I have one, and only one, experience with sailing.

In my senior of college, one of my friends invited a number of us to his family’s lake house near the coast of North Carolina for one last weekend together before graduation. The house sat on a cove tucked just off the ocean shore. Down by the water sat the family’s beautiful (and expensive) two-person sailboat, tied firmly to a post.

The more experienced went out first. Several of my classmates had grown up close to the ocean, and knew how to handle a sail. They raced up and down the cove, making it look easy. When they were done, another first-timer and I stepped up to take the ropes. Once we pushed ourselves away from shore, we swung and tugged, leaned and lunged, stood and sat — and barely moved. The others, of course, took even more joy in our floundering than they had in their sailing. After a while, our titanic struggle left us tired and hungry, so we pulled the boat ashore and went in for dinner.

Early the next morning, a couple of aspiring sailors woke us, asking where we left the boat. “Down by the shore, of course. Where else would we leave it?” “Did you pull it into the grass?” “Umm, no.” “Did you tie it up?” “Umm, no.” “Well, the boat is gone.” Any experienced sailor (or just a man of common sense) knows what I learned that day: the tide rises at night, so you have to anchor your boat or it will drift away. I immediately started counting every dollar I owned. (It didn’t take long.)

A couple of us went out in the motorboat, driving up and down the shore, desperately looking for any sign of the sailboat. Surely it had been damaged, maybe even destroyed, after all these hours. After another hour or two, we’d come up empty. We saw nothing. And no one we saw had seen anything. I still remember the long ride back. I was sick to my stomach.

That boat came to mind again recently when I read Tim Keller describe a tool he used over the years to help him discern the health of a soul (and particularly the health of a person’s prayer life).

Which Boat Describes You?

Keller paints the nautical picture this way: “Imagine that your soul is a boat, a boat with both oars and a sail” (Prayer, 258). Into that scene, he asks four pointed questions: Are you sailing? Are you rowing? Are you drifting? Or are you sinking? In terms of my story, does your spiritual life resemble my master-sailor friends gliding up and down the cove, or the two first-timers working hard and going nowhere, or the empty sailboat drifting aimlessly away?

The tool’s helpful in two directions. First, it helps us assess and maintain our own boats. How often have we assumed that we’re rowing when we’re actually drifting, or that we’re drifting when we’re actually sinking? Second, the tool gives us a window into the boats of others. It’s a simple, vivid question that cuts through shallow places (where we often prefer to swim in our relationships) to the heart of a person, to how he is really doing.

Keller doesn’t attach particular texts to the four different boats, but the Psalms came to mind as potential examples because they model, with unusual vulnerability and emotion, the highs and lows of the human soul. So I’ve attempted to identify at least a few lines that give voice to each of these four spiritual conditions.

1. Are You Sailing?

When you think about your spiritual life right now, do you feel the wind at your back? Does prayer feel easier and more enjoyable than normal? Does daily Bible reading sparkle like a treasure in the field? Do you find yourself on Monday, Tuesday, Wednesday actually looking forward to Sunday morning and the opportunity to sing and serve with your local church? Do you find spiritual conversation natural and gratifying?

If you’re currently in the sweet thrill of sailing, you might pray like King David does in Psalm 16:6–9:

The lines have fallen for me in pleasant places;
     indeed, I have a beautiful inheritance.
I bless the Lord who gives me counsel;
     in the night also my heart instructs me.
I have set the Lord always before me;
     because he is at my right hand, I shall not be shaken.
Therefore my heart is glad, and my whole being rejoices;
     my flesh also dwells secure.

As we’ll see, David didn’t always feel this kind of spiritual high. He often struggled and had to fight hard for faith. At times, he fell into valleys of despair. In these verses, however, we can almost feel the wind lifting and driving his sails. Anyone who’s riding a spiritual breeze can identify with what he’s describing, and anyone who isn’t would want what he’s experiencing.

2. Are You Rowing?

If you’re rowing, you’re still making progress, but it’s a slower, hard-fought progress. You’re moving forward, but you’re really earning each passing wave. “Rowing,” Keller writes, “means you are finding prayer and Bible reading to be more a duty than a delight” (259). They’re chores you keep doing, but they honestly feel like chores. You keep attending worship, and discipline yourself to listen, engage, and even sing, but you often walk out distracted and tired. You want your heart to be in a different place, and you put effort into feeling differently, but you haven’t felt a strong wind in a while.

If you’re currently in the wearying work of rowing, you might pray like David does in Psalm 63:1:

O God, you are my God; earnestly I seek you;
     my soul thirsts for you;
my flesh faints for you,
     as in a dry and weary land where there is no water.

