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HBO and The Ringer's Bill Simmons hosts the most downloaded sports podcast of all time, with a rotating crew of celebrities, athletes, and media staples, as well as mainstays like Cousin Sal, Joe House, and a slew of other friends and family members who always happen to be suspiciously available.
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I was forced into retirement 3 weeks ago. This is the raw, unfiltered truth about what it's really like.
Three weeks ago, I lost my job at 56. Instead of jumping back into the brutal job market, I made the decision to retire early. This isn't a polished video with a script — it's an honest conversation about what I'm learning in real-time.
What I cover in this raw talk: • Why I chose retirement over job hunting in today's market • The critical importance of having 3-6 months of savings • How to create structure when your work routine disappears • Healthcare options when you lose employer coverage (COBRA, ACA) • The identity crisis that comes with losing your job title • How sudden retirement affects your relationships • Financial planning when retirement wasn't planned • Why this job market is particularly brutal for people over 50
This isn't about having all the answers — it's about sharing the journey as Ifigure it out.
🎯 New video format: Mondays = polished content, Thursdays = casual conversations like this one
💡 Join the journey: I'm documenting every step of this unexpected retirement transition — the mistakes, the wins, and everything in between.
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Your Reinvention After 50 Guide:
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Job Loss After 50: Your Emergency Action Guide
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Scam - How to Protect Yourself:
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