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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Episoder(65)

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 Mar 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 Des 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 Des 202517min

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