Lessons Learned From My Time At San Quentin

Do NOT read this if you don’t have a teenager or young person in your life that you have concern for.

How listening and emotional sharing can help at-risk youth to avoid prison and manage anger.

I had the privilege to go to San Quentin along with the SQUIRES program on a spectacularly picturesque day this weekend. The setting itself of the prison is breathtakingly beautiful. Once inside the prison walls, the environment is breathtakingly painful.

The SQUIRES program brings inner-city youth, and concerned adults into the prison for a day of face-to-face and heart-to-heart discussions with inmates, with the purpose of keeping the young guys out of the penal system. It is not a scared straight program where the kids get yelled at in their face, but one of sitting in a circle with the inmates, listening to their stories and sharing about one’s own personal struggles. The rules for the participants are to maintain confidentiality, to have respect for self and other, and to be 100% real (a good code of behavior for anyone).

By the end of the day, (and actually, within 10 minutes of being with the inmates we met with) I was completely impressed with the quality of character of these inmate Squires, as they are called.

The inmates very graphically and honestly speak to the kids about what their crimes were (most had killed someone) that got them to San Quentin, and about what life is really like in the prison, day after day for 20+ years and counting.

The most moving and painful part of the discussion was to hear the inmates’ personal stories – usually one of loss, trauma, extreme challenge – that got them into the position to commit a crime in the first place. Many of them had committed crimes as teenagers (including murder) or as young adults, and had already spent more than half their lives in San Quentin.

Each inmate referenced childhood trauma, insurmountable loss, violence witnessed in their family or neighborhood, poverty, insecurity in life, that seemed to lead to hanging out with the wrong people; feeling lonely; escalating drug and alcohol use; making poor decisions. Most had anger issues that had showed up in their attitude, or they did poorly in school; or got bullied and beat up. Several had poor attendance at school; or were always late; or rejected parents and adult figures they felt ashamed of, rejected by, or who had abused them.

Then the inmates got the young guys talking – first inquiring about the challenges they face in their every day lives. Most of the young guys portrayed a sense of cool…Everything is OK. I get in trouble sometimes because of someone/something else. I get mad. But nothing’s too challenging. I’m cool. I ain’t no punk.

Gradually their tone changed. One young man acknowledged “Yeah, I don’t do so well in school. Yeah, I miss a lot of school or get there late. The bus makes me late. (I have to take a longer bus ride so I can avoid the kids who call me names and want to fight at the closest bus stop.) Yeah, I could improve my attitude. I just get mad. But nothing really bothers me… Oh yeah, a cousin of mine was killed a few weeks ago… Oh yeah – and my dad was killed four years ago.” When queried further by the inmate about his mom, he admitted she had died too – the year before his dad did.

I and the other adults in the room silently wept – bearing witness and grieving for this 14-year-old boy who had already suffered so much loss in his short life. No wonder he’s been acting out. We mourned his lost childhood. And the potential dismal future he may have if he keeps getting too close to the edge. Tears ran down my face as I realized I was in a roomful (actually a prison-full) of young and middle-aged men – mostly males of color- with similar stories – most with no outlet for all of that emotional pain.

The inmates were artful in knowing what was underneath the kids’ suppressed anger or the Joe cool attitudes of the young visitors. They probed, shared their own experiences, probed some more, and soon had the kids identifying and speaking more about their own pain. It was beautiful and poignant to see the young guys unfolding about the hurt and trauma they were living currently – and acknowledging that they were trying their best to hide that pain by seeming angry or tough. Best way to protect themselves, that ultimately doesn’t work.

The inmates powerfully made the connection between the underlying emotional suffering, the lack of healthy emotional outlet or true listening, and the outward expression of anger, violence,  addictions that took place for them and landed them in prison. They talked about how important it is to let your emotions out, to give voice to what hurts you, even though the kids clearly did not want to hear that.

After hearing them out, the Squire inmates took us all on a tour of the prison.

I was struck by the beautiful murals on many of the walls outside. And by some inmates who seem to be in their 70s or 80s, hobbling around. I was struck by how, when a death row inmate was escorted nearby us, the inmates (murderers with 20 years to life sentences themselves) with us, had to turn and face the wall – and not look into the face of the shackled presumed psychopath. I was touched by how open and responsive the inmates with us were in answering questions or sharing about their situations. I appreciated the accountability and responsibility they seemed to take for their own actions.

I was struck by the dehumanization that occurs for the prisoners, from the time they are processed in; receive their sentences, and live for years in their cells. It was sobering (and horrible) to go into their cells – realizing the space was smaller than my bathroom at home – in which two men lived and shared a complete lack of privacy. I soaked in the clear blue sky, and wind on my face, every time I was outside, knowing that this was the only sense of freedom the inmates could experience.