“The vast majority of drifters and sinkers drift and sink alone.”

In these verses, he’s not praying from the pleasant places of Psalm 16. Now he’s kneeling in the wilderness — “in a dry and weary land where there is no water.” But as the spiritual winds died down and the ground under him dried up, he didn’t give up and lie down in the boat. No, he kept his eyes on God and started rowing: “Earnestly I seek you.”

3. Are You Drifting?

From a distance, drifting may look and feel like rowing, but swim up closer to the two boats and you’ll notice one massive difference: effort. The drifter stops trying. You stop praying earnestly. You stop reading the Bible regularly. You stop paying attention during church gatherings (or stop attending altogether). Tired and discouraged and maybe even disillusioned, you set your oar aside and passively wait for some gust of wind to come along to save you.

This condition is probably the hardest to pair with a psalm, mostly because the psalms themselves are prayers. So even at their darkest, they model what it looks like to row in the dark — to keep praying, keep gathering, keep seeking. But in Psalm 42, dangerous circumstances have prevented the psalmist from attending the temple (“When shall I come and appear before God?” verse 2), so though he’s still able to pray, he’s cut off from other vital means of grace.

When shall I come and appear before God? . . .
These things I remember,
     as I pour out my soul:
how I would go with the throng
     and lead them in procession to the house of God
with glad shouts and songs of praise,
     a multitude keeping festival.
Why are you cast down, O my soul,
     and why are you in turmoil within me? (Psalm 42:2, 4–5)

The drifter has desires for more, and he can remember times when he experienced spiritual health and community, but he’s lost the will to keep fighting. His soul is cast down, and so his boat wanders aimlessly, from app to app, from show to show, from task to task, from meal to meal, from week to week. He wakes up farther and farther from where he wants to be spiritually, and yet with less and less resolve to change course.

4. Are You Sinking?

Is the boat within you quietly taking on water? You drifted for a time, but then you hit something hard — a job loss, a breakup, an illness, a death — and water started trickling in. Now, weeks or months later, your faith is gasping for air. You’re not longing for former days of stronger, more satisfying faith. You’re questioning whether it was ever real. You’re not thinking about restarting your prayer life, or looking for a Bible-reading plan, or joining a small group. You’re looking elsewhere for answers (or you’re avoiding the questions altogether).

Again, even psalmists dealt with sinking moments in the soul. Listen to the heartache and despair in Asaph’s voice when he thinks back on a dark night in his own soul:

All in vain have I kept my heart clean
     and washed my hands in innocence. . . .
But when I thought how to understand this,
     it seemed to me a wearisome task. . . .
When my soul was embittered,
     when I was pricked in heart,
I was brutish and ignorant;
     I was like a beast toward you. (Psalm 73:13, 16, 21–22)

He remembers a time when he was living in spiritual peril. Do you feel your heart slowly growing embittered to God? Has your pain crystallized into self-pity? Has confusion mutated into bitterness and resentment? Have your doubts ripened into apathy? Is your boat filling with water?

Obviously, any boat that’s sinking needs some serious attention. One of the blessings of a tool like this is simply putting a sinking boat on someone else’s radar. How many souls sink without anyone ever knowing, at least until it’s too late?

Drifting and Sinking Alone

Later that long day, when we had nearly given up hope finding my friend’s sailboat, a neighbor from down the cove phoned. It had landed on their shore. Amazingly, no damage. The boat had drifted more than a mile.

For all our failures aboard that extraordinarily expensive piece of fiberglass, my first-timer friend and I did one thing right that day: we went out together. When it comes to our spiritual health and joy, the vast majority of drifters and sinkers drift and sink alone. And the vast majority of rowers and sailors row and sail with others.

Keller ends his book on this note:

Those who enjoy sailing might find these nautical images helpful. However, a metaphor used more often in the Bible to describe fellowship with God is that of a feast. . . . Eating together is one of the most common metaphors for friendship and fellowship in the Bible, and so this vision is a powerful prediction of unimaginably close and intimate fellowship with the living God. It evokes the sensory joys of exquisite food in the presence of loving friends. The “wine” of full communion with God and our loved ones will be endless and infinite delight. (260–61)

The image of the feast gets at the satisfying fullness of sailing. It also gets at the togetherness, though. Somebody might eat alone, but nobody ever feasts alone. And, spiritually speaking, nobody sails alone either. Richer communion with God requires richer communion with other souls, in the church.

So, if we feel ourselves drifting or worse in our walk with God, our first step to righting the ship will be to steer our boat into more crowded waters, where the sailors and rowers live.