DiscoverEarly Retirement RoadmapThe Biggest Retirement Mistake? Working Past 60
The Biggest Retirement Mistake? Working Past 60

The Biggest Retirement Mistake? Working Past 60

Update: 2025-08-18
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Working past 60 might seem smart, but it could be the biggest retirement mistake you make. In this video, we reveal the hidden costs of working past 60 — from lost health years to missed financial opportunities — and how to find your perfect retirement timing.


You’ll learn why the payoff for working longer can shrink after age 60, how taxes and Medicare premiums eat into those extra earnings, and why your healthiest years may be slipping away. Plus, I’ll share real-life examples, surprising data, and a practical framework for deciding when it’s truly time to retire.


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Resources Mentioned:


📊 New York Life Study: https://time.com/3821757/this-is-the-retirement-regret-nobody-talks-about/


💼 My Favorite Retirement Planning Tool! If you’re serious about planning for retirement, you’ve got to check out Boldin. It’s a powerful tool that helps you map out your financial future—whether you’re a DIY planner or just want to stress-test your retirement strategy.


👉 Try Boldin here: https://go.boldin.com/earlyretirementroadmap


Disclosure: This is an affiliate link, which means I earn a small commission if you decide to go on the paid plan after a free 2-week trial, or you can remain on the free plan, but I highly recommend the paid plan to use all its robust features! I personally use it for my retirement planning and love it! This link doesn’t cost you anything extra and helps to support the content I create. Thank you!


📺 When you're not on the go, check out my Early Retirement Roadmap YouTube Channel: https://youtube.com/@EarlyRetirementRoadmap?sub_confirmation=1


🌐 Visit my website for all my media, including my blog or to contact me about sponsorship or other business opportunities: https://mikeupland.com/


☕ Support: [Buy me a coffee](https://buymeacoffee.com/mikeupland.com)


DISCLAIMER: This podcast is for educational purposes only and reflects my personal experience and research. It is not financial, tax, legal, or investment advice. Always consult with qualified professionals before making major retirement or financial decisions. I am not responsible for any loss or damages resulting from reliance on this information.


#WorkingPast60 #RetirementPlanning #EarlyRetirement

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The Biggest Retirement Mistake? Working Past 60

The Biggest Retirement Mistake? Working Past 60

Mike Upland