The Second Shift

You built the career. You earned the title. Now you're wondering what comes next.
Second Shift is for high achievers at a crossroads - physicians, pilots, executives, founders - who are financially ready to move on but emotionally stuck. Hosts Bryan Jepson (retired ER physician turned financial planner) and Aaron Milledge (fighter pilot turned advisor) interview people who've navigated the transition from identity-defining careers to whatever comes after.
No fluff.
No retirement fantasy.
Just honest conversations about purpose, relevance, and building a life that doesn't depend on a title.

Seeking former high-achievers like physicians, pilots, or executives who have successfully transitioned from their career-defining roles to new, fulfilling life chapters, ready to share their honest experiences and insights on our podcast, Second Shift.

Note: Guest insights are created with AI assistance.