Sailing / rowing

By Harp, good trouble substack

"Your soul is a boat—with both oars and a sail." — Tim Keller

 I've been sailing once in my life. I pastored a church in Oklahoma City, and one of my parishioners fancied himself a sailboat captain. One afternoon, he invited me out on his boat. Lunch packed, we drove to the marina and set sail. Sort of.

After a quick nautical lesson and a new vocabulary [bow, stern, port, starboard, mast, boom, beam reach, broad reach, and running], we put out in the water. Except, there was no wind. Ever. We sat in the hot Oklahoma sun for hours. It may be the only windless day on record in the Sooner state.

It was miserable.

And yet, despite my sailing fail, the activity is incredibly symbolic. Tim Keller once used a sailboat to give a vivid pastoral metaphor—a diagnostic tool disguised as a parable for the soul. Keller's "Which Boat Describes You?" is deceptively simple, but like all Kellerisms, it opens a door into the heart. It blends biblical wisdom, soul-care, and practical theology with the precision of a seasoned pastor who wants you to make it home.

Let me offer a few reflections that may be helpful as you integrate or consider this framework in your own life and ministry…

The Four Boats: A Diagnostic for the Soul

Keller envisioned our souls as being boats, and we have both a sail and oars. And we are all in one of four positions:

You're Sailing – The Wind is at Your Back

This is a soul at rest and in rhythm with the Spirit. This rest and rhythm is not spiritual triumphalism, it is spiritual vitality. The Word is alive. Prayer is sweet. The wind of God's presence is real. In this state, obedience flows from delight, not duty.

The by-product of sailing:

So, where is your heart/soul? As I reflect on these four positions, I confess that I feel as if I have been rowing for the last two years, especially when it comes to leading my wife and children well. Disciplines and rhythms are in place, but they often feel dry and disheveled. 

Joy is hard fought, and the smallest irritation destroys what peace I fight for. 

In some ways, the church has lost its wonder. My mind wanders when it should be focused on worship.

Instead of running my race, at times, I am crawling.

But, I am crawling forward. And I am crawling with others. In fact, it is the others that keep me going.

Here is what I've noticed about drifters and sinkers: the vast majority of them drift and sink alone. And the vast majority of rowers and sailors row and sail with others.

My encouragement... If your boat is in trouble, don't wait for the wind or white-knuckle the oars. Instead, reorient—steer your soul into community. Cry out to the crowded waters where saints sail and row side by side.

It is in the presence of God and others that grace fills the sails again.

Rowing with you and towards you,

— Harp

https://open.substack.com/pub/charper/p/hows-your-heart?r=43vew&utm_medium=ios