What to Write to People in Prison: A Guide to Compassionate Correspondence

New Book Provides Valuable Insights on Corresponding with Incarcerated Individuals

In March 2017, Doug Cupery walked into the Crossroads office for his first day as the church mobilization director. As a former Crossroads student, he understood the deep impact of encouraging letters from mentors. The mystifying part to him was the mentors. He couldn’t explain their commitment to writing letters every week.

“I was asking myself, ‘Why would someone do what they do?’” he recalled.

In those early months, Doug sat down with mentors across the United States to learn why they chose to mentor through Crossroads.

“I remember sitting in a mentor’s living room in California with a group of mentors and their spouses, just talking and getting to know them,” he said. “As we talked about what they do and why they have been doing it for all these years, they mentioned that they struggled with keeping their letters fresh.”

He explained, “That was the birth of the Just for Mentors. I came back from California thinking about that.”

After talking with a colleague, he was encouraged to start writing to mentors. The first issue of Just for Mentors, a newsletter to support mentors in their work, was mailed in September 2017. Since then, Doug has written more than eighty issues of the monthly newsletter, providing encouragement and insights to Crossroads mentors as they correspond with their students.

“Along the way, people started to suggest to me that I should turn the newsletters into a book,” Doug said. With the encouragement and support of staff members and the mentor community, Doug began compiling the columns by categories to see which themes emerged. This process also helped him see which columns stood out in conveying the significant themes of grace, forgiveness, trust, identity, and restoration.

“As I thought about it, I wanted it to be a book for our mentors but also for people who have the opportunity to write to the incarcerated and aren’t quite sure what to write or how to write. I wanted to create something meaningful and biblically based that would help them understand the needs of those they write to and what they are going through,” he said.

I See You: Remembering the Incarcerated Through a Living Letter is written in such a way that anyone can apply its message and tips to their letters. The book is not only for Crossroads volunteers but also for family members, friends, pastors, or anyone looking to write to someone who is incarcerated. It is also broadly applicable to anyone who is struggling to have meaningful communication with a lonely, isolated person.

Each brief chapter addresses emotions we all experience at different points in our lives, highlighting the humanity of people behind bars. It can be used as a daily devotional or for small group discussions.

I See You isn’t just a book title. It’s a promise that every letter matters. It means that someone behind bars, through their mentors’ words, feels seen, heard, and understood.

Order your copy on Amazon!

Doug is planning a travel itinerary for 2024, intending to visit different communities of mentors nationwide. He hopes to encourage and empower them to share their stories and experiences as Crossroads mentors. If you would like to arrange a visit to promote the ministry in your area, please reach out to Doug or his assistant, Alaina Zwiernikowski, at 616-208-1480 or mentor@cpministries.org.