Tenacity with a Heart: A Conversation with COL (Ret.) Timothy Lee Sheppard

For four decades—from May 1977 to September 2017—Colonel (Ret.) Timothy Lee Sheppard served our nation with a blend of grit, humility, and steady conviction. In our recent AristaValor interview, Tim opened up about formative moments, hard calls, and the quiet disciplines that turn raw potential into enduring leadership. His story reminds us that valor isn’t just about combat decorations—it’s about perseverance, integrity, and the will to build others up.

Finding a Family—and a Standard

Having lost his father at just two years old, Tim Sheppard grew up especially close to his mother—the center of his world, and the gentler influence in his family. Her sudden death when he was eighteen shattered him in ways he couldn’t yet grasp. “I thought, well, I’m eighteen, I’m an adult, I can handle this,” he said. “But I didn’t realize how close we were until I lost her.”

Without her steady hand, Tim spiraled. “I was living kind of fast and loose,” he remembered. “The prescription I gave myself for getting over her loss was alcohol and drugs—and I took them liberally.” The grief and isolation left him in a dark place, and he knew it couldn’t continue. “I was desperate and in a place I didn’t want to be,” he shared. “Inside, I knew that wasn’t who I was.”

Then one day, a friend came to him with an idea that changed everything: “Hey, I think we should join the Army.” Tim said yes immediately. “I decided I’d experience a different kind of pain,” he reflected. “Within a few weeks, I was a member of the United States Army.”

His first assignment was with the 101st Airborne Division at Fort Campbell, Kentucky—a legendary unit with a history that inspired awe. “I thought, what’s this crazy kid from Oshkosh, Wisconsin, going to do at the 101st? They’re going to find me out and kick me out.” But instead, he found belonging. Surrounded by disciplined soldiers and strong mentors, he discovered purpose, structure, and self-respect.

The 101st’s proud legacy and demand for excellence became his new foundation. “I developed a sense of duty and dedication,” he said. “It took me away from that wild side to a very disciplined, competent soldier.”

Mentors Who Change Trajectories

One of Tim Sheppard’s earliest mentors—a first sergeant—taught him that respect is earned through consistency, competence, and accountability. Early on, that same first sergeant made him company clerk and handed him a chaotic stack of handwritten shot records with a simple order: “Fix this.”

It was no small job. Long before digital systems, every immunization had to be logged by hand, and no soldier could deploy without being medically cleared. Tim tackled the problem head-on: he rebuilt the filing system by hand, organized the data, worked with platoon sergeants to schedule every immunization, and got the entire unit medically deployable. “If you don’t have the right shots, you can’t go anywhere,” he explained. “I made sure they could go.”

That experience gave Tim something deeper than administrative skill—it was the first time he realized his ability to lead, organize, and deliver results under pressure.

A few years later, a company commander changed his life in another way. When Tim planned to re-enlist and request a tour in Germany, the commander stopped him. “No,” he said, “you’re going back to school to finish your degree, and then you’re going to Officer Candidate School.” Tim tore up his re-enlistment papers, enrolled at the University of Wyoming, and began a new chapter as an officer.

Grateful for the commander’s guidance that steered him toward Officer Candidate School, Tim embraced the opportunity to grow as both a leader and a teacher. Later, as a TAC officer training officer candidates for four years, he found himself passing on the very lessons that had shaped his own career. Immersed in Army doctrine—drill, ceremonies, fitness, and leadership—he instilled discipline and confidence in others while continually reinforcing those same standards within himself. That experience not only confirmed his commander’s wisdom but also forged the leadership principles he would carry into every command that followed.

Leading Through Resistance

When Tim Sheppard took command of the 133rd Engineer Company in Laramie, he quickly noticed something off: the unit’s field gear—helmets, vests, and other protective equipment—was collecting dust in lockers. “We had all this stuff,” he said, “but I never saw anyone using it. Why do we have it if we’re not going to wear it?”

Determined to change the culture, he told his soldiers that from then on, they would wear full combat gear for every mission—road projects, airfield work, and especially during annual training. The pushback was immediate. “It was almost a mutiny,” he recalled. “They thought it was too heavy, too hot, too awkward.”

As tensions grew, the company gathered for an evening operations meeting where frustration was boiling over. Then, as Tim described it, thankfully, a respected senior advisor—Warrant Officer Grady Wright, who had just returned from school—walked into the room. “Someone stood up and said, ‘If we have to wear this gear the whole time, you’ll lose half the unit.’ And Grady spoke up and said, ‘No—you’re all wrong. The captain is right. This is what good units do.’”

That moment changed everything. With Grady’s clout behind him, Tim’s standard stuck. The soldiers complied, then adapted, and soon took pride in their discipline. “Eventually,” he laughed, “they learned to hate to love it.”

By the end of his command, the 133rd had reached the highest readiness level possible—a combat-ready engineer company known for doing things the right way, gear and all.

Valor in the Archives

The habits Tim learned from early mentors—take ownership, persist, finish—showed up years later in a different arena. While serving as Chief of Staff of the Wyoming Army National Guard, he was asked by the Adjutant General to determine whether a Korean War artillery unit had truly earned the Presidential Unit Citation—the nation’s highest collective combat honor, awarded for extraordinary heroism against an armed enemy. With no staff to spare and unwilling to pull soldiers from current missions, Tim took it on himself—off duty and on his own time.

