Sister Joins Shelterwood Staff Inspired by Brother’s Transformation: Kiley’s Story

God used Shelterwood to change the heart of Kiley Crossland, while her younger brother, Nate, was a student. She came to know the school’s healing power through his journey and her own.

Kiley, the oldest of four siblings, was away at college when Nate enrolled as a Shelterwood student. “Over the course of a few hard years, my parents decided he needed extra care. Although I was at college, I was still super connected to my family and to him,” Kiley remembers. Kiley visited her brother a few times while he was at Shelterwood, and those visits put a desire in her heart to serve as a Big Sister/Mentor one day herself.

“My mom and dad would both say the hardest thing they’ve ever done in their lives was drop Nate off at Shelterwood,” Kiley continues. “But the fruit of that tough love was amazing. Sometimes love forces you to make someone you love uncomfortable, and Nate needed to be uncomfortable to grow. Shelterwood had a huge impact on our whole family.”

What especially struck Kiley was the Life-on-Life Discipleship model at Shelterwood, in which young adult, “Big Brother,” mentors walked alongside Nate. “The mentorship component was so impactful for Nate. Shelterwood intentionally places struggling teens alongside young adult men and women to offer perspective and guidance,” Kiley says. Even after his Shelterwood graduation, Nate’s Big Brothers remained connected, even driving overnight to attend his Eagle Scout ceremony. “These guys just really invested in Nate’s life.”

Fast forward several years — Kiley graduated from The King’s College and was working full-time. She was accepted to law school, then completed a fellowship, but questioned whether law school was the right place for her. “Long-term, I wasn’t sure this was what I wanted to do with my life.” So she did some soul-searching.

“I’d always said that if God opened up a year in my life where I could be a Big Sister/Mentor at Shelterwood, I’d love to take advantage of the opportunity,” Kiley says. Although her background in economics and philosophy didn’t seem like a fit, she applied anyway. “I was so thankful to be accepted.”

To say it was a life-changing year is an understatement, Kiley says. “I don’t think it’s possible to be at Shelterwood for a year and not have it impact your life. It was transformational in so many ways.”

Central to Kiley’s role as a Big Sister/Mentor was daily life with Shelterwood’s teen girls. “Doing life on a daily basis with 30 teenage girls . . . was very impactful. Still today, I continue to reflect on that year and how it’s changed me.”

Of the many ways she grew at Shelterwood, Kiley points first to her perspective on relationships. “The reality is that relationships are long-term commitments. It’s lots of days talking, being supportive and small interactions over the course of time, that’s how trust is built.”

The Shelterwood girls changed Kiley’s life too. “A lot of students arrive at Shelterwood hopeless, trying to understand how to find hope when things are at their worst. They taught me about grace, perseverance and hope.”

In both Nate’s experience and her own, Kiley believes Shelterwood’s program is successful due to its community centered approach. “It’s not just getting teens on track with school, getting the right diagnosis or the right medication, but looking at each teen as a whole person. Shelterwood offers incredible professional counseling, a really strong education component and this passion to see students understand and know the Gospel.”

“At Shelterwood, I saw lives change significantly and for real. The reality is that long-term change is a marathon, not a sprint. Shelterwood is committed to working a longer path with these students,” Kiley says. “There is hope and the Holy Spirit works in people at Shelterwood.”