If you sail, you learn to pay attention to the wind. Because sailing wasn’t part of my childhood, I didn’t learn to pay attention to the wind. We were motorboat people. Point the bow of the boat in your desired direction, throttle up, and go. 

My father, the ever-present danger named Carl, took me out on a small sailboat—a Sunfish—once. I was seven or eight. The boat was stored in a shed at the lakeside cottage we were renting. All I remember is coming to the surface in a panic, gagging out the lake water I had half-inhaled, half-swallowed when the Sunfish, wrong way to the wind by no fault of its own, bucked and flipped. My dad couldn’t read the wind either. 

Wind is alive. 

There’s so much more, but the beginning of discernment is an awareness that there are lives outside you, and that those lives outside you make claims. The wind is one of those lives. It has moods and seasons: the autumn bluster spinning dry leaves, the summer breeze rippling the pond, the winter gale. 

As without, so within. God’s Spirit will fearsomely spin us and mercifully gather us, will disturb our dust and blow us clean. God’s Spirit animates clay into living souls and breathes life into dry bones. We learn awareness of the Spirit as we attend to the life of his seasons in us. If you seek to discern God’s will, you learn to pay attention to the breath of the Spirit. How is he moving? Where is he leading? 

Before departing from shore, ask: How is the wind today? Because if you are doing discernment, you’re aiming to align your will with the will of the wind. 

We are motorboat people in a motorboat world. The wind doesn’t matter. Motorboat people don’t discern. We decide. 

We who would prefer to paddle, row, or sail can’t help being motorboat people to some degree. I have a little three-horsepower Honda that helps me manage my sailboat alone. The motor allows me some freedom from depending on the wind, and on other people. While I don’t want to be a motorboat person, I am. A little. Or maybe more than I want to admit. 

Motorboats feed the illusion that we are self-directed little captains of our own little boats who steer our own course according to our own desires. Who needs to pay attention to the wind when you’re self-propelled? Who needs to pay attention to the wind when you’ve got an internal combustion engine and a full tank of gas? Just cut through the wind. You can go anywhere you want. 

Motoring is a monologue. The pilot is constrained by shoals, no-wake zones, and other boaters, of course: the pilot must be aware of what’s happening around him. But in the motorboat world we live in, what’s outside the motorboat is an obstacle, not a conversation partner. The reference point is the sovereign self, standing amidships, inscrutable behind mirrored sunglasses with one hand on the throttle and one hand on the wheel. All things are defined in relation to him—that is to say, us. The logic, the inner coherence, of the motorboat world always leads back to the first principle: the autonomous self. He speaks to himself alone and acts in obedience to his own word. In this world his separateness is the freedom by which he can be, authentically, a self. 

By contrast, sailing is a conversation. The wind makes an assertion, and the sails take in what the wind has spoken; the boat tilts, as if cocking an ear in response. The helmsman listens, and seeks to connect the wind’s assertion and the boat’s response to the course this conversation is on, contextualizing the exchange, making meaning. The helmsman may affirm what the wind has said or remain silent. Or he may introduce a new idea entirely, bringing the boat through the eye of the wind, continuing the conversation now from a fresh angle. The wind, the boat, and the sailor listen to one another and respond. 

This conversation is not small talk; these are not idle words. On the contrary, the conversation is constitutive. It makes something new. It is through the conversation that boat, wind, and sailor have life. You can see each distinctly, but you can’t see them separately. They make each other who and what they are, in communication with each other. 

Discernment is a logical and therefore practicable possibility in this dialogical world of sailing. In this world the self is essentially relational; we are authentically ourselves only by being in conversation with others. Discernment, the essence of which is a communication between self and Spirit, is a coherent notion, and a reasonable practice, only in this kind of world. 

By “world” I mean a comprehensive conceptual field of meanings and their logics that defines the proper relations between things, determines what makes sense and what doesn’t, and shapes how we see. A “world” is a metaphysical scaffolding, a cosmos. Discernment is not possible in the monological world of motoring; it’s an incoherent concept, and therefore practicing it is the definition of insanity. In the motorboat world, discernment is crazy. You’re hearing voices, but it’s not possible that anyone is speaking to you. 

