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)

Future-Proof Your Lazy Retirement: My 9 Habits of Thriving Retirees

Future-proof your retirement with habits of thriving retirees, early retirement planning tips, and simple retirement investing strategies to help you feel confident about the decades ahead. In this ep...

1 Des 202514min

My Lazy Retirement Investing Plan

Lazy retirement investing made simple: early retirement, index funds (VTI, VOO, VUG, VIG, VYM), withdrawal rate guardrails, 2–4 year cash liquidity runway, Roth conversions, MAGI/ACA & IRMAA tax strat...

10 Nov 202512min

Does Retiring Early Reduce Social Security? The Truth.

Does retiring early reduce Social Security? The truth—how benefits are really calculated: the 35-year rule, Average Indexed Monthly Earnings (AIME), bend points, indexing only through age 59, and why ...

3 Nov 20259min

7 Signs You Should Retire Earlier Than You Think

Retirement planning, early retirement, 7 signs you’re ready to retire, retire earlier than you think, retire in your 50s, how to retire early—here’s how to know if the numbers and lifestyle say YES. I...

27 Okt 202510min

🚨No Subsidies in 2026? Plan A vs Plan B (DO THIS)

2026 health insurance: If Affordable Care Act (ACA) subsidies end, Plan A vs Plan B. Open Enrollment Nov 1; enroll by Dec 15 for Jan 1. MAGI targets, 400% FPL, on-exchange vs off-exchange. In this vid...

27 Okt 20259min

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

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

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