Early Retirement Roadmap

Early Retirement Roadmap

Welcome to the Early Retirement Roadmap podcast, your audio guide to preparing for and thriving in early retirement!

If you’re dreaming of retiring early but feeling overwhelmed about where to start, or if you’re already retired and looking to make the most of your freedom, you’re in the right place.

I’m your host Mike Upland, and I successfully retired at 55 in 2024. Through this podcast, I share my personal early retirement journey—the victories, the challenges, and all the essential lessons I’ve learned along the way.

Each episode delivers practical strategies and real-world insights on crucial topics like financial planning, health insurance, tax strategies, developing the right mindset, and finding purpose in retirement. You’ll hear candid discussions about the realities of early retirement, actionable tips for building and managing wealth, and inspiring stories to help you navigate your own path to early retirement or thrive in it if you're already there!

Whether you’re just starting to explore early retirement or fine-tuning your existing plans, this podcast provides the roadmap you need to build a financially secure and fulfilling post-career life.
For visual guides and additional content, be sure to check out the Early Retirement Roadmap YouTube channel, where I share complementary videos and resources to support your early retirement journey.

Your early retirement journey starts here—subscribe or follow now to ensure you never miss an episode!

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I Retired at 55: 10 Things You Need to Know

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

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

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? 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

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 Mars 15min

I Retired at 55: 7 Early Retirement Mistakes I Missed

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 Mars 17min

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

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 Mars 19min

Retire Now If You Can Answer Yes to These 6 Questions

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 Mars 18min

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