Facing an eight-year prison sentence, Alex Senegal wasn’t planning to become an ambassador for the Enneagram or one of its most compelling proponents. But that’s exactly what happened. And the awakening – if we can call it that – came at a particularly low point in Senegal's life. “I was drowning in guilt and shame when the Enneagram came into my life,” he says.  

At this point, Senegal had already spent over 20 years of his life incarcerated on drug and assault-related charges. Released from prison after his last 13 year stint, he swore that he would never repeat the behaviors that landed him behind bars. For a while, he lived up to these promises. Senegal worked hard to build a new life, cleaning up and graduating college. He became a drug and alcohol counselor and worked at the Salvation Army as part of their intake team. He became one of the leaders in his church. 

But after 10 years on the straight and narrow, Senegal slipped. Every destructive behavior he had before his transition came roaring back. Eventually he got busted in possession of a large amount of drugs and wound up back in jail, this time with an eight-year sentence. “I ended up locked up with people who I had counseled! I felt ashamed, betrayed by myself, and confused. I had a sense of total hopelessness. My biggest question was “Why on earth did I do that?” And I had no answer.”

“That seems like a cult!”

To listen to Senegal speak today, you would never know that he had the cards stacked against him from a young age. He tells his story with the wisdom and clarity of a community elder, not a former criminal. But as he shares his story, it becomes clear he was never going to have an easy path in life.

Senegal’s mother put alcohol in his baby bottle to keep him quiet. By the time he was five years old, he was an alcoholic. The oldest son of six siblings from four different fathers, he grew up in a chaotic household in Compton, Los Angeles and fell into the gang scene there. He was running the streets by the time he was seven years old. “I grew up with a lot of self-doubt and neglect,” Senegal recalls. “I was raised in a violent household, so I stayed away from home as much as possible. I got involved in gangs, and I started to link my value to my ability to be violent.”

Fast forward to his relapse and now facing another eight-year prison stretch, Senegal was persuaded by a chaplain friend to give himself another chance. Unsure of the path forward, he began taking classes as part of the Regimental Correction Program. “One day, this little white lady with a poster showed up. She was teaching the Enneagram, and I remember thinking, “I’m not taking that class… That seems like a cult!” The Enneagram symbol made me uncomfortable at first.” 

But an intuitive voice inside him said, “No. Take that class.” He wrestled with himself, going back and forth, until he eventually pushed open the classroom door and walked in. That open door became his introduction to the Enneagram, and he began attending Susan Olesek’s weekly self-awareness training program at Elmwood Correctional Facility in Santa Clara County. 

That’s when everything changed.  

The Enneagram Prison Project is Born

The “little white lady” with a poster is a force of nature. In 2007, Susan Olesek learned the Enneagram in a parenting class and was struck by the power and depth of the system. She never intended to teach the Enneagram in jails, but her open heart led the way. “In 2009, when I was approached to bring the Enneagram to the inmates of Cleveland Correctional Facility in Texas, everything in my heart said “yes!” I am what they call an Idealist, the Type 1 on the Enneagram and so a prison, of all places, felt like the right place to be.”

Olesek’s instincts proved right. Over 100 residents attended her very first class. Despite being inexperienced and newly certified to teach the Enneagram, she knew she had found her calling. “As soon as I set foot in the prison, I knew I wanted to come back again and again. What came crystal clear to me as I spoke in that first session was how we are all in a prison of personality. And it was so powerful because I was explaining this metaphor to a room full of people who were literally in prison, and navigating the confines of their own minds.” 

From crisis to opportunity

After that pilot program in 2009, Olesek continued teaching at the prison just outside of Houston, Texas, commuting two or three times a year from her home in California. But in 2012, the prison’s administration decided to stop using the Enneagram and use the Myers-Briggs personality system instead. Olesek was devastated because her Enneagram prison training had become one of her favorite things to do. But her termination turned out to be a blessing in disguise. 

“I would have stayed happily, supporting that one program offering the Enneagram a few times a year for a weekend at a time. But after being replaced, I began Googling prisons and jails in the Bay Area,” Olesek says. 

In 2012, she found a jail called Elmwood Correctional Facility just a few miles from her house in Los Gatos, California. After multiple meetings, she was offered the opportunity to run a pilot class on a volunteer basis. This is the class Senegal attended. 

The real work began

With Senegal, the unlikely student, and Olesek, the inexperienced teacher, the real work began. Alex struggled to find his Enneagram type but eventually recognized himself as a Type 9 when he was asked, “what do you need right now?” and couldn’t answer.

