"How did you go from being a philosophy professor to a digital strategist?" It's invariably one of the first three questions I get at every job interview, every client meeting, every networking event. It's a simple question with an answer that is at once both simple and complicated. Simple in that there's a one-line motivation—I want to make longform research and scholarship work on the Internet. Complicated in that the journey to get from there to here is winding, and fueled more by luck than by any sort of conscious plan. Act I, the Long Digression That Initially Seems Irrelevant But Eventually Makes Sense My story begins on an early fall morning in upstate New York. It is the sort of crisp, clear day on which you cheerfully wave goodbye to the last of August's humidity and start looking forward to falling leaves and hikes through red and golden forests. It is both early in the fall and early in the morning. At the United States Military Academy—West Point—classes begin at 7:35. In the morning. It is a time that is entirely bewildering to me, a civilian and newly-minted PhD who has defied the odds and actually landed a job as an assistant professor of philosophy. I teach two sections of Introduction to Philosophy back-to-back at 7:35 and 8:40. It's a required course for all sophomores—"yearlings," in West Point parlance. I'm a moral and political theorist. My dissertation is on John Stuart Mill. I am far more concerned about getting my interpretation of Mill right than I am about whether Mill was right. Applied ethics courses—bioethics, military ethics, business ethics—keep philosophy departments in business. It is the price you pay to be able to do the interesting theoretical stuff. Because it is early in the semester, we're still covering logic. Later in the semester, we'll get to moral theory before diving in to just war theory and military ethics. Today we're discussing informal logic. The first class of the day has gone without a hitch, and I'm well into the second, when there's a knock at the door. A cadet I've never seen before, his face flushed. "Sir, the commandant requests that you turn on the television." Each classroom at West Point is equipped with a television. The week before, I had used it to show a courtroom scene from A Few Good Men. My students had reconstructed the argument using formal symbolic logic. When not playing videos, the TV shows CNN. It is an odd request. The commandant runs the military side of West Point. He doesn’t typically interfere with the academic side. That is the dean's purview. Still, the commandant has a star on each shoulder and I am in my third week. I turn on the television. For the remaining few minutes of the class, I sit with my cadets watching smoke rising from the World Trade Center. Later, I sit with my colleagues—captains, majors, and a few lieutenant colonels in the United States Army—and watch as the towers collapse. Groups will peel off every hour or so, heading to classrooms around post to lead classes on British literature, on metaphysics, on art history. Tragedy is a fact of life when you're a soldier. You do your duty regardless. West Point is one of the few colleges in the United States to hold classes on September 12. I would leave West Point in 2003, bound for a tenure-track position at a regional branch in the UNC system. During my two years at West Point, I will teach 16 sections of future officers. In most of those 16 sections, we will cover just war theory. During those same two years, my military colleagues will rotate out of their teaching positions to go to Afghanistan. Nearly all of them will end up in Iraq at some point. Some will not return. Afghanistan is fairly easy to square with the principles of just war theory. Iraq, not so much. Act II, the Part That Is (Eventually) About the Web I spend three more years as an academic, most of them being reasonably successful. I win a teaching award. I publish papers regularly. Some of those papers are even on just war theory. One of them argues that officers have a moral obligation to refuse deployment to an unjust war. That one gets reprinted in a couple of textbooks. Its title is 98 characters long, and partially in Latin ($). Its readership runs well into the 10s. Back in Washington, the Bush Administration makes up a whole new category of people—"enemy combatants"—specifically to exempt suspected members of al-Qaeda from the ordinary rules of war. That's a nice way of saying that Bush and company decide to torture suspected terrorists, and appropriate the language of just war theory to cover their asses. Philosophers object. But, again, we are mostly writing for other philosophers. And we pretty much all agree with each other anyway. It is incredibly frustrating to sit day after day reading and writing finely nuanced arguments about making war (slightly) less hellish, and then watch my country hypocritically deploy the language of morality in the service of making war even worse than it already was.So I left academia. This is the part where I got very lucky. The managing partner at an ad agency saw through my four-page cover letter (Four. Pages. Of. Cover. Letter.) and somehow thought, "yeah, this guy could probably write copy." That experience writing political ads would later land me a gig at FactCheck.org, where I learned journalism from some very patient editors—editors who later cleared my schedule so I could figure out how to redesign FactCheck’s website. Since then, I've been privileged to help a lot of really smart people—economists at the Congressional Budget Office, sociologists at The Century Foundation, scientists at the EPA—repackage their work for wider audiences. The frustrations are different now. Economists and sociologists and scientists really like their PDFs. And their line charts with 14 lines of notes at the bottom. And their jargon. And their footnotes. Some days it seems that they've never met a lede they didn't bury. Usually in a footnote. But it is a better class of frustrations. My clients genuinely want their work to improve public policy. They may not always quite know how to do that, but the fact that they have hired people to help is a huge step. On a really good day, I get to play a teeny tiny role in creating better policies. So far, I haven't really seen many philosophers embracing the digital world. It's not hugely surprising. This is a discipline that has been (not inaccurately) described as "a series of footnotes to Plato." For that matter, its core methodology is named for the guy who taught Plato. It is not a discipline that is quick to embrace change. Still, I hold out some hope that some day I'll get to help an old colleague produce Snow Fall, but for just war theory.