The Question We Stopped Asking
“Who are your best friends?” There was a time in our lives when this was one of the most important questions we had to answer, the core concern of where we stood in the social construct that we inhabited. It was often the catalyst for fights and arguments, particularly around birthday parties, where the status of “bestie” carried much weight. My youngest daughter is still in that stage, with her answer to the question shifting every school semester.
But it does not end with elementary and middle school. In our teenage years, the search for best friends—or, more accurately, a tight-knit circle of confidants—is especially intense. If we are lucky, they become our lifeline through turbulent times. A similar dynamic develops during college years, with the added pressure of ensuring the group is one we can live with.
And then it stops. At some point, we are less preoccupied with who our best friends are. We stop asking the question. It may be because, by then, we assume we already have our core group of friends. It may be because the post-college expansion of our social circles through work and our partners (and, often, their friends) renders the question moot. But maybe it's exactly the question we should have kept asking.
I have been thinking about this for some time. Part of it has to do with a recent visit to DC by one of my longtime friends and the candid but invigorating conversation we had over dinner. Part of it has to do with recent struggles that one of my college friends is facing. But what pushed me to write was a recent episode of Arthur Brooks’ podcast, Office Hours.1 In it, Brooks argues that the quality of our friendships may be one of the most consequential—and most neglected—dimensions of a well-lived life. “I want you to take your friendship as seriously as you do your diet and exercise and work habits,” he tells us, because our ability to fend off loneliness, and all that comes with it, may depend on it.
That Brooks is expanding on this topic should come as no surprise to those who follow his work. In his 2022 book, From Strength to Strength, he made a statement that has stayed with me: “The top two loneliest professions, according to the Harvard Business Review, are lawyers and doctors.” And for good reason. The vicious cycle runs something like this: the habits that make strivers successful lead to workaholism. Workaholism breeds anxiety—the fear of falling behind, the conviction that success demands maintaining the same punishing pace indefinitely. And that pace crowds out friendship, which become casualties.
Brooks’ theory in From Strength to Strength is that to avoid getting into that vortex—or to have any chance of getting out of it—we must develop real friends outside of marriage. Not “deal friends,” but rather friends who share a passion or belief with us—friends we can be vulnerable with. Deal friends are fine, and even necessary. But they are not a substitute for real ones.
Brooks expands on these themes in his recent podcast. He starts by examining the three types of friendship in Aristotle’s Nicomachean Ethics.
You have friendships of utility—necessary and often appealing—the colleagues, clients, and contacts who populate our professional lives. But they are ultimately insufficient. There are no emotional bonds, so if you stopped working or doing business together, you wouldn’t stay in touch.
Then you have friendships of pleasure. These are friends we actually admire. They are entertaining, smart, or funny. But these friendships are still transactional at their core—a means to an end, even if that end is simply pleasure or good company.
At the highest level, you have friendships of virtue. They are not utilitarian at all, but rather useless in the best way—you love these friends independent of what they can do for you. These are the real friends, the friends for life. And you are going to be lonely if you don’t have friends of virtue, if your friendships “are all deal and no real.”
Brooks offers three prescriptions. First, give yourself a friendship audit: ask yourself who would notice if something were wrong—who would actually call. List a few people, excluding your spouse, with whom you’re comfortable being vulnerable and discussing a weakness. Second, have deeper conversations—talk about things that actually matter to you, not trivialities to pass the time. Third, make more friends whom you don’t need. Go outside your networks of utility—beyond the workplace and the alumni networks.
I’ve been open about my struggles with workaholism in my early years in Big Law. I lived the vicious cycle Brooks described—the anxiety, the lack of sleep, the fear of decline, the sense of isolation. I think I survived it. And I realize now that I was lucky not to have lost my friends along the way. But I think I came close. I distinctly remember the time one of my real friends called me out—told me, firmly, that we always have time for the people who matter, no matter how busy we tell ourselves we are. I didn’t react well. But it made an impact. He’s still my real friend. And a constant reminder that we have to find time for friendship.
Beyond my own experience, the question of friendship deserves more deliberate attention for two reasons. First, because of its connection to loneliness. The loneliness epidemic in the US, and particularly among attorneys and other professionals, is still not talked about openly enough. Even with a heightened attention to wellness and mental health, loneliness and its effects tend to get shortchanged. And yet we know that loneliness can be a cause or at least an accelerator of addiction and substance abuse. It can erode our mental and physical health, shorten our lives, and hollow out the sense of purpose that drives us in the first place. And, in a cruel, ironic twist, it is heightened when our laser focus on work leads to burnout—that moment when the very thing we sacrificed our friendships for stops giving back what it once did.
It is also important because maintaining and deepening our friendships requires deliberate effort. That can feel impossible when we are stretched thin and managing so many competing demands. But friendships of virtue don’t maintain themselves. They require investment. They require showing up—in person, in the small moments, in the hard ones. The friend who called me out about not calling back wasn’t just venting. He was signaling that real friendships have a cost, and that cost is time, presence and vulnerability. The alternative to that hard work is worse: arriving at midlife to discover that loneliness is nearly impossible to climb out of—because we have many deal friends but no real ones.
The good news is that it’s rarely too late. Friendships can be repaired. New friendships can be made. But it starts with the question we stopped asking somewhere along the way: Who are your real friends? Not your deal friends. Not your network. Your real ones. And are you being one in return?
Thank you my friend!