I Retired at 55: 10 Things You Need to Know

Early retirement, retirement planning, retired at 55, and what to know before retirement—here are 10 lessons I’ve learned after 17 months of early retirement that could help you plan smarter.

When I retired at 55, I thought the hard part was getting the numbers to work. But after 17 months of actually living early retirement, I’ve learned that the money plan is only part of the story.

In this episode, I share 10 things I’ve learned about early retirement, including how retirement really feels, why time matters more than most people realize, how spending changes, why taxes and health insurance get more strategic, what market downturns feel like when you’re no longer earning a paycheck, and why identity, relationships, and health matter just as much as the financial side.

If you enjoy honest early retirement journeys and real-world retirement planning insights from someone actually living it, this video is for you.

If this video helped you, subscribe for more videos on early retirement, retirement planning, Affordable Care Act health insurance, taxes in retirement, Roth conversions, Social Security, and building a retirement life that actually works.

🎧 Episode mentioned during this podcast listen to next: The Cash Runway Plan: Build It, Store It, Refill It (Season 3, Episode 9)

✅Free Resources available on my Patreon!:

📊Free MAGI calculator Excel template

📊Free 12-Step Early Retirement Planning Checklist

📊Free eBook: ACA Premium Shock Fix, 10 Ways to Pay Less for Marketplace Coverage All Year Long

👉 To get these free downloads, go to my Patreon here: https://www.patreon.com/cw/earlyretirementroadmap then click Join for Free, then click on the Tools collection. You can download any of them there.

💼 My Favorite Retirement Planning Tool, and that I mentioned in this episode! 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!

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

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DISCLAIMER: This episode 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.

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