Reviewing tennis star Tracy Austin’s memoir, David Foster Wallace memorably wrote that the elite athlete must “be blind and dumb about it,” must fundamentally lack the propensity for introversion.

Before Mississauga-born illustrator and writer Leanne Shapton was the art editor at the New York Review of Books, her life was measured in 5:30 a.m. practices, damp swimsuits, analog pace clocks, ...