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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The Top 10 Retirement Myths That Could Cost YOU Thousands!

The Top 10 Retirement Myths That Could Cost YOU Thousands!

Think you need $1 million to retire? That Medicare covers everything? Or that your expenses will drop after you stop working? In this episode of the Early Retirement Roadmap Podcast, I bust the top 10...

7 Juli 202522min

🚨Roth Conversion Warning: Miss This 2025 Window, Regret It FOREVER!

🚨Roth Conversion Warning: Miss This 2025 Window, Regret It FOREVER!

🚨 Roth Conversion Warning: Miss This 2025 Window, Regret It FOREVER! In this episode, I break down why Roth conversions in 2025 are more important than ever—and how early retirees, those already reti...

1 Juli 202511min

STOP Worrying About Running Out of Money in Retirement!

STOP Worrying About Running Out of Money in Retirement!

Are you constantly worried about running out of money in retirement? You’re not alone—and the good news is, the truth might surprise you! In this podcast, I reveal what most people get wrong about ret...

24 Juni 20258min

How Much Do You REALLY Need to Retire on $10K a Month?

How Much Do You REALLY Need to Retire on $10K a Month?

Want to retire on $10K a month? This episode shows exactly how much you need saved in 2025 and beyond—factoring in taxes, healthcare, inflation, Social Security, and investment risk. We’ll break down ...

17 Juni 202512min

Will ACA Subsidies Disappear After 2025? What You NEED to Know!

Will ACA Subsidies Disappear After 2025? What You NEED to Know!

⚠️ Are ACA subsidies really going away after 2025? If you're planning to retire early or already living off your investments, this could impact your healthcare costs in a big way. In this episode, I e...

10 Juni 20256min

If You’re in Your 40s, 50s, or 60s: 25 Life Lessons from 70+ Year-Olds

If You’re in Your 40s, 50s, or 60s: 25 Life Lessons from 70+ Year-Olds

If you're in your 40s, 50s, or 60s, listen to this! In this podcast, I share 25 life lessons from people over 70 — timeless wisdom for navigating midlife, retirement planning, relationships, purpose, ...

5 Juni 202511min

How Your Kids Can Derail Your Retirement (Unless You Plan for It)

How Your Kids Can Derail Your Retirement (Unless You Plan for It)

Many early retirees forget to factor in their adult children when planning retirement. From weddings and tuition to ongoing support, the financial impact can be substantial—especially when you no long...

4 Juni 20257min

Claim Social Security at 62, 67, or 70? The Answer May Surprise You!

Claim Social Security at 62, 67, or 70? The Answer May Surprise You!

Should you claim Social Security early, wait until full retirement age, or delay until 70? In this podcast, we walk through a real retirement case study and run the numbers to show how your claiming a...

27 Maj 20259min

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