When I Retire, I Will... A Financial and Life Planning Conversation

Perfect Game Retirement · Oct 1, 2026 · 15m

There's a 7-minute animated short that got nominated for an Oscar this year called Retirement Plan. It's free on YouTube, narrated by Irish actor Domhnall Gleeson, and it follows a middle-aged man named Ray who spends his days listing everything he plans to do once he finally retires. Ryan uses the short as a jumping-off point for a bigger conversation about the expectations we build around retirement and the life we’re living right now.

Here’s what we discuss in this episode:

💵 Pension Planning: Why understanding your retirement benefits matters before making permanent decisions

✈️ Travel…