Whenever I need to drive somewhere, I use Waze. The app saves me a lot of trouble, because it aggregates information to which I have no access and even plans how to distribute the traffic rationally to avoid clogging the roads. It has a lot of pop-up ads, but I try to ignore them because they seem a minor annoyance.

Waze does, however, have some debatable features. First, it doesn’t tell me where to go, which is, supposedly, entirely up to me. If my desires are misbegotten, it facilitates their fulfillment as readily as if they weren’t. Waze is Jeremy Bentham for the digital-consumer age: The Potbelly Sandwich Shop is as good as the poetry bookstore. Second, Waze does not create infrastructure; by planning its users’ routes on roads that already exist, it thereby augments the illusion that what we have is satisfactory for our needs and that we require the state less than we might think we do. Most troubling, Waze entrenches our reliance on automobiles even further and postpones a collective reckoning with its consequences for the climate, including who ought to bear them in our unequal society.

But whatever its drawbacks, Waze marks a triumph for “navigability,” the ungainly term that Cass Sunstein uses in his new book, On Freedom, to describe how easy or difficult it is to get from here to there and, in the metaphorical sense, to achieve a goal once you’ve set one for yourself. For Sunstein, government ought to be more like Waze, helping people fulfill their desires and dreams, especially when they themselves are blocking that fulfillment. But any inquiry into navigability is inseparable from a much bigger theory of where our desires come from and how society fits them together not just with others’ but also into a common scheme of life. For too long, liberals have abstained from inquiring into what people want and have ignored how most obstructions come from neither the state nor the self but from a deregulated market and an unreformed society in which oppression is the rule.

Born in 1954, Sunstein has been America’s foremost law professor for decades. On the strength of his achievements, he has stepped out as one of America’s leading public intellectuals, co-writing the 2008 wonk best seller Nudge. In it, he and University of Chicago economist Richard H. Thaler argued for a new and simpler form of government that seeks to influence choice through information, signaling to individuals rather than coercing them directly. A mentor and friend of Barack Obama, Sunstein served in his administration, working on regulatory policy from 2009 to 2012. In a bid for pop-culture relevance, he also wrote a book on the Star Wars films, although the less said about it, the better. Once the companion of philosopher Martha Nussbaum, Sunstein is now married to former US ambassador to the United Nations Samantha Power, which means that he surfaces from time to time in the gossip columns (such as when Henry Kissinger attended an elegant party for one of his books).

Among the most prolific academics of our time, Sunstein, to his credit, has disproved Heraclitus’s dictum that you cannot step in the same river twice. He began his career as a liberal adept of administrative law, but ever since his early years at the University of Chicago, he has steeped himself in the libertarian economics made famous there and offered a more or less stable worldview. If you haul out one of his several dozen books at random—by my count, some eight books by Sunstein have been published in the last two years—you will usually find the same propositions.

First and foremost, Sunstein argues that the libertarian sage Friedrich Hayek was fundamentally correct: Government, aside from always courting tyranny, lacks the ability to centralize information so as to plan the best social outcomes (which raises the burning questions of how Waze works and how government could do anything competently). Correspondingly, Sunstein insists that the free market is king, though he does not entirely reject the state. In recent years, he has forcefully criticized the extremist skepticism of government that culminated in the Tea Party movement and its intellectual emanations. But his faith in the market has also made him skeptical of many forms of state intervention, and he tends to panic most of all at the frightful prospect of overregulation, insisting that the primary purpose of rules must be to maximize efficiency.

For Sunstein, the state exists to help citizens achieve their private ends; through its nudging, it can influence and shape, in a paternalistic manner, the attempts by citizens to fulfill these desires, but it should do so only if it respects their need to be “free to choose”—a phrase that Sunstein borrows from the economist Milton Friedman and uses repeatedly in his new book. For example, a law might require that you be shown the calorie counts for the different items listed on a fast-food menu, but this is justifiable, since you already care about your weight—and it is still up to you to order whatever you want on cheat day.

