Oakland McCulloch is helping people create a leadership legacy worth having that focuses on servant leadership and work-life balance.

Prioritizing Well-Being and Excellence: A Leadership Legacy with Oakland McCulloch – BtR 399

Retired U.S. Army Lieutenant Colonel, Oakland McCulloch, strives to prioritize well-being and excellence, facing the challenge of building a lasting leadership legacy with servant leadership.

Building a Leadership Legacy

With a career rooted in the military, Oakland McCulloch’s leadership journey took an unexpected turn that reshaped his understanding of success. Through personal anecdotes and pivotal lessons, he discovered the profound impact of prioritizing well-being and fostering trust in his team.

As he delves into the emotional and relatable aspects of his narrative, Oakland’s journey offers valuable insights for aspiring leaders. Join us as we uncover the twist that transformed Oakland’s leadership approach, leaving a lasting legacy that continues to inspire.

In this episode, you will be able to:

  • Discover the keys to building a lasting leadership legacy that inspires and motivates others.
  • Learn how servant leadership prioritizes the well-being of your team, leading to trust and excellence.
  • Uncover the secrets to setting and maintaining high standards in leadership, driving continuous improvement and growth.

My special guest is Oakland McCulloch

Retired Lieutenant Colonel Oakland McCulloch brings a wealth of experience in military leadership to the table. With a career spanning over multiple decades, Oakland has led in combat zones and deployed in peacekeeping operations, providing him with invaluable insights into the essence of leadership and building a lasting legacy.

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His journey from West Point to the ROTC program and his diverse roles in the military showcase his commitment to fostering trust, excellence, and well-being within his teams. Throughout his career, Oakland has embodied the principles of servant leadership, prioritizing the needs of those he had the privilege to lead.

Oak’s dedication to understanding and connecting with people on a personal level has been pivotal in establishing trust and achieving mission success, making him an invaluable resource for leaders seeking to leave a positive, enduring impact.


00:05:01 – Pivotal Leadership Advice

00:08:18 – The Three M’s and Emotional Capital

00:10:22 – Building Trust and People-Centric Leadership

00:12:58 – Building Emotional Capital

00:14:45 – Delegating and Empowering Teams

00:17:40 – Legacy and Integrity

00:24:58 – Impact of Leadership Actions

00:25:32 – Leading by Example and Setting Standards

00:29:21 – Building Relationships and Taking Care of People

Importance of Trust and Integrity

Trust and integrity are foundational pillars for effective leadership. Leaders gain respect and credibility by demonstrating consistency in their actions, living by their words, and showing genuine concern for their team’s welfare. Upholding these virtues in every decision and interaction builds a strong rapport with team members and paves the way for open communication, enhanced cooperation, and heightened productivity.

Building a Lasting Legacy

In leadership, creating a lasting legacy transcends personal achievements to include the development and inspiration of future leaders. A leader’s impact is seen not only in their career milestones but also in the lives they positively influence. Leaders, such as Oakland McCullough, instill values of trust, integrity, and excellence, inspiring others to carry forward this legacy in their own leadership journey.

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Servant Leadership Transformation

The concept of servant leadership fosters a profound transformation in traditional leadership roles. Instead of exerting authority, leaders like Oakland prioritize the well-being of their team, encourage personal growth, and cultivate an environment of trust and respect. This approach to leadership not only enhances team performance but also fosters a sense of shared purpose and commitment, integral for long-term success.

Robert J. (1996). “Path-goal theory of leadership: Lessons, legacy, and a reformulated theory”. Leadership Quarterly. 7 (3): 323–352. doi:10

About LTC(Ret.) Oakland McCulloch

LTC Oakland McCulloch‘s journey into leadership began with his military experience, transitioning from West Point to the ROTC program and eventually becoming an officer in the army. Through his deployments and peacekeeping operations, he learned a pivotal piece of advice from Lieutenant Perkins, emphasizing the importance of prioritizing the three M’s: money, meals, and mail to ensure the team’s well-being and mission success.

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Oakland’s insights into emotional capital and trust-building shed light on the impact of nurturing a positive work environment. His personal anecdotes, from holding his colicky daughter to the lessons learned from fellow soldiers, create a relatable and emotional narrative that resonates with the audience. This blend of military wisdom and personal experiences makes Oakland’s leadership journey both compelling and inspiring, providing valuable insights for aspiring leaders.

Oak McCulloch married Kelly Smyth at Fort Sheridan, IL in 1987. They now live in Daytona Beach, FL and have two children, Oakland Vincent McCulloch and Caileigh Nicholson. They also have a granddaughter, Ryleigh Jade Nicholson, and two grandsons, Christopher Bryce Nicholson and Oakland Maverick McCulloch.


Book LTC(Ret.) Oakland McCulloch for your next leadership development event, https://www.ltcoakmcculloch.com/

Get a copy of Your Leadership Legacy: Becoming the Leader You Were Meant to Be on Amazon today!

Follow Oak on LinkedIn and Facebook.


Subscribe to Beyond the Rut Podcast on your favorite podcast player.

Other episodes and articles you’ll enjoy:

7 Pillars of Servant Leadership: How to Lead with Empowerment, Compassion and Integrity

JERRY’S SHORT: Stake Your Leadership T.E.N.T.

Building Trust and Open Communication: The Power of Psychological Safety with Salomé Trambach – BtR 398

Connect with me:

Leave a voicemail at (469) 608-0355.

Send an email to [email protected].

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Hosted and Edited by Jerry Dugan


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