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Perfect Game Retirement
Ryan Ledden
When I Retire, I Will... A Financial and Life Planning Conversation
OCT 1, 202615 MIN
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Description
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 Goals: Turning “I’ll travel more someday” into an actual financial plan
❤️ Giving Back: Using retirement assets strategically when charitable giving matters to you
⚖️ Life Balance: Saving for the future without sacrificing everything you could enjoy today
🕰️ More Time: Learning how to say yes—and no—when retirement gives you greater control of your schedule
🌅 Present Living: Why the film’s message about being “aggressively present” hits especially hard
📝 Your Own List: Using the short film as inspiration to think about what you want retirement to look like
“Retirement Plan” (2026 Oscar Nominee) | The New Yorker -
https://www.youtube.com/watch?v=2Mqa4zfJdx4
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