Behind the Bird: Digital Skills Advice from a Reentry Manager and Peer

Behind the Bird: Digital Skills Advice from a Reentry Manager and Peer


We are excited to share ‘Behind the Bird,’ additional content around the theme of our most recent edition of Fortune News, Digital Literacy and Equity. These articles highlight additional guest writers and include extended versions of pieces in the publication. 

The Last Mile is a partner organization providing Grow with Google‘s Career Readiness programming to individuals returning home from incarceration.


During my three years of incarceration, my behavior adapted to my environment in several ways. I kept a meticulously planned schedule, accounting for every minute of the day, practicing algorithmic toy problems, mnemonics memory exercises and two full, two-hour workouts each day. I would read the letters I received from my daughters repeatedly, cherishing every word.

After I was released in 2019, I quickly learned that schedules, communication and information have very different rules and expectations in the free world. I found that shifting from a rigid structure to a more flexible and agile schedule worked better with the new, competing priorities vying for my time.

Digital communication operates at unprecedented speeds, and the world expects immediate responses across most platforms. Slack, texts, emails and social media messages can overwhelm someone in the reentry process. Even language itself has become shorter and faster. The meaningful words I once cherished in letters from my daughters have been replaced primarily with emojis and acronyms. 

When I came home, I began my career at The Last Mile. This non-profit organization opens opportunities for justice-impacted folks through a groundbreaking in-prison education and technology training program.  

As the reentry manager at The Last Mile, I provide peer-based support for recently released program participants navigating the reentry process. While our program helps fill the tech gap by teaching coding and web development, returned people still face challenges with time management and keeping up with various digital communication streams. 


Bridging this skills gap is vital for anyone looking to reenter the workforce and society more broadly.

When surveying our returned participants about the biggest, most unexpected reentry challenge, the most common answer was ‘time.’ Because of this, the first app I always suggest is a digital calendar. 

Whether someone has been incarcerated for two years or 20, the world will have been adapting to technological advances. Unfortunately, people who are not justice-impacted often have implicit expectations about the skill level that everyone else ‘should’ have. Since the jump from 2 and 3G to 4G LTE, the world has steadily increased the speed and capacity of their gadgets. Returning people who missed these tech evolutions should be mindful of the challenges they will face and the available resources and support.  

I suggest that almost immediately after release, those looking to enter today’s workforce start using a digital calendar and find a safe person with whom to practice daily communication across multiple platforms. They should immerse themselves at a rate just outside their comfort zone and raise it as it becomes comfortable.  

I still receive a daily text message from someone I supported over a year ago. It may sound silly, but the communication divide for those who struggle with these skills contributes to the feelings of otherness commonly felt among the formerly incarcerated population.


Written by Carrie Murchison 

Reentry Manager at The Last Mile  

Turn 2 U Inc. dba The Last Mile (TLM) is an Oakland, CA based 501(c)3 organization whose mission is to provide opportunities for personal and professional growth for justice-impacted individuals through education and technology training. Through prison education, transitional support and workforce reentry, TLM is disrupting the system of mass incarceration across the United States. In-classroom curricula and course material prepare students for meaningful employment in modern job roles including web development, software engineering and audio and video production. Students cultivate personal and professional development in alignment with the technical education and with the support of TLM reentry staff, volunteers, and a community founded on shared lived experience.

The Last Mile is celebrating more than a decade as an organization, originating with its first program in San Quentin State Prison in California. The Last Mile has continued to leverage the power of public-private partnerships with Departments of Corrections and industry leading companies. Programs are currently operating in 6 states and 16 facilities across the United States. TLM has been able to expand its purpose, To Imagine, Build and Open Doors, into other facilities through these partnerships as well as funding and employment opportunities from the technology sector, including, Slack, GitLab, Stand Together, Bank of America, Apple and more.

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