Building Lasting Legacy Through a Life of Service and Leadership
What drives a person to choose a life of service over chasing after financial success? In this blog, we dive deeper into what it takes to build a legacy as a servant leader. We’ll explore the inspiring journey of Oak McCulloch, a retired Army officer whose life has been a testament to selflessness and strong leadership. His story shows how trust, perseverance, and dedication to others can make a real impact, whether on the battlefield or in everyday life.
A Life of Service: Oak’s Story
After 23 years in the Army, Oak didn’t just hang up his uniform and walk away. Instead, he continued serving in unique ways that helped shape the lives of others. From playing a key role in disaster relief operations across the U.S. to working with Army ROTC at a university, Oak has been a mentor to hundreds of future leaders, guiding them as they move forward in service to both the military and the country.
His transition from military service to running a food bank only deepened his commitment to serving others. Leading disaster relief operations during crises like the Gulf oil spill, Oak helped expand the food bank, doubling its truck fleet and staff to keep up with the rising demand. These efforts were shaped by the lessons he learned in the Army: resilience, resourcefulness, and leadership.
Having traveled to 45 countries, Oak credits his military career with helping him build a global perspective on leadership and service. The same mindset that guided him through international assignments continues to influence how he leads today.
Now, Oak is channeling his passion for service into writing. His second book, Arm Yourself for Success, explores how leadership transcends situations—whether it’s a high-stakes military operation, a humanitarian effort, or a day-to-day civilian challenge. Oak’s commitment to leadership and service defines everything he does, inside and outside of his career.
Lessons in Trust and Mentorship
Building trust and caring for your team are at the heart of effective leadership. Looking back, Oak fondly remembers his early years in the Army, especially the mentorship he received from retired generals who helped shape his leadership philosophy. They taught him that leadership isn’t a right but a privilege. Trust is the foundation of any successful team, and you can’t lead without it.
Mentorship has been a constant thread throughout Oak’s journey. His mantra has always been: “Have a mentor, be a mentor.” He believes that learning from people in other fields provides fresh perspectives and innovative ideas that you wouldn’t otherwise encounter.
Leadership, according to Oak, is about humility and openness. True leaders are always willing to learn from others and grow, regardless of their experience level.
The Decline of Trust in Institutions
There’s a troubling trend these days: trust in major institutions like government, the military, and the justice system seems to be dwindling. This loss of trust affects not just our faith in institutions but our collective sense of purpose. When trust fades, people disengage. Whether it's a decline in faith in voting systems or a rise in people leaving traditional jobs for freelancing, it's clear that many feel let down by the systems they used to rely on.
Oak believes that one key to rebuilding trust is fostering a sense of unity. Leaders must show that the success of an organization—be it a company, a government, or the military—depends on everyone working together for a common cause. It’s vital that people feel valued and motivated to contribute to something greater than themselves.
Leaders need to trust their teams to make the right decisions and uphold the organization’s core values. In turn, teams need to believe that their leaders are working with integrity and putting the collective good first.
At the core of trust lies integrity. Leaders who act with integrity naturally inspire trust, simply by doing the right thing because it’s the right thing to do—not because they’re being watched. Unfortunately, many leaders today fail to meet this standard, which only fuels the decline of trust in leadership.
The Power of Connection
When leaders don’t take the time to understand their people—both their strengths and challenges—it can lead to poor decision-making and missed opportunities. One of Oak’s key pieces of advice is to prioritize personal connections. He has a simple practice that he’s followed for years: make it a point to learn something new about each person on your team every day. Not work-related stuff, but personal details. This opens the door to natural conversations that can lead to better teamwork and deeper trust.
Oak also credits one of his mentors, a retired three-star general, for teaching him the importance of humility in leadership. His advice was simple yet profound: “Never turn down the chance to get your own cup of coffee.” It’s a small act that shows you’re no better than anyone else on your team. Plus, when you’re at the coffee pot, you get the chance to talk with your people and build relationships in an informal, low-pressure setting.
“A team is not a group of people who play together. A team is a group of people who trust each other.” - Vince Lombardi
Finding the Right Mentor
Mentorship plays a crucial role in leadership. A good mentor provides guidance, wisdom, and perspective that can help you grow both personally and professionally.
When searching for a mentor, consider these tips:
Find someone with the experience you need: Look for someone who has the skills or knowledge that will help you move forward.
They need to be invested in you: A mentor must genuinely care about your growth and be willing to invest time in helping you.
Seek mentors from outside your field: Sometimes the best mentors come from completely different industries. They offer new insights that can benefit your professional and personal life.
Remember, mentorship isn’t just about receiving help—it’s about giving back. Once you’ve gained wisdom from your mentor, it’s important to pass that knowledge on to someone else. Leadership is about paying it forward.
For those just starting out, don’t wait for a mentor to find you. Seek one out. There are people who are eager to help; they may just not know you need guidance yet.
Leadership & Legacy
For Oak, leadership has always been about more than just getting results. He views leadership as a lifelong journey of growth, responsibility, and giving back to others. Early in his career, he began to realize the importance of leaving a leadership legacy. A conversation with Master Sergeant David Powell solidified this belief. Powell shared a quote that Oak carries with him to this day: “Great leadership, handed down from generation to generation, is what develops great nations.”
This insight reinforces the belief that leadership isn’t just about immediate success. It’s about shaping the next generation of leaders who will carry forward the values and principles that create lasting impact.
In light of Oak’s new book Your Leadership Legacy, he explains that legacy is not just about what you achieve—it’s about the leaders you develop. The true legacy is in the people you guide, mentor, and prepare to take the reins when you’re gone. These individuals will continue to shape the organization for decades after you’ve moved on.
Leadership is not about titles or positions. It starts with leading yourself and inspiring those around you, no matter where you are or what your role is.
The First Steps in Creating a Leadership Legacy
Oak recommends that anyone looking to make a lasting impact start by focusing on a few core principles:
Servant Leadership: Lead by serving others. When you focus on the needs of those you lead, you build trust and inspire loyalty.
Communication: Listening is just as important as speaking. Leaders must be able to listen to their teams and understand their needs.
Problem-Solving and Decision-Making: Leadership often means making tough choices. How you approach challenges shapes your ability to guide others through them.
Professional Development: Invest in your own growth. Whether through books, courses, or mentors, continue to develop your skills and knowledge.
Reflection and Self-Discipline: Regularly reflect on your actions and decisions. The best leaders continuously evaluate themselves to grow and improve.
Believing in Yourself as a Leader
Leadership isn’t just about natural ability—it’s about dedication, responsibility, and putting others first. Great leaders are made through experience and effort. By focusing on self-awareness and building confidence in your abilities, you can strengthen your leadership, whether it’s in your family, career, or community.
In the end, leadership is about taking action. It’s about choosing to lead yourself and others with integrity, listening, thinking critically, and striving to be better every day.
When you do this, you not only create your own legacy but also inspire those around you to do the same.
What’s your takeaway? Let us know in the comments.
For a deeper dive into my conversation with Oak, tune in to the podcast episode here: Building Lasting Legacy Through a Life of Service and Leadership
