Early Retirement Roadmap

Welcome to the Early Retirement Roadmap podcast — a practical guide for people planning for early retirement, navigating financial independence, or learning how to thrive after leaving full-time work. I’m your host, Mike Upland. I retired at 55 in 2024, and this podcast shares the real-world lessons I’ve learned before and after making the leap into early retirement. If you’re in your 40s, 50s, or early 60s and wondering whether you can retire early — or if you’ve already retired and want to make the most of your freedom — you’re in the right place. Each episode explores practical, relatable topics like early retirement planning, retirement income strategies, health insurance before Medicare, Affordable Care Act planning, taxes, Roth conversions, Social Security decisions, withdrawal strategies, market risk, spending, purpose, mindset, and the emotional side of life after work. You’ll hear candid discussions about the victories, challenges, surprises, and trade-offs that come with early retirement — along with actionable ideas to help you build a financially secure and fulfilling post-career life. For all my media in one place, check out the Early Retirement Roadmap YouTube channel and visit mikeupland.com. Support the channel and get bonus resources on Patreon: https://www.patreon.com/cw/earlyretirementroadmap Your early retirement journey starts here — subscribe or follow now so you never miss an episode.