A new beginning starts here · Planned reentry initiative

The Jail to Possibility Program

A second chance should begin before someone walks out of jail. Our vision brings together compassionate leadership, a personal roadmap, Angel volunteers, and the resources people need to build a meaningful life after release.

Currently in development. This program is not yet operating. We’re bringing together specialists, partners, and funding to build it.

The heart of Jail to Possibility

Your Life. Your Strengths. Your Roadmap.

Every participant would complete a structured Life Roadmap Assessment—a carefully designed test developed with qualified specialists. It would help uncover individual strengths, learning preferences, goals, practical barriers, and areas where professional guidance may be useful. The purpose is not to label someone, but to understand the person and build a plan together.

Take the assessmentDiscover strengths and needsBuild a personal roadmapConnect to servicesWork with an AngelCelebrate progress
01 · PARTICIPANT ASSESSMENT

Understand the whole person

Strengths & skillsLearning & communicationFamily & supportEmployment & educationHousing & childcareRecovery & wellness referralsGoals & aspirationsPractical reentry needs

Participants would take the assessment with appropriate support. Qualified professionals would help develop and interpret the tool; it would not substitute for clinical evaluation or make automatic decisions about a person’s eligibility or future.

02 · PERSONALIZED LIFE ROADMAP

Turn insights into a plan

First 30 days

Immediate essentials: documents, housing needs, appointments, and a trusted support contact.

First 90 days

Build routines around employment, recovery or therapy referrals, childcare, and probation requirements.

1-, 3-, 5- and 10-year goals

Build a long-term vision for stable housing, family relationships, education, meaningful work, financial confidence, service, and personal aspirations—with goals chosen and revisited by the participant.

Illustrative milestones only. Each roadmap would be developed with the participant and adjusted to their circumstances.
Connect today · Bring services together tomorrow

The Right Support, From the Right Organization

The Life Roadmap Assessment is envisioned to help identify not just a person’s goals and needs, but the types of existing community services best suited to support them. An Angel would then help the participant explore appropriate referrals, make connections, and follow through.

Jobs & training

Explore employment and skills support through organizations such as local clubhouse programs and other qualified workforce providers.

Healthcare

Explore healthcare services through established providers such as People’s Health Clinic.

Safety & shelter

For people experiencing abuse, connect with qualified organizations such as Peace House for confidential support and appropriate safety services.

Family & everyday needs

Find existing resources for childcare, housing navigation, education, recovery support, transportation, and volunteering.

Our longer-term vision: The Mall of Dreams campus could bring independent community organizations and their services together in one welcoming, coordinated setting. This is a future aspiration, not a claim of current co-location or formal partnerships with the organizations named above.

03 · SHARED GUIDANCE, WITH CONSENT

The participant and their Do Hard Things Angel would use assessment results and the roadmap to identify appropriate existing providers, organize referrals, and follow through on next steps. With appropriate permission, relevant information could also help probation officers, case managers, and qualified service providers coordinate support—while each professional retains their own responsibilities.

No one should navigate reentry alone

Angels Who Walk Beside Participants

A Do Hard Things Angel is envisioned as more than a mentor who hands someone a list of phone numbers. Angels would help participants turn their personal roadmap into everyday action—one appointment, resource, and milestone at a time.

Probation & Court Requirements

With the participant’s permission and appropriate authorization, Angels could attend meetings alongside participants, help them prepare questions, understand expectations, track deadlines, and communicate with probation officers.

Recovery, Therapy & Wellness

Help participants connect with qualified providers and community programs, including opportunities such as Work Out for Recovery where appropriate, and support consistent participation.

Family, Childcare & Essentials

Connect people with organizations offering childcare, food, transportation, family support, and other basic needs—then help them navigate the next steps.

Employment & Financial Stability

Support practical goals such as job applications, training, obtaining identification, opening a bank account, and building healthy financial habits.

A better experience of accountability

From Fear to Forward Progress

Probation can feel intimidating, especially when someone is trying to rebuild a life while managing many new responsibilities. We are not seeking to replace probation or reduce accountability. We want to help people succeed within the system by making expectations clearer and support easier to access.

By encouraging constructive communication between participants, probation officers, Angels, and service providers, we hope to replace unnecessary fear and confusion with understanding, encouragement, responsibility, and steady progress.

Accountability and encouragement can work together.
Chabree smiling in a recent portrait
A participant’s story

A Path Forward, One Step at a Time

After leaving jail, Chabree moved into sober living, found a job with High Valley Transit, and made a home of her own through workforce housing. Proud of her sobriety and her ranch roots, she has also helped with the equestrian program and worked with Romeo.

