When it comes to criminal justice reform, few voices carry the weight of lived experience combined with professional leadership like Tyler Boyd. After navigating the challenges of incarceration and reentry himself, Tyler has transformed his journey into a mission of support, growth, and systemic change. Today, as Senior Manager of Development & Growth at The Last Mile, and founder of Another Day Down, he brings both authenticity and vision to the fight for justice-impacted individuals.
In this Clutch Justice Q&A, Tyler opens up about his path from personal struggle to professional leadership, the role of family and community in his transformation, and the urgent need to reframe how society approaches “second chances.” He also shares how his lived experience fuels his approach to program design, advocacy, and building compassionate reentry pathways for others.
Q: In 2-3 Sentences, tell me what the world needs to know about Tyler Boyd.
Hmmm- I would say I am a dedicated and supportive voice in criminal justice reform, driven by a passion for helping others navigate the challenges of incarceration. Having experienced a profound personal transformation over the last five years, I am committed to being the resource that I could not find during my own time of need. Through the right support and guidance, I believe individuals facing incarceration can not only manage their time inside but also grow in ways that set them up for success upon release.
Q: As someone who has both lived through the justice-impacted experience and now serves as Senior Manager of Development & Growth at The Last Mile, how has your personal journey informed the way you approach program development and outreach within the organization?
Having lived through the justice-impacted experience myself, I bring a perspective to my role at The Last Mile that goes beyond advocacy. I’ve sat in the classroom, experienced the challenges and opportunities firsthand, and truly understand the light and hope that The Last Mile can bring to students.
This lived experience allows me to speak authentically with funders and partners about the transformative impact of our programs, not just in theory, but through the lens of someone who has benefited directly from them.
My personal journey also informs how we design and adapt programming to truly meet our students’ needs. I know that what the outside world sees is not always the reality inside the classroom or the facility, so I prioritize ensuring that our programs are practical, relevant, and directly supportive of the students’ goals. By combining firsthand insight with data and feedback from our current students, I help shape initiatives that build not only essential job skills but also the confidence and resilience needed to succeed upon release.
Q: You often mention your wife and your two bulldogs as central to your life outside of work; how has your family supported you through the challenges of your past, and how do they continue to motivate your mission today?
My wife and my two bulldogs, Tupac and Biggie, are truly the “Big 3” in my life and have been my constant through tremendous change over the past few years. Amid the challenges of my professional life, the stigmas of being justice-impacted, and the grief and regret I carry, they provide a space where I can simply exist and recharge.
I met my wife while on bond, preparing for trial, and I’m deeply aware of the strength it took for her to stand by me through that journey, including my decision to accept a plea deal and willingly walk into prison. She has been my anchor and she motivates me every day to continue my work helping others navigate the justice system with hope and support.
Q: As a justice-impacted individual who’s now leading efforts in development and growth, what changes would you like to see in how society frames second-chance opportunities, and what role do you believe programs like The Last Mile can play in that shift?
This is a question I spend a lot of time thinking about…
One thing I’ve learned is that the term “second chance” often doesn’t capture the reality for many justice-impacted individuals. For a large portion of our students, and many others who are or have been incarcerated, they never had a “first chance.” The skills they gain while incarcerated and the opportunities we provide upon reentry often represent their first real opportunities to build a meaningful career and life.
Programs like The Last Mile are delivering high-level training and skill-building that equip students not just to survive reentry but to thrive. I believe this work should shift the conversation with employers from “Please consider hiring our alumni” to “You have the opportunity to hire our alumni.” That’s the mindset I’m working to instill every day, and it’s a shift I’m already beginning to see take hold.
Q: Your website, Another Day Down, speaks powerfully about offering honest, lived-experience support for people facing incarceration, especially for the first time. Could you share the vision behind that initiative and how it complements or intersects with your work at The Last Mile?
The vision behind Another Day Down grew out of my own search for guidance and support while facing incarceration — a resource I struggled to find in my time of need. I see Another Day Down as a complement to The Last Mile.
While The Last Mile provides top-tier in-prison programming and reentry support, Another Day Down serves as the first chapter of that journey. It offers honest, lived-experience insight for those entering prison, helping take some of the unknown out of the experience while also providing guidance to create a plan for both personal and professional growth during their time away.
Q: Having been released in June 2023 after what could have been a significant sentence, what were the key turning points or supports that helped you rebuild your life and how do you incorporate those lessons into creating more compassionate re-entry pathways for others?
Although my time in prison was under two years, any time incarcerated is too long, and reentry presented challenges I hadn’t fully anticipated. Upon release, I initially thought I could pick up where I left off in my career, but after numerous interviews and setbacks due to background checks or gaps in my resume, I realized I needed support.
Reconnecting with my Reentry Coach at The Last Mile was a turning point — their guidance and encouragement helped me find direction and rebuild my life. Those experiences now shape how I approach new hiring partners and organizational collaborations at The Last Mile, ensuring we align with partners who share our vision for what is possible for justice-impacted individuals, rather than advancing their own agendas. Fortunately, we’ve been able to build strong partnerships that truly reflect that shared mission.
Q: Looking ahead, what are your hopes for the broader justice-impacted community? And what impact do you aspire to make through your dual roles with The Last Mile and Another Day Down to support that vision?
Looking ahead, my hope for the broader justice-impacted community is to continue shifting the conversation around opportunity and potential. As I touched on earlier- I want to shift the conversation.
Instead of us asking, “How can we get our students into your pool of applicants?” the question should become, “Why should we put this opportunity in front of our alumni?” It may sound ambitious, but that’s how deeply I believe in our students, our curriculum, and the transformative work of The Last Mile.
In terms of how Another Day Down intersects with The Last Mile, I see it as the pre-incarceration resource — the first step in providing guidance, insight, and support for individuals facing prison. The Last Mile then continues to drive and shape in-prison programming and reentry support, creating a full continuum that helps justice-impacted individuals grow personally and professionally throughout their journey.
With your two bulldogs at home: if they could each have a job title at Another Day Down, what would they be, and why?
Great question! If I could give Biggie a job at Another Day Down, it would definitely be in fundraising — at just three years old, he’s full of energy and enthusiasm, and with his lovable face, it’s nearly impossible to tell him “no.”
Tupac, on the other hand, is nine and would make the perfect mascot. While he prefers to sleep at least 15 hours a day, refuses to eat without yogurt in his bowl, and occasionally gets into a “dust up” with the local deer, he embodies the spirit of resilience and character that makes him unforgettable.
I’ll definitely have to feature them in a video or update one of these days!
Be sure to check out The Last Mile and most definitely support Another Day Down.
