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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Jaksot(80)

Gen X Followed the Rules. Then the Rules Changed.

Gen X was told to work hard, be loyal, save for retirement, and follow the rules. But somewhere along the way, the rules changed. In this interview, I talk with author Mark Ross about work, retirement...

5 Loka 26min

Retiring in the Next 5 Years? Get These 5 Things Right

The final five years before retirement can make or break your plan. After retiring at 55, I’m sharing five essential retirement planning steps to help you prepare for early retirement. Many people spe...

28 Syys 24min

I Retired at 55—Why It Felt Wrong

I retired at 55, but early retirement still felt wrong. In this episode, I explore why retiring before 65 can bring guilt, social pressure, and the uneasy feeling that you haven’t worked long enough. ...

21 Syys 12min

I Paid Off My Mortgage—Then I Learned About This Scam

Paid off your mortgage? Deed fraud, deed theft, and home-title fraud can still create a costly mess. I explain how this property deed scam works—and the free alert that can help you catch it early. Af...

14 Syys 16min

I Quit the Rat Race at 55 — Here’s What I Got Back

I quit the rat race at 55 and retired early. Nearly two years later, I’ve learned that life after work gives you back things you may not even realize your career has been taking from you. After decade...

7 Syys 15min

Why Gen X is So Burned Out at Work

Why is Gen X so burned out at work? After decades of corporate America, constant connectivity, doing more with less, and watching work consume more and more of our lives, many Gen Xers are starting to...

31 Elo 20min

Why Gen X is Quietly Done With Work

Why is Gen X quietly done with work? As an early retiree, I break down 7 reasons Gen X is rethinking careers, early retirement, financial independence, and the value of time. I retired at 55, and bein...

24 Elo 17min

I'm 57 Now. Here's What I'd Tell My 40-Year-Old Self.

After retiring at 55, I discovered that early retirement is about more than money. Here are the retirement lessons I wish I knew at 40 about time, health, work, freedom, and family. When I was 40, I t...

17 Elo 23min