I WENT to graduate school for two reasons: to study Heidegger, and because there was a wealthy university in Texas that inexplicably offered to fund such study. Who could resist four more years to keep reading big books and thinking deep thoughts, even if it meant trading picturesque San Francisco for hot and humid Houston? After only a couple months of pondering in the air-conditioned comfort of the university library, I realized that it wasn’t really Heidegger I was interested in — it was Heideggerians. What a strange lot, and why would anyone want to be counted amongst them, myself included?

Once you start looking for them, Heideggerians are everywhere. But identifying what they had in common with each other wasn’t easy. It was hard to tell who even counted as a Heideggerian, anyway, especially in the United States — a nation for which Heidegger himself had little positive to say throughout his life (among other things, we had too much technology and too little history, he thought). Catholics read him, but so too did Protestants and Jews. Existentialists claimed him as one of their own, despite his protests, but deconstructionists did the same, and by then he was no longer around to protest. Pragmatists sometimes made their peace with him, and occasionally poets and novelists played around with his wordplay-filled writings. I found that those last ones generally had the most fun, partly because they didn’t take it all so terribly seriously. Critical Theory, Hermeneutics, and Phenomenology — theoretical paradigms predicated on seriousness — each genuflected in Heidegger’s direction at one point or another, sometimes skeptically, sometimes not. There was hardly a corner of the American academy that hadn’t been infiltrated by some kind of at least latent Heideggerianism —except, of course, actual philosophy departments, where Heidegger often remained simply too foreign and too suspicious. One had better luck finding him in anthropology, literature, or theology.

As an undergraduate I was (un)lucky enough to have landed in two departments — one history, the other philosophy — where Heidegger was taught in a serious, and, occasionally, fun way. But even my professors couldn’t agree about how, or more importantly, why, to teach Heidegger. Was he a philosophical role model, a representative intellectual-historical figure, or did he represent something else entirely, perhaps even a kind of morality tale for the modern era — how else could one explain the fact that one of the greatest philosophical minds of the 20th century had also been a Nazi? Looking back on it now, I take it as a remarkable sign of my teachers’ commitment to free and open inquiry that they made the question of teaching Heidegger as important as the question of being, which according to Heidegger was the only question that really mattered.

Whether or not the question of being or Seinsfrage is the only properly philosophical question worth asking, the question of how, let alone whether, Heidegger’s works should be taught is now, in light of the recent publication of his private notebooks — the so-called Schwarze Hefte, or black notebooks — inescapable. Some 40 years after his death, Heidegger continues to scandalize; the fallout from the publication of the black notebooks has been felt in seminars and reviews both far and wide (see Gregory Fried’s “The King Is Dead” and Santiago Zabala’s essay “What to Make of Heidegger”). Providing a window onto Heidegger’s most private philosophical musings, the notebooks offer troubling evidence not just of his pervasive anti-Semitism, but also his abiding commitment to certain strands of National Socialist ideology. By the time of his death in 1976, Heidegger surely knew that the notebooks in which he scribbled his philosophical and political reflections were riddled with dubious, even incriminating remarks. So why, then, did he decide not just to include them in the edition of his collected works that would ensure his fame, but also, and more importantly, to dictate that they appear as the culminating volumes of the decades-long project? What could he have been thinking?

As the editor of the black notebooks, German philosopher Peter Trawny knows their contents perhaps more intimately than anybody else, and it is precisely that question that he tries to answer in his short little book, Freedom to Fail: Heidegger’s Anarchy. I’m not sure he answers it, exactly, but as a kind of Rorschach test, his essay certainly proves useful. How you respond to it will tell you what kind of Heideggerian you are, or if you are one at all anymore.

One of the strengths of Freedom to Fail is that its author is not an orthodox Heideggerian, but that may not be saying much these days. The black notebooks may have made the idea of a strict fidelity to Heidegger’s writings moot — they have become, as Trawny puts it, “an unavoidable point in question for anyone who would like to encounter Heidegger’s thinking.” Bemoan them, criticize them, lament them, but there is no avoiding them. The black notebooks exist. Although the remark is buried in a footnote, Trawny suggests that “unconditioned partisanship of Heidegger’s own thinking” is now out of the question. It is time to face the facts — well, sort of.

