John of the Cross
Joining the Reform of Teresa of Ávila

John was ordained as a priest in 1567. He subsequently thought about joining the strict Carthusian Order, which appealed to him because of its practice of solitary and silent contemplation. His journey from Salamanca to Medina del Campo, probably in September 1567, became pivotal. In Medina he met the influential Carmelite nun, Teresa of Ávila. She was staying in Medina to found the second of her new convents. She immediately talked to him about her reformation projects for the Order: she was seeking to restore the purity of the Carmelite Order by reverting to the observance of its "Primitive Rule" of 1209, which had been relaxed by Pope Eugene IV in 1432.

Under the Rule, much of the day and night was to be divided between the recitation of the Liturgy of the Hours, study and devotional reading, the celebration of Mass and periods of solitude. In the case of friars, time was to be spent evangelizing the population around the monastery. There was to be total abstinence from meat and a lengthy period of fasting from the Feast of the Exaltation of the Cross (14 September) until Easter. There were to be long periods of silence, especially between Compline and Prime. Simpler, coarser, and shorter habits were to be adopted. There was also an injunction against wearing covered shoes (also previously mitigated in 1432). That particular observance distinguished the " discalced ", i.e., barefoot, followers of Teresa from traditional Carmelites, and they would be formally recognized as the separate Order of Discalced Carmelites in 1580.

Teresa asked John to delay his entry into the Carthusian order and to follow her. Having spent a final year studying in Salamanca, in August 1568 John travelled with Teresa from Medina to Valladolid, where Teresa intended to found another convent. After a spell at Teresa's side in Valladolid, learning more about the new form of Carmelite life, in October 1568, John left Valladolid, accompanied by Friar Antonio de Jesús de Heredia, to found a new monastery for Carmelite friars, the first to follow Teresa's principles. They were given the use of a derelict house at Duruelo, which had been donated to Teresa. On 28 November 1568, the monastery was established, and on that same day, John changed his name to "John of the Cross".

Soon after, in June 1570, the friars found the house at Duruelo was too small, and so moved to the nearby town of Mancera de Abajo, midway between Ávila and Salamanca. John moved from the first community to set up a new community at Pastrana in October 1570, and then a further community at Alcalá de Henares, as a house for the academic training of the friars. In 1572 he arrived in Ávila, at Teresa's invitation. She had been appointed prioress of the Convent of the Incarnation there in 1571. John became the spiritual director and confessor of Teresa and the other 130 nuns there, as well as for a wide range of laypeople in the city. In 1574, John accompanied Teresa for the foundation of a new religious community in Segovia, returning to Ávila after staying there a week. Aside from the one trip, John seems to have remained in Ávila between 1572 and 1577.

At some time between 1574 and 1577, while praying in a loft overlooking the sanctuary in the Monastery of the Incarnation in Ávila, John had a vision of the crucified Christ, which led him to create his drawing of Christ "from above". In 1641, this drawing was placed in a small monstrance and kept in Ávila. This same drawing inspired the artist Salvador Dalí 's 1951 work Christ of Saint John of the Cross.
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