Reentry: Staying Safe on the Outside – Coping, Thriving, and Surviving
Updated: Nov 5, 2025
“The real test of freedom isn’t breaking out — it’s learning how to live once you’re free.”— Adapted from Viktor Frankl’s principles on resilience
Recently, several people reached out who work in the jail system, sharing stories about the unique challenges individuals face when transitioning back into the community. Their experiences inspired me to create this new activity, “Reentry: Staying Safe on the Outside – Coping, Thriving, and Surviving.”
While the idea started with reentry in mind, this activity isn’t just for people coming out of jail or other controlled environments. It’s also for anyone working to make positive changes, avoid setbacks, and strengthen recovery. Whether you’re leaving a treatment program, completing a mandated course, or simply trying to stay on track after a rough patch, the lessons here apply to real life.
The featured reading, “Promises – Promises,” explores how easy it is to say “never again” when life hits hard — and how much harder it can be to keep that promise once the pressure fades. For anyone who has ever made heartfelt promises in moments of clarity, this exercise offers practical tools for following through.
Participants will explore the risks that come with freedom and transition, such as relapse triggers, stress, financial strain, and loss of structure. They’ll also identify strengths like resilience, gratitude, patience, and self-awareness — the qualities that help turn survival into growth.
Like many Taking the Escalator activities, this one balances realism with hope. It encourages reflection, planning, and discussion on how to prepare for life’s outside pressures while staying grounded in recovery and personal change.
For Members
The full Reentry: Staying Safe on the Outside – Coping, Thriving, and Surviving worksheet is available for download- It includes:
The “Promises – Promises” reading and reflection.
A guided discussion on real-world risk factors.
Insight and motivation-building exercises.
Practical prompts for self-honesty, planning, and support.
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