When the Questions Begin to Change

One of the most meaningful parts of our Woodhaven Family Program is seeing families use what they have lived through to support one another.

Our monthly dads group is facilitated by two experienced fathers whose sons were Woodhaven’s first two residents. They bring the perspective and understanding that come from having walked this path from the very beginning. For tonight’s conversation, one of them created a reflection around five words: Win, Wonder, Wrinkle, Wisdom, and Wish.

Each word invites us to consider a different part of our lives. What can we celebrate? What questions are we carrying? What remains difficult? What have we learned? What do we hope for our loved ones beyond sustained recovery?

As I considered my answers, I realized how much my questions have changed.

Several years ago, when my loved one was in early recovery, I wondered whether he would stay sober and whether his recovery would last. I wondered whether he would graduate from high school. During the most frightening moments, I wondered whether he would stay alive. Our relationship had traveled some bumpy roads, and I did not know how it would evolve.

Those questions did not disappear all at once. They changed gradually, often so gradually that I did not recognize the change while it was happening.

Here are my answers today.

Win

After three years of planning, we have officially moved to Pennsylvania.

Every box is unpacked. We still have televisions to hang, stereos to install, and spaces to organize, but we live here now. It already feels like home.

Being closer to Woodhaven was at the heart of this move. It was something we talked about and worked toward for years. Now it is real. I can be present for the daily life of Woodhaven in a way that was never possible when I lived in another state.

There have been smaller wins too. Yesterday, my loved one called to tell me that he had bought me a little gift. The gift itself was almost beside the point. What mattered was that he had thought of me.

My daughter’s phone calls have become less frequent this past week. Strangely, that feels like a win too. I miss hearing from her, but fewer calls may mean she is finding her own rhythm and building a life on the other side of the world.

After years of imagining this chapter, I am finally living it. It is still taking shape, but we are here.

Wonder

For most of Woodhaven’s existence, I was also managing another demanding career. More recently, life has included helping my daughter prepare to move across the world, planning summer events, packing a house, and moving to Pennsylvania.

Even with every box unpacked, we are still settling in. Our daughter remains a central part of our lives from the other side of the world. My loved one is building an independent life of his own. Our family is still close, but closeness looks different now.

I find myself wondering what balance will look like in this next chapter.

How do I remain deeply involved in work that means so much to me while making room for myself and my family? When will my husband and I begin finding common hobbies, forming friendships, and becoming part of our new community? What might I discover that is mine simply because I enjoy it?

There was a time when my questions were about survival. Today, I have room to wonder about balance, connection, and enjoyment.

I am grateful to have room for those questions now.

Wrinkle

My loved one and I are living near one another and seeing each other regularly for the first time in years. I value that closeness, but it can make it easy to slip back into familiar roles and patterns.

Neither of us is the person we were several years ago, and our relationship cannot simply return to what it was then.

We do not go back to where we were. We develop where we are going.

Recently, my loved one became overwhelmed and lost his cool with me. I recognized the reaction because I am capable of it too. Instead of continuing the exchange, I said that I needed a moment and took a walk.

When we spoke again, he took responsibility for the way he had reacted.

Neither of us handled every part of the moment perfectly. We would both prefer to avoid those blowups. But his willingness to return, acknowledge what happened, and take ownership felt significant.

An adult relationship does not depend on getting every moment right. It depends on recognizing our part, repairing what happened, and continuing to learn how to relate to one another differently.

Years ago, I wondered whether our relationship would survive. The questions are different now, and that difference reflects how much has changed.

Wisdom

On my nightstand, I keep a small dish that says, “Life doesn’t need to be perfect to be wonderful.”

It sat beside my bed in our old house, and now it has a place in our new bedroom. I have read those words many times, but they feel especially meaningful right now.

For a long time, it was easy to believe that I could exhale once everything was okay. But “okay” can become a moving target. There is always another concern, another transition, or another part of life that has not gone according to plan.

We moved into our new home late last week, and my husband is already back in New York for two days because his work is also there. That is not how I pictured our first full week, but it is where we are right now. I can use the time to catch up on work so that I can be more available when he returns.

The wisdom I am carrying into this chapter is simple: I do not have to wait for perfection before deciding that life is good.

Sometimes the wonderful life we have been waiting for is already happening. It just does not look exactly the way we pictured it.

Wish

My wish is that my loved one eventually returns to college.

Education has always mattered deeply to me. I believe in the opportunities it creates and the ways it can expand a person’s understanding of himself and the world.

At the same time, I do not want that wish to overshadow everything he is already accomplishing. He has found purposeful work, and he is good at it. He is building a relationship, creating a home of his own, and growing in independence and responsibility.

Returning to school could build upon the life he is already creating. It could give him additional knowledge and opportunities while broadening the impact he can have through whatever work he chooses.

More than anything, I want him to have choices. I want his future to remain open.

The path belongs to him. My wish is that, when he is ready, college becomes part of that path again.

The Questions We Carry

As I considered these five words, I realized that my answers are all connected.

My win is that we have finally arrived. My wonder is how to build a life here that includes more than work. My wrinkle is learning how to build a new kind of relationship with my loved one. My wisdom is that none of this needs to be perfect to be wonderful. My wish is for a future filled with choices and possibility.

The Five Ws came from a father who understands this journey and chose to use his experience to help other families. The words are his. These answers are mine. Each family’s answers will be different.

Some families reading this may still be asking the questions I once asked. Will my loved one stay sober? Will he be safe? Will our relationship survive?

I cannot promise another family when those questions will change or what their answers will be. I can only say that change does not always announce itself. Sometimes we recognize it when we pause long enough to notice that the questions we carry today are not the same ones we carried years ago.

Life has not become perfect, but we have grown, our relationships have evolved, and hope has had room to become something larger than survival.

What is your win?

What are you wondering?

What wrinkle are you working through?

What wisdom are you carrying?

And when you look beyond sustained recovery, what do you wish for your loved one?

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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