How Pilgrimage Helped a Business Woman and Fashion Designer Experience Transformation

By Jeannie Carpenter (with Sue Reeve)

Pilgrimage is a Sacred Encounter

Spiritual Director and Pilgrimage Guide, Lacy Clark Ellman, explains that pilgrimage helps us discover answers to “sacred questions,” such as:

Who am I?
Who is God?
Where is God?
What is the meaning of life—
In the bigger picture?
In the day-to-day?
What makes me come alive?
What do I long for?

“Throughout history,” Ellman says, “those who asked these sacred questions with intention and actively engaged the search that burned within set off on pilgrimages: journeys of Sacred Encounter …. These literal journeys … called forth the vulnerability through which Sacred Encounter and transformation often occur.” 

Pilgrimage Enriches the Spiritual Climb

Making a pilgrimage to a well-known sacred site is one requirement for the Certificate in Spiritual Direction Training Program of Sherpa: Guidance for the Spiritual Climb, and in the Sherpa blog, we will regularly explore aspects of pilgrimage. 

In today’s post, we have extracted excerpts of a paper written by Jeannie Carpenter about her pilgrimage to Spain in 2018. (Jeannie’s paper, a requirement for her ATGS Master of Divinity program, is comprehensive and excellent. She received an A+ from Dr. Gill, and if you would like to read in its entirety, Jeannie graciously agreed to send it to you. Contact her at

Introduction to Jeannie’s Journal (Jeannie’s exact words in italics): 

In August 2017, I received an emailed invitation for a spiritual pilgrimage and silent prayer retreat. Dr. Gill, the writer questioned:

  • Are you interested in learning the life stories of three spiritual giants who knew God in an intimate way?
  • Would you like to walk in the very footsteps of Spanish saints who launched spiritual movements that continue to influence the Church 500 years later?
  • And most of all, are you hungry to know God better and to learn to hear his voice today?

All my answers were an enthusiastic “yes!” I had no inkling what a silent prayer retreat would entail, but it did not matter. I was an adventurer with a heart always desiring to move toward God. Could I receive a transformational experience? Immediately, I started researching the life and writings of the three sixteenth-century Spanish mystics: St. Ignatius of Loyola (1491-1556); St. Teresa of Avila (1515-1582); and St. John of the Cross (1542-1591).

Embarking on pilgrimage to a sacred site in hopes of transormation means exploring the unknown—not only to a foreign land such as Spain, but also into the recesses of our own soul. Before, during, and following the Spain pilgrimage, Jeannie asked questions, such as: 

    • What is a contemplative? Do I want to be one? Will I become one, or am I already one?
    • And mysticism? Would I want to be called a mystic? My roots are deep in the Pentecostal movement. Do these terms belong with Eastern religions and New Age cults?
    • I am used to a crowd of vibrant, loud worshippers. What value is a retreat of solitude and silent prayer?

Part 2 of Jeannie’s Pilgrimage Journal:  

  • Day One:  Madrid to Toledo –  Eleven modern-day pilgrims traveling from the northeast, northwest, and mid-south regions of the United States met in Madrid …. commonality of a quest for personal transformation would bind us together in a life-long sisterhood …. We began the tour as physically weary pilgrims, but our spirits were excited with the anticipation of the next ten days.
  • Day Two: Avila – Home of St Teresa, Avila.  Our tour guide pointed out numerous historical and beautiful spots as we walked through the city thinking about the life and times of Teresa and John of the Cross. 
  • Day Three: Segovia – It was quite a trek from the heights of the Alcazar to the cave where St. John, San Juan de la Cruz, spent many hours in prayer. The view of the city was enthralling, but even more captivating was my personal experience in the cave. My emotions were taken captive by the Holy Spirit, and I received a custom designed, supernatural experience that would never be forgotten. 
  • Day Four: Manresa – We arrived at our destination, the Retreat House at the Cave of St. Ignatius. We were introduced to our retreat director, Javier Melloni. I left with his words, “Pray for the grace of inspiration to our transformation.” 
  • Days Five – Eight: Prayer Retreat at Manresa. Our first day’s schedule included one and one-half hours of contemplation of nature in the garden followed by thirty minutes of meditation. The walking breaks would be quiet slow walks in silence focusing on kissing the earth with every step and focused breathing. The total for the day would be six and one-half hours of meditation. One day we visited Montserrat where we saw the image of St. Mary in the Basilica. The next day, Javier led the pilgrims on a trek to the Well of Illumination where Ignatius experienced understanding that made him feel as if he were another man. Dr. Gill explained the “well is always going deeper and wider. It is not finished.” 
  • Days Nine & Ten – We were going to Barcelona. Our first stop was Antonio Gaudi’s Basilica of the Sagrada Familia. Begun in 1882, it remains in process and will not be complete for many years. The Pilgrims shared a final meal and time of sharing. The next morning, nine of the pilgrims left early. One sister pilgrim and I remained together several hours. Earlier we identified each other as extroverts and laughed about the conflict of our natural personalities with solitude and silence. It was fun sharing how we individually processed the pilgrimage. 


One of my travel companions told me a tourist is concerned about viewing things and a pilgrim’s concern is more about the journey and less about the sites. I may have begun the journey to [sacred sites in] Spain as a tourist, but the spiritual transformation will be what remains. 

There will  not be a conclusion to the reflection of my study of the Three Sixteenth-Century Spanish Mystics. My original questions were answered, but the seven months of research invited more. I see a continuous beginning rather than a finale. 

Jeannie’s experience in Spain mirrored mine as well as those of the other pilgrims, several of whom became members of Cohort 1 Sherpa: Guidance for the Spiritual Climb’s first cohort. Friendships forged through shared experiences and individual sacred encounters created deep bonds of friendship as we discovered that pilgrimage to a sacred site is indeed transformational. 

To learn more about how you can participate in a Sherpa pilgrimage, contact Dr. Deborah Gill at ____________________________. Another pilgrimage to Spain is scheduled for 2025. 

Jeannie’s background was in the business world–first as a designer of women’s evening gowns and later as co-owner of athletic clubs. A lifelong Jesus follower, after the unexpected death of her beloved husband Curt in 2014, Jeannie committed to a higher level of spiritual formation. She is a graduate of Sherpa Cohort 1, completed Spiritual Direction Supervision training, and has been on pilgrimages to Spain, Turkey, and Egypt. Jeannie is known as a great friend and cheerleader to those pursuing the “Spiritual Climb.”



2. Cova Saint Ignasi

Jeannie Carpenter