He came to the monastery and became a novice when he was about 16 years old, and when he died in 649 he was the monastery's abbot. He wrote a number of instructive books, the most famous of which is The Ladder of Divine Ascent. (It is because of this book that John is known as "Climacus", which means "of the ladder".) It describes how to raise one's soul to God, as if on a ladder. This book is one of the most widely read among Eastern Orthodox Christians, especially during the season of Great Lent which immediately precedes Easter.
An icon known by the same title depicts several people climbing a ladder; at the top is Jesus, prepared to receive the climbers into Heaven. Also shown are angels helping the climbers, and demons attempting to shoot with arrows or drag down the climbers, no matter how high up the ladder they may be. Most versions of the icon show at least one person falling.