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.

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Episoder(65)

I Retired at 55: 10 Things You Need to Know

Early retirement, retirement planning, retired at 55, and what to know before retirement—here are 10 lessons I’ve learned after 17 months of early retirement that could help you plan smarter. When I r...

27 Apr 25min

The Hidden Social Security Math That Changes Early Retirement

Social Security is a much bigger part of early retirement planning than most people realize. In this episode, I share early retirement planning tips on claiming age, portfolio pressure, and how Social...

20 Apr 18min

Your Roth Conversion Window Closes Faster Than You Think

Early retirement planning tips matter a lot when it comes to Roth conversions. In this episode, I explain why your Roth conversion window can close faster than you think — and how ACA subsidies, Socia...

13 Apr 19min

Retiring Soon? Don’t Make this Mistake

Retiring soon? In this episode, I cover the biggest retirement planning mistake people make before retirement and the 7 things to figure out now, including spending, taxes, health insurance before Med...

6 Apr 12min

Your Net Worth is the Wrong Number

Early retirement planning is not just about net worth. In this episode, I break down the retirement number that matters more, plus ACA health insurance, taxes, spending, and sequence risk. Most people...

30 Mar 15min

I Retired at 55: 7 Early Retirement Mistakes I Missed

Early retirement planning tips from someone who actually did it: I retired at 55, and in this episode, I share 7 early retirement mistakes I missed so you can retire early with fewer surprises and avo...

23 Mar 17min

How Much Do I Need to Retire Early? 5 Numbers That Tell You

How much do I need to retire early? In this episode, I walk through the five numbers that really determine whether early retirement works — including spending, healthcare costs, taxes, your retirement...

16 Mar 19min

Retire Now If You Can Answer Yes to These 6 Questions

Early retirement + retirement planning made simple: Can you retire now? In this episode, I share 6 questions to test your financial independence and retirement readiness—before you make the leap. If y...

11 Mar 18min