I Retired at 55 — 8 Regrets I Refuse to Have at 80

I retired at 55, and I’m thinking about the retirement regrets I want to avoid by 80. These 8 early retirement lessons cover spending, taxes, cash, health, travel, marriage, and changing the plan as life changes. I could make sound financial decisions and still regret how my wife and I used our years. After hearing about regrets people shared in their 80s, I asked myself which ones could become mine—and what I can do about them now. In this video, I talk about eight regrets I’m working to avoid: 1. Saving the best years for later 2. Making a permanent move too soon 3. Planning taxes one year at a time 4. Following someone else’s retirement plan 5. Confusing cash with complete safety 6. Taking health for granted 7. Assuming my wife and I want the same retirement 8. Treating the retirement plan as finished Some of these choices involve money. Others involve how we spend our time, protect our health, and build a retirement that works for both of us. I’m sharing my approach as someone living through early retirement, not a plan for everyone to copy. 👇 Comment Below: Which of these regrets concerns you most? Let me know in the comments. 👉 Watch next (video I mentioned): 📺I Retired at 55 — Here's What I Wish I Knew at 40: https://youtu.be/xAdq9WfFqYw ❤️ 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 #retirement #retirementplanning Chapters: 00:00 Will their regrets become mine? 01:14 Regret #1 03:49 Regret #2 06:17 Regret #3 08:23 Regret #4 10:48 Regret #5 12:16 Regret #6 14:01 Regret #7 15:28 Regret #8 16:59 What Future Me Needs Now