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!

Episoder(57)

ACA MAGI: How to Calculate & Manage It for Big Savings!

ACA MAGI: How to Calculate & Manage It for Big Savings!

ACA MAGI explained: how to calculate and manage Modified Adjusted Gross Income (MAGI) for Affordable Care Act (ACA) subsidies—step-by-step, with a free MAGI calculator to lower premiums and maximize p...

22 Sep 202516min

Roth Conversions or ACA Subsidies? The Early Retirement Dilemma No One Talks About

Roth Conversions or ACA Subsidies? The Early Retirement Dilemma No One Talks About

Roth conversions vs. ACA subsidies is the early retirement dilemma no one talks about. If you’re planning for early retirement, you need to know how Roth IRA conversions can raise your MAGI and cost y...

8 Sep 202511min

5 Things I Wish I Knew BEFORE Retiring Early at 55

5 Things I Wish I Knew BEFORE Retiring Early at 55

Early retirement at 55 comes with financial and lifestyle challenges most people don’t expect. In this video, I share 5 things I wish I knew before retiring early, including lessons on retirement plan...

25 Aug 20258min

The Biggest Retirement Mistake? Working Past 60

The Biggest Retirement Mistake? Working Past 60

Working past 60 might seem smart, but it could be the biggest retirement mistake you make. In this video, we reveal the hidden costs of working past 60 — from lost health years to missed financial opp...

18 Aug 20257min

One Big Beautiful Bill: 2025 Retirement Tax Shake-Up for Retirees & Future Retirees

One Big Beautiful Bill: 2025 Retirement Tax Shake-Up for Retirees & Future Retirees

Wondering how the 2025 tax law changes affect your retirement strategy? This video breaks down the One Big Beautiful Bill Act, a landmark tax bill signed into law by President Trump — and its HUGE imp...

3 Aug 20259min

How to Tap Your IRA or 401(k) Early —NO IRS PENALTY! | Rule 72(t) Explained

How to Tap Your IRA or 401(k) Early —NO IRS PENALTY! | Rule 72(t) Explained

Want early access to your 401(k) or IRA before age 59½ without getting slammed by the IRS 10% penalty? In this episode, I’ll walk you through the IRS Rule 72(t)—a little-known but completely legal loo...

27 Jul 20258min

Countdown to Retirement: Are You Really Ready to Take the Leap?

Countdown to Retirement: Are You Really Ready to Take the Leap?

Are you really ready for retirement? As your retirement countdown begins, I reveal the critical steps you must take to ensure you're fully prepared to retire confidently and securely. From defining yo...

20 Jul 202511min

6 Reasons to Retire AS SOON AS YOU CAN!

6 Reasons to Retire AS SOON AS YOU CAN!

Thinking about early retirement? Here are 6 powerful reasons to retire early—covering retirement planning, financial freedom, health, and why waiting longer could cost more than money. Whether you're ...

14 Jul 202511min

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