“The self-forgetting part was what hit home to me that I am a Type 9,” Senegal says. “The Enneagram introduced Alex to Alex. Before learning the Enneagram, I really didn’t know myself.”

Layer by layer, habit by habit, and gift by gift, Senegal befriended himself. Like many Type 9s, Senegal had grown up with no clear identity. He didn’t know who he was. In the violent environment he was raised in, he became violent to fit in. 

The Enneagram showed him what was right about himself and gave him a light to follow. “The Bible tells you to change, but it doesn’t tell you how to change. The Enneagram gave me some practical tools to become the best version of myself. The system showed me what was good about me, which was a big departure from the regular narrative of what was wrong with me.”

The hustle for investment

While Senegal was proving the effectiveness of the training, Olesek was hustling hard to keep the program going. 

In 2012, she created a name for the program, the Enneagram Prison Project (EPP), and filed to be recognized as a 501(c)(3) not-for-profit organization. Only now, Olesek began to feel like a human bridge. She would leave her volunteer position at the Elmwood Correctional Facility and change out of her EPP shirt into a blouse in her car. She would then take the same curriculum, with a different branded poster, to teach at a Silicon Valley mansion or a Fortune 500 company.

“Eventually we applied and were awarded a $280,000 grant spread out over three years from Santa Clara County. Up until then, all of our work in the prisons had been pro-bono. This is really when EPP started to walk on its own,” Olesek says. 

After that initial grant, the stars started to align. In 2013, a Harvard-educated businessman named Lance White was in the audience when Olesek and her ambassadors presented at the Denver International Enneagram Association Conference. White was in the process of selling his business, and EPP’s presentation made an impact on him. “After I saw Susan’s presentation, it stayed with me. I kept thinking about it, and I could see the depth and the breadth of where it could go. I thought of it as investing not just in the future of the EPP but in the future of the world.”

Democratizing the Enneagram

EPP had special resonance for White. In 2003, his 17-year-old son was sentenced to 10 years in prison. He knew the pain and the confusion of the incarcerated and their families. White and his wife went on to become EPP’s first investors, and White currently sits on EPP’s Board of Directors.

But beyond prisons, White aligned with EPP’s goal of democratizing the Enneagram. “All of our programs are donation based because we want everyone to be able to learn these valuable tools. Some inmates go on to become guides, and they want to get certified to teach the Enneagram. But how do they pay for that when they are also trying to figure out how to pay their rent? The goal of EPP is to make this curriculum available to everyone who wants it. ”

To date, over 5,500 residents have participated in EPP programs. The program’s success is measurable: early statistics taken in 2015 revealed the recidivism rate (the rate at which people return to prison) to be under 10%, far lower than the U.S. national average of 44%. And with any student who took the EPP program more than once, the recidivism rate drops even lower.

Says White, “If we can ensure that those who leave the prison don’t come back, there’s a payback in that. Whether you are politically liberal or conservative, there is a business case to want the Enneagram in prisons. We’re taking the Enneagram programs to high school students now, too. We’re trying to reach people before they end up in prisons.”

Senegal’s story serves as the model for what is possible. He qualified for early release and currently serves on the EPP Board and as an EPP Ambassador. EPP Ambassadors are formerly incarcerated men and women who used the Enneagram training to turn their lives around. They act as change agents, providing hope and inspiration not just for those still behind bars but for all who seek a more compassionate world. “I would not have a heart of compassion if I hadn’t been through what I’ve been through,” Senegal says. 

Learn more about the Enneagram Prison Project and listen to Alex Senegal’s interview for Freedom Beyond Bars.

Truity provides free or low-cost career and personality assessments for charities, nonprofits and schools that are focused on helping people find their paths, including The Right Way Foundation, which provides programs for foster youth that support successful employment and healing, Project WeHOPE, which supports services for the un-homed and The Last Mile, which provides opportunities for personal and professional growth for justice-impacted individuals. For more on Truity's nonprofit program or to apply, visit here.

Lynn Roulo
Lynn Roulo is an Enneagram instructor and Kundalini Yoga teacher who teaches a unique combination of the two systems, combining the physical benefits of Kundalini Yoga with the psychological growth tools of the Enneagram. She has written two books combining the two systems. Headstart for Happiness, her first book is an introduction to the systems. The Nine Keys, her second book, focuses on the two systems in intimate relationships. Learn more about Lynn and her work here at LynnRoulo.com.