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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Episoder(68)

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 Mar 17min

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 Mar 19min

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 Mar 18min

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 Mar 19min

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 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

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 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