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!

Avsnitt(57)

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 Mars 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 Feb 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 Feb 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 Jan 10min

ACA Premium Shock? Pay Less All Year

ACA Premium Shock? Pay Less All Year

ACA premium shock for 2026? If your Marketplace/Obamacare health insurance premium jumped, this video shows 10 practical ways to pay less all year by controlling MAGI (modified adjusted gross income) ...

12 Jan 18min

2026 401(k) & IRA Limits Are Up—But Maxing Out Can Backfire (3 Rules)

2026 401(k) & IRA Limits Are Up—But Maxing Out Can Backfire (3 Rules)

2026 401(k) and IRA contribution limits are rising from 2025—but maxing out can backfire if you’re planning early retirement. In this episode I break down 3 rules to fund the right accounts in the rig...

5 Jan 10min

Monthly Dividend ETFs: The Paycheck Illusion (3 Tests to Avoid a Costly Mistake)

Monthly Dividend ETFs: The Paycheck Illusion (3 Tests to Avoid a Costly Mistake)

Monthly Dividend ETFs for retirement income can look like a paycheck—but it’s often an illusion. In this episode, I share 3 tests to avoid costly mistakes and keep Affordable Care Act (ACA) taxes in m...

15 Dec 202512min

6 Levels of Retirement Wealth – Which Level Are You?

6 Levels of Retirement Wealth – Which Level Are You?

Wondering if you really have enough to retire? In this early retirement planning episode, I break down 6 levels of retirement wealth—from Survival to Fulfillment—so you can see which level you’re at a...

8 Dec 202517min

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