When it comes to government helping people achieve fulfillment, Sunstein insists that technocrats must rule. With a palpable sense of relief, he has confessed that he finds politics mostly a distraction and not so much about contending collective visions of the good life or about calling out the oppression that claims to expertise can mask. “Immersion in the facts made people’s political convictions look a little like background noise,” Sunstein explains, with more than a whiff of condescension, regarding what he learned during his years in the Obama White House.

Sunstein’s combination of pro-market enthusiasm and technocratic instincts comes linked to a patriotic endorsement of American civilization within its current institutional carapace. James Madison was right (or, in Sunstein’s adolescent description, he “rocked”): If unleashed, the people are fundamentally dangerous, and so democracy requires a big dose of oligarchy. Sunstein once penned a heated and still-relevant challenge to reactionary zealotry on the Supreme Court, Radicals in Robes (2005), but he later came to regret this excess, and while he has warned against overreach, he admires the high court’s power to keep democracy within the proper bounds.

This more conservative impulse can be seen in various other ways. During the Obama years, Sunstein served on a high-level commission that largely signed off on massive global surveillance in the name of national self-defense. His conservative streak has also led him to plead for tolerance on left-wing campuses allegedly hostile to ideological diversity. He has even gone so far as to praise the “intellectual dark web” site Quillette for counteracting progressive groupthink. Asked whether his approach inherently favors conservative conclusions, he answers, “I don’t think [my approach] has a conservative bias. If it ends up going in a conservative direction, that tells us something important. What it tells us is that the conservative view is correct.”

By dint of his central role in American intellectual life in recent years, Sunstein, who has taught at Harvard Law School for a decade, deserves respectful attention. Yet it is revealing that a man routinely celebrated by liberals (and sometimes denounced by Fox News) in the 1990s and early 2000s has come to look very different in a rapidly evolving debate. Like so many liberals in recent decades, Sunstein joins progressive stances on social issues with a libertarian economics. A longtime feminist, he edgily broached the possibility of giving animals legal rights, apparently disqualifying himself for a Supreme Court appointment as a result. But in thrall to his Cold War libertarianism, he has also advocated for an unquestioning devotion to free markets and has championed a national-security establishment committed to America’s role in protecting them around the world.

Unsurprisingly, the appearance and increasing popularity of Bernie Sanders, who calls both of these things into question, has ruffled Sunstein’s neoliberal equanimity. In a 2015 sally for Bloomberg, he equated Sanders to Donald Trump, alleging that their denunciations of the political establishment were compelling to many voters because of the human propensity to “think fast,” or hastily and impulsively. Conversely, more sober and cautious reflection, or “thinking slow,” would lead voters to resist their demagogic lure. In his more recent columns, Sunstein has suggested that Sanders plays on the irrationality of people (especially the young) to incline toward candidates who are not perceived as boring, and he has praised Trump for dismissing “socialism”—as if the great leader were worth endorsing, no matter the risks, when his impulses approached Hayekian principle. Sunstein does, however, appear to have a soft spot for Beto O’Rourke, whom he credits with the “grace” of Ronald Reagan in giving voters a rhetoric of national unity instead of stark division.

And now comes On Freedom, with its titular shout-out to John Stuart Mill’s On Liberty. “When life is hard to navigate,” Sunstein begins, “people are less free.” Social theory, meet Waze: Sunstein is interested neither in examining how humans routinely look for fulfillment in the wrong places nor in clearing obstacles beyond those that individuals put in their own way. As Sunstein’s book proceeds, it turns out that the point of thinking about navigability is to defend his old brief for government nudging from a variety of individualist and libertarian objections—even though his approach is already strongly individualist and libertarian. And while he answers these challenges plausibly, he does so only by ignoring the deeper objections to his account.