What followed became a seven-year labor of persistence and pride. For the first three and a half years, Tim spent his evenings and weekends combing through decades-old reports, orders, and field logs—chasing faint paper trails through military archives. The deeper he went, the more resistance he met. Army historians and chroniclers repeatedly insisted the record was correct and should remain untouched. “It would have been easy to say, ‘Okay, the historians win,’” he recalled. “They didn’t want to correct the record—they wanted to leave it as it was. But they were wrong. And I could prove it.”

His persistence finally paid off. Tim’s exhaustive research proved beyond doubt that the 300th Armored Field Artillery Battalion had indeed earned the Presidential Unit Citation, and that a clerical error had denied them the honor for decades. The Army corrected the record—and the soldiers of the 300th, along with their families, finally received the recognition that had been long overdue.

But Tim didn’t stop there. In the process of securing that distinction, he uncovered evidence that two additional units had also been wrongly overlooked. Determined to finish what he started, he devoted another three and a half years to verifying their records and ensuring justice was done.

In all, nearly 2,000 soldiers and families were finally recognized. What kept him going through years of late nights and bureaucratic pushback wasn’t ambition—it was conviction. “It was a labor of love,” he said simply. “They deserved it.”

Growing What Matters

The same persistence that carried Tim Sheppard through seven years of archival research later defined his approach to leadership in the field. When he stepped into the Chief of Staff role, the Wyoming Army Guard’s strength stood at about 1,372 soldiers. Tim believed it could grow—and needed to. “It’s what’s in the best interest of our soldiers, their units, our state, and our country,” he said. But the Adjutant General, a close colleague and former classmate from Officer Candidate School, was skeptical. “Tim,” he said, “we’ve been down that road. The Guard isn’t going to grow.”

Tim didn’t argue; he made a proposal. “How about you let me have it,” he said. “I’ll show you in numbers that we can grow.” The general agreed—but warned, “I think you’re going to fail.” Tim smiled as he recounted it: “Well, I didn’t fail.”

What followed was another uphill climb—but in just over three years, the Guard grew from 1,372 to 1,875 soldiers—proof that culture, accountability, and a little humor could move mountains. That growth, combined with Tim’s relationships within the National Guard Bureau, helped secure the Army’s last remaining Fires Brigade for Wyoming, preserving the state’s proud field-artillery tradition for future generations.

Lessons in Leadership—Then and Now

Reflecting on his years in uniform, Tim Sheppard says the qualities that matter most in today’s Army—and in leadership anywhere—are flexibility and adaptability. “You have to be ready to adapt,” he explains. “The environment changes fast. You can’t cling to what worked before.” He points to how the U.S. military evolved in Iraq and Afghanistan, adjusting on the run to reduce casualties and succeed.

He’s candid about the constraints leaders face—legacy equipment and procurement realities driven by congressional processes. You may be told to maintain systems that aren’t ideal for the next fight, he notes, but the mission still demands agility: accept the constraint, plan around it, and be ready to pivot the moment conditions change.

Recruiting also weighs on him. Interest among 17- and 18-year-olds remains strong, he says, but medical and entry standards are tougher than ever. “With my old foot injury, I probably wouldn’t get in today,” he admits—and he supports keeping the bar high.

Above all, he believes leadership—military or civilian—begins with character and fundamentals. “Know what’s right,” Tim says, “and do what’s right, always.” Keep your foundation, carry your values forward, and find where you fit so you can serve well.

Continuing the Mission

Today, Tim continues to serve—just in a different uniform. As Executive Director of the Wyoming Veterans Commission, he advocates for veterans and their families across the state.

He also serves as an International Trustee for Kiwanis International, coaching three districts across North America. About 70 percent of his time is spent mentoring leaders and helping them grow membership and impact; the rest goes to international governance. And through the First Lady’s Hunger Initiative, he supports statewide efforts to combat food insecurity among children and families.

Whether in uniform or out, Tim’s approach hasn’t changed: measure what matters, help people succeed, and never stop serving. “My superpower,” he says, “is growing organizations—and helping people grow with them.”

A Legacy of Care

Asked what he’s most proud of, Tim circles back to a simple truth: he never forgot “Private Sheppard.” Throughout his career, he carried that young soldier with him—staying close to the troops, investing in their readiness, and caring about their futures. He also held himself to the same standard he asked of others: lifelong physical readiness. In his words, he stayed “very physically fit,” scoring the maximum on the Army fitness test for his entire career—falling short only once, three months after major back surgery. That blend of care for people and uncompromising self-discipline—more than any rank or ribbon—is his legacy of valor.

At AristaValor, we call that “tenacity with a heart.” It grows people. It grows units. It corrects the record. And it reminds us that leadership isn’t about being the loudest in the room; it’s about being the last to give up on what’s right.

AristaValor.org was founded to honor that same spirit—celebrating the stories of service members whose courage, humility, and perseverance continue to shape their communities. Our mission is simple: to bridge military valor with civilian leadership, helping veterans and active service members share their stories, mentor others, and keep serving long after the uniform comes off.