Steven Sheppard’s journey into the military was shaped by a combination of personal history, family inspiration, and a practical desire to secure a stable future. Growing up as the son of an Air Force veteran, Steven was immersed in the military lifestyle from a young age. His father’s service left a lasting impression on him, and as he approached adulthood, Steven found himself drawn to the same path. Reflecting on his decision to enlist, Steven shared, “There was always that tether to military life, even after my dad retired. I started to see the military as a way to build a future—one that offered both stability and the opportunity to learn a trade.”
In late 2003, Steven made the decision to visit an Air Force recruitment office, initially driven by curiosity but soon realizing the potential benefits of a military career. He recalls a defining moment during a visit to Nellis Air Force Base with his father, where the affordable meal prices at the base cafeteria piqued his interest in the lifestyle. “My small brain at the time thought, ‘Man, I can get free food,'” Steven joked. But beyond the humor, he recognized the military as a viable option to gain skills, receive an education, and follow in his father’s footsteps. “The military seemed like a no-brainer at the time,” he added.
Steven’s military career began in earnest in 2004, and over the next two decades, he rose through the ranks, ultimately achieving the position of Master Sergeant (E-7). His early years in the Air Force were focused on IT and cybersecurity, where he excelled as a System Administrator with a server focus. “I got the job I wanted, which was IT, and I was fortunate to be in a field that I enjoyed,” Steven explained. As he advanced in rank, his responsibilities grew, and he transitioned into leadership roles, overseeing larger teams and more complex operations.
One of the most impactful assignments in Steven’s career was his first posting at Sheppard Air Force Base in Texas. Though initially disappointed with the assignment, he quickly realized it was a blessing in disguise. “At first, I thought it was a cruel joke—Sheppard at Sheppard—but it turned out to be the best start to my career. The relationships I built there have lasted a lifetime,” Steven recalled. The camaraderie and friendships formed during this time laid the foundation for his military journey, and to this day, many of his closest friends are those he met at Sheppard.
One of the most pivotal assignments in Steven’s career was his tenure in San Antonio from 2014 to 2019. This period marked a significant milestone, as he was acknowledged for his exemplary contributions and leadership. “Those five years in San Antonio were when I truly came into my own,” Steven reflected. “I was honored as NCO of the Year twice and earned a promotion that allowed me to take on greater responsibilities.”
Deployments played a crucial role in shaping Steven’s career, each presenting its unique challenges and rewards. Of the three deployments he undertook, his 2016 mission to Guantanamo Bay, Cuba, during his San Antonio posting, was particularly noteworthy. “The mission at GTMO was intense, but also gratifying. We were extremely busy, but we found time to enjoy ourselves too. It was a true ‘work hard, play hard’ atmosphere,” Steven shared. This deployment, along with his final assignment at Creech Air Force Base, where he served as a senior enlisted leader, were defining moments in his career. “Being trusted to lead an entire squadron was a significant responsibility, and it was a role I embraced fully.”
While his career was marked by professional achievements, it was not without its challenges. Time away from family, particularly during deployments and a remote tour to Korea, where family was not allowed to visit, was the most difficult aspect of his service. “Being away from family was tough. My remote tour to Korea, right before we had our first child, was incredibly challenging,” Steven reflected. However, he credits his wife, Darla, for providing unwavering support throughout his military journey. “Having a good partner was huge. Darla was instrumental in helping me balance the demands of military life with our family.”
Steven’s leadership skills evolved naturally over the years, influenced by his experiences and the mentors he encountered along the way. From being appointed dorm chief in boot camp—a role assigned based on his physical presence—to leading a squadron at Creech, Steven consistently demonstrated his ability to lead and inspire others. “Leadership came naturally, but it was also something I honed over time. I learned a lot from the mentors who took the time to guide me,” he said.
Among those who had a significant impact on Steven’s development as a leader were Jim Truman and Senior Master Sergeant Sheldon Milligan. Jim Truman, a retired Senior Master Sergeant who became Steven’s flight commander at Nellis Air Force Base, played a crucial role in shaping Steven’s approach to leadership. “Jim Truman was more than just a leader—he was a mentor who took the time to teach us the nuances of both technical skills and leadership,” Steven recalled. Truman’s experience as a senior enlisted leader allowed him to provide invaluable guidance on career progression, writing effective evaluations, and understanding the broader scope of leadership. “He was the only leader who made it his sole purpose to ensure we were taken care of in both categories—technical and leadership. His mentorship gave me the blueprint to succeed.”
Senior Master Sergeant Sheldon Milligan was another influential figure in Steven’s career, particularly in his later years. Milligan, who chose to retire rather than advance to the rank of Chief, embodied a leadership philosophy that resonated deeply with Steven. “Milligan showed me that it wasn’t always about the rank—it was about what you could accomplish with people,” Steven explained. Milligan’s focus on mentorship, both professionally and personally, left a lasting impression on Steven. “He taught me a lot about leading people, but also about being a father and balancing family life with military duties. His guidance was instrumental in how I approached the latter part of my career.”
Throughout his service, Steven learned valuable lessons about teamwork and camaraderie, which have continued to influence his life. “Without teamwork and camaraderie, the mission suffers. I’ve seen toxic leadership and the damage it can do to morale and productivity. It’s essential to build strong relationships and be a genuine leader,” he emphasized.
As Steven prepares to retire in December after 20 years of service, he reflects on the impact his military career has had on his personal life. The time spent away from family was a significant sacrifice, but he managed to maintain a work-life balance, even during demanding assignments. “It was always about managing time and ensuring that family life was taken care of,” he said. His military experience also shaped his values and outlook on life, particularly the importance of family and the need to recognize when to prioritize them over work.
Looking ahead, Steven is exploring opportunities for his post-military career. With the official retirement date approaching, he is weighing options between working as a contractor with Lockheed at Creech Air Force Base or pursuing a remote position with a company based in Boston. The transition to civilian life has been an eye-opener for him, and while he’s excited about the future, he acknowledges that the adjustment has been challenging.
As he prepares to embark on the next chapter of his life, Steven remains open to sharing his experiences and offering guidance to those interested in following a similar career path. He encourages anyone considering a military career to do thorough research and understand the opportunities available. “The Air Force is a great way to start your adult life. It sets you up for success, and I think anyone interested should look into it,” he advised.
For those who wish to learn more about Steven’s journey or seek advice on a military career, he is willing to discuss his experience and what can be expected. He is available to connect via email at stevencksheppard@gmail.com.
