Check Your Assumptions
For Master Sergeant Arthur Raymond Jackson Jr., effective leadership comes down to three words: “Check your assumptions.”
The principle emerged from a confrontation that could have ended his career. As a younger airman in the AWACS community, Jackson noticed equipment testing was taking 45 minutes to an hour, eating into crucial training time for his troops. The procedure had been in place for decades. Senior NCOs with 20 years of experience were running it the same way they always had. Jackson was about to challenge all of them.
“So many times in leadership, you find that you get to a place and they have organizational knowledge of what they’ve been doing for so long,” Jackson explains. “Nobody ever checks the assumptions.”
Jackson’s solution wasn’t complex technology or additional resources. He simply talked to the programmers. “I said, ‘Hey, I need you to set this up so that when I’m done, it loops back to the very beginning and I have the option to go test two different things, not loop back and erase everything and start all over again,'” Jackson recalls. “That’s what took up all the time.”
The improvement cut testing time to 30 minutes. The resistance was immediate and personal. “A lot of the NCOs ahead of me were very upset because they had spent 20 years doing that,” Jackson says.
But Jackson had uncovered something crucial: the old procedure wasn’t just inefficient — it was actively harming mission readiness. Troops weren’t getting the training they needed because equipment testing consumed their time. When they actually needed to use the equipment in real situations, they didn’t know how to operate it. The senior NCOs weren’t incompetent. They were victims of organizational drift — continuing procedures because “that’s what we’ve always done” rather than questioning whether those procedures still served their purpose.
That confrontation taught Jackson something that would shape his entire career: true leadership requires evolution beyond simply following established procedures. “When you get to a certain point in leadership, it’s not about just following rules, it’s about setting rules,” he explains. “And I think sometimes people forget that part. They just want to be in charge.”
The key is asking the right questions. Jackson constantly challenges his people and himself: Why are we doing this again? Too often, the answer reveals organizational drift. People continue procedures simply “because that’s what we’ve always done” — which Jackson calls “a bad answer.”
This principle extended far beyond that single procedure improvement. It became the foundation for everything Jackson did, from managing presidential aircraft missions to developing the troops who would eventually serve in the Presidential Airlift Group. “I’m always telling people, check your assumptions,” Jackson says. “Just make sure that what you’re doing and you think it’s right, it’s right because you’re doing it for the right reason, not just because that’s what we’ve been doing. Ask questions.”
Jackson’s willingness to challenge assumptions while delivering results earned him significant recognition. He holds four Air Medals — unusual for enlisted personnel — awarded during special operations duties in Afghanistan. “I’m proud of that because there were certain things that we did that kept a lot of people from dying,” Jackson says. He also holds Achievement Medals across multiple categories: VIP transport, flight test, and AWACS operations. Few people have earned recognition across such diverse specialties.
The Crisis Hidden in Plain Sight
When Jackson retired in 2017, he discovered a statistic that reveals a crisis hiding in plain sight: 80% of veterans leave their first civilian job after military service. The reason isn’t money. It’s meaning.
“You get to a point where you don’t care about recognition anymore,” Jackson explains. “All you care about is that what you do matters. It has to be something of value.”
Jackson has watched this pattern repeatedly among his peers. Veterans who find meaningful work tend to stay. Those who take high-paying jobs without purpose often leave to become firefighters, police officers, or return to military service. “I’ve known plenty of guys that got jobs that were high paying, but they didn’t enjoy the work and the work really wasn’t valuable,” Jackson says. “A lot of times when guys get out, they’re just trying to get a job to pay the bills. It’s not until they’ve been there for a while that they realize, ‘I really would rather go be a fireman or be a police officer.'”
Jackson was fortunate. He immediately transitioned to civilian contractor work maintaining the same aircraft he’d supervised as military crew. The work had clear value and direct connection to his military experience. “As long as you’re doing something that has some value, you’re going to be okay, you just can’t go out and punch a clock anymore because you’ve been there and done that.”
