Volunteering With The Last Mile

A few months ago I applied to volunteer at The Last Mile which is a program that works with prisoners to help them build relevant skills in technology and other areas so that they can more easily transition to productive employment once they are out of prison. It all started after hearing Catherine Howe of Defy Ventures speak on the Reboot Podcast (one of my very favorites). Everything she was saying resonated so deeply with me, I knew immediately I had to figure out how to be involved with this type of reform. I actually applied for a job and applied to volunteer (I was incredibly eager), but never heard back. Now that I knew such programs existed, I wouldn’t take no (or no response) for an answer. I continued to google and that is when I came across The Last Mile. The program seemed like a great fit, and they were responsive!


A week later, we were making plans for me to speak at the Folsom Women's Facility about female entrepreneurship, my career and how I started and built my own company. I prepared 5 pages of bullet points, was hoping for the best but truly had no idea what to expect. I was nervous that it would be a larger culture shock than I expected, that no one would be friendly, but most of all, that I didn’t have anything of importance to say, and this would be a waste of their time. But I trusted myself and my experience, arriving ready and willing to be as thoughtful, transparent and real as I could.

There were about 10 people in the class, all of whom greeted me as I walked up. We chit chatted as the door was opening and I immediately felt at ease, everyone was so friendly. We went into a room with about 15 desks with computers and each person took their seat, grabbed notepads and I began.

I spoke for about 30 minutes about successes, failures, pitfalls, lessons learned and stories about the wild ride that has been owning my own company. Knowing I had some time left, I asked for questions. Any other time I have spoken to a crowd, I normally get one or two questions, but here, almost every person raised their hand. And this is where it really got good.

We went through one by one having deeper and more in depth conversations about the most pointed topics such as hosting a website, filing taxes, registering a business, how much of a social life you have when you are starting a business, how to balance time, etc. Clearly, they had been reading books, educating themselves and learning as much as they could.  These were smart women who were trying to understand the practical side of running a business. They had purpose and drive and really wanted to know what it takes to make it. It was so inspiring.

After speaking, I was able to visit some of the students one-on-one and check out their projects, hear more about their pitches and learn more about their stories. One was working on an e-commerce site and was trying to figure out how to collect payments. Another was pitching me her idea of a way to save and foster cats. They built out websites, thought through the logistics of their business idea, and were working toward an end goal.

They were learning how to program, without the internet. They were learning how to make their website responsive (something multiple students showed me, they were very excited about this), how to add payments, how to think through a business idea and make money. All without the internet. Learning an entirely new skillset, especially something as technical as programming is incredibly challenging, to do so without the internet is incredibly impressive.

I have no experience with prisons, the day-to-day stresses, or the pressure they are under. I'm sure that it can be incredibly hard, and I want to acknowledge that. The thing I found interesting was that in this classroom with these students, you'd never know the stresses, or that you were even inside of a prison. They are resilient, pushing through despite all the excuses, stresses and day-to-day issues and were actively working toward their futures. I heard from a few that in that space, they felt an escape, their minds could focus on something creative and bigger than themselves. That really rings true for me, so I can only imagine how accurate that could be in this setting.

I had read a lot about the program, but I truly had no idea what The Last Mile was doing until I was in that room seeing their projects, hearing their stories, and experiencing the change it was creating in each of these women’s lives. Their creativity, entrepreneurial thinking, inquisitive nature, resilience,  it was all so inspiring. The work this program is doing to create change, to support a group of people that no doubt are going to have a harder finding work and giving them a skillset they can use is work that I am so honored to be a part of.

I am not entirely sure what my next career move is, but the positive energy and this feeling of helping others is letting me know I'm on the right track. It is something I'm looking for in my next phase of life. In the meantime, I am going to continue to volunteer and expose myself to new situations like this. Next up, I'm training as a crisis counselor for a crisis text line. More on that later!

To learn more or help The Last Mile, check out their website. They also have an interesting program called The Last Mile Works which is a development company giving The Last Mile students real world work and experience while building out your project (which I'm planning on using next time I need development help). And finally, there is a new podcast out of San Quentin called Ear Hustle which is a new favorite of mine. Check it out! Photos by The Last Mile.