The 13 Big Ideas:

• The First Mountain We Climb

• The Second Mountain We Climb

• Society Prioritizes Individualism Over Connection

• Unlimited Freedom Can Mean You Aren’t Committed to Something

• Without Connection and Meaning, We Fall For Superficial Thrills

• The Telos Crisis

• Go Outside

• What Are You Motivated To Do Over The Next Decade?

• Daemon: A Calling, An Obsession

• Your Vocation Is About Finding A Match Between Your Desire And A Social Need

• Self-Discipline is a Form of Freedom

• Vocation Is Doing The Same Thing, Day After Day

• Thick Communities

My Highlights From the Book:

The First Mountain We Climb

I often find that their life has what I think of as a two-mountain shape. They got out of school, began their career or started a family, and identified the mountain they thought they were meant to climb:

People climbing that first mountain spend a lot of time thinking about reputation management. They are always keeping score. How do I measure up? Where do I rank? As the psychologist James Hollis puts it, at that stage we have a tendency to think, I am what the world says I am.

The goals on that first mountain are the normal goals that our culture endorses—to be a success, to be well thought of, to get invited into the right social circles, and to experience personal happiness. It’s all the normal stuff: nice home,…

The Second Mountain We Climb

Then something happens. Some people get to the top of that first mountain, taste success, and find it…unsatisfying. “Is this all there is?” they wonder. They sense there must be a deeper journey they can take.

At this point, people realize, Oh, that first mountain wasn’t my mountain after all. There’s another, bigger mountain out there that is actually my mountain. The second mountain is not the opposite of the first mountain. To climb it doesn’t mean rejecting the first mountain. It’s the journey after it. It’s the more generous and satisfying phase of life.

On the first mountain you tend to be ambitious, strategic, and independent. On the second mountain you tend to be relational, intimate, and relentless.

Society Prioritizes Individualism Over Connection

Our society suffers from a crisis of connection, a crisis of solidarity. We live in a culture of hyper-individualism. There is always a tension between self and society, between the individual and the group. Over the past sixty years we have swung too far toward the self. The only way out is to rebalance, to build a culture that steers people toward relation, community, and commitment—the things we most deeply yearn for, yet undermine with our hyper-individualistic way of life.

Unlimited Freedom Can Mean You Aren’t Committed to Something

Political freedom is great. But personal, social, and emotional freedom—when it becomes an ultimate end—absolutely sucks. It leads to a random, busy life with no discernible direction, no firm foundation, and in which, as Marx put it, all that’s solid melts to air. It turns out that freedom isn’t an ocean you want to spend your life in. Freedom is a river you want to get across so you can plant yourself on the other side—and fully commit to something.

Without Connection and Meaning, We Fall For Superficial Thrills

People generally go through a familiar process before they can acknowledge how comprehensive their problem is. First, they deny that there’s something wrong with their life. Then they intensify their efforts to follow the old failing plan. Then they try to treat themselves with some new thrill: They have an affair, drink more, or start doing drugs.

The Telos Crisis

Only when all this fails do they admit that they need to change the way they think about life. THE TELOS CRISIS

This is a telos crisis. A telos crisis is defined by the fact that people in it don’t know what their purpose is.

The normal reaction to a season of suffering is to try to get out of it. Address the symptoms. Have a few drinks. Play a few sad records. Move on. The right thing to do when you are in moments of suffering is to stand erect in the suffering. Wait. See what it has to teach you.

Understand that your suffering is a task that, if handled correctly, with the help of others, will lead to enlargement, not diminishment.

Go Outside

At the moment when you are most confused about what you should do with your life, the smartest bet is to do what millions of men and women have done through history. Pick yourself up and go out alone into the wilderness.

In the wilderness, life is stripped of distractions. It is quiet. The topography demands discipline, simplicity, and fierce attention. Solitude in the wilderness makes irrelevant all the people-pleasing habits that have become interwoven into your personality.

What Are You Motivated To Do Over The Next Decade?

That may be fine if you’re willing to settle for something meager like a career. But if you are trying to discern your vocation, the right question is not What am I good at? It’s the harder questions: What am I motivated to do? What activity do I love so much that I’m going to keep getting better at it for the next many decades? What do I desire so much that it captures me at the depth of my being?

Daemon: A Calling, An Obsession

The Greeks had a concept, later seized by Goethe, called the daemonic. A daemon is a calling, an obsession, a source of lasting and sometimes manic energy.

The daemon identifies itself as an obsessive interest, a feeling of being at home at a certain sort of place, doing a certain activity—standing in front of classroom, helping a sick person out of bed, offering hospitality at a hotel.

When you see an individual at the peak of her powers, it’s because she has come into contact with her daemon, that wound, that yearning, that core irresolvable tension. This is especially obvious in writers and academics. There’s often some core issue that obsesses them and they scratch at it for their entire lives.

Your Vocation Is About Finding A Match Between Your Desire And A Social Need

First, it’s not about creating a career path. It’s asking, What will touch my deepest desire? What activity gives me my deepest satisfaction? Second, it’s about fit. A vocation decision is not about finding the biggest or most glamorous problem in the world. Instead, it’s about finding a match between a delicious activity and a social need. It’s the same inward journey we’ve seen before: the plunge inward and then the expansion outward.

Self-Discipline is a Form of Freedom

H. A. Dorfman is one of the great baseball psychologists. In his masterpiece, The Mental ABC’s of Pitching, Dorfman says that this kind of structured discipline is necessary if you want to escape the tyranny of the scattered mind. “Self-discipline is a form of freedom,” he writes. “Freedom from laziness and lethargy, freedom from expectations and the demands of others, freedom from weakness and fear—and doubt.”

Vocation Is Doing The Same Thing, Day After Day

Vocation can be a cure for restlessness. Mastering a vocation is more like digging a well. You do the same damn thing day after day, and gradually, gradually, you get deeper and better. “In silence, in steadiness, in severe abstraction, let him hold by himself,” Emerson wrote, “add observation to observation, patient of neglect, patient of reproach; and bide his own time, happy enough if he can truly satisfy himself alone, that this day he has seen something truly.”

Thick Communities

The second-mountain society is a thick society. The organizations and communities in that society leave a mark. And so I’ve been thinking a lot about what makes an organization thick or thin.

The thick communities have a distinct culture—the way the University of Chicago, Morehouse College, the U.S. Marine Corps do. A thick institution is not trying to serve its people instrumentally, to give them a degree or to simply help them earn a salary. A thick institution seeks to change the person’s whole identity. It engages the whole person: head, hands, heart, and soul.

Thick institutions have a physical location, often cramped, where members meet face-to-face on a regular basis, such as a dinner table or a packed gym or an assembly hall. Such institutions have a set of collective rituals—fasting or reciting some creed in unison or standing in formation.