What happens when career ambition collides head-on with family life? In this episode, Tim sits down with Connor — a first-time dad, commercial pilot, and former aspiring Air Force aviator — for an honest conversation about the choices that define us as fathers.

Connor shares what it was like to grow up as the oldest of four boys in a military family, watching his stoic, often-deployed dad lead by example. He opens up about his own years-long pursuit of becoming an Air Force National Guard pilot — and the pivotal moment when his wife's pregnancy helped him finally see how far his priorities had drifted from what mattered most.

From missing church every Sunday during airline training to leaving home just days after his son Cooper was born, Connor reflects on the cost of unchecked ambition — and the unexpected peace he found in letting it go.

The conversation also dives into the lost art of rites of passage, the book The Intentional Father by Jon Tyson, and Connor's plans to walk his son through meaningful milestones — from the first shave to learning to fly.

In this episode:

• Growing up in a military household and learning to lead by example
• Why the Air National Guard dream nearly cost Connor his family
• Life as a reserve pilot and navigating an unpredictable schedule with a newborn
• The power of rites of passage and why modern boys are missing them
• Extracurriculars, sports, and finding the balance between pushing and allowing kids to choose
• What being truly present looks like with a 4-month-old

Father and Friend is a podcast for dads who want to show up, love deeply, and make a lasting impact on their families. Visit fatherandfriend.com to connect.