On The Other Side - Daily Love with Mastin Kipp

On The Other Side

tlm icon-1By Caleb Hunter

Returned Citizen


Two weeks ago, I left San Quentin State Prison. Nearly eight years after entering California’s Department of Corrections, sentenced for auto theft, I returned to my hometown to begin rebuilding my life.

There was never a time in my life when I thought I’d be in prison. Prior to incarceration, I relished my career as a tech professional with good friends and living in the incredible city of San Francisco. The experience of going to prison was so vastly different from any other in my life that the whole of my sentence was spent focusing on getting through the next day. While there were thoughts of the future, they were relegated to the background while managing to stay mentally intact in a chaotic environment took up my foreground view.

There was a framework for the future in place. It had built up over time. Return to school, pursue a Master’s Degree, try rebuilding family connections, reconnect with a select few people from my past, nurture a budding relationship. There was no step-by-step plan laid out. Planning is my default mode, yet on this most important issue my post-release future, precious few details had been fleshed out. Even tougher, CDCR isn’t known for helping individual inmates plan for the successful transition from cell to street. How do you prepare people who’ve all-too-often lost all means to shelter or support themselves? The legwork of finding the right plan and resources for reentry is pretty much left up to each incarcerated person to make it happen for themselves.

No amount of planning would ever be sufficient. That’s known beforehand. The knowledge comes from lessons learned in the CDCR. The unexpected must always be expected. All the planning in the world would likely have to be tossed out or it would need to be endlessly flexible to account for the plethora of unforeseen factors like parole conditions, financial resources, and what my parole agent found acceptable. There were times, in the dark of night, when I’d allow myself to wonder how successful I’d be at getting a job or jobs that would allow me to stay in the ever-expensive San Francisco. Or how would I explain a conviction in a job or school application? How do I restart conversation with my estranged family? There were a lot of questions. To avoid stress and letting my mind get too far away from me, I purposely limited those times of speculation.

With the help of The Last Mile, an innovative and unique program educating inmates to become entrepreneurs, I’ve tapped into my core strengths again and am applying myself with a renewed focus and passion. The curriculum is demanding, but it prepares program participants for unique opportunities to be amazing and innovative individuals, free to work in various ventures or to start their own. It’s with the support of The Last Mile that I know that my future will be a bright one.

When I walked out of San Quentin, there was nervousness but also relief. The relief stemmed from having the worst period of my life definitively come to an end. The nervousness was from returning to a life that’s advanced without me being present. Though I didn’t actively think about it, I did wonder what it would feel like to finally leave prison; to be home again in San Francisco after being so far removed from everyday society. I’d watched the city change from afar via newscasts, newspapers and magazines. Though I was previously a tech professional, tech, by it’s very nature, had advanced. I wanted to find my way, but was self-conscious about appearing to be a country boy visiting the big city for the first time.

On the other side, removed now for two weeks I can say that re-immersion wasn’t as tough as I thought it might be. The experience of re-engaging with society has been pretty calm and uneventful. There’s mostly the feeling of needing to reacquaint myself with the changed physical landscape. While some places are the same, many in the downtown core have changed. No one seems to notice but me.

Tech has advanced in my absence. Palm doesn’t make phones anymore, self-checkout is no longer a novelty, and Siri can tell me what the weather is outside.  Map apps are so much richer in their content, and speaking your mind in 140 characters is in vogue. Who would have thought?!

The one thing I’m not, is stressed out. Passing people on the street, I always say hello or offer a nod. Crossing the streets of San Francisco can be a dicey proposition, but it’s made smoother with eye contact with the driver and a little wave. Everyone in a service job, from waitress to cashier gets a heartfelt salutation from me, because it’s such a blessing to just be here. To be able to interact with and connect with everyone from locals to world travelers is a unique opportunity to practice humanism, something we as harried individuals can lose sight of if we’re not mindful.

I’m no longer told what to do or not do; now I’m a citizen: Citizen Caleb. Fully engaged, and wholly responsible to be the best person I can be. Returning home after such an absence is a tough experience, but I’m not alone on this road. I’m blessed to have the support of my loved ones and the network that is The Last Mile. I’ll continue exploring my city, discovering how technology has changed, and strive to find my footing with new and old acquaintances, but know that one thing I’ll have no problem with is positive support while I find my way.


All communications between inmates and external channels are facilitated by approved volunteers since inmates do not have access to the internet. This program is part of The Last Mile San Quentin. Twitter:  @TLM