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!

Jaksot(53)

Why Net Worth Won’t Tell You If You Can Retire

Why Net Worth Won’t Tell You If You Can Retire

Early retirement planning is not just about net worth. In this episode, I break down the retirement number that matters more, plus ACA health insurance, taxes, spending, and sequence risk. Most people...

30 Maalis 15min

I Retired at 55: 7 Early Retirement Mistakes I Missed

I Retired at 55: 7 Early Retirement Mistakes I Missed

Early retirement planning tips from someone who actually did it: I retired at 55, and in this episode, I share 7 early retirement mistakes I missed so you can retire early with fewer surprises and avo...

23 Maalis 17min

How Much Do I Need to Retire Early? 5 Numbers That Tell You

How Much Do I Need to Retire Early? 5 Numbers That Tell You

How much do I need to retire early? In this episode, I walk through the five numbers that really determine whether early retirement works — including spending, healthcare costs, taxes, your retirement...

16 Maalis 19min

Retire Now If You Can Answer Yes to These 6 Questions

Retire Now If You Can Answer Yes to These 6 Questions

Early retirement + retirement planning made simple: Can you retire now? In this episode, I share 6 questions to test your financial independence and retirement readiness—before you make the leap. If y...

11 Maalis 18min

Your First 5 Years of Retirement Decide Everything

Your First 5 Years of Retirement Decide Everything

Your first 5 retirement years decide everything—retirement planning, withdrawal strategy, taxes, health insurance, spending, purpose, relationships, and the mistakes that derail early retirees. Here a...

2 Maalis 19min

The Cash Runway Plan: Build It, Store It, Refill It

The Cash Runway Plan: Build It, Store It, Refill It

Build a cash runway for retirement so you’re not forced to sell stocks in a down market. Learn how many years you need, how to build it, where to hold it (HYSA, CDs, T-bills), and simple refill rules....

9 Helmi 22min

ACA Subsidy Payback: The Tax-Time Trap

ACA Subsidy Payback: The Tax-Time Trap

ACA subsidy payback at tax time? Form 8962 + 1095-A reconciliation can trigger a surprise bill when your MAGI ends up higher than expected. In this episode, I’ll you'll learn why it happens, how to fi...

2 Helmi 12min

Choppy Markets? Use This Retirement Defense Plan

Choppy Markets? Use This Retirement Defense Plan

Market volatility and choppy markets can wreck retirement plans—if you react the wrong way. In this episode, I share a simple framework to stay calm, avoid panic selling, and protect your long-term in...

26 Tammi 10min

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