On Elegance, Failure, and the Con of Being Yourself

Chabon had chosen the place — a defunct print shop in the Temescal neighborhood of Oakland that someone had converted into a coffee bar without fully committing to the conversion. The old Heidelberg press still occupied the back third of the room, hulking and grandiose, its rollers caked with sixty-year-old ink. The espresso machine, by contrast, was immaculate. The juxtaposition was either ironic or accidental, and I suspected Chabon had picked the spot because it was both.

He was already seated when I arrived, at a table made from a compositor’s cabinet, the little brass-handled drawers still labeled with point sizes. He was drinking something with oat milk and reading a battered paperback of The Hot Rock with the kind of attention that suggested he was not reading it for the first time but was rather rereading it to confirm a suspicion.

Towles arrived precisely on time. Not early, not late — on time, which is itself a kind of statement. He wore a blazer that fit the way blazers fit in photographs from 1962, and he surveyed the room with an expression I would describe as interested tolerance. He sat down, ordered a double espresso, and waited for it to arrive before speaking.

“I have been thinking about heists,” Towles said, “and I believe the fundamental problem is that the genre requires forward momentum while the best stories require something closer to lateral movement. A heist narrative says: here is the plan, here are the obstacles, here is the execution. It is essentially a train on a track. The pleasure is in watching it go.”

“The pleasure is in watching it derail,” Chabon said, closing his paperback. “Westlake understood that. In The Hot Rock, Dortmunder’s crew steals the same emerald four times because every heist goes wrong in a different way, and each failure requires a completely new architecture of theft. The train doesn’t just derail — it derails, and they rebuild the train out of the wreckage, and it derails again, and the rebuilding becomes the story. The planning is the action.”

“That is amusing. But amusement alone is thin.”

“Amusement is never thin. Amusement is one of the hardest effects to achieve and sustain. You know this. A Gentleman in Moscow is, among many other things, very funny, and its humor does structural work — it makes the confinement bearable, both for the Count and for the reader. Without the wit, the hotel is a prison. With the wit, it becomes a civilization.”

Towles conceded this with a slight incline of his head, which I was beginning to understand was his equivalent of a standing ovation. “The Count’s humor is a strategy for survival. It is not incidental to his character — it is the mechanism by which he converts limitation into liberty. A confined man who can be witty about his confinement has not been fully confined. So. If our heist keeps failing, the humor must serve a similar function. It must be the characters’ way of surviving the failure.”

“Or refusing to acknowledge the failure,” I said, seeing an opening. “What if the comedy comes from their absolute unwillingness to admit that they are bad at this? Each failure gets reframed as a strategic pivot. They never say ‘we screwed up.’ They say ‘the situation has evolved.’”

Chabon laughed — a full, generous laugh that made the barista look up. “That’s corporate language. That’s the language of the mission statement. ‘The situation has evolved’ is what they say in board meetings when the product has failed and they need to pretend it was always going to be a different product.”

“Which connects to Melville,” I said, pressing the advantage. “To the Confidence-Man. Because what is a confidence game except the insistence that reality is other than what it appears? The con artist doesn’t just lie — he creates an alternative framework of interpretation in which the lie is the truth. If our characters are running a heist and the heist keeps failing and they keep insisting it is not failing, they are running a confidence game on themselves.”

Towles set his espresso down with a precision that suggested the cup had a designated location on the saucer and he intended to find it every time. “Now you are in interesting territory. The con directed inward. But I want to be careful about something. The Confidence-Man is a deeply strange book — deliberately, almost aggressively opaque. Melville wrote it as a series of encounters on a Mississippi riverboat in which no one can be trusted and identity itself dissolves into performance. It is not, despite what some critics claim, a satire of American optimism. It is something worse. It is a demonstration that trust is impossible and that we proceed anyway, and that this proceeding-anyway is the only faith available to us.”

“That’s bleaker than I expected from you,” Chabon said.

“I am not a sentimental writer. I am frequently mistaken for one because I write about beautiful rooms and well-tailored suits and the proper way to serve a cocktail. People confuse an appreciation for form with an absence of darkness. The Count is under house arrest for thirty years. Katey Kontent’s sister has tuberculosis. Emmett Watson’s father is dead and his brother is a con artist. My characters endure. Endurance is not sentimentality.”

