William “Jack” Stephens ‘77

William “Jack” Stephens ‘77

Often it takes years for alumni to reconnect with St. Johns. This was certainly the case with Jack, but once he and the School were reconnected, boy did he have a story to share. He describes his time at St. Johns as an escape from his life outside school. He built relationships with peers and teachers and worked hard to keep up with the demanding academics. Jack recalls Miss Edith Cowles who taught English and was his homeroom teacher senior year, “She was known as being tough, but I enjoyed being a storyteller and she made it a challenge.” 

After graduating, Jack went to Jacksonville University where he majored in marketing and economics. He had one goal—to find a good-paying job. He found that job in distributing and logistics in Jacksonville, and he also found his wife, Cindy. Jack and Cindy inspired each other to explore, so a few years after college they both quit their jobs and left for a 30-day trip to Alaska. They spent the next six years there and started their own marketing distribution company. 

Jack and Cindy’s life in Alaska didn’t alleviate their need to travel and explore the world. They enjoyed different landscapes and moved from here to there only allowing themselves a few years in each place. When they were in their thirties, they decided to slow down and Jack pursued a career in the pharmaceutical industry. He became an executive vice president for Express Scripts, a pharmacy benefits management organization, and was a private industry consultant for the Drug Enforcement Agency in Washington D.C. At this point, he and Cindy resided in Dallas and he spent many days on the road away from home. 

By their mid-forties, Jack and Cindy were about to move yet again—this time to Albuquerque, New Mexico—when a life-changing tragedy changed the entire course of their lives. Jack’s wife was in a terrible car accident on the highway. Cindy recovered after suffering multiple life-threatening injuries, but the life she and Jack had been living changed drastically. They sold everything, gave up their careers, and moved to Argentina, where they have lived now for the last fifteen years. They spent their first nine years living in wine country, where Jack explored different interests and hobbies, including coding a website, publishing writing pieces, and building his own home in the Andes Mountains. 

Jack published his first novel, Where the Green Star Falls, in 2017, and he quickly started getting letters from people all over the world wanting to know more about the characters. Since then, he has released another novel, Andalusian Legacy: The Complete Novel. He has sold the rights to these novels and an upcoming third novel to an executive producer in Hollywood and looks forward to continuing to write about adventures and emotions from his own experiences because, as he puts it, “writers influence lives.”

Jack and Cindy still live six months out of the year in Argentina and the other half of the year in Alabama surrounded by friends and family. His advice for having it all and changing course is  “Don’t be afraid to learn things. Don’t feel like you will be stuck in your profession for the rest of your life. I kept growing and changing until I found something that made me happy because what I wanted in life kept changing.” He also emphasizes the importance of learning another language. “I’ve been fortunate to accumulate friends from all over the world and the ones who are most successful and make the most interesting companions are those who speak several languages,” he says. “The world is a very big place and only 13% of it speaks English! I believe the young leaders who will truly change this world for the better, are the ones who can converse with, and understand people from other cultures.” 

 St. Johns is thrilled to have reconnected with Jack and is excited to see where his next adventure takes him as a published author!