By Kristen Daniels, Chief Development Officer
Shelter Youth & Family Services

Every summer, as Chicago grapples with youth violence and families navigate long months away from school, we’re reminded how much stability matters. The conversation often turns to accountability. It should also turn to opportunity. By the time many young people enter the juvenile justice system, years of instability, trauma, and unmet needs have often narrowed the choices available to them.

Every young person makes mistakes. What differs is the stability and support they have as they learn from those mistakes.

I’ve come to believe we often begin the conversation too late.

Recently, I sat down with Gilbert Cuellar, one of Shelter’s Transitional Living Program (TLP) caseworkers. He shared the story of a young man who entered Shelter’s TLP after receiving one final opportunity through Cook County’s Supporting Education and Employment Development (SEED) program. This program is an alternative to incarceration for emerging adults, typically ages 18 to 26.

Without a stable place to live, the young man moved from one family member to another. He struggled to keep appointments and simply manage the demands of daily life. Gilbert shared what changed once he entered the TLP.

“He was hopping around and did not have financial support or even transportation to get to his appointments,” Cuellar said. “When he came to us, he could focus on completing the (SEED) program instead of putting his energy into getting his basic needs met.” Within six months, he had graduated.

Cuellar’s story isn’t unique. Influential child and family policy research organization Chapin Hall has found that young people experiencing homelessness often move among unstable living situations while also navigating challenges within the child welfare, behavioral health, and juvenile justice systems. As Chapin Hall’s study concludes, “We are missing opportunities to ensure that all young people can reach their full potential.”

Behavioral economist Sendhil Mullainathan and cognitive scientist Eldar Shafir, leading researchers on scarcity and decision-making, have found that when people are consumed by the demands of surviving day to day, “the present presses automatically on you. The future does not.”

Cuellar sees that reality every day.

Stable housing provides far more than shelter. It creates the foundation for young people to focus on school, work, counseling, healthy relationships, and the everyday decisions that shape their future.

Today, The young man Cuellar is employed and preparing for independent housing. Gilbert told me this isn’t unusual. It’s what he has witnessed time and again when young adults finally have the stability to focus on something beyond food, shelter, and their health.

Of note, approximately 80 to 90 percent of residents in Shelter’s TLP are managing mental health or medical challenges. About half have experienced involvement with the juvenile justice system, and every young adult in the program has experienced severe housing instability.

Those numbers don’t define the young people we serve. They remind us that many arrive carrying burdens most of us never see.

Caitlyn Lierman, Director of Residential Programs, explains: “Shelter is working to expand its Transitional Living Program because the need for these services continues to exceed the available capacity—not only within our program, but throughout our community.”

Every additional bed represents more than a place to sleep. It represents another young adult with the opportunity to finish school, keep a job, and begin building a stable, independent life.

The more I reflect on my conversations with Gilbert and Caitlyn, the more it crystallizes my belief that this work is about much more than housing. It’s about creating the conditions that allow young people the time and space to learn from their mistakes, discover their strengths, and build a future.

Before we finished our conversation, I asked Gilbert one final question.

“What can people do?”

I expected him to talk about volunteering, mentoring, or supporting organizations like Shelter.

Instead, he simply said:

“Give people grace.”

I’ve thought about his answer often.

During Juvenile Justice Month, we’ll continue talking about accountability, and we should.

But we should also remember that we rarely know the path that brought a young person to where they are today.

The first thing we should offer isn’t judgment. It’s support. And perhaps most importantly, grace.

See the work in action. Watch our Transitional Living Program video series to hear firsthand how Shelter Youth & Family Services is helping young people build stability, confidence, and brighter futures.