David Brooks is one of those talented people who has managed to get himself disliked in many circles. As a resident conservative at the New York Times, he has the unenviable task of defending a political outlook that few of his readers agree with, and makes such an effort to speak to them that he’s pretty easily labeled a Republican In Name Only by the right. Sometimes he pursues balance for its own sake to the extent that seems like one of those annoying kids yelling “yeah, but” on the playground, and his willingness to dabble in anything can lead him to be painfully wrong about some things, most notably foreign policy.

Such is life as a syndicated columnist, as he must churn out new ideas twice a week, every week. Much of his longer work is a far better sample of what his real interests and concerns are, from the acute diagnosis of upper middle class America in Bobos in Paradise to the social science-heavy study of life in The Social Animal. Brooks has been on a steady turn inward as his career has gone along, a process that culminated in his most recent book, The Road to Character. He’s long been capable of profound reflections on the costs of a lack of reflection on one’s own self—see the classic “Organization Kid” essay, which should be required reading for anyone entering an “elite” college—but only recently has he taken the step from detached takedowns of people who don’t do this to exploring what it means to actually do so. (His own recent divorce probably spurred this all along, too.)

I had the good fortune to attend a lecture by Brooks when he was in the early stages of conceiving The Road to Character, a 2011 talk called “The Era of Self-Expansion” put on by Georgetown University’s Tocqueville Forum. In it, he recalled a column he’d written earlier that year, an especially memorable piece for a soon-to-be college graduate in which he talked about how people find their callings. When I asked him about it in the receiving line, he admitted he’d somewhat made it up, but was impressed with how well it had resonated.

In the column, he blasts the tiresome myopia of the follow-your-own-dreams rhetoric so common in life advice today. However noble in its desire to tell us to be ourselves, these words foment a worldview that places the self and its ambition at the center of it all. The universe revolves around me, even as I purport to go forth and do “good” in the world, following the passions I have deemed worthwhile, in my infinite wisdom. And when I do try to do this, life inevitably gets in the way, whether in the form of my own limitations or the failures of other people or forces beyond my control. Suddenly, I’m powerless, and I’m pretty angry about it. Before long, I’m defeated, or perhaps more mundanely, I’ve discovered that the dreams of my younger self are no longer the dreams of my older self, and I’ve spent however many years chasing the wrong thing. The world refuses to cooperate and revolve around me.

The fruits of Brooks’ search don’t come in this takedown of selfishness, though. This is easy, and not terribly original. He needs an alternative, something else to aspire to. He now champions excellence over happiness, and the pursuit of something a bit more complete than just the self-expression celebrated in some of his earlier work. This drive doesn’t come from within, but from something that happens to people: one’s circumstances leave one with passions, and mark people by the things that jar them into awareness, whether as witnesses or the things they endure. It may seem like a small distinction, but it is essential. The turning points in life are rarely moments of great happiness or accomplishment, but instead in suffering and failure, and a desire to overcome it, perhaps even build off of it. This, and not the blind whims of dreams, defines who we become.

It is now fairly easy to go through childhood, and even much further into life, without ever coming face-to-face with this sort of adversity. It’s a triumph of affluence, I suppose, of good health, suburban living, wealthy schools (public or private), and other comforts that allow us to live out that pursuit of happiness extolled in Brooks’ early work. It’s not a bad life, clearly, and I don’t necessarily begrudge anyone for pursuit it.

The trouble comes in pursuing it alone, and nothing else. Deep within this comfort there is a moral poverty: everyone plays out the string as they see fit. Forget complaints about moral relativism; there is no moral dimension at all, as the whole language necessary to even make these distinctions falls away. People become lost and have no means to figure out why. Even the humanities, designed with this express purpose, often fails, aiming instead for aesthetic, utilitarian, or political arguments to justify its existence. It’s no wonder these departments are collapsing left and right. But there are encouraging signs, Brooks’ latest book among them, that people are starting to realize something is missing. Hopefully the new book offers some models, and some ways to cultivate that character necessary to pursue the truly good life. If Brooks can do that for people, it would amount to a legacy far greater than his scattered collection of brief columns.

Sometimes, though, one of the sparks that helps a jaded kid make sense of the disparate threads of life, one that plays off those turning points and fuses them with ongoing interests, comes from an unexpected place. In that lecture I attended four years ago, Brooks dropped in a book recommendation: Jane Jacobs’ The Death and Life of Great American Cities. I jotted it down at the time, picked it up a year or two later, and the rest is history.