Saint John of the Cross begins the commentary on his poem with these words:

Before embarking on an explanation of these verses, we should remember that the soul recites them when it has already reached the state of perfection — that is, union with God through love — and has now passed through severe trials and conflicts by means of the spiritual exercise that leads one along the constricted way to eternal life, of which our Savior speaks in the Gospel (Mt. 7:14). The soul must ordinarily walk this path to reach that sublime and joyous union with God. Recognizing the narrowness of the path and the fact that so very few tread it — as the Lord himself says [Mt. 7:14] — the soul’s song in this first stanza is one of happiness in having advanced along it to this perfection of love. Appropriately, this constricted road is called a dark night, as we shall explain in the later verses of this stanza. The soul, therefore, happy at having trod this narrow road from which it derived so much good, speaks in this manner:

One dark night, fired with love’s urgent longings — ah, the sheer grace! — I went out unseen, my house being now all stilled.

John here sets up the big picture: if the goal of our lives is union with God through love, how are we going to get there? What path should we follow in order to arrive at this union? John tells us that, ordinarily, the soul must walk through what he calls a “dark night.” Doesn’t sound very inviting right off, does it?

When I was very young, maybe five or six years old, some of my brothers tried to encourage me to try water skiing. We lived on a lake and had our own ski boat. My brothers, all older than me, were accomplished skiers, and in their enthusiasm for water skiing, they wanted me to learn.

I had watched them ski often, and it did look fun, but I had a fear of the water that bordered on dread. I knew what it would take to get up on the skis: more than likely, it would involve at least a few false starts, getting dragged through the water at high speeds, face first, water down the nose, etc. This was not my idea of a good time. When I was younger, I had been playing in waist-deep water at our beach with some friends of the family. One particular man thought it would be funny to dunk my head underwater to see how I would react, so he did, and he held my head under for what seemed like an eternity. It’s hard to describe the panic I felt that day, and this probably was at the heart of my reluctance to try water skiiing.

At any rate, I couldn’t grasp why my brothers were so insistent that I try it. I wasn’t a brave kid, and if I could avoid pain, I would always choose that route. To me, the joy of water skiing just wasn’t worth it. “Maybe another time” was my constant refrain.

Eventually — by some means I do not recall — they prevailed upon me to try. I did have some false starts, but one time I refused to let go of the rope, ignoring the evidence around me that I would not succeed. When I did rise out of the water, I experienced a joy I had no way of anticipating. Part of the joy was knowing that I had passed through an obstacle that had held me back for months from this experience.

At some subconscious level, every time I am facing a challenge I don’t feel equal to, or that I would rather avoid, I recall what it felt like to get up on water skis for the first time. Before I did this, the only sort of freedom I knew was the freedom of not having to face the fear. I had no idea how this would pale next to the freedom that would come from overcoming the fear.

So, from this simple experience, I can imagine why John recommends the dark night, and why Christ tells us to follow the narrow road: it is the path to true freedom.