Military service taught Jackson a fundamental skill that transcends any specific career: the ability to learn rapidly and adapt to new challenges. His technical training exemplified this approach — nearly two years of school in Mississippi covering 33 different training blocks. Each block required mastering new concepts, from basic electronic principles to complex circuits and computer systems, all with demanding 85% passing standards.
“I have to learn this stuff I’ve never seen before, get tested on it, pass at a certain degree, then move to the next,” Jackson recalls. “If you learn to do that over and over again, you get better at being able to pick up and drop knowledge.” This adaptability became Jackson’s professional superpower, enabling him to excel across AWACS operations, presidential aircraft missions, and special operations in Afghanistan.
“That translates to civilian life, there’s not much that I don’t feel like I can’t learn. Give me enough time and enough resources to give me what I need, I can probably pick it up.” But here’s what makes Jackson’s approach different: he combined rapid learning with assumption-checking. He didn’t just learn procedures — he questioned whether those procedures were optimal.
The Kansas-to-Oz Problem
Jackson addresses a reality many veterans face: the difficulty of returning to a home that no longer feels familiar. “It’s very weird,” Jackson explains. “If you’re giving your life for a couple of decades and you spend a lot of time overseas, when you come home, it may not feel like home anymore.”
He uses a powerful analogy: “You were living in Kansas, and then there was a tornado. You went to Oz. You come back and everything is kind of changed.” Many veterans don’t return to their original hometowns because those places no longer exist as they remember them. The high school friends have moved away, the local economy has shifted, and the veteran has fundamentally changed through their service experience.
Finding new community becomes essential for successful transitions. Living in Hawaii, Jackson actively connects with organizations supporting veterans in transition. He works with the Black Vet Project, the Organization of Black Aerospace Professionals, Spitfire Elite through his Air Force Academy connections, and local VFW chapters.
But Jackson emphasizes that formal organizations aren’t the only solution. “If you’re in the military for a long period of time, you’re going to make friends from other services,” he says. “That ends up being your peer group — Navy, Army, Marines.” These informal networks matter crucially, especially given suicide rates among Iraq and Afghanistan veterans. Jackson’s generation maintains group chats and regular check-ins.
“We try to communicate and keep tabs on our friends and make sure we check in,” Jackson explains. “Especially after the Iraq Wars, we were having a lot of guys losing them to suicide and all types of things like that for PTSD.”
Jackson’s most urgent message centers on something he sees lacking in today’s military and veteran community: intergenerational mentorship. “I had a lot of mentors who were older than me when I came to the military who reached down and looked out for the guys who were younger,” he explains. “That makes all the difference in the world.”
The decline of mentorship isn’t just a military problem — it’s a societal crisis affecting young men across America. “The problem they’re finding with young men in the country now is that they’re afraid they’re not being able to bond with their fellow Americans,” Jackson observes. “Part of that is because the generation in front of them hasn’t reached down to them. They’re kind of like, ‘Oh, they’ll take care of themselves.'”
This mentorship gap helps explain both veteran transition struggles and broader social isolation among young people. The assumption that “kids will figure it out” is proving catastrophically wrong. Jackson’s message to struggling veterans is direct: “There are people above you that care about you and want to reach out to help you out. It’s just they may not be able to get to you right away.”
Beyond the Uniform
When discussing PTSD and military trauma, Jackson offers perspective that challenges common assumptions about military mental health. “I’ve gone through it, but I was already one of those people who had a very tough upbringing, so I was able to compartmentalize a lot,” he explains. “I was able to separate things early. So by the time I got to the military, I was like, ‘Yeah, this is just another thing I got to put over in this box and leave it there.'”
Jackson’s approach worked for him, but he doesn’t prescribe it for others. What matters is recognizing that military service itself doesn’t create resilience — it reveals and refines resilience that people bring with them or develop through support systems. “Putting on the uniform isn’t like a superpower,” Jackson explains. “It doesn’t protect me from depression. It doesn’t protect me from financial challenges. But the tools that I’ve learned, the resilience, the support systems — that’s the superpower.”
