We Start Again

We had been through a few challenging days as a community. The night before, we ended with a difficult community meeting. I think some of the boys expected that conversation to continue when we met again in the morning.

I understood why they might. There were still things to think about and conversations we would need to return to. But our morning group meets right before school starts, and I wanted us to begin the day differently.

I had asked our chef to prepare some fresh fruit. He brought in a tray of sliced apples and grapes for the boys to enjoy while we gathered.

Then I asked them to close their eyes. A risky move, since several of them had just woken up.

I invited them to think about the day ahead and how they wanted to approach it. There would be things they could not control. They could not change what had happened the day before or decide what someone else would do. They might still be carrying feelings they could not simply set aside.

But there were choices they could make.

When they opened their eyes, we talked about what was within their control. Some mentioned exercise, running, or going to the gym. One said he could call a friend. Another said he could talk to a peer.

I read the first chapter of Admiral William McRaven’s Make Your Bed. We talked about the routines that can help us begin a day. We brush our teeth. We get dressed. We make our beds. We show up where we are supposed to be.

On some mornings, these things happen almost without thought. On others, they take effort. Making a bed will not resolve a hard conversation. Talking to a peer may not bring the answer we want. But each is something we can do while we figure out the rest.

As the time for school drew close, I ended group a few minutes early. I told the boys to brush their teeth and make their beds. We had talked about the choices they could make throughout the day; now they had a few minutes to take care of two things right in front of them.

Then school began.

I thought about the difference between our conversation that morning and the one we had held the night before. The community meeting had been necessary. We needed to be honest with one another. Beginning the next day with fruit and a book did not take any of that away.

It gave us somewhere to go from there.

I have had to learn this in my own life, too. When someone I care about is struggling, I want to understand everything at once. I go back over conversations and wonder what else I should have asked or said. Sometimes I do need to return to those conversations. Sometimes I have to wait until there is more to know. Sometimes I just need to let unanswered questions stay that way.

While I am waiting, the next day still arrives. The people I care about are still in front of me. I can listen to what they need and decide what I have to offer. Some mornings, that may be another difficult conversation. Other mornings, it is a fresh start with fruit, a chapter from a book, and a few minutes to take care of ourselves.

Hours later, I was driving when I heard one of the boys ask another from the back seat, “Why didn’t you brush your teeth like Jill said this morning?”

My first thought was, Oh. You listened.

It reminded me of my own children. I could say something and have no idea whether it had reached them. Then, sometime later, I would hear one of them bring it up and realize they had carried it with them after all.

I do not know what each of the boys did with those few minutes before school. I do not know whether the boy he asked ever brushed his teeth. But I was glad to hear that our conversation had stayed with them, even as the day went on.

There will be more difficult conversations. Beginning again does not mean pretending they never happened or leaving them unfinished. We can tell the truth about where we are. And when morning comes, we start again.

Dr. Jill DeRosa

Dr. Jill DeRosa is Co-Founder and Director of Education and Family Programs at Woodhaven Recovery. With more than three decades of experience as a teacher, principal, and Assistant Superintendent, she brings a rare combination of educational leadership, lifelong personal understanding of addiction and recovery, and deep commitment to her work with young people and families.

Her perspective is shaped by both professional expertise and lived experience. She co-founded Woodhaven Recovery to create a supportive environment where teen boys and their families can find healing, connection, and the foundation for lasting recovery.

At Woodhaven, Jill helps shape academic and family programming, contributes to the broader vision and daily life of the program, and works directly with residents across many aspects of their growth, including recovery, education, college and career planning, and transitions. She also works closely with parents, offering guidance and insight as they navigate their own role in the recovery process.

As a mother who has lived alongside addiction and recovery throughout her life, Jill writes from a place of genuine understanding. Her work reflects a deep belief in the capacity of young people and families to heal, grow, and build meaningful lives in recovery.

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When the Questions Begin to Change