What I Learned From Prison Inmates

The other day, I spent my morning volunteering an the San Quentin prison with a program called The Last Mile. As Wired recently reported, this nonprofit seeks to help inmates prepare to get a job on the outside. I was as shocked as anybody when a friend of mine called up asking me to teach advanced computer science topics to their level two class.

I took a few weeks to prepare a lecture on algorithm design (a class which most students do not take until the second or third year of university). My friend told me that I would be surprised about how diligent and well-prepared the students were, and boy was he right.

I arrived around 9am and faithfully handed over my cell phone. Inside, I also had to give up my notebook (because it had a hard cover). The metal clip binding my papers together also had to go. We walked through “the yard” to see a scene out of any prison movie or TV show: groups of inmates with their shirts off doing body-weight workouts. Then we turned the corner, went through a door, and were suddenly inside a computer science lab with a bunch of guys diligently coding away. I spent the rest of the morning with this class, and here’s what they taught me.

inmates coding with The Last Mile

Expect Nothing

“Is this your first time in prison?” the program coordinator asked me. I told him it was.

When I entered the prison, I had no idea what to expect. All I know about “the inside” comes from movies, books and TV shows. But I had no illusions that Prison Break or Oz would prepare me for what I was about to see.

I quickly learned to take on the same attitude I do while traveling. It’s tempting to come in to these situations with value-judgements at hand. When traveling, foreign culture can feel different and wrong. It takes a conscious effort to remove expectations. So, too, with prison.

The atmosphere in the classroom was, quite simply, studious. The inmates did not have access to an internet connection. They casually told me about how this made some of their server architecture work rather difficult. Or how they had to request documentation. They had to make formal requests for the sorts of information I would have Googled, solved and moved on from in minutes.

Soon, I found my impressions changing…

Impressions Can Be Obstacles

Several of the students in my class had neck/chest tattoos, or other things which would make me think they’re “hardcore.”

Maybe this is true. I have no idea. I cannot speak to the rest of their lives.

What I do know is that in the class, these very same people were some of the most thoughtful and articulate members. There’s a phrase in psychology called cognitive dissonance, when two different impressions of something conflict and cause mental turmoil. By expecting nothing, I had prepared myself for this dissonance. Still, the contrast was striking.

As a teacher, I expected to need to dwell on the basic idea of an “algorithm.” Or to explain why time-complexity analysis is important. Instead, the inmates dove into questions like “is merge sort O(n lg n)? Why?” within minutes. If you haven’t studied computer science, suffice to say that this represents an advanced understanding of underlying mathematical concepts.

At the same time, I expected to get a certain “who is this dude?” vibe from the inmates. I thought I’d need to prove myself or something. Instead, I felt welcomed and instantly comfortable around them. They were, quite plainly, eager to learn and discuss what they’d learned.

Again, like with travel, I found my impressions breaking down. I forgot that I was inside a prison. I never thought to ask questions like “what did this guy do to get here?” until after the entire session was over. While I was there, we were just a group of people interested in the same topic.

How To Use Time

At one point, I inquired as to the time.

51HsuPnTbrL._SX329_BO1,204,203,200_One inmate laughed and said something to the effect of “you’ve got all the time in the world, here.” It struck me that he thought about time in an entirely different way.

I happened to just finish reading a book called Deep Work. The hypothesis of the book is that there is a qualitatively different kind of mental work. We all spend most of our distracted days doing “shallow work” like responding to quick emails. Instead, deep work requires hours of disconnected time spent focusing on a single topic in order to understand it completely.

The inmates were naturally forced towards this kind of deep work. Shallow work happens when you feel like you’re limited on time and need to get as much done as possible. Since the inmates were constrained by resources (connectivity, books, etc) instead of time, their mental approach was different. They read and re-read the same limited materials over and over.

With heavy textbooks like Introduction to Algorithms, the only way to truly understand them is to engage in deep work. You can’t just read through them. You need to sit and work with them, fighting your way through the topics and problems until you understand. As I was preparing for the class, I was re-reading the book to remind myself of some key concepts. I had tasked myself with spending a solid un-interrupted hour on the book. Even that was hard. As always, I was distracted by messages on social media, slack, email, etc. Eventually I had to put my phone in the other room so that I could focus on the topic enough to actually make progress.

For better or for worse, the inmates have these constraints artificially placed upon them.

What You Can Learn

There are two main things I’ll take away from this experience:

The first is that working with people from diverse backgrounds is valuable. The inmates had perspectives and questions I hadn’t considered. Study after study has shown that diversity improves creativity in the workplace, and this was a clear example as to why.

The second thing worth learning from the inmates is that artificial constraints are valuable. I’m convinced that the circumstances forced the inmates to do deep work in a way that most of us no longer engage in due to our highly connected culture. If you really want to improve yourself or understand a hard topic, completely removing distractions for hours on end and focusing entirely on the topic is a challenging but effective approach.

I was immensely impressed by The Last Mile program, and hope they succeed at their goal of landing (former) inmates in tech jobs. I’m convinced they could potentially be an incredible asset for the companies they joined.


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