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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.
| Episode | Date |
|---|---|
|
I Retired at 57. America Is Testing My Plan.
|
May 25, 2026 |
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I’m 57 and Retired: 5 Things I Never Tell Anyone
|
May 18, 2026 |
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I Retired at 55: My 7 Layers to Avoid Running Out of Money
|
May 11, 2026 |
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My Gen X Retirement Doesn’t Look Like a Boomer’s
|
May 04, 2026 |
|
I Retired at 55: 10 Things You Need to Know
|
Apr 27, 2026 |
|
The Hidden Social Security Math That Changes Early Retirement
|
Apr 20, 2026 |
|
Your Roth Conversion Window Closes Faster Than You Think
|
Apr 13, 2026 |
|
Retiring Soon? Don’t Make this Mistake
|
Apr 06, 2026 |
|
Your Net Worth is the Wrong Number
|
Mar 30, 2026 |
|
I Retired at 55: 7 Early Retirement Mistakes I Missed
|
Mar 23, 2026 |
|
How Much Do I Need to Retire Early? 5 Numbers That Tell You
|
Mar 16, 2026 |
|
Retire Now If You Can Answer Yes to These 6 Questions
|
Mar 11, 2026 |
|
Your First 5 Years of Retirement Decide Everything
|
Mar 02, 2026 |
|
The Cash Runway Plan: Build It, Store It, Refill It
|
Feb 09, 2026 |
|
ACA Subsidy Payback: The Tax-Time Trap
|
Feb 02, 2026 |
|
Choppy Markets? Use This Retirement Defense Plan
|
Jan 26, 2026 |
|
ACA Premium Shock? Pay Less All Year
|
Jan 12, 2026 |
|
2026 401(k) & IRA Limits Are Up—But Maxing Out Can Backfire (3 Rules)
|
Jan 05, 2026 |
|
Monthly Dividend ETFs: The Paycheck Illusion (3 Tests to Avoid a Costly Mistake)
|
Dec 15, 2025 |
|
6 Levels of Retirement Wealth – Which Level Are You?
|
Dec 08, 2025 |
|
Future-Proof Your Lazy Retirement: My 9 Habits of Thriving Retirees
|
Dec 01, 2025 |
|
My Lazy Retirement Investing Plan
|
Nov 10, 2025 |
|
Does Retiring Early Reduce Social Security? The Truth.
|
Nov 03, 2025 |
|
7 Signs You Should Retire Earlier Than You Think
|
Oct 27, 2025 |
|
🚨No Subsidies in 2026? Plan A vs Plan B (DO THIS)
|
Oct 27, 2025 |
|
5 Things to Sell BEFORE You Retire
|
Oct 20, 2025 |
|
7 “Assets” Rich Retirees Avoid
|
Oct 13, 2025 |
|
How I Retired at 55: Do These 5 Things
|
Sep 29, 2025 |
|
ACA MAGI: How to Calculate & Manage It for Big Savings!
|
Sep 22, 2025 |
|
Roth Conversions or ACA Subsidies? The Early Retirement Dilemma No One Talks About
|
Sep 08, 2025 |
|
5 Things I Wish I Knew BEFORE Retiring Early at 55
|
Aug 25, 2025 |
|
The Biggest Retirement Mistake? Working Past 60
|
Aug 18, 2025 |
|
One Big Beautiful Bill: 2025 Retirement Tax Shake-Up for Retirees & Future Retirees
|
Aug 03, 2025 |
|
How to Tap Your IRA or 401(k) Early —NO IRS PENALTY! | Rule 72(t) Explained
|
Jul 27, 2025 |
|
Countdown to Retirement: Are You Really Ready to Take the Leap?
|
Jul 20, 2025 |
|
6 Reasons to Retire AS SOON AS YOU CAN!
|
Jul 14, 2025 |
|
The Top 10 Retirement Myths That Could Cost YOU Thousands!
|
Jul 07, 2025 |
|
🚨Roth Conversion Warning: Miss This 2025 Window, Regret It FOREVER!
|
Jul 01, 2025 |
|
STOP Worrying About Running Out of Money in Retirement!
|
Jun 24, 2025 |
|
How Much Do You REALLY Need to Retire on $10K a Month?
|
Jun 17, 2025 |
|
Will ACA Subsidies Disappear After 2025? What You NEED to Know!
|
Jun 10, 2025 |
|
If You’re in Your 40s, 50s, or 60s: 25 Life Lessons from 70+ Year-Olds
|
Jun 05, 2025 |
|
How Your Kids Can Derail Your Retirement (Unless You Plan for It)
|
Jun 04, 2025 |
|
Claim Social Security at 62, 67, or 70? The Answer May Surprise You!
|
May 27, 2025 |
|
How Early Retirees Can Pay WAY Less for Health Insurance!
|
May 20, 2025 |
|
Retirement Stats That’ll Make You Rethink Working Another Year
|
May 14, 2025 |
|
Why You’re Closer to Early Retirement Than You Think
|
May 05, 2025 |
|
The $12,900 Health Insurance Loophole for Early Retirees!
|
Apr 28, 2025 |
|
5 Retirement Regrets You’ll Want to Avoid
|
Apr 22, 2025 |
|
What Vanishes When You Retire (And How to Get it Back!)
|
Apr 14, 2025 |
|
Thinking About Retiring Early in 2025? Think Again.
|
Apr 07, 2025 |
|
The Retirement Wake-Up Call: What the Study AND My Story--Reveals!
|
Apr 01, 2025 |
|
How a Mutual Index Fund Cost Me $17K in Taxes (And How to Avoid This Mistake)
|
Mar 24, 2025 |
|
Scared to Retire? Overcome Your RETIREMENT FEARS!
|
Mar 17, 2025 |
|
The Perfect Retirement Announcement: A Step-by-Step Guide
|
Mar 17, 2025 |
|
The ONE Retirement Mistake That Could RUIN You!
|
Mar 11, 2025 |
|
Health Insurance Options for Early Retirement: What You NEED to Know
|
Mar 04, 2025 |
|
Retirement Tax Mistakes that Could Cost You Thousands!
|
Mar 04, 2025 |
|
How Much Do You REALLY Need to Retire?
|
Feb 19, 2025 |
|
Ready to Ditch the 9-to-5? Your Early Retirement Checklist
|
Feb 19, 2025 |
|
10 Powerful Reasons to Retire Early (Don't Wait Too Long!)
|
Feb 19, 2025 |