The transition from a highly controlled environment to community life can be overwhelming.
WHAT THEY’RE FEELING AND EXPERIENCING
REENTRY IS A MARATHON, NOT A SPRINT.
- Feeling exhausted: They may be dealing with trauma and other mental health challenges, prefer small spaces, and have trouble sleeping. This makes it hard to keep appointments, maintain health care, and understand social cues.
- A heavy mind: Constant stress, lingering cravings, and past hurts can make open spaces and simple tasks feel overwhelming, like going to the store, taking a bus, or even waiting in line.
- Stigma and fear of alienation: Fear of being judged by neighbors, employers, or strangers can lead to chronic distrust of others, preventing people from seeking support, treatment, work or social connections.
- Safety risks: Changing drug supply, reduced tolerance and seeing people they used to use with can be triggering. It takes time to feel “normal” again.
HEALTHY BOUNDARIES ARE AN ACT OF LOVE, NOT REJECTION
Be clear about what you can and cannot do: Setting limits is a way to take care of both of you. It’s okay to say what you are able to help with (e.g. rides, reminders, listening) and what you cannot do, like lending money or tolerating unsafe behavior.
Self-Care First. You cannot pour from an empty cup. Strengthen your own well-being and remember you can’t do everything. Your role is to help set the pace so you all stay strong for the journey ahead.
PRACTICAL PROBLEMS
- Money and home: Not having stable employment and affordable housing is a major stressor, and can lead to relapse or return to jail.
- Systemic Hurdles: Managing parole/probation obligations, unreliable phone or internet, restricted access to housing and social services, and navigating healthcare take a lot of time and energy. One missed step or seemingly small hurdle can quickly become a major setback.
- Difficult paperwork: They may no longer have a valid ID, and filling out forms for housing, jobs, health care and other vital services can be confusing and draining.
- Getting around: Not having a license, reliable car, or access to a dependable bus makes it hard to keep a job or stick to appointments.
WAYS TO OFFER SUPPORT
Feelings of hope, grief, stress and fear are normal when returning to the community. Family and friends can help ground them while setting clear limits.
- Listen with love: Find a quiet place to talk. Ask simple questions like, “How is today going, so far?” and just listen without judging, interrupting or trying to fix everything for them.
- Work together on small steps: Help them with tangible goals, like navigating parole or probation obligations, getting a ride to court, preparing for a job interview, or organizing the paperwork for healthcare or housing.
- Ask about their support team: Help them stay connected with providers, peers and supportive friends.
- Respect their autonomy: As a formerly incarcerated person, your loved one needs space to learn how to make decisions again. Support their agency by encouraging them to lead their own recovery and reentry goals.
HEALTHY BOUNDARIES ARE AN ACT OF LOVE, NOT REJECTION
Be clear about what you can and cannot do: Setting limits is a way to take care of both of you. It’s okay to say what you are able to help with (e.g. rides, reminders, listening) and what you cannot do, like lending money or tolerating unsafe behavior.
Self-Care First. You cannot pour from an empty cup. Strengthen your own well-being and remember you can’t do everything. Your role is to help set the pace so you all stay strong for the journey ahead.
YOU AREN’T ALONE.
Other families are going through this too. It’s okay to ask for help for yourself, like talking with a professional or joining a peer group where you can share your experiences. Your loved one is more than the struggles they face.
RESOURCES FOR YOURSELF AND YOUR LOVED ONE:
- 2nd Street, 2nd Chances: For individuals who have been incarcerated- no matter how recent or long ago that time was. 2nd-street.org
- Learn 2Cope: For people and families who have been impacted by substance use. learn2cope.org
- SADOD: For people who have lost a loved one to substances. sadod.org
- Peer Recovery Centers:
Have Hope (North Adams),
Living in Recovery (Pittsfield)
South County Recovery Center (Great Barrington),
George B. Crane Center (Pittsfield) all have resources for both families and individuals.

