For the Rosbrughs, it wasn’t their son signing the papers that felt so heavy. It wasn’t his orders arriving in the mail. The moment that felt like a ton of bricks was those last hugs at the airport before sending him off to basic training.
The Rosbrughs — made up of dad, Sonny; mom, Missy; oldest son, Dalton; and three younger sisters — would not have considered themselves a military family before that moment. But when Dalton enlisted with the South Dakota National Guard last year, this family’s point of view shifted dramatically. “Our exposure to the military really wasn’t that much,” explained Missy, who is the Office Manager at Crossroads Wesleyan Church in Rapid City. “My grandpa was in the Air Force and I have a cousin who is in the National Guard, but other than that, we really weren’t a military family.”
Dalton, like most kids in their senior year of high school was faced with the common but profound question of his post-graduation life. “He wasn’t certain on what he wanted to do,” Sonny, who is the Lead Pastor at Crossroads said. “And I think that bothered him.” Dalton, of course, had his options. A smart young man with several interests, he considered his path forward — but one possibility stood out.
Finding a Guide
Long time family friend, Sgt. 1st Class Lyn Waldie, is a recruiter for the South Dakota National Guard. He and his family have called Crossroads their church home for over 15 years. So when questions came up about Dalton potentially enlisting, the Rosbrughs found a new reason to be grateful for their friendship with Lyn.
“That was such a blessing,” Missy said. “We knew we could trust him and what he was telling us.” For any family who is walking through the possibility of their son or daughter enlisting, finding an expert like Lyn, according to the Rosbrughs, is a must.
Lyn’s advice to families contemplating enlistment is simple: don’t guess. Don’t rely on noise. Don’t get lost in opinions from people. “Every branch is a little different,” he explained. “You’ve got to figure out your goals first, then see which one actually fits those goals.”
Lyn encourages families to do the work of exploring, not just Googling and hoping for clarity. “A face-to-face conversation with a recruiter goes a long way,” he said. “Google doesn’t always tell you what questions to ask.” That grounded approach mattered for the Rosbrughs. Because as soon as Dalton started moving toward enlisting, the voices started coming. Well-meaning ones. Concerned ones. But ones that were maybe a little mistaken.
“Even people who have served might say things like, ‘You’re letting him do what?’” Lyn said. “That happens more than people think.” It’s part of the process. Big decisions — and Lyn is clear, the military is a big decision — tend to collect big opinions. But those decisions can get clearer through intentional conversations with your recruiter.
The Benefits
When it comes to benefits, Lyn pointed out that the Guard offers both tangible support and long-term development.
On the practical side, South Dakota Guard members — both Army and Air — can receive up to 100% tuition coverage at state universities, technical schools and select private institutions. Health insurance, steady income and eligibility for the GI Bill all factor into the decision as well. Those who pursue active-duty service in the U.S. Air Force can also take advantage of tuition assistance while serving and full GI Bill benefits after their service, offering another strong path to pay for college. “There’s a real financial piece that matters for a lot of families,” Lyn said. “College benefits alone can change the entire equation.”
He also pointed out what doesn’t show up on a benefits sheet. “The intangible part is harder to quantify,” he said. “Job skills, leadership, being part of something bigger than yourself, those things stay with you. That’s what the Guard tends to do. It gives people a direction they didn’t always know they were looking for.”
He’s seen it firsthand over years of service, including a deployment to Iraq, where he says the relationships built under pressure often outlast the experience itself. “It’s the people you serve with,” Lyn said. “That’s what sticks.”
Treasure your Time
His signing ceremony was a proud moment. His orders brought anticipation. But none of it compared to the airport. “That was emotional for everyone,” Missy said. “We were sending him off into the unknown.” It wasn’t just Dalton stepping into something new. It was the whole family stepping into a new chapter.
At the gate, everything slowed down in a way no one was ready for. The final hugs didn’t feel final until they were. And then he was off. “We just had to step back and say, ‘OK God, you’ve got him,’” Sonny said.
For the sisters, it hit in its own way. One moment stuck with Sonny in particular. “Our oldest daughter hugged him and then said, ‘I think I wasted time with him.’” The reminder is simple, but not easy: you don’t get unlimited ordinary days. Pay attention while they’re still happening.
Commit and Encourage
Basic training stripped life down to structure, discipline and endurance. Dalton pushed through long days, strict routines and physical challenges that tested everything from strength to mindset. The final test was called “The Forge” — a multi-day, 30-plus-mile march with a 40-pound pack, layered with exhaustion, sleep deprivation and nonstop movement.
It was the kind of thing you don’t really understand until you’ve lived it. He made it. And in that process, something else began to take shape. Discipline, yes. But also confidence. Leadership. And connection. Because nobody goes through that alone. The people alongside him became something more than classmates or unit members. They became a kind of brotherhood — built through shared challenges. The kind that doesn’t fade when the experience ends.
For the Rosbrughs, the transformation wasn’t just what Dalton learned. It was who he was becoming. They saw it in the stories he told. In the way he carried himself. In the way he began to step into responsibility with a new kind of steadiness.
In letting go. In the trust. In learning to encourage from a distance instead of trying to control what can’t be controlled anymore. This isn’t just a son leaving home, but a family learning how to hold on differently. And discovering, somewhere in the middle of it all, that love doesn’t shrink with distance. It grows through it.
By Stephen Simpson
Photos courtesy of the Rosbrugh family and McKayli Simpson