Is a state that nudges on a slippery slope to totalitarian rule? No, Sunstein counters: All human endeavor takes place in settings that limit choice, and governments can therefore defensibly work to shape these landscapes. After all, absent government, nature itself imposes limits on liberty and encourages choice. (A hill on my hike in effect nudges me to navigate around it.) If so, policy-makers can also intervene when it comes to influencing the public’s decisions, especially if their aim as “choice architects” is to assist citizens in achieving their ends. Like Waze, the state can help everyone get where they want to go, as long as it does not substitute new goals chosen by the planners themselves. But even if all this makes sense as a response to libertarian critics of government, Sunstein neglects two bigger questions: Should liberals focus on restricting government to a Waze-like function of helping people successfully get where they want to go in life? And do individual foibles really constitute the main obstacles to that success?

“Oh, the places you’ll go,” once proclaimed that prophet of navigability, Dr. Seuss. But like others influenced by contemporary economics, Sunstein assumes that the formation of preferences is a black box that allows no examination into its workings, in spite of the many traditions in social theory that have concurred that what we say or think we want is potentially irrational.

For a long time, Western philosophy has rejected a blind trust in human desire. The Christian tradition asserts that sinful inclination lurks most where people claim to be making free choices, and many modern social theorists—notably, Karl Marx and Sigmund Freud—have insisted that people’s conscious desires can be ascribed to ideology and rationalization. However, Sunstein simply ignores these traditions and assumes that people’s desires are credibly their own.

One of the most striking features of On Freedom is, therefore, that Sunstein has written a book about liberty that ignores how, even without government interference, the most insidious threats to it transpire when people believe they are in pursuit of their own preferences. The main problem in today’s society is not, as Sunstein maintains, that the state tends to transgress its bounds and overregulate; instead, it is that in the state’s absence, private coercion often holds sway, allowing powerful forces like the “free market” and structural injustice to reduce humankind to servitude, both in choosing its ends and in fulfilling them.

Blinded by fears of government overreach, Sunstein doesn’t recognize that the advertising business and the consumerist revolution already exercise this kind of extraordinary power. Long before Sunstein reconceived government activity around nudging, Madison Avenue and marketing companies had deployed very similar methods to sway consumers. Although he invokes Mill throughout his books, Sunstein seems to have missed the most momentous claim in On Liberty: that it is not government but one another whom we should most fear, precisely for usurping our power to determine the course of our lives. “The mind itself is bowed to the yoke,” Mill noted of social nudging:

Even in what people do for pleasure, conformity is the first thing thought of; they like in crowds; they exercise choice only among things commonly done: peculiarity of taste, eccentricity of conduct, are shunned equally with crimes: until by dint of not following their own nature, they have no nature to follow: their human capacities are withered and starved: they become incapable of any strong wishes or native pleasures, and are generally without either opinions or feelings of home growth, or properly their own. Now is this, or is it not, the desirable condition of human nature?

The state acting beyond its proper boundaries is not the only or even the main threat to human freedom; unchecked power outside of it is. At a critical point in On Freedom, Sunstein cites Aldous Huxley warning that the worst kind of totalitarian rule would be “a population of slaves who do not have to be coerced, because they love their servitude.” But Sunstein raises this possibility, which he associates with the state, merely to conclude that it is not an objection to the theory of freedom he wants to build in defense of state nudging. But of course it is. This is not because nudging creates a slippery slope to totalitarianism; it is because, if nudging merely helps people navigate to places in a world that social tyranny has made for them, the result is not freedom but its opposite.

Obstacles to navigability have been the great blind spot in the Western philosophical tradition,” Sunstein writes. It is disappointing that, despite this insight, he fills the gap mainly with a theory of how government can permissibly act to help people through self-imposed obstacles. The best use of government action, he insists, is when it helps me from becoming my own worst enemy—in cases in which I already know what I want but need help getting it in spite of myself, as in the assist that the state can provide in reminding me to lay off the Big Gulps and Big Macs in order to stay trim.

It is not obvious, to begin with, how Sunstein can celebrate people’s personal goals without question but then fret so much that they will fall prey to self-imposed obstacles on their way to realizing them. If I am subject to irrationality and need help, it is hard to see why the trouble would set in only when it is time to satisfy my preferences. And if you grant that my desires are trustworthy, it is hard to see why my problems in satisfying them are most likely to be a problem with me rather than with the world. Sunstein’s obsession with self-control makes On Freedom often read like a book about piloting a boat through shark-infested waters that focuses mainly on the government’s role in encouraging the passengers not to drink so much that they fall overboard. Sunstein is not interested in the sharks.

