Dexter Peggins Jr: Life and Leadership Lessons I Learned In The Military

Be in the right place at the right time — there have been a number of opportunities that have been afforded to me largely because I was in position.

As a part of my series about “Life and Leadership Lessons Learned In The Military”, I had the pleasure of interviewing Dexter Peggins Jr.

Dexter Peggins Jr. is a husband, father, combat veteran, and business owner. Dexter’s personal mandate is to help people get clarity concerning their purpose, overcome life’s what-ifs, and win in difficult situations. The diversity of his experiences has made him a sought-after speaker in the areas of leadership and personal development, as well as a trusted advisor for those dealing with life’s most crucial issues.

Thank you so much for doing this with us! Can you tell us a bit about your childhood “backstory”?

I believe I had a fairly common upbringing. I am the oldest of three boys and we grew up in a two-parent home. My father was a career military man, which means that we moved a lot, and whenever my father would have to go on an assignment, I would get the infamous “You’re the man of the house speech”. As a type-A personality, even thought I was a young, I took the charge of being a man to heart and projected myself as being older than what I was. In this regard, I feel like I grew up early, but in hindsight I wouldn’t change anything.

And what are you doing today? Can you share a story that exemplifies the unique work that you are doing?

These days I wear a several hats that keep me quite busy. I am a public speaker and leadership coach; however, it’s my work with at-risk youth that keeps me on my toes. Through my nonprofit, City of Refuge Enterprise, I am able to work with area youth who are in need of mentoring services. Through our organization we aim to help transform the lives of juveniles who are in the system and in danger of being incarcerated.

Can you tell us a bit about your military background?

I am a 15-year Army Veteran with 3 combat tours in support of both Operation Iraqi Freedom and Operation Enduring Freedom (Afghanistan). I initially began my career as Air Condition Refrigeration Mechanic, and eventually reclassified into Military Intelligence.

Can you share the most interesting story that you experienced during your military career? What “take away” did you learn from that story?

I have no shortage of interesting stories; however, my first deployment was a real eye opener. Someone once told me that in the Army you don’t have to pay to be miserable because they issue misery for free, and my first deployment was a master class in hardship. I remember having to go on several dangerous convoys along this highway called MSR Tampa.

One time I was in a 4-vehicle convoy headed to support members of our unit on another base. As we were getting ready to leave the base there was a small skirmish outside of the gate which delayed our ability to leave the area. Once the skirmish ended and the all-clear was given, we made it about 10 miles outside of the base, only to stop again because one of the vehicles had a flat tire. In 100 plus degree heat alongside one of most dangerous roads in the world, there we were changing a tire and pulling security at the same time. When we finished changing the tire, my company Commander said that he had seen enough for the day and made the decision to return to base. Later that day we found out that there was a huge explosion along the same route that we would have taken to visit the other base. Ironically, we estimated that had it not been for the events that held us up we would have been in that location around the time of the explosion.

During my deployment I learned a lot about resiliency and this story highlighted how fortunate I really was.

I’m interested in fleshing out what a hero is. Did you experience or hear about a story of heroism, during your military experience? Can you share that story with us? Feel free to be as elaborate as you’d like.

If you are in the military for any length of time, you’re going to become familiar with a few stories of heroism. Whether it’s Audie Murphy and his exploits during WWII, Roy Benavidez and his heroic acts during Vietnam, or even Michael Murphy and his Seal team while serving in Afghanistan, there are so many men and women who have worn the uniform that can be considered heroes. Ultimately, I believe a common trait that you will find within all of their stories is someone who was willing to go beyond themselves for the benefit of others.

Based on that story, how would you define what a “hero” is? Can you explain?

I would define a hero as someone willing to sacrifice their own personal convenience and even their own safety to protect someone or something else. The heroes that many of us are familiar with in many instances wouldn’t deem themselves as heroes; however, their actions say otherwise. In a lot of instances their acts of heroism were split second decisions, which demonstrated a selflessness that speaks volumes of their character.

Does a person need to be facing a life and death situation to do something heroic or to be called a hero?

No. Life and death circumstances are not and should not be the only measure for what makes someone a hero. As I stated before, I believe the truest measure of a hero is someone that is willing to sacrifice themselves for others. This sacrifice can be in time, resources, or even in personal comfort.

Based on your military experience, can you share with our readers 5 Leadership or Life Lessons that you learned from your experience”? (Please share a story or example for each.)

1. Be in the right place at the right time — there have been a number of opportunities that have been afforded to me largely because I was in position.
2. Celebrate your team in the open and correct them in private — far too often leaders do a good job of critiquing their people publicly but a bad job of offering public praise.
3. If there is an expectation, don’t forget the demonstration — far too often leaders live in the place of assumptions rather than confirmation. If you expect something from your team, make sure they know how to do it.
4. Don’t be the single point of failure — In the military, at least 2 people knew how to do your job. In this regard, the mission continues even in the absence of a team member.
5. Welcome feedback — a leader that knows it all, is a leader that is not growing.

