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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How Early Retirees Can Pay WAY Less for Health Insurance!

How Early Retirees Can Pay WAY Less for Health Insurance!

Want to pay WAY less for health insurance in early retirement? This follow-up to my previous very popular video (link below in watch next) shows how smart retirees legally slash ACA premiums by strate...

20 Maj 202512min

Retirement Stats That’ll Make You Rethink Working Another Year

Retirement Stats That’ll Make You Rethink Working Another Year

Is working longer really worth it? In this episode, I break down 3 retirement stats and insights that could completely change the way you think about work, wealth, and health in retirement. If you're ...

14 Maj 20257min

Why You’re Closer to Early Retirement Than You Think

Why You’re Closer to Early Retirement Than You Think

Are you wondering why it feels like everyone else is retiring early — and you're not? In this episode of Early Retirement Roadmap, we uncover the real reasons people delay early retirement, even when ...

5 Maj 20258min

The $12,900 Health Insurance Loophole for Early Retirees!

The $12,900 Health Insurance Loophole for Early Retirees!

What if you could save over $12,000 a year on healthcare—just by choosing the right account to withdraw from to fund your retirement? In this episode, I (early retiree and tax-planning nerd) break dow...

28 Apr 202511min

5 Retirement Regrets You’ll Want to Avoid

5 Retirement Regrets You’ll Want to Avoid

If you’re planning for retirement — or already enjoying your golden years — this episode is a must-listen. Dive into the five most common financial regrets retirees face, drawing from personal experie...

22 Apr 20256min

What Vanishes When You Retire (And How to Get it Back!)

What Vanishes When You Retire (And How to Get it Back!)

You’ve worked hard, saved diligently, and now retirement is here! But nobody warns you about the six major things that disappear the moment you leave the workforce. If you’re not prepared, these chang...

14 Apr 202510min

Thinking About Retiring Early in 2025? Think Again.

Thinking About Retiring Early in 2025? Think Again.

Planning for early retirement in 2025? Before you hand in your notice, this episode of Early Retirement Roadmap is your essential guide to navigating the biggest risks facing early retirees this year....

7 Apr 20257min

The Retirement Wake-Up Call: What the Study AND My Story--Reveals!

The Retirement Wake-Up Call: What the Study AND My Story--Reveals!

Thinking about early retirement or already living it? This episode is your wake-up call — and your roadmap. In this powerful and personal episode of The Early Retirement Roadmap, I talk about the reti...

1 Apr 202513min

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