There are some answers you hear differently when you’re sitting across from someone.
Today, James Regan is a husband, father and owner of Valor Legacy Wealth, but long before building a family and career here in Arizona, he spent seven and a half years serving in the military.
When I sat down with James in his family home to talk about military service, gratitude and the life he has built since returning home, our conversation unfolded amid the familiar rhythm of a busy family evening. His wife, Merian, prepared dinner for their children while little voices and footsteps moved through the house. Every so often, one of the kids appeared with a question or a request for Dad.
It was ordinary family life happening around us—and perhaps that is what made one moment in our conversation so powerful.
I asked James if there were things he once took for granted that carried an entirely different meaning after serving.
His answer was one word.
“Life.”
The emotion came quickly.
James served seven and a half years in the military, including approximately 18 months overseas through three deployments—Kuwait in 2002, Qatar in 2004 and Iraq in 2006. During his final deployment in Iraq, he witnessed a side of war that never completely leaves you.
He recalled watching Black Hawk helicopters arrive and, across the flight line, seeing coffins being loaded onto aircraft to carry fallen service members home.
“We didn’t bring everybody home, it’s something I carry with me all the time,” he said.
As he spoke, the sounds of his own family continued around us. His children were calling for their dad and filling their home with activity. Sitting with him years later, I could see that his gratitude for the life he has today isn’t abstract. It is deeply personal.
For James, joining the military felt almost inevitable. Service runs through generations of his family.
Both of his parents graduated from the U.S. Air Force Academy—his father in the Class of 1979 and his mother among the Academy’s FIRST classes of women. His grandfather served in the Air Force, and both of his brothers also followed the family tradition of military service.
“Service was something that was in our blood,” James said.
A self-described history buff, he grew up fascinated by World War II and the Civil War. His father took the family to Civil War battlefields, and when James had the opportunity to choose a special trip while he was in high school, he wanted to go to Normandy.
He remembers walking the invasion beaches and visiting the cemeteries of those who made the ultimate sacrifice. Long before James wore a uniform himself, he had developed a deep respect for those who had.
He enlisted in 1999. Then came September 11, 2001.
Suddenly, the history he had spent his childhood studying no longer felt so distant. James remembers that period happening incredibly fast. His focus became his unit, the mission and the commitment not to let down the people serving beside him.
James doesn’t believe the military created his sense of gratitude. Instead, he says it deepened something already there. Serving overseas gave him a firsthand understanding of sacrifices he had previously encountered through history.
It also gave him an appreciation for something far more fundamental: getting to come home.
James described his military years almost as another lifetime. He was young when he served, and when that chapter ended, he returned home and eventually began building an entirely different life. He compared it in some ways to the young men who returned from World War II, raised families and often spoke very little about what they had experienced.
Now, James is the dad being called from the other room.
There was something poignant about witnessing the life he was describing his gratitude for while it was happening right in front of me.
“I thank God every day for the blessing of my wife, Merian,” he said.
When James thinks about what he wants his children to understand about his military service, he doesn't focus on where he went or what he accomplished. He thinks about what those experiences taught him about navigating life.
“Life is hard, and you will face adversity,” James said.
The military taught him that sometimes there is no shortcut through a difficult season. When life feels especially challenging, he believes the way forward is often simple: keep moving, one step at a time.
It is a lesson he hopes to pass along to his children. While he wants to give them a wonderful childhood, he also knows that preparing them for adulthood means teaching them how to face challenges of their own.
Military service will always be part of James’s story, but when I asked him about legacy, his answer had little to do with medals, deployments or titles.
It was about his children.
He thinks about these formative years and the responsibility he and Merian have to shape their children’s upbringing. He hopes to give them what his own parents gave him: a foundation that allows them to grow into adults who participate in the world and give something back.
James shared a quote from historian Victor Davis Hanson that he says he lives by: “We will and must die, therefore character matters.”
For James, those words have become increasingly meaningful as he considers the example he is setting at home.
“I really think about my character as a man, as a husband, as a father to my children,” he said. “That’s the legacy I think about going forward.”
When I asked what he would tell the young man who first entered the military, knowing everything he knows today, James paused. He wasn't sure he would change anything about the path ahead. Even the difficult experiences helped shape the man he eventually became.
“I would just say thank you,” he said. “And be safe.”
Although family, work and raising young children now account for much of his time, James continues to find ways to support the military community. He previously served on the board of Military Assistance Mission and supports efforts that send care packages to deployed service members—something particularly meaningful because he remembers receiving them himself.
“Those little trinkets of home, man, they go a long way,” he said.
He has also participated in placing wreaths at the Wreaths Across America Ceremony as the Air Force veteran each holiday season. For James, giving back does not necessarily have to be grand. Sometimes it is a package. Sometimes it is a wreath. Sometimes it is simply remembering.
Before we finished, I asked James to complete one sentence:
Today, I am most grateful for...
“My wife and my children,” he said.
Then he added one more.
“And freedom.”
After spending time with James and his family, those words carried a different weight. I had watched his eyes fill with emotion as he remembered those who didn't get to come home. And throughout our conversation, his children called for their dad—a simple family evening unfolding around a conversation about sacrifice, gratitude and life.
Today, James is exactly where he is most grateful to be: home with Merian and their children.
"Today I am most grateful for my wife and children."
“I really think about my character as a man, as a husband, as a father to my children. That’s the legacy I think about going forward.”