I repeatedly noticed my sadness at the waste of human life that occurred here. I was rattled when we walked by the yard where the most recently sentenced inmates were, who were grabbing the fence and yelling threats, pleas, obscenities, at us, like underfed, abused and brutalized animals might. I could see the recent recognition of the misery of their long-term future settling into them. I kept trying to meet some eyes and reflect some warmth, simple human regard and compassion to them. I could meet very few eyes. Some of the young kids on the trip recognized relatives behind that fence. And they cried from both sides of the fence.

We ate a tasteless prison lunch in the chow hall. The adults sought and gave solace to one another for all we had witnessed and felt so far. The Squires sat and ate separately with the boys, getting their impressions, listening and talking more with them. They kept saying they don’t want to see these young men in this place.

We returned to the classroom for more deep dialogue among inmates and kids. More 100% real talk. More listening. More emphasis on the processing of deep wounds and painful feelings. The boys had been profoundly impacted. The adults had been visibly shaken and moved toward deeper understanding.

I felt emotionally drained – and I am someone who is familiar with and used to bearing witness to the deep emotional expression of pain. (I often say my “best days at work“ are when I’ve made people cry and connect with their deepest feelings). This day was heart-wrenching on so many levels. And so uplifting as well, as the boys unloaded, and the inmates presented the incredible deep personal work they’ve been able to do, in the most inhumane of conditions.

Everything they said about their own experience and in relating to the kids was so psychologically sound. I came away thinking they were really decent and beautiful human beings. And hoping against hope that none of the young men with us – who had been equally courageous and open and taken risks to reveal their inner pain – would ever set foot within these walls again and not be able to leave at the end of the day.

After a day “in prison“, I came away with the following lessons and takeaways…truths that are applicable to any young person…

  1. Men in prison have and show a lot of anger outwardly. If you look behind their ‘Wizard of Oz’ curtain, you see underneath that anger there is an even greater amount of emotional pain and hurt – which often goes unseen…And real men cry. And it’s good.
  2. 30 seconds of an adolescent’s bad decision can lead to 30 years of a bad life, once incarcerated. Many bad decisions come from not being able to process painful emotions or experiences adequately.
  3. We all have the capacity to make better decisions and must accept responsibility for our bad decisions.
  4. Listening is a powerful way to help someone else and to help oneself to heal. The Squires knew the value of listening deeply to themselves, to each other, and to the young men to facilitate healing.
  5. Expressing one’s feelings about the frustrations, hurts, losses, aggravations, traumas, pain and suffering is hard but empowering.
  6. Daily morning reflections, breathing exercises, prayer and meditations are a helpful and necessary way of staying sane when one’s basic freedoms do not exist and one has to face a world of chaos.
  7. Helping others to heal from their pain is also healing to the individual who is helping.
  8. Incarceration strips beautiful young men (too many of color) of their dignity and humanity, treat them like animals or objects, and is not a humane way to rehabilitate anyone.

I’d love to hear from you. What takeaways do you get from this blog? What might the Teens in your life be struggling with?

If you have a teen or young person in your life who is struggling and needs help before making too many irreparable bad decisions, please contact me about adolescent or parenting therapy.

For more ideas on how to bring more calm and less worry into your life, click here for a free email course on Mindfulness.

Listening with Heart
Cindi Rivera, MFT
Marriage, Family Therapist
[email protected]
(510) 482-4445


  1. Kennedy Golden on January 24, 2018 at 9:40 am

    Thank you for sharing your day and thoughts with us. How powerful. And, the same rules and situations pertain to our young women- they just end up somewhere else, but they, too benefit from all of the above wisdom.

    Having had a family member in “Q” as he transitioned through to his “long term” placement for 10 years, the reality of this tragedy struck home in reading your words. Oh, if only so many of those who end up there had some support, someone who would listen, and some opening where they could reach out as, or before, they got so deeply into a mess. Although my family member is now out in society, his life (AND THOSE OF HIS FAMILY and friends) has been changed FOREVER. He “found God” while in prison, but that has not undone the damage for anyone. Families were torn apart and young women’s lives changed in ways that impact their ability to be in healthy relationships, to have friends, to trust anyone. Sadly, I believe he needed to spend time thinking about his crimes, but more sadly, I wish that something could have been different within him and he could have had whatever it was he needed so that he would never have done what he did.

    Thank you for your openness to talk about this tough but important day Most of us never have the opportunity to experience this first hand.

    Here’s hoping that it all sank in for those youth who were with you and that they never spend any time there, either for their actions, or even to visit friends and family. (I do have a number of friends/colleagues who spend time at prisons helping inmates in many ways. That is different and badly needed.) Wouldn’t it be wonderful if someday there was less to no reason for prisons? Your post may help us get there.

    Be well, and thank you.

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