Ali Smith has twice already been shortlisted for The Man Booker Prize (for The Accidental and Hotel World), losing each time. But with her wondrous new Mobius strip of a novel, How to be both (2014), the third nomination may well be the charm.

Fans of Smith’s writing will know what to expect here: the usual soul-stirring alchemy of structural mash-ups and wordplay. Smith has always filled her fiction with puns, non sequiturs, riddles, and all other manner of textual derring-do, but in this, her most formally audacious novel to date, Smith has married her literary gamesmanship to a pair of stories about art, loss, and love — among many other lofty subjects — to create something truly extraordinary.

The first thing to mention is the book itself: How to be both is split into two parts: one involving a 15th-century artist, the other set in present-day Cambridge, and which section comes first in your copy is strictly a matter of chance (the electronic versions offer both iterations so you can make the choice yourself). As Smith will fully explore, that arbitrary decision will unalterably affect how you view the work as a whole.

(A clerical note: my copy begins with the contemporary story, so just for convenience’s sake, I will refer to it here as “the first part,” and the 15th-century story as “the second,” though, of course, you may encounter them in reverse order.)

The first part focuses on George (short for Georgia), a precocious, erudite teenager still deeply mourning the sudden death of her mother the previous year. She has taken to watching the same pornographic video on her iPad of a young girl being drugged so that she can bear “witness [. . .] of all the unfair and wrong things that happen to people all the time,” and arranges a series of photographs of her mother on the wall to mask a leaky roof.

When the section begins, her mother, a marketer of “subversive” art, who is also convinced that she is being spied upon by a friend, poses a moral conundrum to George about an ancient artist who worked on a royal project with other artists but believed he was worth more.

She takes George and her brother to Italy to view the artwork at the Palazzo Schifanoia, specifically that of the artist Francesco del Cossa, who specialized in the fresco tradition. She tells them that after the Great Flood of 1966, the plaster on the wall in the palazzo began peeling, revealing images hidden underneath that had been unseen for nearly 500 years.

Which came first? her mother says. The chicken or the egg? The picture underneath or the picture on the surface?

The picture below came first, George says. Because it was done first.

But the first thing we see, her mother said, and most times the only thing we see, is the one on the surface. So does that mean it comes first after all? And does that mean the other picture, if we don’t know about it, may as well not exist?

As the title implies, How to be both is interested in exploring the dualities of life around us: how something can appear one way to someone and another way to someone else, both true at the same time. In fact, each part of this book is labeled One, as if the two stories were just flip sides of the same coin.

I was so invested in George’s story that when it ended, seemingly sans-resolution, I had a hard time getting into the next section, which begins with an extended sequence in the disembodied voice of a figure being forced out of the ground, told in poetic sentence fragments zig-zagging across the page. When the figure’s voice fully materializes, it is in a museum observing a young girl (whom it mistakes for a boy) staring at another picture.

The figure turns out to be Francesco del Cossa, the same artist George’s mother took her children to see in Italy. Once I settled into del Cossa’s account, which explores the circumstances of how the artist’s legendary fresco came to be, I began to make connections and understand why Smith would so abruptly leave George.

Toward the end of the first part, George and her friend Helen are tasked with a creating an empathy/sympathy presentation and decide focus on del Cossa. It turns out the Renaissance-era artist shares several links with the grief-wracked teen: both George and Francesco’s mothers have died prematurely. Both are girls mistaken at times for boys (in Smith’s reimagining, Francesco del Cossa was born a girl but had to pass as a boy to survive as an artist). Francesco appears to be the subject of the conundrum laid out at the beginning of the first section, that of the artist who is convinced she is being underpaid for her work.

Francesco also happens in her narration to drop in oddly contemporary lingo (“just saying”): does this mean the entire second part is a projection of George’s imagination? By burrowing inside the mind of her mother’s favorite artist, might George be trying to keep her mother close at heart?

But how would a reader who received Francesco’s story first know any of this? When del Cossa observes the “votive tablet” the boy is thumbing through, I know it’s George’s iPad as she stakes out her mother’s friend only because I read it first.

Francesco’s story, therefore, is and is not George’s story. Both at once.

I hope I haven’t presented this book as one elaborate gimmick; Smith’s novel is much too smart for that. Behind all the stylistic razzle-dazzle is a big thumping heart finding new ways to direct the novel. Besides, I’ve barely scratched the surface at all the connections to be made between the two stories, but you’ll want to discover them for yourself.

As for the Booker prize, I’ve now read half the shortlisted titles (I’m rather bearish on the two American entries), and though I usually don’t get caught up in literary prizes-as-validation, I find myself rooting hard for Ali Smith. I’m sure the other three novels are crown-worthy (Richard Flanagan’s in particular looks like a must-read), but How to be both deserves to be read and teased over by literature lovers everywhere, and I’m hoping this is the occasion that gives her the audience she so richly deserves.

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