“No,” Chabon agreed, though he looked like he wanted to qualify the agreement. “But your characters endure with style, which creates a certain… buoyancy. The reader trusts that things will turn out, if not well, then at least with a kind of grace. Whereas in Melville — particularly in The Confidence-Man — there is no buoyancy at all. There is only the river and the masks.”

“And which do you prefer?”

“Both. I want both in the same story. I want the buoyancy and the masks. The pleasure of watching clever people improvise their way through a collapsing plan, and underneath that pleasure, the growing suspicion that the cleverness is itself a mask, and that what it is masking is — ”

“Incompetence,” Towles said.

“No. Terror.”

The word sat between them for a moment. I watched Chabon turn his paperback over in his hands, running his thumb along the spine in a gesture that was either nervous or proprietary.

“Let me tell you what I mean,” he said. “In The Amazing Adventures of Kavalier & Clay, Joe Kavalier is an escape artist. He can get out of anything — chains, trunks, frozen rivers. But the one thing he cannot escape is his own grief. The escapes are not metaphors for freedom. They are performances of freedom conducted by a man who is not free. The audience applauds the escape. The escape artist knows that the trick is getting into the chains in the first place, and that the real confinement is the one that does not have locks. I want that for this story. I want the heist to be dazzling on the surface and terrified underneath.”

“You want the characters to know they are failing,” I said.

“I want at least one of them to know. The others can be genuinely deluded — genuinely convinced that this is going according to plan, that each setback is a detour rather than a collapse. But one of them sees it. One of them is performing confidence while fully aware that the whole enterprise is doomed, and they keep performing because the alternative is stopping, and stopping means confronting what they are actually doing with their lives.”

Towles was quiet for a moment, and in the quiet I could hear the espresso machine cycling and, faintly, the sound of traffic on Telegraph Avenue. When he spoke, his voice had shifted — not softer, exactly, but more considered, as though he were selecting each word from a finite supply.

“In the Metropol Hotel,” he said, “the Count builds a life from constraints. He cannot leave, so he deepens his engagement with what is available. The hotel becomes sufficient — more than sufficient. It becomes a world. What you are describing is the opposite. Your character is free to leave — free to abandon the heist, free to walk away — but they stay because the performance of competence is more bearable than the freedom of admitting they have none. The hotel is a prison that becomes a home. The heist is a home that becomes a prison.”

I wrote that down. I had been writing very little — the conversation had moved too fast and in too many directions for note-taking — but this I wrote down because it had the quality of an equation: the heist is a home that becomes a prison. It was not the whole story, but it was a load-bearing wall.

“So the failures,” I said. “Let me make sure I understand the architecture. We are talking about a heist that goes wrong multiple times — Westlake’s structure, the escalating comedy of reinvention. But each failure is also a revelation. Not just ‘the plan did not work’ but ‘the plan did not work and in the process we learned something about ourselves that we did not want to know.’ The comic surface and the psychological interior running on parallel tracks, occasionally intersecting.”

“Occasionally colliding,” Chabon corrected. “Intersection is too gentle. I want the comedy to crash into the psychology. I want a moment where something is simultaneously hilarious and devastating — where the reader laughs and then feels the laugh curdle. Westlake gets close to this sometimes. There is a scene in The Hot Rock where Dortmunder realizes the emerald is inside a police station, locked in an evidence locker, and his face as Westlake describes it is the face of a man confronting the absurdity of the universe. It is funny. But it is also the face of Sisyphus.”

“Sisyphus is a stretch,” Towles said.

“Sisyphus is never a stretch. Every human endeavor that fails and must be attempted again is Sisyphus. The question is whether the character is aware of the boulder.”

“The question,” Towles said, and I could hear him deciding whether to say what he was about to say, “is whether awareness of the boulder makes it lighter or heavier. In my experience — which is the experience of writing about people who endure — awareness helps. The Count knows he is trapped. The knowledge does not free him, but it gives him something to work with. He can be ironic about his situation because he sees it clearly. Irony requires distance, and distance requires clarity.”

“And in my experience,” Chabon said, “awareness makes the boulder heavier. Joe Kavalier knows exactly what he has lost. The knowledge does not help. It makes every escape more desperate and every audience more unbearable because they are applauding a trick when what is happening is a man drowning in public.”

“Then the question for our story,” I said, “is which kind of awareness our characters have. The kind that creates irony or the kind that creates desperation.”

