Early Retirement Roadmap

By Mike Upland

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Category: Investing

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Subscribers: 3
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Episodes: 61

Description

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
I’m 57 and Retired: 5 Things I Never Tell Anyone
May 18, 2026
I Retired at 55: My 7 Layers to Avoid Running Out of Money
May 11, 2026
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