Empowering Women to Reach Career & Education Goals After Incarceration

By Aimee McPhail, Research Associate, and Pavithra Nagarajan, Senior Research Associate

A New York City program is providing support to formerly incarcerated women as they reenter the community. College and Community Fellowship’s (CCF) Build-Out of Student Services (BOSS) project offers access to education, employment, and mentoring services to help women reenter the community more successfully.

People returning to the community after incarceration often face a complex web of challenges. Without the right kind of support, they face heightened risk of unemployment, homelessness, substance use, and further criminal legal system involvement.[1] Women reentering, in particular, often face unique obstacles compared to their male counterparts: they are more likely to be economically disadvantaged and a parent to a child under 18 years of age.[2] Yet, many reentry programs are designed with formerly incarcerated men and their needs in mind. This gap has created a pressing need for gender-informed reentry programs that can effectively provide services and support to mitigate these challenges faced by formerly incarcerated women.

This gap has created a pressing need for gender-informed reentry programs that can effectively provide services and support to mitigate these challenges faced by formerly incarcerated women.

Seeking to fill this gap, College and Community Fellowship’s (CCF) Build-Out of Students Services (BOSS) project provided formerly incarcerated women in New York City with educational and employment services to help them overcome financial and, for some, caregiving obstacles. Funded by CUNY ISLG and the Manhattan District Attorney’s Office through the Criminal Justice Investment Initiative (CJII), BOSS includes three main components: the Academic Support Program (ASP), which aided women currently enrolled or hoping to enroll in college; the Career Advancement Program (CAP), which offered employment assistance and job placement; and Uplift Mentor (UM),[3] which connected women to post-release peer support consisting of 1:1 and group mentoring with program peers.

Through CJII, CCF enhanced its existing program offerings of ASP and UM as well as launched the new CAP program component. Participants could engage in more than one component at a time as relevant and needed. From July 2019 through September 2022, CCF’s BOSS project served 220 participants – most of whom were served through ASP.

As part of CJII, the Vera Institute of Justice conducted a process evaluation that details participants’ appreciation for the BOSS program responsiveness to their specific needs. In particular, and across all program components, participants reported positive relationships with staff and the impact of financial support as particularly beneficial as they worked toward their academic and career goals. Out of the 175 that participated in the study, 21 received a post-secondary degree or credential and 13 secured a job or internship placement.

Staff Were Crucial: “I would not have a college degree without CCF.”

Participants enrolled in any of BOSS’s three services receive case management in which staff assess and provide supportive services directly (e.g., financial counseling) or through referrals (e.g., for housing, healthcare, legal advice). During interviews, participants reported that their experiences in the program were overwhelmingly positive and indicated high levels of satisfaction with the services and support provided by the program in helping to achieve their goals, particularly those enrolled in ASP and CAP. As one ASP participant stated: “When I first started school, it was a new world to me, and my counselor at the time helped me so much. I would call her stressed out due to not understanding something, and she always took her time to listen to me and direct me. I would not have a college degree without CCF.”

Participants also expressed appreciation for the program’s commitment to supporting them with meeting the requirements of the various program components. Specifically, program staff were described by participants as being flexible and tailoring support to meet each participants’ individualized needs. For example, ASP participants who are parents or caregivers were eligible to receive multi-generational services—such as family-centric events, stipends, and workshops tailored toward parenting skills, relationships, and more—to assist them as they pursued their college degrees.

A CAP participant specifically described their career coach as “phenomenal, patient, and understanding with the barriers that a formerly incarcerated or returning citizen might have”.

Furthermore, staff encouragement and advising helped participants “feel seen and important.” Participants highlighted how understanding and responsive BOSS staff and the program were in addressing their needs, especially those needs related to having been formerly incarcerated, such as guidance navigating the reentry process and finding housing. A CAP participant specifically described their career coach as “phenomenal, patient, and understanding with the barriers that a formerly incarcerated or returning citizen might have”.

Financial Supports Laid Foundation to Pursue Goals

Before setting off on accomplishing career and academic goals, participants needed to establish stability. Financial support provided by CCF—such as stipends, transportation and housing aid, and other economic resources—helped them do so. Between December 2020 and December 2022, the program distributed $72,750 in stipends to participants. Participants described how these stipends and education-related funding (i.e., money to pay for books, tuition, transcripts) alleviated their stress while applying to and while enrolled in post-secondary education. Within CAP specifically, participants most commonly received MetroCards, professional clothing, and job-retention bonuses. Participants noted that these were critical supports as they searched for and eventually secured employment. 

Participants from interviews and focus groups identified financial hardship as one of the greatest challenges they faced in participating in the program. To this end, they credited these financial supports and resources as the most important and impactful aspect of participating in BOSS, because it gave them the opportunity to focus on working toward their goals while alleviating some of the stressors faced as part of the reentry process.

As one participant described, “[Since] being released from prison, we are behind many others [in terms of] social economic status…and the lack of funds can be a major stress and can deter us from achieving our goals. Survival [or] having stability and basic necessities seem far more important.”

About the Program and Evaluation

CCF continues to provide women returning from incarceration with necessary education supports and counseling through ASP in order to help participants achieve their higher education aspirations.

This blog accompanies the Vera Institute of Justice’s process evaluation report of CCF’s BOSS project, drawing from interviews with program participants and staff, participant surveys, program observations, and a description of program data.

About the Criminal Justice Investment Initiative

The Manhattan District Attorney’s Criminal Justice Investment Initiative (CJII) focuses on three investment areas—crime prevention, diversion and reentry, and supports for survivors of crime. CCF’s BOSS program and this evaluation were funded through CJII’s investments in diversion and reentry support.

The CUNY Institute for State and Local Governance manages and provides technical assistance to CJII contractors, and conducts oversight and performance measurement throughout the lifetime of the initiative.


[1] Phillips, L. A., & Spencer, W. M. (2013). The challenges of reentry from prison to society. Journal of Current Issues in Crime, Law & Law Enforcement6(2).

[2] Miller, H. V. (2021). Female re-entry and gender-responsive programming. Corrections Today13.

[3] Previously referred to as CCF’s Peer Mentoring Program (PMP).

Photo by Jacob Lund on Adobe Stock.

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