FAIRCHILD AIR FORCE BASE, Wash. -- Staff Sgt. Kailen Singleton’s story had a more rocky start than most. It began with hardship, missteps, and a series of choices that could have defined the rest of his life, but he chose to not let his circumstances define him.
Born in Tacoma, WA, Singleton experienced instability at a young age. Around seven years old, family circumstances led to him being separated into the foster system. After spending a summer there, the courts determined it was safe for him to return home. His brother left home a few years later and left behind a path that he did not want to follow. The fractured relationship between them would become one of the early chapters in a life that would later be driven by a determination to break cycles rather than repeat them.
As a teenager, Singleton found focus in the pool. He began swimming and eventually competed at the state level as a junior in high school. His first career goal was where he imagined a future in the automotive world and enrolled at Minnesota State University to study automotive and manufacturing engineering. However, poor decisions and his newfound independence began to interfere with those plans.
Struggles with underage drinking and legal trouble compounded during the 2009 recession. With only six classes left before graduation, financial pressures forced him to leave school. He found work where he could, but instability followed him. In June 2010, after a DUI in Mankato, he lost nearly everything: his job, his car, his license and his home. He spent 32 hours in jail, a time he describes as the moment he truly hit bottom.
“I remember sitting in that cell realizing I had run out of excuses,” he said.
After his release, Singleton lived for several months in an abandoned mobile home without power or water. He learned how to just focus on getting by one day at a time. That same summer, in July 2010, he met the woman who would become his wife and pull him back from the path he was on. By September, they were building a life together with her son from a previous relationship that Singleton was determined to be a good example for.
Singleton took whatever honest work he could find. He sold knives door-to-door, worked in a fundraising call center, and spent a year at a manufacturing plant. He stocked shelves at Target and built up to working more than 70 hours a week so his wife could attend school full time while they stayed afloat financially.
When she graduated and secured stable employment, Singleton earned a supervisor position at Target. Leadership appealed to him for a simple reason: he wanted to help people grow. The role gave him his first structured opportunity to mentor others, develop teams, and learn how to balance expectations with compassion. He had his first interaction with military recruiters there and he was very interested in joining after hearing service stories from his wife’s family, but was told he would not be able to enlist due to his record.
He later transitioned to Home Depot, where he spent nearly six years building departments, improving processes, and eventually stepping into an assistant store manager role. He gained extensive experience in operations and people management. Though sometimes leadership also required difficult decisions. After taking a stand on issues he believed were morally right, his career there stalled. Ultimately, he chose to walk away.
He didn’t know it at the time, but that decision would lead him down a new path for his career. In 2018, Singleton visited a recruiter to explore joining the Air Force Reserve. This time, the answer was different. The Reserve path would allow him to serve while remaining present for his family, especially his son as he was determined to be the kind of father he hadn’t always had.
In November 2018, he enlisted as an aircraft structural maintenance specialist with the 934th Airlift Wing in Minneapolis–St. Paul. After time in the delayed entry program, he shipped to Basic Military Training in June 2019, followed by technical school.
He approached his new career the way he now approaches everything.
“If I’m going to do something, I’m going to do it right the first time and not just rush and have to repeat it,” Singleton said.
He volunteered more than 200 hours while in training and graduated as the top graduate of his class. He sought additional leadership opportunities early, completed Airman Leadership School ahead of schedule and continued improving every section he joined.
In 2022, an opportunity arose to transition to active duty. Singleton chose to pursue SERE instructor training. The selection process was demanding, and administrative hurdles delayed his start, but he remained patient and steadfast. Throughout the SERE selection process, he was able to persevere by focusing on one small victory at a time.
His transition to this new life wasn’t without challenges. He had to shift from a civilian leadership mindset to a military one which involved embracing standards, structure, and a different rhythm of accountability. After the selection process, he moved to Fairchild Air Force Base to attend the SERE apprentice course, knowing that failure would mean losing his opportunity to serve given the circumstances in which he joined.
During Christmas exodus while still in training, Singleton and his wife learned that their seven-month-old nephew was facing placement into foster care. After experiencing the foster care system himself, they came to the decision that they would bring him into their home. While balancing court proceedings and a new career field, Singleton completed his training and earned his place as a SERE specialist.
His start to the new career didn’t come as he expected as he initially worked in SERE logistics while finalizing instructor certifications. After being promoted to staff sergeant, he returned to logistics and was entrusted with responsibilities typically held by a Master Sergeant, becoming the logistics flight chief in a brand-new role. Drawing heavily from his civilian leadership and operational background, he built the section from the ground up. Under his leadership, the team earned squadron team of the year honors and developed a solar-powered mobile command post now used in SERE training and other Air Force missions.
Even with increased responsibility at work and home, Singleton had his sights set on OTS and returned to his unfinished education, taking one class at a time.
He was recently selected to attend OTS and will serve as a Force Support Officer, a role that aligns closely with what his motivation from the beginning, taking care of people first.
He often shares two beliefs that guide his leadership philosophy.
“Take care of your employees, and they’ll take care of the mission,” he said. “And leadership isn’t just attributes — it’s a philosophy built on principles that guide how you lead.”
He credits much of his success and decisions to the people who he wouldn’t be here without. His wife Ariel and their children Karac, Kielian, Khyler, and Bodhi.
For Singleton, service isn’t about erasing the past. It’s about using it. From a childhood marked by instability, to a jail cell that forced self-reflection, to leading Airmen, and building new capabilities for the Air Force, his path reflects steady, intentional growth. One small step at a time.