Ep. 309: Karen Kendra Holmes: 40 Years Wandering, Then Finding Home as a Transgender Military Veteran

E309 - Ep. 309: Karen Kendra Holmes: 40 Years Wandering, Then Finding Home as a Transgender Military Veteran

Published: September 10, 2026

Duration: 54:59

Zach sits down with Karen Kendra Holmes — U.S. military veteran, TEDx speaker, author, and longtime transgender advocate — for a wide-ranging conversation about her decades-long path to living authentically. Karen shares that she began privately exploring her gender identity at age 13 but didn't transition until 53, describing the internal and religious struggles that shaped those "40 years of wandering." She discusses her 24-year military career (including roles with the Maryland Defense Force and U.S. Veterans Reserve Corps), the carefully planned rollout of her transition across a 47-office federal agency, and her work bridging the transgender community and law enforcement through the...