Blake Bailey has forged a renowned career by making sense of messy lives. He is the author of the NBCC Award finalist A Tragic Honesty: The Life and Work of Richard Yates, NBCC Award winner and Pulitzer Prize finalist Cheever: A Life, and 2013’s Farther & Wilder: The Lost Weekends and Literary Dreams of Charles Jackson.

Literary biographers are an inquisitive, meticulous, unflinching bunch. What we know about their own histories, however, is typically relegated to the indirect information gleaned from the choices they make in selecting and portraying their subjects.

That’s what makes Bailey’s latest, a memoir entitled The Splendid Things We Planned, a most intriguing undertaking. It is the portrait of not only the biographer as a young man, but of the whole Bailey family. Burke Bailey, an NYU law scholar from Vinita, Oklahoma, met Marlies, a fresh-faced German immigrant, in Manhattan. “She and my father met on a blind date. Both were escaping from a home life they found oppressive, unworthy of the personages they hoped to become. Then my mother got pregnant,” Bailey writes. Son Scott is a squalling infant who grows into a ruffian on the way to drug addiction, prison and suicide.

Then there’s young Blake, fate TBD—though not according to Scott: “ ‘I know you,’ he went on. ‘I know what you’re like. You’re gonna be just like me. You’re gonna be worse.’ ” Bailey writes.

While Bailey has handled difficult subjects before, it’s much different when the story’s yours, he says. “Memoir is a totally different exercise. When I write biography, I am a true empiricist. I have no preconceived notions about the subjects I’m writing about,” he says. “I’m working on Philip Roth now, and I’ve accumulated thousands of pages of research about Philip, and it has not affected my judgment of him one way or the other. I don’t allow it to. It’s very easy to be objective about biographical subjects. You come to them because you enjoy their work, and you’re curious about what sort of human being wrote that work.

“It’s virtually impossible to be objective and accurate about people who’ve had such a profound impact on your life. It’s very difficult to craft a narrative—or it was for me,” he says.

While Scott is the destabilizing force in the family, he is the narrative glue. The stress of his compounding crises contributes to the divorce of his parents, who develop the coping mechanisms of enablement and estrangement, respectively. “ ‘When a child is young,’ Burck explained one night (perhaps he was relating to Hauber’s analogy), ‘you can catch him if he falls. Then he gets a little older and falls from a higher place. Maybe you can still catch him. But finally he’s a full-grown adult and falls off the top of a building—then you have to decide: either get out of the way or be crushed,’ ” Bailey writes.

Not coincidentally, a penchant for heights was among Scott’s threatening behaviors. “My brother used to hang from the horizontal flagpole atop this 13-story building in suburban Oklahoma City. Whether he was doing that for kicks because he was stoned out of his gourd, or because he was seriously suicidal are all possibilities. Eventually he went back to the building with the object of throwing himself off, but they had learned by then to lock the door,” says Bailey.

Deadpan delivery and some dark zingers add touches of mirth. “I don’t want readers to think this is all bleak. It’s a funny book, I’ve been told,” he says.  “Ultimately, what lent me perspective on this very dark material was the ability to see the humor in it.”

In addition to humor, an education buoyed Bailey through adolescent apathy, truancy and beer binges. At Tulane he uncovers the twin gifts for writing and researching that will beget professional success. Scott tries work, relationships, born-again Christianity and a stint in the military without commensurate avail. His end is tragic, and The Splendid Things We Planned grew from a painful reckoning. “When you’re casting about for something to work on, you want to find something that’s meaningful to you. I knew that my brother would not be around much longer, given the way his life was going, and I knew I would not see him again. I was grieving about that, I had thoughts about that that I wanted to work out,” he says.

Megan Labrise is a freelance writer and columnist based in New York. Follow her on Twitter.