Reflecting on his career, Jackson admits to a discovery that surprised him. “My career surprised me because I didn’t think I was going to enjoy it as much,” he says. “I had planned to come in and do my little four years and get out. But I really did enjoy what I did for a living, and I was good at it.”
The combination of enjoyment and competence created a career foundation that lasted 24 years. But Jackson credits mentorship for making that possible. “It also helped that I had a lot of mentors who were older than me who reached down and looked out for the guys who were younger,” he reflects. “That makes all the difference in the world.”
Three Applications That Change Everything
Jackson’s “check your assumptions” philosophy applies to three crucial areas that can transform both veteran transitions and civilian leadership:
First, organizational effectiveness. Question procedures that exist simply because “that’s how we’ve always done it.” Jackson’s 30-minute testing solution saved countless hours and improved training quality — similar opportunities exist in every workplace. Second, career transitions. Don’t assume your first civilian job will provide the meaning you need. Eighty percent of veterans leave their first job, but those who find meaningful work tend to stay. Third, personal development. Challenge assumptions about what you can learn and what careers might suit you. Jackson went from confused recruit to presidential aircraft specialist — none of it planned, all possible through questioning assumptions about limitations.
“There are people above you that care about you and want to reach out to help you out,” Jackson emphasizes. “It’s just they may not be able to get to you right away. So you don’t have to be afraid.” He doesn’t minimize the challenges veterans face — financial strain, depression, isolation, and difficulty finding meaningful work.
But Jackson’s core message is empowering: “Check your assumptions, take care of your people, and remember that leadership isn’t about following rules — it’s about making the right rules for the right reasons. That works whether you’re at 40,000 feet with a president or in a civilian office trying to figure out your next move.”
Today, Jackson continues supporting the aircraft he once commanded as a civilian contractor. Former crew members from his Hawaii unit have gone on to prestigious assignments, including serving as personal attendants to the Obama family. “I’m very proud of my time doing VIP Special Air Missions,” Jackson reflects. “A lot of my former troops went on to do big things. That’s what good leadership creates — not just mission success, but people who go on to create their own success.”
Master Sergeant Arthur Raymond Jackson Jr.’s legacy demonstrates that effective leadership comes from the courage to question assumptions, the commitment to develop people, and the wisdom to create better systems rather than simply following existing ones. The man who kept presidents safe at altitude now keeps fellow veterans grounded in purpose, community, and hope.
Jackson’s message to those still serving: “Thank you for your service, thank you for the support, and keep it up.” For those transitioning, he emphasizes that the same attention to detail that protects world leaders can help guide their own futures — if they’re willing to question their assumptions about what’s possible.
Resources for Veterans and Families
Veterans Crisis Line
Dial 988, then press 1 | Text: 838255 | Chat: veteranscrisisline.net
Confidential, 24/7 support for veterans, service members, and their families in crisis.
Military OneSource
Phone: 800-342-9647 | militaryonesource.mil
Free, 24/7 support for service members and their families, including counseling, relocation help, financial advice, and more.
Black Vet Project | Community organization connecting Black veterans and providing support networks.
Organization of Black Aerospace Professionals (OBAP) | obap.org
Supporting both civilian and military aviation professionals through networking and career development.
Iraq and Afghanistan Veterans of America (IAVA) | iava.org
Advocacy and community building for post-9/11 veterans.
Team Red White & Blue | teamrwb.org
Physical and social fitness programs connecting veterans through community activities.
National Alliance on Mental Illness (NAMI) HelpLine
Call: 800-950-NAMI (6264) | Text: “HELPLINE” to 62640 | nami.org/help
Mental health education, support, and advocacy for individuals and families.
Student Veterans of America | studentveterans.org
Educational support and networking for veteran students.
Hire Heroes USA | hireheroesusa.org
Employment assistance specifically designed for veterans and military spouses.