John’s first education was at a school for the poor. This was like an orphanage where the children received food, clothes and lodging and were taught Christian doctrine.  Later, he had the opportunity to become an apprentice and learn a trade. While here John was chosen by the priest in charge to be the acolyte in the sacristy of the nearby monastery of Augustinian nuns. He did not seem to have an aptitude for any trade but Don Alonso, the director of the hospital, noticed his great gentleness and patience for the poor who had infectious diseases. John was employed there, nursing with great compassion the poor people whom others did not wish to come near. Don Alonso continued to take an interest in John and had him enrolled in the Jesuit school where he would be given an excellent education, obtaining a knowledge of grammar, rhetoric, Latin, Greek and the Spanish Classics – tools which would facilitate his later work as a Spanish poet.

At this time it looked as though John might, with Don Alonso’s patronage, be ordained and become the chaplain to the hospital, which would lift his mother and brother out of their poverty. However instead, in 1563, at the age of twenty one he entered the newly founded monastery of the Carmelites at Medina del Campo. Perhaps he was drawn to the contemplative life.  His devotion to Mary already had a significant place in his spiritual life. After his novitiate year he was sent to Salamanca University to study philosophy and theology. The professors at Salamanca at this time were among some of the most brilliant and renowned scholars in Europe. During his time at university John was noted for ‘his outstanding talent’ and reliability and so was made prefect of studies while still a student.

John became dissatisfied with the academic world of intellectual brilliance with its temptations to ambition and self-excellence. It was this that had moved him to ask to be admitted to the Carmelite Order. He began to think of the Carthusian life but God’s providence however, continued to bless John. St.Teresa was at this time in the city making arrangements for her second foundation of the Reformed Carmelites at Medina del Campo. She had permission from the General to found a monastery of Reformed Carmelite Friars who would minister to the spiritual needs of her nuns and she was looking for vocations for this new venture. She had one, Fr. Anthony of Jesus, the Prior of the monastery of the Carmelites of the Ancient Observance in Medina, but then she met John and was struck with his exceptional qualities and his desire for a more recollected life. Teresa persuaded him to join her friars, pointing out the advantages of living a more contemplative life while remaining within the Carmelite family. St.Teresa was not disappointed with her diminutive little friar for John was very short in stature; his virtues and his gifts for guiding souls to perfection were immensely valuable, not only for Teresa’s nuns but for all those who came to him for help.

Some people have misunderstood St. John of the Cross’s personality. He has come across to some as inhuman in his insistence on negation and complete detachment. Possibly this has come about by their reading some of his writings such as the Ascent of Mount Carmel and the Dark Night, which deal with the radical purification and prolonged spiritual darkness that chosen souls have to undergo before the soul can reach perfect union with God. These works are often read without a proper understanding or without balancing them with John’s sublime spiritual poetry about the soul’s passion for God and the commentaries he wrote for these poems. John was in fact a very gentle and humane person and he condemned any type of excessive penance that did not result in helping a person to become more gentle, humble and Christlike. Incidentally, St. John of the Cross ranks as one of Spain’s most distinguished poets.