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!

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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 Mars 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 Mars 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 Mars 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 Mars 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 Mars 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 Mars 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 Feb 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 Feb 202512min

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