This article was written by Tommy Winfrey, a graduate of The Last Mile prison education program. He is an artist and aspiring web designer, with an eye on the future.


On May 11, 2017, I walked out of San Quentin State Prison as a free man after two decades of incarceration. The world has changed immensely in so many ways since I left. The biggest difference for me has been the evolution of technology during the past twenty years. My first time on the internet was the day of my release.Thankfully I was prepared. My preparation involved several invaluable principles that have been been the roadmap to my successful reentry into society.

  1. Focus on the positive: I remained focused in prison and did not get distracted by the negative influences that I encountered on a daily basis. In prison, if you have focus and purpose, you will get respect.

  2. Follow your passion: I also learned that I need to follow my passions in life, and I realized that I loved art. Every day, even in prison, I would wake up excited to see what I could create. Yes, its possible to be excited every day, even in prison.

  3. Leverage opportunities: I learned front end computer coding and web design. I was apprehensive about my ability to grasp the concepts, however I knew that these skills would be key to my future success.

  4. Build your Confidence: I lacked confidence when I first entered prison, but I knew that I had to overcome my fears if I was going to become a successful small business owner on the outside. I was encouraged by volunteer mentors, and my fellow inmates.

  5. Unyielding determination: My journey through the prison system taught me that it takes determination to succeed. It took hard work for me to change my life on the inside, a quality I know will make me effective on this side of the wall

  6. Create a network: I had to build a network of positive influence in prison to help shield me from all of the negative. I also met many volunteers, who were willing to dedicate their time to my success. Who knew that I would meet Mark Zuckerberg inside prison? He visited San Quentin and listened to my story. This network has continued to evolve since I have been free.

  7. Learn from experience: I know it sounds crazy, but I am thankful for the time I spent in prison. It really helped me get my life together. I was lost and confused, and on a path to destruction. Sometimes I think that if I hadn't gone to prison I may not be alive today.

  8. Seize the day: I wake up every day inspired to create. I am no longer the same young kid that walked in those prison gates years ago. I brought that zest for life to my new home, and I hope people can appreciate and benefit from it.

My transition has not been the easiest. Life has thrown its curve balls at me. However, I have dealt with them. The tools I have learned have allowed me to deal with stress and disappointments, and stay on a positive path.

As an artist my passion lies in creating, and my drive to build my own business is wrapped up in this passion. Tommy Winfrey Art is a digital design and web development firm that I founded.

I know this new leg of the journey has just begun for me, but I see my future and it looks bright. I'm committed to making my business work. Today, I define my life by the choices I make; to work hard, live right, and enjoy life.

Design and development are more than just passions of mine, they are a way of life.