Some careers become part of your identity. For retired Lieutenant Colonel Oakland McCulloch, the Army was not just a profession. It was structure, service, mission, camaraderie, and a way of seeing himself in the world.
In this episode of Why I Left, Brian talks with Oak about what it means to leave an institution that shaped your entire adult life. Oak shares the moment he knew it was time to retire, the grief that came with no longer putting on the uniform, and the challenge of entering civilian leadership spaces where urgency and mission did not always mean the same thing.
The conversation moves beyond military transition. It is about values, loyalty, ego, leadership, and the question many professionals eventually face: when does staying become self-betrayal?
Oak’s story is a grounded reminder that purpose can survive a transition. But sometimes, you have to rebuild it without the title, the rank, or the institution telling you what matters.
Enjoy!
Stay connected with Oak McCulloch
Website: www.ltcoakmcculloch.com
LinkedIn: www.linkedin.com/in/oakland-mcculloch/
Work with Brian Aquart
Storyline by Kingswood helps leaders and professionals make sense of career transitions, identity shifts, and the stories they’re telling about their work.
Learn more: https://drive.google.com/file/d/1IT1-NDl51cZbhNUzUO4lCyjVJiVcmvxS/view?usp=drive_link
Stay connected with Why I Left
Visit: https://www.WhyILeft.co
Subscribe:
YouTube: https://www.youtube.com/channel/UCMgQI4X0kEp8-o7Z9D3tRmg
Apple Podcasts: https://podcasts.apple.com/us/podcast/why-i-left/id1613667100
Spotify: https://open.spotify.com/show/0TE4Y626idPxNeewpCG6Ef
Follow:
Instagram: https://www.instagram.com/officialwhyileft/
LinkedIn: https://www.linkedin.com/company/why-i-left/
Connect with Brian: https://www.linkedin.com/in/brianaquart/
Rate us 5 stars and share feedback: https://podcasts.apple.com/us/podcast/why-i-left/id1613667100
Your story deserves to be told with clarity and impact. That’s why I created Storyline by Kingswood, an executive branding and narrative strategy service for high-impact professionals who are stepping into a new chapter. Elevate your leadership. Command your story.
Interested in sponsoring Why I Left?
Learn more about partnership opportunities here: https://whyileft.co/sponsor-why-i-left-podcast/