“Different characters, different kinds,” Chabon said immediately. “That is where the ensemble earns its keep. You need the one who endures with style — that is your character,” he said to Towles. “The one who treats every catastrophe as an invitation to improvise, whose composure is genuine and whose grace under pressure is not a mask but a talent. And you need the one for whom every failure peels away another layer of performance until what is left is not competence but raw need. That is my character. Those two people in the same heist, reacting to the same failures in opposite ways — that is the engine.”

Towles was looking at the Heidelberg press in the corner. “There is a third kind,” he said. “The kind who does not know they are failing. Who genuinely believes, against all evidence, that this is going well. Who walks through the collapsing building pointing out the nice molding. That is the one Melville would write. The confidence man. Not a liar — a believer. Someone whose faith in the plan is so absolute that reality cannot penetrate it.”

“That is the most dangerous character in the story,” I said.

“Dangerous to whom?”

“To the others. Because faith is contagious. The one who genuinely believes — who radiates certainty while the building falls — that person keeps everyone else in the building. They cannot be reasoned with because their position is not reason. It is conviction. And conviction in the face of overwhelming counter-evidence is either madness or charisma, and sometimes there is no difference.”

“There is always a difference,” Towles said. “Madness does not know it is performing. Charisma does.”

“Does it?” Chabon leaned forward. “Does the con artist know? Does the confidence man on Melville’s riverboat know he is conning people, or has he conned himself first? That is the question the book refuses to answer, and the refusal is the point. If you can determine whether the confidence man believes his own pitch, the spell breaks. The uncertainty is the spell.”

We sat with that for a while. The barista was closing up, wiping down the portafilter with a cloth, and the late afternoon light through the windows had turned the Heidelberg press into something almost ecclesiastical — a relic, a monument to a technology of reproduction that the espresso machine had not so much replaced as outlived. I thought about the story, or rather I thought around it, circling the shape of it without trying to pin it to a surface.

“I want the failures to escalate,” I said finally. “Not just in practical difficulty but in what they cost. The first failure is comic — a door that won’t open, a timing mistake, something physical and solvable. The second failure is logistical — they have to rebuild the plan from scratch, and the rebuilding reveals that they disagree about what they were doing in the first place. The third failure is personal. Something about who they are, not what they know. And by the fourth attempt they are no longer the same people who started, and the thing they are stealing may not be the thing they set out to steal.”

“That fourth point is strong,” Towles said. “The object of the heist shifting beneath them. They walk in to steal a painting and walk out having stolen something they cannot name.”

“Or having been robbed,” Chabon said. “The heist reverses. They go in as thieves and come out as victims. Not of an external force — of the process itself. The repetition strips them. The comedy strips them. You cannot fail this many times and remain intact.”

“Can you not?” Towles asked, and there was something in his voice — not defiance, but a genuine question, posed from a position of intellectual conviction that resilience was real and not merely a narrative convenience. “I believe people can fail repeatedly and remain themselves. I believe, in fact, that repeated failure is one of the mechanisms by which the self is confirmed. You discover who you are by discovering what you do when the plan collapses. The Count lost everything — his estate, his freedom, his place in the social order — and what remained was the Count. Not diminished. Clarified.”

Chabon opened his mouth, closed it, opened it again. “I want to argue with that,” he said. “I want to argue with that very badly. But I am not sure I can. Not because you are right — I am not prepared to concede that — but because the argument itself is the story. The question of whether repeated failure clarifies or erodes. Whether these people, by the fourth attempt, are more themselves or less. Whether the con has stripped them down to something essential or stripped them down to nothing.”

“And you do not need to resolve it,” Towles said.

“Oh, I know. The unresolved question is always the better story. The resolved question is an essay.”

The barista had turned off the overhead lights. We were sitting in the remnant daylight and the amber glow of a single pendant lamp that hung, for reasons no one in the room could have explained, directly above the Heidelberg press. Chabon was still holding his paperback of The Hot Rock. Towles had his hands flat on the compositor’s table, his fingers resting in the grooves where the type drawers slid in and out, a gesture that was either absent or deliberate, and I suspect with Towles there is no meaningful distinction between the two.

“One more thing,” I said. “The title. ‘Amateur Hour.’ It suggests incompetence, but it also suggests a beginning — the hour when amateurs are allowed on stage, before the professionals take over. What if the story is about that threshold? The hour before competence, when everything is possible because nothing has been proven.”

“The hour when you can still be anyone,” Chabon said, “because you have not yet demonstrated what you are.”

“And when the hour is over?” Towles asked.

Nobody answered. The barista jangled her keys.