Those who appreciate Charles Taylor’s work will recognize the monologue/dialogue distinction, which I am mapping onto the typologies of motoring and sailing. In tracing the genealogy of ideas, Taylor fair-mindedly reminds us that the motorboat world in which we live today arose from a reforming movement that aimed at human flourishing. The movement was well-intentioned. It’s worth pausing for a moment to summarize this development, to remind ourselves when the world that supported discernment ceased and the motorboat world began. It wasn’t immediate. 

In this reformist vision of flourishing, so the story goes, the individual, liberated from stale tradition, binding oppression, and stultifying conformity, becomes free to seek the good and listen for the stirrings of the Spirit, deep within himself. Whatever date or historical moment you might assign to this shift, it’s the shift to modernity. Discernment is still possible at this point. Seeking the movement of the Spirit deep within myself retains the sense that what I seek is transcendent, is an Other who speaks to me. This world still supports dialogue with the Spirit who is beyond me; what’s changed is that in modernity this dialogue has shifted location. Instead of being “out there,” the conversation is now “in here.” The conversation of self and Spirit is now deep within, and anyone can participate, without the need of a mediator. 

The line of demarcation is when the Spirit—or any kind of authoritative theological or a-theological transcendence (like the good)—begins to feel superfluous to the story. This transcendence—call it the Spirit—becomes an unnecessary complication, an extra character off to the side, without any role in the action onstage. The depth of my own self becomes the authoritative guide for decision-making, the benchmark for authenticity, and the final judge of my flourishing. In an increasingly materialist, rationalist modernity, Spirit eventually becomes an embarrassment to reason, a ghost in a haunted house. I know what I need, if I can free myself from the artificial constraints and traditionalist bugaboos that keep me from knowing my own truth. Deep down, I know where I am going. As long as I am in communication with my own depths, I am on the right course. Talking to myself is no longer a misstep: talking to myself has become the point. Here begins the monological motorboat world. 

In The Ethics of Authenticity, Taylor describes this ideal of human flourishing as rising from “self-determining freedom,” a notion of freedom evident in Jean-Jacques Rousseau’s political philosophy. This kind of freedom goes beyond even negative liberty (being “free from” constraints) to make a claim on what forms the basis of a good life: “I am free when I decide for myself what concerns me. . . . Self-determining freedom demands that I break the hold of all such external impositions, and decide for myself alone.” 

Something good is in this self-determining freedom. A person who claims independence from an oppressive power—a bully, a domineering spouse, a tyrannical boss—and seeks to define oneself as separate from that power is courageous and dignified. However, if self-determining freedom is taken as the sole correct way to understand authentic living at all times and in all conditions, then we’re living in the world of the monological self. We’ve motored into the cove of inwardness so far that we’ve lost sight of the world outside us, as though each of us travelled further into our own individual inlets as the sun went down, increasingly in the dark, increasingly disconnected from the reality of other people and other things, cut off from God, who speaks but can’t get our attention. Technology—the motor and its gas—feeds the illusion that we’re independent rather than dependent. We’ve ended up in the backwaters of egoism, driving in self-referential circles. 

Hit the ignition and throttle up. We are motorboat people. We ignore the wind. Discerning the movement of the Spirit and adjusting course to his leading is wrong-headed and nonsensical. I decide where I’m going, in conversation with myself. 

The sailboat world where discernment is possible is a world of dialogue. People and things move more slowly in the sailboat world, because conversation takes time: a motorboat person makes a decision; a sailboat person enters into a process of discernment. The sailboat world is a quieter place, where listening is more important than speaking. Even to begin to hear the voices outside yourself—let alone to tell which are of God and which are not—you need to practice being still and quiet. This is prayer. You need to learn how to be a good conversation partner. The sailboat world is relational. 

In this sailboat world in which “being-in-relationship” is the fundamental category defining selfhood, practices related to quiet listening constitute the higher virtues. Everyone knows that good listening requires setting your ego aside in order to open yourself to the thoughts and feelings of an other. While discernment is more than overcoming egoism, it is also no less than that. The good news is that daily life gives us multiple opportunities for overcoming our natural self-preoccupation. If you are a new parent, catching a pungent whiff of your baby’s full diaper presents you with a choice: Will you respond to the need, or will you continue lying on the couch watching Netflix, hoping your spouse will act? A baby’s diaper to a new father; the wind to a sailor; the Holy Spirit to a Christian disciple: all remind you that there are beings and persons outside you, and that these beings and persons make claims on you. Responding to these claims with grace requires setting your ego aside. 

