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!

Jaksot(57)

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

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 Joulu 202514min

My Lazy Retirement Investing Plan

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 Marras 202512min

Does Retiring Early Reduce Social Security? The Truth.

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 Marras 20259min

7 Signs You Should Retire Earlier Than You Think

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 Loka 202510min

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

🚨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 Loka 20259min

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 Loka 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 Loka 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 Syys 202521min

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