As if to signal the danger inherent in these culminating volumes of Heidegger’s collected works, the three epigraphs Trawny chooses to introduce his essay — from Hölderlin, Heidegger, and Paul Celan, respectively — dwell on things “monstrous,” “tragic,” and, in Celan’s case, a combination of the two. In a direct reference to the Holocaust, the third epigraph speaks of “the monstrousness of the gassings.” The original German title of Trawny’s book, Irrnisfuge, or “Errancy Fugue,” deliberately echoes Celan’s famous poem “Todesfuge,” or “Death Fugue,” from which the epigraph is drawn. That poem describes “death” as a “master from Germany.” In another celebrated poem titled “Todtnauberg,” a reference to the location of Heidegger’s celebrated Black Forest hut, Celan immortalized a famous postwar meeting with the philosopher, during which the poet’s hope for a word of contrition and/or explanation — a word literally “to the heart” — from his host never came. For a philosopher who made mortality, our “being-towards-death,” a cornerstone of all philosophizing, such silence surely spoke volumes to Celan, who lost both his parents in the Holocaust. “Todtnauberg” was published only after Celan’s suicide, in Paris, in 1970.

In deciding to render Irrnisfuge as Freedom to Fail, Trawny’s English-language translators have obscured this explicit reference to Celan, but otherwise their decision cannot be faulted (they explain their reasons in a brief and helpful introduction). The book really is about the freedom to fail, not just in a pragmatic, everyday sense, but in a kind of grand gesture of philosophical experimentation. Trawny’s essay can be read as a retelling of the story of Icarus, with Sein in place of the sun, and Heidegger taking over for the winged highflyer. But where some might see hubris at work, others see only a willingness to push the envelope, and it is clear from the very beginning that Trawny would rather have his philosophers be daredevils than hall monitors — Nietzsche rather than Kant, Kierkegaard instead of Descartes. In trading “drama” and “poetry” and “tragedy” for mere “argument,” contemporary philosophy has, Trawny thinks, totally lost its way. Or as he puts it: “The drama of thinking has vanished in the world of the argument.” Freedom to Fail is a lament — not for Heidegger’s mistakes, but for a philosophical epoch that, as he sees it, avoids mistakes at all costs.

According to Trawny, Heidegger’s commitment to thinking leads him into a realm beyond argumentation. It also led him into a realm beyond good and evil. Rhetorically, but also dramatically, Trawny asks if Nietzsche, who first surveyed this territory, was “Heidegger’s master” and then spends the next 80 pages answering his own question. Many of these pages make for captivating reading, but a shorter route could have been taken simply by quoting Heidegger’s late confession, as reported by his student Hans-Georg Gadamer, that “Nietzsche hat mich kaputt gemacht” — or, to translate it a little loosely, “Nietzsche broke me.”

On one level, Trawny’s essay is a meditation on the necessity of brokenness and failure for philosophical thinking. It takes as its lodestar Heidegger’s infamous — and undeniably self-serving — postwar declaration that, “He who thinks greatly must err greatly.” Without failure, success is meaningless. Without endings, no new beginnings. Without daring and danger, no true safety nor security. One could go on to list any number of productive oppositions: darkness and light, concealing and revealing, calculating and poetizing, erring and thinking. Heidegger’s understanding of truth as aletheia, or unconcealment, was predicated upon this chiaroscuro-like interplay of opposing forces — things were revealed one minute, only to slip into darkness and oblivion the next. Who was to say when something stood in the light of truth and not, in fact, in the shadow of error? “Is there an absolute criterion for the assessment of a philosophy?” Trawny asks, once again more rhetorically than not.

There probably isn’t any “absolute criterion for the assessment of a philosophy,” but we can probably agree that certain statements, whether “philosophical” or entirely prosaic, do or do not describe the world in ways that we find helpful, inspiring, or thought-provoking. Take, for instance, Heidegger’s remarks about “world Jewry” throughout the black notebooks. Trawny makes no bones about the fact that Heidegger certainly “harbored a private ressentiment against Jews,” which “cannot be understood otherwise than as anti-Semitic.” But he thinks that such sentiments cannot be used to “condemn his entire thought.” We can’t be done with Heidegger because philosophy “cannot be brought to a conclusion.” The only cure for philosophical errancy? More thinking, and more errancy, clearly.

