Early Retirement Roadmap
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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)

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 Mai 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 Mai 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 Mai 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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