“Not all of us who’ve been in combat are as fortunate as I am. I had school, a church community, my family, and my buddies around me. I didn’t feel as isolated as some vets do.”
As an 18-year-old who grew up in the worst parts of Chicago during the crack epidemic, three months’ boot camp in San Diego was a way out for Captain Caleb Ra. He’s now a member of the U.S. Army Reserves serving as Medical Readiness Officer In Charge and Training Safety Officer In Charge, alongside his career as a clinical case manager serving chronically homeless veterans via the U.S. Department of Veterans Affairs Eastern Colorado Health Care System. Specifically, the Housing and Urban Development-VA Supported Housing program is a collaborative effort between the HUD and VA to end veteran homelessness.
“I started out clueless,” recalls Caleb, who will be a panelist at the foundation’s October 17 event – Up Close: The Veteran Experience in Boulder County. “At that age, you don’t have any idea what you’re getting yourself into.
“The culture at that point was definitely different then, too. After a couple deaths, changes were made to ‘instructional training’ that used to include a lot of physical and excessively exhausting training.”
Caleb formally trained as a combat engineer and deployed to Iraq in February 2003 in support of Operation Enduring Freedom and Operation Iraqi Freedom I. In 2004-2005, he deployed in support of Operation Iraqi Freedom II-II, leading a quick-reaction team. His responsibilities included designing the defensive perimeter of the Forward Observation Base in Trebil, Iraq; leading multiple security missions to disarm road obstacles that prevent convoys from reaching their objectives; supervising the disposal of more than 500 pounds of un-exploded ordinances; and heading up a four-man assault team and participating in contingency operations in Iraq/Kuwait in support of Operation Iraqi Freedom … and much more.
Having endured digging latrines, living out of tents sans running water, not eating well, and other hardships, Caleb also remembers what it felt like to experience the site of the historic Babylonian Empire … and meeting an Iraqi interpreter who learned English through U.S. music and pop culture. “He was in his 30s and I was in my 20s,” continues Caleb, having retired from the Marines in 2007, completing graduate studies in social work at the University of Illinois two years later. “We were two completely different people speaking the same language. He told me that ours were the first conversations he’d had, where he wasn’t afraid he was being spied on, or that he’d be turned in.
“There was a connection there, and it felt really good to experience that.” Not to mention, Caleb’s growing connection to his military buddies, now lifelong friends.
“I really wanted to get to know the guys, from those who came from the city like myself, to a guy who came from a small farming community in Illinois. Ultimately, my experiences set me on my current professional path, and formed my life conviction.”
In particular, Caleb remembers Tyler “Ty” Ziegel, a U.S. Marine Corps sergeant who suffered severe burns during the Iraq War, and who received a Purple Heart medal. “He got it pretty bad,” Caleb says of Ty, who died in 2012. “But the type of person he was really influenced me. He was a no-nonsense guy who would always speak his mind, getting to the essence of things. He inspired me to always carry on, and to do the best I can.”
Caleb started working with veterans experiencing homelessness at the San Diego VA Medical Center, and moved to Colorado in 2015 to continue that work here in Boulder County.
“Not all of us who’ve been in combat are as fortunate as I am,” he says. “I had school, a church community, my family, and my buddies around me. I didn’t feel as isolated as some vets do.
“In my work, I see vets who have burned bridges with their families, who aren’t able to support themselves, and who don’t have a place where they feel comfortable going. Isolation and desperation like that can lead to everything from substance abuse to tormented family lives.
“Beyond helping to address vets’ mental health needs and other immediate needs, I try to mentor them and help them make informed choices based on my own experiences. There are a lot of vets out there who are struggling, who need to find ways to engage professionally again, too.
“One challenge is getting them to change their thoughts, to realize that the freedom they fought for is now theirs to enjoy.”
Among Caleb’s numerous special trainings and awards are completing the Veteran Health Administration’s Leadership Development Institute, as well as earning Crucial Conversations certification. He’s also the recipient of eight VA Medical Center Performance Awards, two VA Medical Center Special Contribution Awards, a Global War on Terrorism Service Medal, an Iraqi Campaign Medal, and an Armed Forces Reserve Medal.
Community Foundation Boulder County Awards $231,000 in 2026 Through the School Readiness Initiative
View a downloadable press release here. 14 organizations to receive School Readiness Initiative grants, including 11 nonprofits receiving multi-year funding BOULDER, Colo., Nov. 9, 2026 – Community Foundation Boulder County announced today the 2026 grant recipients of the foundation’s School Readiness Initiative Fund. 14 grantees will receive a total of $231,000, with 11 organizations receiving […]
In the spring of 2025, Community Foundation Boulder County conducted the first Boulder County Nonprofit Survey to better understand how funding cuts and policy changes were impacting the local nonprofit sector. The data confirmed that our local, community-driven organizations were having to work harder and make difficult decisions to meet greater needs with fewer resources. […]
Meet Luisa, the community foundation’s new Operations & Communications Associate. Having called Boulder County home since 2016, Luisa is excited to give back and contribute to the foundation’s work of bringing people together to address community needs. Whether greeting guests at the front desk, helping to keep operations moving smoothly, or supporting the foundation’s storytelling […]
Donor Perception Report: Center for Effective Philanthropy Survey Results
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National Estate Planning Awareness Week is coming up from October 19 through 25. This comes on the heels of August’s Make-A-Will Month. A reminder to “make a will” is good advice, of course, but a thoughtful estate plan usually involves much more than a single document. And if charitable giving is important to you, making […]