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(68)

5 Things to Sell BEFORE You Retire

5 Things to Sell BEFORE You Retire

Retirement planning: 5 things to sell before you retire—downsize the house, cut support for adult children, ditch RV/boat “toys,” drop the second car, and release your work identity with my Keep-Sell-...

20 Okt 20259min

7 “Assets” Rich Retirees Avoid

7 “Assets” Rich Retirees Avoid

Retirement planning, early retirement, money traps: timeshares, vacation homes, high-fee annuities, whole life insurance, long-term care insurance, high-yield bonds, high-fee active funds, cash flow, ...

13 Okt 20258min

How I Retired at 55: Do These 5 Things

How I Retired at 55: Do These 5 Things

I retired early at 55. In this episode I show exactly how to retire early with 5 proven keys to early retirement: the mindset that powers compounding, how to raise your savings rate, the income multip...

29 Sep 202521min

ACA MAGI: How to Calculate & Manage It for Big Savings!

ACA MAGI: How to Calculate & Manage It for Big Savings!

ACA MAGI explained: how to calculate and manage Modified Adjusted Gross Income (MAGI) for Affordable Care Act (ACA) subsidies—step-by-step, with a free MAGI calculator to lower premiums and maximize p...

22 Sep 202516min

Roth Conversions or ACA Subsidies? The Early Retirement Dilemma No One Talks About

Roth Conversions or ACA Subsidies? The Early Retirement Dilemma No One Talks About

Roth conversions vs. ACA subsidies is the early retirement dilemma no one talks about. If you’re planning for early retirement, you need to know how Roth IRA conversions can raise your MAGI and cost y...

8 Sep 202511min

5 Things I Wish I Knew BEFORE Retiring Early at 55

5 Things I Wish I Knew BEFORE Retiring Early at 55

Early retirement at 55 comes with financial and lifestyle challenges most people don’t expect. In this video, I share 5 things I wish I knew before retiring early, including lessons on retirement plan...

25 Aug 20258min

The Biggest Retirement Mistake? Working Past 60

The Biggest Retirement Mistake? Working Past 60

Working past 60 might seem smart, but it could be the biggest retirement mistake you make. In this video, we reveal the hidden costs of working past 60 — from lost health years to missed financial opp...

18 Aug 20257min

One Big Beautiful Bill: 2025 Retirement Tax Shake-Up for Retirees & Future Retirees

One Big Beautiful Bill: 2025 Retirement Tax Shake-Up for Retirees & Future Retirees

Wondering how the 2025 tax law changes affect your retirement strategy? This video breaks down the One Big Beautiful Bill Act, a landmark tax bill signed into law by President Trump — and its HUGE imp...

3 Aug 20259min

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