Trawny repeatedly portrays Heidegger as the living embodiment of the philosophical life, as somebody who did everything for, and through, philosophy — even the bad stuff. But this runs the risk of taking everything Heidegger said at face value, of taking all too seriously the act that Heidegger was always performing, which was that of the academic outsider, the philosophical rebel who showed up to conferences and lectures still wearing his ski clothes. Many of Heidegger’s most famous students, from Hannah Arendt to Herbert Marcuse, were taken in by this image, but they also eventually came to see its limitations. Even the first Americans to hear about him or to see him teach, such as Sidney Hook and Marjorie Grene, knew that Heidegger was putting on a show. He may have railed against academic philosophy, but he still participated in it. Unlike Nietzsche, his “master,” Heidegger never abandoned his academic post and, when he got the chance, he even tried to reorganize the venerable University of Freiburg along Nazi party lines. What kind of academic outsider goes into university administration willingly, and then tries to militarize it? The one who errs greatly, of course.

Trawny makes a big deal of Heidegger’s preference for poetry and tragedy over technology and ethics. It was a preference that, supposedly, motivated his enthusiasm for overhauling university education: not necessarily more of the former and less of the latter; more like, some of the latter, but only in service of the former. What the university needed, what Germany needed, was a grand narrative to latch onto. The one Heidegger offered was one that, as Trawny admits, had a lot in common, though not everything, with Oswald Spengler’s The Decline of the West. It was a narrative of operatic proportions. “Heidegger wanted to narrate this history to the Germans,” Trawny suggests. “He wanted to determine a role for them to play in it.” He would connect the dots between the history of being — as it played out in everything from Ancient Greek tragedy to the poetry of Friedrich Hölderlin — and 1930s geopolitics. In Trawny’s formulation, “the narrative imperative runs: Be Oedipus! Be tragic! Yet it came about altogether differently.” That last line might be a bit of an understatement.

Heidegger’s tragic, overblown interpretation of Nazism may have been unique to him, but he was certainly not the only 20th-century philosopher to think that poetry and tragedy might preserve something integral to human experience that was in danger of being swallowed up by the forces of reason and demystification. Even somebody as different from Heidegger in temperament and orientation as the analytic philosopher Bernard Williams — a reader of Nietzsche who also went into university administration, but with far better and more humane results to show for it — thought that we could learn more about how to live from Sophocles than from Socrates and Aristotle.

But Williams never went so far as to proclaim that his own philosophical works were themselves the results of a tragic, world-historical narrative. And here is where Heidegger’s self-conception sets him, and those Heideggerians who follow too closely in his footsteps, apart. Whereas for Williams the lessons of Greek tragedy emphasized the contingency and frailty of even our best intentions (hence his famous idea of “moral luck”), for Heidegger they pointed towards the inescapability of fate and destiny. True philosophy wasn’t a matter of luck or chance at all: it was predestined, scripted even, by the historical unfolding of being itself. Heidegger was just the first and only thinker to recognize as much. He knew that history was tragedy and he thought he knew what roles he and the German people were supposed to play in it. He may have been miscast.

“The truth of being is onto-tragic,” Trawny writes at one point in Freedom to Fail. Following Heidegger, he thinks that the tragic history of being can be traced back “to the first of all inceptions, the inception of the history of being” itself. Heidegger thus came to see his life and his philosophy as part and parcel of the tragic narrative that resulted from this inception, an inception that pre-dated Socrates and stretched back to Heraclitus and maybe even all the way back to Daedalus, Icarus’s father, who gave him those wings in the first place. The history of being was, for Heidegger, the history of the forgetting, the oblivion of being. Tragedy was the only genre that suited it.

Once one begins to think in world-historical and onto-tragic proportions things often get dicey — never more so than when you start to think of yourself in such terms. Hegel had enough hubris to think that he stood at the end of history; Heidegger likewise considered himself the first true philosopher since Heraclitus, precisely because he alone had seen the tragic unfolding of the history of being leading up to him. Heidegger also thought he was alone in recognizing how, like Greek tragedy, the onto-tragedy of being contained within it the possibility of a new beginning. (In the black notebooks he also recognized that the names Heraclitus, Hegel, and Hölderlin each began with the letter “H.” So too did Heidegger and Hitler, of course. Was it fate?)