Do you think your experience in the military helped prepare you for business? Can you explain?

Yes! The military taught me the value of systems and partnerships. From the moment you join the military you discover that everything is systematized. In basic training there is a system that helps transition you from a civilian to a solider, and even transitioning out of the military there is a system. As a business owner I understand the importance of creating step-by-step structures, largely because I saw the value of them while in the military.

In the military, you work in teams with individuals who have different specialties or job assignments. This dynamic creates environments in which cross-training is prevalent, and as a business owner I recognize that the right partnerships can cultivate growth opportunities.

As you know, some people are scarred for life by their experience in the military. Did you struggle after your deployment was over? What have you done to adjust and thrive in civilian life that others may want to emulate?

I have encountered a number of situations that have undoubtedly changed me. After my first deployment I felt like I was in a fog for several months after my return. For me, prayer has always been a vital component in my ability to get clarity and gain peace. As a civilian, I still maintain a posture of prayer and meditation. I have also learned to leave the job at the job and not bring my frustrations home. This attitude has helped me to be more present and available for my family and friends.

Are you working on any exciting new projects now? How do you think that will help people?

At the moment, my nonprofit is getting ready to facilitate another 10-week long session with a new group of young men. Using my book, “Dear Son: The Words of a Father to the Heart of a Son” I am also gearing up for a new series dealing with fatherhood that will take place around Father’s Day.

What advice would you give to other leaders to help their team to thrive?

Pace yourself! There is normally a compulsion to try and do everything all at one time; however, it has been my experience that this causes undue tension and frustration. As a leader, emphasize that which is critical and systemize what can be done over the course of time.

What advice would you give to other leaders about the best way to manage a large team?

Acknowledge the ability of your subordinate leaders and don’t be afraid to delegate authority. I adhere to a system of 12s, which suggest that a manager’s immediate team should not be larger than 12 individuals, a supervisor should oversee no more than 12 managers, and a director should have no more than 12 reporting supervisors. If done correctly, the senior leader should be able to get a pulse of the organization through their interaction with the directors.

None of us are able to achieve success without some help along the way. Is there a particular person who you are grateful towards who helped get you to where you are? Can you share a story about that?

There are a number of people that I can highlight; however, with respect to what we have discussed today I would be remiss to not acknowledge my late friend, SSG Ricky Crockett. There was a time well before my first deployment that I wanted to be selected for the Army Corporal Recruiting Program; however, I was struggling to pass the run portion of my physical training (PT) test. At the time SSG Crocket was my section supervisor and he told me if I was serious about becoming a recruiter that he would help me get ready for the process. Three times a week after having worked long hours in the motor pool, we would go running. He sacrificed his time and energy to help me get ready for the process. Due to the deployment, I couldn’t submit my recruiter packet; however, his selflessness spoke volumes to me. Tragically, he was killed in Iraq the following year. Nevertheless, to this day I try to model his example in a lot of the things that I do.

How have you used your success to bring goodness to the world?

I have been able to use my success by highlighting causes that are important to me. I am passionate about helping marginalized communities. For the past 7 years I have served as a mentor for at-risk youth. I’ve tutored in after school programs, been on the board for the My Brother’s Keeper Initiative, been an advisor for the juvenile prison system, and in 2020 founded a nonprofit that provides mentorship services. In working with this population, I understand the necessity of young people having an active father/male presence in their lives and in this regard, I have been helping men to understand their value, while encouraging them to get involved in their communities.

You are a person of great influence. If you could inspire a movement that would bring the most amount of good to the most amount of people, what would that be? You never know what your idea can trigger. :-)

I believe that everyone has a responsibility to give back. In this regard, we can all be heroes by serving our communities. With that being said, find a cause you are passionate about and start serving!

Can you please give us your favorite “Life Lesson Quote”? Can you share how that was relevant to you in your life?

“It is better to be prepared and not have an opportunity, than to have an opportunity and not be prepared.” This quote is helpful reminder to maintain a position of readiness for the opportunities that I say I want.

Some of the biggest names in Business, VC funding, Sports, and Entertainment read this column. Is there a person in the world, or in the US with whom you would love to have a private breakfast or lunch with, and why? He or she might just see this if we tag them :-)

As a society we are rapidly making a lot of technological advancements, and I would be interested in having a conversation with Elon Musk. As a leader in that space, I’d like to ask some questions about some of the work that he is doing.

Thank you so much for these amazing insights. This was truly uplifting.