Ready for Any Path After Prison: Inside The Last Mile’s Expansive New Curriculum

By Robert Roche, VP of Marketing at The Last Mile.

The world of work is changing faster than most people can keep up with. Artificial intelligence is reshaping entire industries, altering entry-level roles, and changing the skills employers expect from new hires. For someone returning to the workforce after years away, that shift can make an already difficult transition even harder.

This August, The Last Mile launched PATH at San Quentin Rehabilitation Center to meet that moment. PATH (Professional Advancement, Training & Hiring) expands how we prepare students for careers after prison, integrating digital literacy, artificial intelligence, project management, sales, and entrepreneurship into a comprehensive workforce curriculum. The program represents a major evolution of an idea that has guided The Last Mile since 2010: the skills taught inside prison must reflect the opportunities students will encounter when they come home.

PATH also tells a deeper story about who should shape the future of prison education. Much of the curriculum was developed and tested by people who once sat in TLM classrooms themselves. In this article, we explore why The Last Mile built PATH, how lived experience influenced its design, what students are now learning, and why this launch could mark the beginning of a much broader approach to career preparation after incarceration.

A Mission Built Around Employment

When The Last Mile opened its first classroom at San Quentin in 2010, the program centered on business and entrepreneurship. A few years later, the technology economy created a new opportunity: software companies needed developers, and TLM began teaching coding inside prison. Web Development and Audio/Video Production eventually became defining parts of the organization’s career training.

At every stage, the programs changed because the opportunities outside changed. That responsiveness has always been part of the model.

“When we started The Last Mile, we had a mission, which has never changed,” Co-Founder Beverly Parenti explained. “Our mission is to provide marketable skills that result in gainful employment.” She added that TLM has a responsibility to keep “looking ahead so we know where the opportunities lie, and therefore we provide the training that matches those opportunities.”

By mid 2025, looking ahead revealed a very different economy. Artificial intelligence was moving rapidly into workplaces. Entry-level technology roles were shifting. Employers increasingly expected workers to communicate across teams, navigate digital systems, solve unfamiliar problems, and learn new tools as they emerged. Executive Director Kevin McCracken described the volatile job market that people are entering after incarceration. “Everything about the job market is changing very quickly, much more quickly than most of us even expected.”

That created a familiar challenge for The Last Mile: identify where opportunity is moving, then prepare students to meet it.

PATH grew from that challenge. It expands career preparation beyond a single occupational track and equips students with skills they can carry between industries. In many ways, it returns to the question Co-Founder Chris Redlitz remembers asking at San Quentin from the beginning: “What’s the preparation people need for when they get out?” This question recently led us to one of the most expansive evolutions of The Last Mile’s curriculum in our history.

Building PATH for the Workforce Students Will Enter

PATH begins with a broader question than any single career track: What does someone need to enter the modern workforce confidently?

Karly Stark, TLM’s Senior Remote Instructor, helped shape that answer. Early in the design process, Karly reviewed nearly 1,200 pages across PATH’s five modules. Karly then helped develop and test the Remote Instruction lesson plans that would bring the curriculum to life.

“The scale was really enormous in my head, which is super exciting,” Karly recalled. As the pieces came together, the breadth of PATH became clear. “This is a lot of really useful content. This is a lot of skills that we’re teaching. These are a lot of soft skills and hard skills, all integrated.”

That breadth was intentional. Sierra Robinson experienced TLM first as a student while incarcerated. Years later, she helped lead PATH as TLM’s Academic Data Analyst and Curriculum Manager. For Sierra, expanding the curriculum means giving students more freedom to follow opportunities wherever they emerge.

“I think it’s so cool that now our students are gonna come home much more broadly prepared,” Sierra said, with “different pathways or avenues that they can explore and really find what their interests are.”

Remote Instructor Natasha Towle brought the same perspective to curriculum writing, quality assurance, lesson-plan development, and classroom testing.

“The rapid rise of AI has fundamentally reshaped the job market,” Natasha explained, making versatile, future-ready skills increasingly important. PATH, she said, gives students an expanded toolkit “designed to help students adapt and succeed in a modern, AI-driven economy.”

PATH prepares students for that uncertainty by widening what they are equipped to pursue.

Built by People Who Know the Prison Classroom

The people building PATH understood that a curriculum can be technically strong and still miss the realities of learning inside prison. Students may have limited internet access, unfamiliar technology, rigid schedules, and years of distance from the workplace they are preparing to enter.

That is why lived experience became part of the design process itself.

The curriculum team included former TLM students, returned citizens, experienced educators, and Remote Instructors who work directly with students inside correctional classrooms. Their perspectives influenced everything from examples and terminology to pacing, assessments, and the identification of where additional support was needed.

Sierra remembers frequent conversations among team members whose incarceration experiences ranged from six years to more than two decades. Those differences mattered. “Having those diverse perspectives really allowed conversations to happen,” she explained, helping the team decide what students truly needed and where assumptions about prior knowledge could create barriers.

Natasha described the difference even more directly. “We design from experience, so we understand where the friction points are,” she said. “We anticipate the frustration before the student even hits it, and we build the supports to guide them through.”

That perspective continues when instruction begins. Karly tells students and teaching assistants something simple when introducing PATH: “This is for you.” Former TLM students had a major role in writing the curriculum, allowing current students to encounter examples, assignments, and learning supports shaped by people who understand their classroom firsthand.

