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Winfrey's path to professionalism

  • Published
  • By Airman 1st Class Pedro Tenorio
  • 82nd Training Wing Public Affairs

SHEPPARD AIR FORCE BASE, Texas – “Perfection is a worthless goal, perfection is a summit of a mountain that can never be reached and even if you could – there is no growth beyond that,” said Staff Sgt. Gregory Winfrey quoting one of his role models, Miyamoto Musashi.

Winfrey has been reading Musashi’s book, “A Book of Five Rings,” since the age of 12 when he was just a wee young lad punching trees in his back yard. Since then he has acquired a goal … a goal of never reaching a goal, but instead always growing to get closer to said goal.

His path to professionalism is littered with the lessons and ideals of the leaders and troops throughout his life, lessons that he takes from each one to help him on his way up the mountain. However he is not just holding them for himself, Winfrey is very generous when it comes to wisdom he has acquired over the years.  

Quiet professional

Winfrey started his patriot career as a machine gunner for the Marine Corps, which is where he met his drill instructor who taught him a valuable lesson, the value of being a “quiet professional.”

“Originally, I went in as infantry but my drill instructor was a machine gunner,” Winfrey said. “I admired him and I wanted to be like this guy. He kept calling himself a ‘quiet professional’ and that appealed to me.”

The mindset of a quiet professional opened Winfrey’s eyes. It became a new way to look at his work. It wasn’t about being recognized.

“So from that, I was like you know what, it’s not necessarily that I wanted to be a hero, It was more of the idea that I could protect my fellow Marines,” he said. “Also, if I’m going into combat, why not have the biggest gun firing the most rounds.”

From then on, Winfrey and his machine gun would be deployed to Fallujah, Iraq, which brought a new problem/teacher – stress. Which is a recurring antagonist on his path to professionalism.

But this time, stress came in the form of Winfrey missing the birth of his step-daughter. A troubling time for the young Marine, the addition of thinking of home and family brought that extra stress to the already stressful battlefield.

“I was 20 and turned 21 during the deployment,” he said. “I did not have the life experience to guide that family through that kind of experience.”

War is dirty, war is not pretty, war is not fun. Yet Winfrey said the roughest seasons are usually where you learn the most valuable lessons.

“It taught me how much family meant,” he said. “Being a father, a husband. It taught me what I was missing, so I ended up getting out of the Marine Corps and moved on to the civilian world.”

Not for me

Winfrey ended his Marine career in 2009 and lived happily in the civilian world … until he started to realize that life was not for him.

“Wearing the uniform meant too much for me,” he said. “The day I got my DD214 from the Marine Corps, I was already talking to an Air Force recruiter. It took me about a year and a half to get into the Air Force.”

In 2011, Winfrey was back into the profession of arms and in an arguably cooler looking uniform. Winfrey wanted to join security forces, but with a little bit of recruiter magic, he was convinced to go into the field of contracting, which at first he looked at as a mistake instead of an opportunity.

“My recruiter looked at my ASVAB scores and he said, ‘Well, we can put you anywhere you wanna go,’ and he suggested contracting,” Winfrey said. “He sold it as some double-O-seven James Bond stuff. You know, walking around with a suitcase full of money. Wheeling and dealing. I thought, ‘Ah yeah that sounds pretty cool’ … nope.”

Although at first Winfrey did not see the glory in contracting, he remembered the phrase “quiet professional” and began to look into all the opportunities that have opened for him in the contracting business.

“During my time in the Air Force, I’ve begun to learn all of the opportunities this job presents to me,” he said. “People think of contracting opportunities as how much money you can make on the outside. Well, there’s also a lot of opportunities on the inside.”

Winfrey fully embraced the contracting business and actually gained unique experiences through his deployments, which gave him more life lessons to be used in his future.

‘Hell yeah I was nervous’

“I was negotiating multi-million contracts for the Air Force in a skyscraper in an undisclosed Middle Eastern location at 26 or 27,” Winfrey said. “How many people in their late 20s can get to do that? Let me tell you, Hell yeah I was nervous, but you learn how to not show that kind of a thing; you learn how to not project your nervousness or insecurity.”

Now, you may ask yourself why would a Marine who had bullets fired at him be nervous of a business deal? Winfrey said his stresses in the Marine Corps and the Air Force were completely different. They could be compared to the differences in fire and water, red and blue, a nice summer breeze to whatever Texas has. Yet, all of these experiences to hone skills that Winfrey gained over time has accumulated to help himself round out into the NCO he is today.

“I often think in reality the stress in combat is a very different stress from the business side,” he said. “I think it’s two different stresses and it requires different stress management skills and communication skills.”

