Retiring in the Next 5 Years? Get These 5 Things Right

The final five years before retirement can make or break your plan. After retiring at 55, I’m sharing five essential retirement planning steps to help you prepare for early retirement. Many people spend decades saving for retirement but wait too long to pressure-test how they will actually leave work, cover their expenses, access their investments, manage health insurance, and handle a bad market. In this video, I walk through five areas to get right before you retire: 1. Choose two possible retirement dates and define three levels of spending 2. Create a withdrawal strategy before the paycheck stops 3. Plan your healthcare bridge and manage MAGI before Medicare 4. Prepare for sequence-of-returns risk and a bad early market 5. Rehearse both the financial and lifestyle sides of retirement I also explain why two households with the same net worth can have very different abilities to retire, why one “normal” year is not enough to create a reliable retirement budget, and why a retirement calculator cannot tell you what Tuesday at 10:30 in the morning will feel like. If you are within five years of retirement—especially if you are considering retiring early—use this video as a practical checklist to identify what is still vague in your plan and where your attention belongs next. 👇 Comment Below: If you are within 5 years of retiring, tell me in the comments which of these five plans feels the least settled for you, or if you have retired, which of these did you plan for particularly well, or wish you had planned for better? 👉 For detailed videos on each topic covered in this video, watch these videos next of mine: 📺The Cash Runway Plan: Build It, Store It, Refill It: https://youtu.be/p7zA8Sp1qq8 📺Check out my playlist on early retirement health insurance and ACA Planning - 9 videos to check out: https://www.youtube.com/playlist?list=PLjvDzlBEZvaYu9lZ9oN2w22xu7jbOCvnD Resources Mentioned: 📊 2026 EBRI and Greenwald Retirement Confidence Survey referenced in the video: https://www.ebri.org/content/full/2026-ebri-greenwald-retirement-confidence-survey ❤️ 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. #retirementplanning #earlyretirement #retirementstrategy Chapters: 00:00 5 Plans to Build 5 Years Before 01:24 Plan 1 05:20 Plan 2 09:35 Plan 3 13:26 Plan 4 17:37 Plan 5 21:17 What Retirement Taught Me 22:16 Five Questions to Ask