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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How a Mutual Index Fund Cost Me $17K in Taxes (And How to Avoid This Mistake)

How a Mutual Index Fund Cost Me $17K in Taxes (And How to Avoid This Mistake)

Investing in index mutual funds sounds like a safe bet, right? Well, I thought so—until I got hit with an unexpected $17,000 tax bill. In this episode of Early Retirement Roadmap, I break down the hid...

24 Maalis 202511min

Scared to Retire? Overcome Your RETIREMENT FEARS!

Scared to Retire? Overcome Your RETIREMENT FEARS!

You’ve run the numbers, planned your finances, and dreamed of early retirement—but fear is still holding you back. You’re not alone! What if I run out of money? What about healthcare costs? Will I be ...

17 Maalis 202516min

The Perfect Retirement Announcement: A Step-by-Step Guide

The Perfect Retirement Announcement: A Step-by-Step Guide

Planning to retire? Announcing your retirement isn’t as simple as picking a date and telling your boss—it’s about strategy, timing, and setting yourself up for success. In this episode of Early Retire...

17 Maalis 202515min

The ONE Retirement Mistake That Could RUIN You!

The ONE Retirement Mistake That Could RUIN You!

You’ve saved up, planned carefully, and are ready to enjoy your retirement—so what could possibly go wrong? In this episode of Early Retirement Roadmap, host Mike Upland reveals a critical mistake tha...

11 Maalis 202511min

Health Insurance Options for Early Retirement: What You NEED to Know

Health Insurance Options for Early Retirement: What You NEED to Know

Thinking about early retirement but worried about health insurance? You’re not alone! Healthcare costs are one of the biggest reasons people delay retirement. But don’t let that stop you! In this epis...

4 Maalis 202514min

Retirement Tax Mistakes that Could Cost You Thousands!

Retirement Tax Mistakes that Could Cost You Thousands!

💰 Are you unknowingly making tax mistakes that could drain your retirement savings? In this episode of Early Retirement Roadmap, host Mike Upland breaks down the biggest retirement tax traps and how ...

4 Maalis 202513min

How Much Do You REALLY Need to Retire?

How Much Do You REALLY Need to Retire?

Retirement planning isn’t one-size-fits-all, and the question of “How much money do I REALLY need?” can feel overwhelming. But don’t worry—I’ve got you covered! In this episode of Early Retirement Roa...

19 Helmi 202512min

Ready to Ditch the 9-to-5? Your Early Retirement Checklist

Ready to Ditch the 9-to-5? Your Early Retirement Checklist

Are You REALLY Ready to Retire Early? This Checklist Will Tell You! 🚀 You dream of ditching the 9-to-5 grind—but are you truly prepared to take the leap into early retirement? In this episode of Earl...

19 Helmi 202512min

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