The impact reaches beyond accessibility. Students can see where the work itself came from. Someone who once sat in a TLM classroom can now design what the next student learns there. That creates another form of career preparation: a visible example of how far their own skills and experience can eventually take them.

Digital Literacy and AI for a Career After Prison

PATH begins with skills that are essential for almost every modern workplace.

Digital Literacy teaches students to navigate software, communicate digitally, manage files, evaluate information, collaborate, and protect data. Students work with productivity tools and learn the fundamentals of HTML and CSS. The goal is comfort, confidence, and the ability to keep adapting as technology changes.

AI Literacy builds on that foundation. Students learn how artificial intelligence works and where errors or bias can emerge. They practice using AI assistants for workplace tasks. Later lessons cover prompt engineering, responsible use, and ethics.

Sierra wrote the AI Literacy curriculum from beginning to end, with colleagues supporting quality assurance. Her approach focuses on concepts that can survive constant technological change.

“If you can learn how to prompt effectively and learn prompting techniques, then you can use any AI tool,” she said. That foundation prepares students to approach future systems with confidence, even as individual products evolve.

Project Management, Sales and Entrepreneurship

PATH also develops professional capabilities that travel across industries, giving students practical frameworks for organizing work, communicating with confidence, understanding people, solving problems, and turning ideas into action. Together, Project Management, Sales, and Entrepreneurship help students build skills they can carry into many different roles, teams, and career paths.

Bringing Secure AI Into a Prison Classroom

For most students outside prison, experimenting with generative AI requires little more than opening a browser. Inside a correctional facility, that same technology presents an entirely different challenge.

Sierra remembers AI Literacy arriving relatively late in PATH’s development because the team was unsure whether meaningful access could work inside a secure classroom. “It was not something that we thought was going to be possible inside of our facilities,” she explained. Sierra ultimately wrote the AI Literacy curriculum and helped develop the simulator students would use to practice it.

The goal was to recreate the experience of working with tools like ChatGPT, Claude, or Gemini without introducing an unrestricted system into a prison. TLM worked with correctional partners to understand what safeguards would make that possible. The development team then built multiple security layers around the experience.

When a student enters a prompt outside the assigned educational topic, the system can reject it before it ever reaches the AI. Instead of ending the exercise, it guides the student back toward a stronger, more relevant prompt. Sierra described that process as giving students repeated opportunities to practice while receiving feedback on “how to better prompt and how to stay relevant and on topic.”

Lived experience shaped those safeguards too. Sierra noted that, aside from the project lead, everyone building the simulators had experienced incarceration. They understood both the restrictions and the educational possibilities of the environment.

That breakthrough reaches beyond AI. The same secure infrastructure can eventually support additional partners and curricula, expanding what students can access without requiring every education provider to solve the technological barriers to prison learning from scratch.

More Possibilities After Release

PATH’s real test begins when students return home and face a workforce filled with choices they may never have been able to explore from inside.

Sierra sees that shift as one of the program’s most meaningful changes. Earlier TLM students often graduated with a highly specialized technical skill set. PATH prepares people to move more freely across industries. “I think it’s so cool that now our students are gonna come home much more broadly prepared,” she said, with more pathways to explore and more opportunities to discover where their interests lead.

That preparation also produces something students can carry into an interview. Throughout PATH, they build a portfolio from the work they complete. “They don’t just have a resume,” Sierra explained. “They have all this proof and evidence that shows that they can apply these skills.” Projects in areas such as project management, personal branding, pitching, and professional communication can become tangible demonstrations of what a student knows how to do.

The deeper goal is confidence: giving students enough experience with technology, communication, problem-solving, and professional environments to imagine several possible futures for themselves.

Natasha hopes students carry that belief with them long after the course ends. “I want them to know that their past doesn’t define their future; their ability to learn does,” she said. “If they can master these concepts in the most challenging environment, they can thrive anywhere.”

That is the promise behind PATH: a career after prison with more skills, more evidence of ability, and more room to choose what comes next.

Launched at San Quentin. Designed for the Country.

PATH’s launch at San Quentin Rehabilitation Center marks a new chapter for The Last Mile, but the larger story begins with what happens next.

A student who starts with basic digital literacy can now move into AI, project management, sales, entrepreneurship, and specialized career pathways. Along the way, they build confidence, a portfolio, and the ability to keep learning as the workforce continues to change.

That matters because reentry rarely comes with a single prescribed path. People return home with different ambitions, different strengths, and different ideas about the lives they want to build. PATH gives them more tools to make those choices for themselves.

The program was built by educators, technologists, and people who once experienced incarceration firsthand. Now, students at San Quentin are beginning to carry that work forward.

Our ambition is to make this opportunity available far beyond one facility.

We want to bring PATH, secure classroom technology, Remote Instruction, and career-connected education to correctional facilities in every state. Reaching that scale will require a community of supporters who believe preparation for reentry should begin long before someone walks through the gate.

You can help build that future. Your support funds the classrooms, technology, curriculum, instruction, and student services that make programs like PATH possible.

Join The Last Mile and help us bring the next generation of career preparation to more students across America. Learn more here. 

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By Robert Roche, VP of Marketing at The Last Mile.

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