I Retired at 55—How I Knew I Had Enough

I retired at 55. How did I know I had enough to retire early? I looked at whether our retirement plan could pay for the life we wanted, bridge the years before Medicare, and hold up in a bad market. I started with the retirement we actually wanted, including travel and the things we enjoy—not a budget stripped down to the bills. Then I had to work out where our spending money would come from in the early years. I explain why the Rule of 55 wasn't my bridge, how our taxable brokerage account helped, and why the accounts you draw from can affect ACA health insurance subsidies. I also share why I built a cash runway of about four years, what an expensive A/C repair taught me in my first year of retirement, and how I decided whether working one more year would meaningfully improve our plan. There was no magic account balance that made the future certain. I needed a plan that could support the life we wanted and give us choices when things didn't go as expected. 👇 Comment Below: What's one part of retirement you wouldn't want to cut just to retire sooner? I'd love to hear from you! 👉 Watch next: 📺Health Insurance Playlist Mentioned in Video: https://www.youtube.com/playlist?list=PLjvDzlBEZvaYu9lZ9oN2w22xu7jbOCvnD ❤️ Like, Subscribe, and Share this video if you found the information in it helpful! ✅Go beyond the YouTube comments and engage with me and other folks preparing to retire early or have already done it by joining the private Roadmap Member community discussion mentioned in this video. This is private, small & respectful space to ask questions, share experiences, compare notes and learn from each other. This Patreon tier is only $5/per month. I'd love to have you join us. And if you like podcasts, it also includes access to all my podcasts ad free and early access to new episodes. 👉 Join my Patreon here: https://www.patreon.com/cw/earlyretirementroadmap You can also join for free via the link above - I have some free tools: checklists, worksheets, ACA Magi Calculator and other resources I've created and you can download for free. Click **Join for Free**, then go to the **Tools** collection. You can download any of the free tools and resources there. 💼 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/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! 🎧 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 Enough for What? 01:58 The Honest Price 03:09 The Years In Between 06:05 When Things Go Wrong 08:53 What Would One More Year Buy? 10:40 How I Made the Call