How tolerant you are of this kind of thinking will determine how persuasive you find Trawny’s defense of Heidegger’s errancy, which entails accepting at least three interrelated things: first, that Heidegger’s errancy was a necessary component of his thinking; second, that his thinking was destined by the history of being going back to Ancient Greece; and third, that this tragic narrative exists not just beyond good and evil, but also beyond guilt and responsibility, in an “abyss of freedom.” In other words, true thinking means never having to say you’re sorry (see critics’ responses to Gregory Fried’s “The King Is Dead”).

At times, Trawny’s meditation on Heidegger’s errancy reads almost like a kind of secularized theodicy. He dwells as much on the inescapability of evil as he does on the inevitability of failure. “For Heidegger,” Trawny writes, “evil belongs to thinking. Insofar as it elucidates being, it elucidates evil. For even evil belongs to the world-narrative.” But does this mean that, insofar as I recognize the role I play in the “onto-tragic” narrative of western history, I do not have to take responsibility for my actions? Is it all being’s fault?

Trawny is sharp enough to recognize that, in the light of day, all this can sound more than a little dubious. “Errancy can operate as an immunization of thinking,” he admits, and there is always the danger of such talk slipping into “farce” or even “buffoonery.” Richard Rorty once suggested that we should take Heidegger’s talk of fate and destiny with a grain of salt, especially when it came to Heidegger’s understanding of his place in the history of philosophy. “Heideggerese is only Heidegger’s gift to us,” Rorty remarked, “not Being’s gift to Heidegger.” But Trawny will not go so far as that.

There’s no room in Trawny’s narrative for Heideggerians who, like Rorty, might want to leaven all this errancy and tragedy with a bit of irony, or even some self-deprecating comedy. Only seriousness prevails. And that’s a shame, for it imposes a with-us-or-against-us mentality that limits engagement with Heidegger’s writings only to those who have demonstrated their full fidelity to the Heideggerian narrative. Readers of Heidegger are asked to “give it everything they’ve got” or “to give up. Isn’t this asking for precisely the kind of “unconditioned partisanship” that Trawny rightly calls into question in his footnotes?

In any case, what would it mean to give Heidegger everything we’ve got? Trawny ends his essay with a Heideggerian lament about how we now live a rational, technological world, one in which argument holds sway over poetry and tragedy. Our intellectual “sobriety,” he thinks, marks the “end of all ‘greatness.’” Maybe he’s right. Maybe academic philosophy today has conceded too much ground to demystifying argumentation, to judgment and quantification. Maybe we do need more poetry in our lives. Maybe films really do represent a last gasp for tragedy and grand-scale thinking in the modern world. (Trawny mentions Terrence Malick’s The Thin Red Line as a suitably Heideggerian work, though its debts to Heidegger, rather than, say, Emerson, are debatable.)

From a current West-coast vantage point, though, it seems clear that, when it comes to failure, there is no need to worry. Or, alternatively, that there is every reason to worry, just not any of those suggested by Trawny’s book. After all, “the freedom to fail” is very much alive and well these days, and that might just be the problem in and of itself, especially because it has taken root in a place that any real Heideggerian would be horrified by: Silicon Valley — the land of Uber rather than the Übermensch. It is in the world of tech start-ups and venture capital, algorithms and IPOs, where the productive and undeniable power of errancy is praised and rewarded most vociferously. Industry mottos such as “Fail fast, fail often” or, in a more Beckettian tone, “Fail better,” encapsulate our current narratives of intellectual daring and innovation. In the domain of digital technology, small failures are seen as a sign of small thinking; large failures, meanwhile, are held up as the hallmarks of revolutionary change. Has “technicity” — as Heidegger called it — co-opted even errancy itself? Or is this just the inevitable farce following the tragedy? Whatever it is, we should remember that, though he may not have failed fast, Heidegger sure failed hard. Maybe there is a lesson in that somewhere, whether you are a Heideggerian or not.

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Martin Woessner is Associate Professor of History & Society at The City College of New York’s Center for Worker Education. He is the author of Heidegger in America (Cambridge UP, 2011) and is currently writing a book about the philosophical films of Terrence Malick.