and the internalized struggle against time and space—reflected in a face. His face. Or hers. (Or theirs.)
In my experiments with AI, I find no apparent fidelity to gender, to biologic fusion, to the merging of male and female. You can’t fertilize an image, but you can blend two images, which is to say, two faces. (Or more than two.).
That’s when the alchemy goes rogue. When I combine sketches (which I often do) I sometimes find a face that does not betray its pronouns.
And so it is with this painting, a softer and Icarus, regretful, preoccupied, lost. I am thinking of Icarus as
a translucent visitor / yearning for the estuary (Eavan Boyland, Cityscape)
Here is Icarus yearning, leaning actually, into his fate. An ascendant martyr, draped in feathers—but what kinds of feathers? Bird feathers? Angel wings? Insect wings?
A wing becomes a plume. A bird feather becomes an eagle feather.
Now I am thinking about the Boy Scouts, about feathers used in ceremonial regalia. The feather as a nod to nature, to a spiritual journey, to achievement.
Ornament (external) becomes engine (internal).
What was Icarus scouting, I wonder? That word itself, scout—in the late fourteenth century, a synonym for a wretch, a rascal, a rogue—male or female.
Sometimes painting unleashes more questions than answers.
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Observed
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Observed
By Jessica Helfand
Jessica Helfand is an artist and writer based in New England. A former critic at Yale School of Art and one of the founding editors of Design Observer, she is the author of several books on visual culture including Self Reliance, Design: The Invention of Desire, and Face: A Visual Odyssey.