Friendship and Solitude - Redfin Real Estate News

Friendship and Solitude

Updated on October 5th, 2020

Have you read the wonderful, deeply counter-cultural lecture on solitude and leadership delivered by William Deresiewicz in spring 2010 to the West Point plebe class? I just found it via David Brooks, and can hardly recommend it enough.
Part of what makes the lecture seem so important is the audience hearing it. West Point students are the kind of people who could have gone to Wall Street or started a company two years out of school but instead will soon find themselves face down in the dirt of Afghanistan on Christmas day, scared and cold, leading people they’ve just met, under circumstances that would overwhelm folks like me.
But mostly, I love the essay because the old professor gives the plebes such strange and good advice. In the plainest terms, the lecture captures everything I’ve been feeling about these charming hoop-jumping robots Redfin has been interviewing at top-flight schools this fall  — smarter, more polished people than I am who’ve never had a goofy moment of pure curiosity, who never blew stuff up for fun or were allowed to make terrible mistakes, who never screwed up their transcript or their resume just to see what it would feel like to stop pleasing everyone else.
Interviewing such poised job applicants, I kept thinking this fall of Wagner’s complaint about Mendelssohn, who was more precocious even than Mozart and more lyrical: that he never lost control of himself. Drawing on decades of grooming Ivy League students, Deresiewicz argues that this control is crucial to being successful in society, but not to being a leader. His students are always thinking of how to get to the next step, but always on someone else’s stairway:
So I began to wonder, as I taught at Yale, what leadership really consists of. My students, like you, were energetic, accomplished, smart, and often ferociously ambitious, but was that enough to make them leaders? Most of them, as much as I liked and even admired them, certainly didn’t seem to me like  leaders. Does being a leader, I wondered, just mean being accomplished, being successful? Does getting straight As make you a leader? I didn’t think so. Great heart surgeons or great novelists or great shortstops may be terrific at what they do, but that doesn’t mean they’re leaders. Leadership and aptitude, leadership and achievement, leadership and even ex­cellence have to be different things, otherwise the concept of leadership has no meaning. And it seemed to me that that had to be especially true of the kind of excellence I saw in the students around me.
The essay argues that what a leader really needs is solitude — the kind you feel when completely absorbed in a creative project, or on a long car ride through an empty place. For me that solitude has come most intensely running up a mountain, all alone in winter, with darkness coming and the snow falling as thick as the air itself, running until I’ve thought through what to do with my life or decided how I really feel about God, running so far that I’ve started to get scared about making it back alive. Deresiewicz worries this solitude is being drowned out by modern life:
“Your own reality—for yourself, not for others.” Thinking for yourself means finding yourself, finding your own reality. Here’s the other problem with Facebook and Twitter and even The New York Times. When you expose yourself to those things, especially in the constant way that people do now—older people as well as younger people—you are continuously bombarding yourself with a stream of other people’s thoughts. You are marinating yourself in the conventional wisdom. In other people’s reality: for others, not for yourself. You are creating a cacophony in which it is impossible to hear your own voice, whether it’s yourself you’re thinking about or anything else.
What I love most about the essay is that it talks about  how the solitude that a leader needs — that anyone needs — is not incompatible with friendship, especially the friendship of one person, someone you know well enough to welcome into your solitude:
Introspection means talking to yourself, and one of the best ways of talking to yourself is by talking to another person. One other person you can trust, one other person to whom you can unfold your soul. One other person you feel safe enough with to allow you to acknowledge things—to acknowledge things to yourself—that you otherwise can’t. Doubts you aren’t supposed to have, questions you aren’t supposed to ask. Feelings or opinions that would get you laughed at by the group or reprimanded by the authorities… Instead of having one or two true friends that we can sit and talk to for three hours at a time, we have 968 “friends” that we never actually talk to; instead we just bounce one-line messages off them a hundred times a day. This is not friendship, this is distraction.
I was lucky to grow up always having a friend like this: until we left one another for college my twin brother and I lived in our own country, unassailable and determined. The French describe a newly married couple as, “alone, just the two of them,” a phrase that perfectly describes the feeling we’ve had together.
Over time, I’ve been lucky enough to make new friends like that, but lately not so much. I don’t know if I’ve gotten too old, or too busy — I’ve often just felt that I’m no longer gooey, that my identity has sadly hardened to the point where it can hardly accommodate the shape of a new personality. But Deresiewicz’s beautiful lecture convinced me that there are, at least, a few more kindred spirits out there, for all of us.

Glenn Kelman

Glenn Kelman

Glenn is the CEO of Redfin. Prior to joining Redfin, he was a co-founder of Plumtree Software, a Sequoia-backed, publicly traded company that created the enterprise portal software market. In his seven years at Plumtree, Glenn at different times led engineering, marketing, product management, and business development; he also was responsible for financing and general operations in Plumtree's early days. Prior to starting Plumtree, Glenn worked as one of the first employees at Stanford Technology Group, a Sequoia-backed start-up acquired by IBM. Glenn was raised in Seattle and graduated from the University of California, Berkeley. He is a regular contributor to the Redfin blog and Twitter.

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