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 video, 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. 👉 Watch next (mentioned in this video): 📺The Cash Runway Plan: Build It, Store It, Refill It:    • The Cash Runway Plan: Build It, Store It, ...   ❤️ Like, Subscribe, and Share this video if you found the information in it helpful! ✅ Free resources available on my Patreon: All Roadmap tools, checklists, worksheets, downloads, and resources are now available to free members — including the ones mentioned in this video: 📊 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 the free downloads, go to my Patreon here:   / earlyretirementroadmap   Click *Join for Free**, then go to the **Tools* collection. You can download any of the free tools and resources there. If you’d like to go a step further, the $5/month Roadmap Member tier includes early access to podcast episodes, ad-free podcast episodes, and access to the private Roadmap Member community discussion space. 💼 My Favorite Retirement Planning Tool, and that I mentioned in this video! 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/earlyretirement... 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! 🎧 Listen on the go: Early Retirement Roadmap Podcast Available wherever you get your podcasts! 🌐 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 video 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. #EarlyRetirement #RetirementPlanning #RetireEarly Chapters: 00:00 How to Live Once You Get There 01:14 Lesson 1 04:09 Lesson 2 07:01 Lesson 3 09:35 Lesson 4 12:08 Lesson 5 13:24 Lesson 6 14:28 Lesson 7 16:26 Lesson 8 17:50 Lesson 9 19:26 Lesson 10 21:45 Free Resources