Chabree did the hard work of building this life, with encouragement and support along the way. She is now saving for a car, another goal she is working toward on her own terms. Her story shows the determination and possibility at the heart of reentry.

Chabree’s journey is her own. The Jail to Reentry program described on this page is still being developed.

A guiding voice for second chances

Sheriff Kacey Bates: Leadership with Compassion

Summit County Sheriff’s Office badgeSummit County Sheriff’s Office badge
Sheriff Kacey Bates
Sheriff Kacey Bates

For several years, Sheriff Kacey Bates has helped influence the vision for Do Hard Things. Her conviction that people need stability after incarceration helped bring transitional housing to the forefront—and housing is now envisioned as the first phase of the future campus.

With decades of experience in the Summit County Sheriff’s Office, including jail leadership, Sheriff Bates brings an understanding of the challenges people face in custody and during reentry.

“Sheriff Kacey Bates is one of the strongest, kindest, and most remarkable women I’ve ever known. She has an incredible instinct for law enforcement, a deep commitment to protecting our community, and the compassion to see the human being behind every circumstance.

What I admire most is that she doesn’t stop caring about people when they leave her jail. She wants to see them succeed, rebuild their families, and create lives they are proud of. She understands that accountability and second chances can go hand in hand.

She’s an extraordinary mother, a dedicated sheriff, and an incredible human being. Her leadership, wisdom, and heart have helped shape this vision, and I couldn’t be more grateful to have her helping guide its future.”— Terrah Lund, Founder, Do Hard Things

As an experienced law enforcement leader, Sheriff Bates brings the judgment and perspective needed to protect the community, uphold accountability, and help guide the Sheriff’s Office into the future. In Terrah’s view, one of Kacey’s defining strengths is that she pairs a sharp law enforcement eye with genuine compassion for the people whose lives intersect with the justice system. Public safety and the opportunity for lasting change belong in the same conversation.

Sheriff Bates will help guide the vision and identify experienced professionals from corrections and reentry who can help design the proposed jail-entry and jail-to-housing programs. Do Hard Things will work to bring together additional specialists, community partners, and funding.

This is a vision being assembled, not an operating program. The experts, program design, agreements, and funding still need to come together before implementation. The housing village is a proposed first phase, not construction currently underway.

Learn more about the Summit County Sheriff’s Office →
Our first campus priority

A Safe Place to Land. A Stronger Place to Begin.

Sheriff Kacey Bates’s emphasis on transitional housing helped make it the intended first phase of the future Do Hard Things campus. A stable place to live can make it easier to keep appointments, maintain employment, reconnect with family, and follow a personal roadmap.

From jail to stability—and toward independence

We envision a carefully designed transitional housing program with guidance from corrections and reentry specialists, appropriate support services, and pathways toward longer-term independence. The housing program would connect with the jail-entry assessment and Angel support model rather than stand alone.

This is a proposed first phase, not a development already under construction. The foundation and Sheriff Bates will need to bring together the right experts, plans, partners, funding, and approvals.

Explore the Housing Vision →

Read Chabree’s Participant Story →

StabilityA dependable foundation for daily life
ConnectionSupport for family and community ties
ProgressPractical milestones toward independence
A program worth building · A future worth investing in

What It Will Take to Build the Program

Do Hard Things is seeking the specialists, funding, and partners needed to develop and carefully evaluate this future program.

01

Specialist-led design

Qualified corrections and reentry specialists would help shape the assessment and roadmap around each participant’s strengths, needs, and goals.

02

Secure tools and evaluation

Funding would support secure software development, careful testing, and evaluation as the model is developed.

03

Prepare Angels

Volunteer training would prepare Angels to help participants navigate referrals and next steps—not provide clinical diagnosis or treatment.

Build the Program with Care

Sheriff Kacey Bates will help bring corrections and reentry experts to the planning process. The program would be designed to support the transition from jail into the community with privacy-conscious practices and qualified guidance.

Fund a Path Forward

Your support can help fund careful program development, including the assessment, roadmap technology, and Angel training.

Support Roadmap Development →Discuss a Major Gift or Partnership →Future-development donations are subject to the Foundation’s published stewardship commitments.
From jail to a brighter future

Everyone deserves a path forward.

Help us build connections that support second chances, stronger families, and a healthier Summit County.

Partner, Volunteer or Support the Mission →