In our age of smartphones, social networks, and search engines, privacy has become a highly contested topic. Though people complain about the lack of privacy online, at the same time, they compulsively post their latest thoughts, photos, and locations for a swath of friends, acquaintances - or perhaps even the entire Internet - to see. And other people "like," comment on, or critique what they post - creating anything from dynamic conversation to a heap of abuse, insults, and threats. Two new books - Privacy in the New Media Age by Jon L. Mills and Intellectual Privacy by Neil Richards - explore the challenges of balancing privacy and free speech in American society, especially in recent decades. Privacy as an American value has had a fraught history, and it has really only entered jurisprudence as a right to be protected in the last century or so. Both Mills and Richards, law professors at the University of Florida and Washington University in St. Louis, respectively, trace the origins of privacy rights from Samuel Warren and Louis Brandeis's seminal article "The Right to Privacy" (4 HARV. L. REV. 193 (1890)), which was inspired by the technology of early photography. As Mills notes, "At the time of its publication, the Warren-Brandeis article was unique not only for its discussion of media privacy invasions but also for its novel treatment of the overall concept of a legal right to privacy." Subsequent decisions finding tort remedies for privacy violations drew heavily upon Warren and Brandeis's reasoning; the U.S. Supreme Court decision in Katz v. United States (389 U.S. 347 (1967)) found a "reasonable expectation of privacy" test to be the method of determining the bounds of the Fourth Amendment's ban on unreasonable searches and seizures. But unlike freedom of expression, which is clearly enshrined in the First Amendment, privacy is not explicitly mentioned in the U.S. Constitution. (Note that in California there is a state constitutional right to privacy (see Cal. Const. Art. I, § 1).) The first Supreme Court case to find a right to privacy, Griswold v. Connecticut (381 U.S. 479 (1965)), has been criticized for its reliance on "penumbras and emanations" from other constitutional rights. And subsequent cases have not fully dispelled these criticisms that privacy, when in conflict with free speech, will often not win the battle. It's into this fray that both Mills and Richards step, attempting to reconcile these two rights in the modern era. Mills, who is also counsel at Boies, Schiller & Flexner, is particularly focused on how individual privacy can be threatened by online content. As a litigator who has represented a range of individuals whose private lives have become part of public discourse, Mills approaches these questions with a specific answer: Freedom of expression is important, but unregulated online "media" can invade privacy without sufficiently strong justifications. The challenge, of course, is in balancing the right to report objectively true information against the privacy rights of individuals who don't want suspect content about them disseminated online, where it may reside in perpetuity. Mills seems especially skeptical of nontraditional media. These are the citizen journalists, whom he idiosyncratically refers to as "iReporters," those who lack traditional training and may run the gamut from prurient gossip hounds to concerned individuals documenting events that escape the notice of the mainstream media. To ferret out spurious motives on the part of online speakers, Mills crafts a balancing test with eight discrete questions to determine how a conflict between media and privacy should be resolved, including who owns or controls the relevant information, how it was obtained, whether it is private and intrusive, and what was the intent of the media in publishing it. Multipronged balancing tests are appealing - as they can encompass a range of concerns in arriving at a conclusion - but they are notoriously difficult to apply in any systematic or objective way. The weakness of Mills's argument is that he does not sufficiently grapple with how discerning minds may answer each of his questions in radically different ways, instead assuming that questions of intent, truth, and control can be answered in unequivocal ways. Given the ascension of the First Amendment in recent jurisprudence, it seems unlikely that a rubric of open-ended questions would do much to tip the scales back in the direction of privacy. In Intellectual Privacy, Richards is far more successful in his efforts to reconcile free speech and privacy concerns, largely due to a more holistic view of how these two rights are intertwined rather than conflicting. Richards argues that privacy is necessary to the development of speech, as it provides a kind of safe space for individuals to create ideas. This concept of intellectual privacy, as he frames it, is "protection from surveillance or interference when we are engaged in the processes of generating ideas - thinking, reading, and speaking with confidants before our ideas are ready for public consumption." Only in promoting intellectual privacy can we promote speech in the way that serves the purposes of the First Amendment. Richards provides two specific solutions on how to promote privacy for an age in which speech proliferates rapidly. In the first, he expands the suite of privacy torts first described by Warren and Brandeis to a suite of "information torts." Unlike Mills's framework, which relies on a new set of questions to resolve the privacy and speech conflict, Richards uses existing legal doctrines to promote privacy while balancing speech rights. However, the real success of his book is in encouraging the development of extralegal norms-codes of conduct for information professionals; guidelines for platforms such as Google, Facebook and Twitter; and a suite of information ethical guidelines - to promote intellectual privacy. Though extralegal norms don't have the scope or power of regulatory regimes, they can be far more responsive to the new challenges of digital media. And, as the work of copyright scholars such as Aaron Perzanowski, Kal Raustiala, and Christopher Jon Sprigman has shown, social norms can be effective in protecting creators without using the blunt club of intellectual property law to pursue perceived wrongdoers. Richards's suggestions demonstrate his nuanced understanding that the answers to balancing privacy and free speech may not be found solely in the law. Of course, these questions are not confined to the legal system in the United States, and they can vary drastically depending on where a possible privacy violation occurs. And this means that lasting solutions to the conflict will almost certainly not be found in traditional legal scholarship. But to the extent that both authors attempt to grapple with a rapidly changing online landscape, they ultimately deserve commendation for recognizing the pragmatic difficulties of addressing the challenges in the first place. G. S. Hans is policy counsel and director in the San Francisco office of the Center for Democracy & Technology.