I Retired at 55 — Here's What I Wish I Knew at 40

After retiring at 55, I discovered that early retirement is about more than money. Here are the retirement lessons I wish I knew at 40 about time, health, work, freedom, and family. When I was 40, I thought retirement planning was mainly about reaching the right financial number. Now that I’m 57 and have been retired for almost two years, I see it very differently. In this video, I share eight lessons I would give my 40-year-old self—including why time disappears faster than we expect, how work can quietly take over our lives, why money only becomes freedom when we define “enough,” and why health, relationships, and purpose belong in every retirement plan. We’ll also discuss: • Why another year of work is also one less year of retirement • How consistency matters more than finding the perfect investment • Why stress and poor health compound just like money • The importance of building a meaningful life before retiring • How to prepare financially without postponing everything that matters • Why financial independence is an opportunity—not the ultimate finish line Whether you’re preparing to retire early, pursuing financial freedom, or already retired, these lessons can help you think differently about money, time, work-life balance, health, relationships, and what you want retirement to make possible. 👇 Comment Below: What do you know today that you wish you could go back and tell your 40-year-old self? I'd love to hear from you! ❤️ 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 for free! 👉 To get the free downloads, go to my Patreon here: https://www.patreon.com/cw/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/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/ 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. #retireearly #earlyretirement #retirementplanning Chapters: 00:00 8 Lessons I'd Tell My Younger Self 01:00 Lesson 1 02:42 Lesson 2 04:48 Lesson 3 07:11 Lesson 4 11:18 Lesson 5 13:27 Lesson 6 15:34 Lesson 7 17:18 Lesson 8 19:29 In the End, Here's What I'd Say 20:33 Freebies/Patreon