Any serious account of threats to freedom would also have to address how civil society and those spheres outside the state stand in the way of fulfilling our individual desires. Neglected by Sunstein, these obstacles were once considered the main target of social planners, since not only do people suffer from social domination without knowing it, but they also face bitter opposition when they struggle to free themselves from it.

In the midst of Sunstein’s narrow reflections on self-control, however, a number of valuable insights for thinking beyond that problem emerge, because it is here that he steps away from his libertarian defaults. He countenances government not merely for the sake of people’s “own” ends but also for the ones that might plausibly need to be imposed on people against their apparent will. Breaking from his usual fears of interference, Sunstein admits that, in those situations where people either dither about what they want or don’t care what they get, the state can justifiably impose its view of the good life. Far from blindly serving freedom as understood by those making the choices, policy-makers in these scenarios can nudge based on their “moral evaluations of options and outcomes.”

Sunstein’s argument on the role that government can play in shaping our preferences is all very enlightening. But in the end, his focus on self-control and its failures is more revealing, because it is so restricted to self-imposed obstacles to navigability. Perhaps the most telling example comes when he discusses how the poor suffer from “insufficient navigability.” In fact, poverty is almost never due to a lack of self-control; domination and exploitation are the culprits. It is therefore very strange for Sunstein to look past structural injustice to say that the poor need help when they want to “find the right track,” “identify the right doctor,” “find the right job,” and “get help in taking care of children.” He cites development economist Esther Duflo to the effect that, however tempting it is to condescend to those in need, it is important to see how much help the well-off get in navigating their life choices by comparison.

Sunstein isn’t wrong when it comes to the rich, but characterizing the situation of the poor as a matter of obstacles to navigation is like saying that the victims of various kinds of oppression just need a little help sidestepping its crushing weight, as if it were not an organized system of coercion, backed by government, that requires government action in order to replace it. To help people find the “right track” out of poverty is a matter of creating good jobs where few exist, giving them adequate health care, and supplying universal free child care—all of which, in turn, require coercing those with money to pay for it. It also requires climate-friendly transportation, without assuming that decaying roads will bear private traffic indefinitely or that the planet will save itself. It trivializes most forms of unfreedom to describe them merely as obstacles in an individual’s path. And addressing such issues adequately requires limits to the freedom of those who most often enjoy its privileges.

To reach better conclusions—call it a Green New Deal—liberals like Sunstein would have to take steps down a road that their assumptions have blocked for decades. Sunstein’s thinking never strays far from the mantra that people are in charge of their own preferences and that the main problem is helping individuals get what they want. But without a bigger theory of how people come by their desires, what forces stand in their way, and what democracy can do to help, no approach to navigability can transcend the status of advice on the Titanic long after it has gone steaming toward the iceberg.

As a first step, Sunstein would have to give up his Cold War estimate of government as the most probable threat to freedom, as if freedom did not depend on eradicating private coercion, too, both when people form their ends and when they try to live them out. He would also have to embrace Mill for real. This would mean dropping Hayek and extending his confidence in the government’s capacity to nudge to other forms of intervention. There is, in fact, no reason that centralized planning is inferior to decentralized activity, as Waze already shows in its way. Indeed, if society—including “the free market”—is the primary threat to liberty, then the state’s justifiable role is far greater than Hayek’s disciples have taught. From nudging, government would have to return to planning.

Sunstein would also have to confront the limits of technocratic nudges when they are allied to a system of oppression that they leave undisturbed. Expertise has a role; any governance depends on it. But as we know, technocrats can serve antidemocratic elites in a counter-majoritarian system as well, inviting an enormous right-wing backlash in the process. You are free to venerate Madison—but not if, like Mill, you repudiate oligarchy and dream of a knowledge class that will serve the people rather than reinforce hierarchy. As for navigability, it is a provocative notion, but emancipation is a better framework for reconceiving freedom.