That discernment requires listening and responding means discernment resembles love. Discernment involves attentiveness to an other, and then acting. Love, understood as overcoming egoism, means being willing to do things that you would prefer not to do (see: stinky diaper, above) in response to the needs of others. Both de-centre the ego and re-centre the focus of mature selfhood in our becoming permeable to the claim-making reality of the beings and persons outside us. 

What is it like to overcome egoism, to move from the monological self to the dialogical self? It’s a shift that can come suddenly, even if it’s been building for a while. Or it can be the slow accumulation of new habits that reshape your character over time. In Iris Murdoch’s novel The Bell, the main character, Dora, has the sudden shift of vision, an epiphany, as she takes in the art at the National Gallery in London. The passage is worth quoting at length: 

Dora’s experience has the character of being a conversion into a new world. While Murdoch uses theological language to describe Dora’s epiphany, it’s not an epiphany of the Christian God. Rather, her conversion is from the monological motorboat world to the dialogical sailboat world. Dora was once in the world of solipsism and subjectivity, the monological world, a world that “seemed to be without interest or value.” Gainsborough’s painting is a portal through which Dora enters a new world that speaks. The pictures are real and outside herself; they make a claim on her, and she responds. Dora is now in the dialogical world where discernment is possible. 

As Murdoch the novelist, so Murdoch the philosopher. Following Plato, the story Murdoch tells is of the authoritative reality of the good, and the veil of human self-centredness that occludes our vision of that good. “Unselfing” is her term for overcoming this egoism. In The Sovereignty of Good she says, “‘Good is a transcendent reality’ means that virtue is the attempt to pierce the veil of selfish consciousness and join the world as it really is.” The world as it really is, for Murdoch, is a world where the good is a reality outside ourselves that speaks to us, draws us. That’s the dialogical world in which discernment is possible. 

A further illustration. Skilled people who work with their hands have an embodied experience of the dialogical world. If you build boats, you become aware of the character of different kinds of wood, so that when you have a piece of white oak or a piece of white pine in front of you, you already know its grammar. You know how to listen for what this piece of fir is saying, through the shape of its grain, the location of its knots, and the character of its species: it will tell you whether it will make a good mainmast. You can’t just decide that this piece of fir is suitable—you have to discern its suitability. If you know how to listen, the wood tells you something. It makes a claim on how it’s to be cut and planed. Responding appropriately to what the wood is saying is the outcome of practiced conversation, over time, in that language. This is akin to discernment. 

The sailboat world and the motorboat world offer different visions of selfhood, different accounts of flourishing, and different hierarchies of virtue. It’s only in the sailboat world, with its vision of a dialogical self whose flourishing is found in relationship, and in which the higher virtues have to do with listening and responding to the claims of other beings and other lives—it’s only in this world that discernment is possible. 

You don’t just wake up one morning and decide to do discernment. As the Jesuit writer Mark Thibodeaux says in his book God’s Voice Within, discernment isn’t a technique. It’s not even so much about making choices or tracing distinctions. Thibodeaux says discernment is less about “what to do” and more about “who to be.” 

To learn to discern is to become a discerning person. That sounds banal, maybe even tautological, but it’s the wisdom in Thibodeaux’s observation. To learn to discern isn’t an acquired skill we plug into our already-formed selves, like adding a funny moustache to a Mr. Potato Head. The practice of discernment is itself formative of the kind of person you will be. 

And what kind of person is that? A discerning person is an indifferent person—in the Ignatian sense. Here “indifferent” doesn’t mean careless, bored, or disengaged. It means being so full of desire to do the will of God that my natural egoism with its worldly desires and predilections becomes muted. Indifferent to a particular outcome, I am available to respond to my Christ whom I adore. He speaks; indebted to others who have taught me, I am practiced at listening. I can hear his voice over all the others. 

We don’t do this alone. We help each other listen, help each other recognize his voice. We adjust our sails to catch the wind. 

Meanwhile, out on the open water, a boat speeds toward rocks. The pilot has decided his course. He can’t hear any warnings over the engine noise; many will be hurt in the crash. Hasn’t it always been this way? 

Yes. There is nothing new under the sun. 

And. For those who are called to be discerning people in a dialogical world, our vocation is to listen and to speak. Let anyone with ears to hear listen.