Early Retirement Roadmap

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)

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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