Winfrey compared his two stresses to the two systems of the brain. System one is the reactionary part of the brain, muscle memory and emotional decisions. He attaches System One type of thinking to his infantry days. He now relies more on System two which he states is like doing long division, thinking through problems and getting mentally exhausted.

Winfrey states this kind of difference in stresses and thinking leads to different stress management skills.

“A lot of my stress management skills right now rely on looking at the good that comes out of the work I do,” he said. “Looking at the people around me, relying on the team, that aspect hasn’t changed. But looking at teaching my juniors and peers and living up to the expectations of my peers and my subordinates. Putting all those together to try and be that NCO. Trying to be that person. That motivates me.”

Coming into the Air Force has really motivated Winfrey to succeed at his NCO duties, which coming from the Marine Corps is a whole different beast.

Different styles of leading

“Coming into the Air Force, the Air Force has a different mission, it’s not that its more lax necessarily, but it’s just that the Air Force has a different view on how the rank structure and how the enlisted force should act to each other,” he said. “That means I have to adjust system one and teach system one: ‘No you can’t just lose your mind.’ And that took a long time and a lot of mistakes.”

When Winfrey left the Marines he was an E-5. He said the transition of how the Marine NCOs corrected their subordinates to how Air Force NCOs corrected their Airmen was a road that led him to think more about what is best for the mission.

“Sometimes the Marine came out without me even knowing that it did,” he said. “That kind of lead to me having a kind of negative reputation among my subordinates. It took years and years for that to wear off and dive back enough for me to actually gain my subordinates’ trust – and actually I shouldn’t be saying subordinate, I should be saying my fellow Airmen’s trust, big A.”

Winfrey said his time as an NCO in the Marine Corps was fun, but coming to the Air Force led him to really look into the meaning of serving those under him.

“Sergeant means to serve,” he said. “I guess it gives you pause to stop and think, as you go up in rank what is that relationship, really?”

Winfrey has embraced the NCO part of his life. Looking to lead from the front and look out for his fellow Airmen, big A. Becoming the NCO his troops can believe in is one of his clearest goals while he is here at Sheppard.

“This is just what’s in my mind right now and other people may disagree with this and they are probably wiser than me, but it’s our belief in this uniform, it’s the belief in what this stands for, it’s our belief in this symbol and our belief that that symbol should mean something,” he said. “That’s what gives power and authority. You have to earn the trust of your troops, they’ll have to believe in you as a leader. They may obey you because they respect your rank, but then they’re falling back on their belief of the value of that rank or their fear of punishment.”

Winfrey believes that leading through trust, belief or respect is much stronger than leading his fellow Airmen through fear. His way to gaining their belief is by building credibility and looking out for the best interests of his Airmen and the mission.

“I’m not simply like I get up in the morning and go, ‘I want to get my troops belief,’” he said. “I get up in the morning and say, ‘I want to see so-and-so succeed.’ If people are only good because they want reward and fear punishment, then we’re pretty sorry, huh. However, the thing is if you can get the belief of your troops, you can get them to do amazing things themselves, and that helps the mission.”

Reaching for the summit

The mission may always change and that will change Winfrey’s short-term goal, but with all the knowledge Winfrey has accumulated, he does not worry if he can or cannot achieve in helping support the Air Force.

“I want to make sure I give credit to all the different leaders because I’ve taken something from, each of them,” he said. “I’ve taken certain lessons, I imagine what they’d say in certain scenarios, I take their advice with me and I could say the same thing for all of my troops. Every single one of my troops has changed me, and I think that’s important for troops to remember that they could be just as influential to their leaders and just as influential to the mission as their leaders and their mission are to them.”

Winfrey’s life has been filled with people he looks up to and admires, which drives him to do better and not worry about the mistakes he makes, but instead helps him on his path of growth.

“Sometimes, as I’m working through my workload, I think back on the workload that some of my troops were doing and how outstanding they did and when I’m feeling like, ‘Oh man, I would just like to clock out and go home.’ I think back at all of the dedication they had to it,” he said. “The fact that I need to step forward and meet that, that motivates me. Yet, I fail constantly at living up to the expectations of others and the examples set by others.”

However, Winfrey’s concept of failure may not be the same as others. It all stems back to the quote from Musashi. Winfrey’s goal is not perfection, but for him to grow on his path to professionalism. Failure is an important part of progress.

“That’s part of being human,” he said. “That’s how we won the American Revolution. We lost how many battles? I mean militarily, that was a huge failure. General Washington, it said he lost as many battles as he won … And yet – ‘Murcia.”