Episode 168 | "The Greats Know The Greats" (Feat. AOCM Ret. Tyese Pressley)

What does it take to succeed in spaces where people believe you don't belong? In this episode of Permission to Speak Freely, Damo and Aaron welcome retired U.S. Navy Captain Dr. Barbara Bell for a conversation about perseverance, leadership, breaking barriers, and the lessons learned throughout an extraordinary career. As a member of the fourth class of women to enter the United States Naval Academy, Barbara experienced firsthand the challenges of entering an institution that was still learning to accept women. Her journey eventually took her into naval aviation, the U.S. Naval Test Pilot School, and efforts to expand opportunities for women in military service. Throughout the conversation, Barbara reflects on the importance of mentorship, the responsibility of being a trailblazer, and why standing out can sometimes be more powerful than fitting in. The discussion also explores leadership development, the role of artificial intelligence in education, and the importance of ethical leadership. Drawing from her book, Flight Lessons: Navigating Through Life's Turbulence and Learning to Fly High, Barbara shares perspectives on navigating adversity, embracing opportunities, and preparing the next generation of leaders.

Captain Marcus A. Canady joins Damon and Damo for a conversation about leadership, connection, trust, and what it means to truly know the people you lead. The conversation centers on Canady’s concept of “Intrusive Leadership,” a leadership style built around intentional engagement with people beyond their professional responsibilities. Canady explains why leaders should understand what is happening in the lives of their people, how trust has to be earned before those conversations can happen, and why being intrusive does not mean ignoring personal boundaries. As he explains during the conversation, leaders can put themselves “on the porch,” but the other person still has to invite them inside. The group discusses emotional intelligence, listening, accountability, mentorship, family, parenthood, diversity, mental health, suicide prevention, and the responsibility leaders have to understand perspectives different from their own. Canady shares stories from throughout his career, including leaders who intentionally invested in him, the impact his wife and family have had on his development, and a conversation with Gen. C.Q. Brown Jr. about a leader who considered Brown’s family while helping map out his career. Damo reflects on his own leadership experiences and how his approach has changed over time, including learning more about the interests of younger Sailors at his command and finding ways to meet them where they are. Canady also challenges military organizations to think more deliberately about how they develop leaders of people, not simply leaders capable of accomplishing the mission.

This week on Permission to Speak Freely, Damon and Damo sit down with NC1 Corey Brennan for a conversation that starts with Navy recruiting and ends up going way beyond it. Corey breaks down what life is really like on recruiting duty, from competing for contracts and managing Future Sailors to MEPS, waivers, Genesis, recruiting ethics, and the things recruiters deal with that the Fleet rarely sees. He also opens up about his transition from QM to career recruiter, his aspirations to make Chief, and the uncertainty surrounding his future in the Navy as he navigates the service’s beard and PFB policies. But somewhere along the way, the conversation leaves recruiting behind. The crew gets into social media, burnout, learning to take care of yourself when everyone depends on you, marriage, fatherhood, separation, and the challenge of finding space for yourself when life never seems to stop. Corey also turns the tables on Damo and Damon with a few questions of his own, leading to conversations about what the anchors actually give a Chief, leadership as access and influence, and what people really mean when they tell Sailors to “drink the Kool-Aid.” Plus: recruiting house calls gone wrong, a 47-pound applicant, Equinox refusing to leave Damo alone, expensive one-year-old birthday parties, and Damon reveals the veteran husband strategy of simply standing up when your wife starts cleaning. Another conversation that went exactly where it was supposed to go.

200 episodes. Damn.

Damo and Aaron are back for a guest-free episode covering Navy leadership, quality of life, money, artificial intelligence, and everything that happens when the conversation goes completely off script.