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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…
Episodes
- Early Retirement Roadmap
Medicare at 50? ACA Enhanced Subsidies Back? What the Election Means for 2027
Medicare at 50? ACA subsidies in 2027? Following the 2026 midterm elections, new Medicare bills and efforts to restore enhanced Affordable Care Act subsidies…
- Early Retirement Roadmap
I Retired at 55. Is Someone Else’s Success Keeping You at Work?
Early retirement, retirement planning, and financial independence can feel out of reach when you compare yourself to others. I retired at 55—here’s why someone…
- Early Retirement Roadmap
I Retired at 55. We've Got Retirement Backwards.
I retired at 55, and early retirement changed how I think about retirement planning, the traditional retirement age of 65, and the real cost of waiting to…
- Early Retirement Roadmap
I’m Gen X, Retired, and I Just Don’t Care
I’m Gen X, retired at 55, and enjoying life after retirement on my own terms. Here’s how early retirement changed my priorities—and why I’m done proving…
- Early Retirement Roadmap
I Retired at 55—How I Knew I Had Enough
I retired at 55. How did I know I had enough to retire early? I looked at whether our retirement plan could pay for the life we wanted, bridge the years before…
- Early Retirement Roadmap
I Retired at 55 — 8 Regrets I Refuse to Have at 80
I retired at 55, and I’m thinking about the retirement regrets I want to avoid by 80. These 8 early retirement lessons cover spending, taxes, cash, health…
- Early Retirement Roadmap
Gen X Followed the Rules. Then the Rules Changed.
Gen X was told to work hard, be loyal, save for retirement, and follow the rules. But somewhere along the way, the rules changed. In this interview, I talk…
- Early Retirement Roadmap
Retiring in the Next 5 Years? Get These 5 Things Right
The final five years before retirement can make or break your plan. After retiring at 55, I’m sharing five essential retirement planning steps to help you…
- Early Retirement Roadmap
I Retired at 55—Why It Felt Wrong
I retired at 55, but early retirement still felt wrong. In this episode, I explore why retiring before 65 can bring guilt, social pressure, and the uneasy…
- Early Retirement Roadmap
I Paid Off My Mortgage—Then I Learned About This Scam
Paid off your mortgage? Deed fraud, deed theft, and home-title fraud can still create a costly mess. I explain how this property deed scam works—and the free…
- Early Retirement Roadmap
I Quit the Rat Race at 55 — Here’s What I Got Back
I quit the rat race at 55 and retired early. Nearly two years later, I’ve learned that life after work gives you back things you may not even realize your…
- Early Retirement Roadmap
Why Gen X is So Burned Out at Work
Why is Gen X so burned out at work? After decades of corporate America, constant connectivity, doing more with less, and watching work consume more and more of…
- Early Retirement Roadmap
Why Gen X is Quietly Done With Work
Why is Gen X quietly done with work? As an early retiree, I break down 7 reasons Gen X is rethinking careers, early retirement, financial independence, and the…
- Early Retirement Roadmap
I'm 57 Now. Here's What I'd Tell My 40-Year-Old Self.
After retiring at 55, I discovered that early retirement is about more than money. Here are the retirement lessons I wish I knew at 40 about time, health…
- Early Retirement Roadmap
I Retired at 55—5 Problems My 401(k) Couldn’t Solve
I retired at 55, and I learned that a large 401(k) alone doesn’t solve every early retirement problem—especially access, ACA health insurance, taxes, and…
- Early Retirement Roadmap
I Retired at 55 — Here’s the Risk Nobody Warns You About
The big question that's always asked when it comes to retirement planning is do you have enough money? But the risk nobody warns you about is retiring too…
- Early Retirement Roadmap
I Retired at 55. My Retirement Plan Is Intentionally Dumb.
I retired at 55 with an intentionally dumb retirement plan—simple retirement planning built around low-cost index funds, cash reserves, flexible spending, and…
- Early Retirement Roadmap
I Retired at 55—6 Signs Work Was Taking Too Much From Me
Working too much can quietly drain your time, energy, health, and relationships. After retiring at 55, I saw how burnout, work-life balance, and early…
- Early Retirement Roadmap
I’m 57. I Retired at 55. Why Am I Still Afraid to Spend Money?
Retirement spending, early retirement, and the fear of spending money can feel strange after decades of saving. I retired at 55, and even with a solid plan…
- Early Retirement Roadmap
I Retired at 55: My 7 Budget Rules That Survived Real Life
Retirement budget rules matter even more when you retire early. I retired at 55, and in this episode I’m sharing the 7 budget rules that helped my retirement…
- Early Retirement Roadmap
I Retired at 55: Don't Let a Calculator Keep You Working
Retirement calculators, Monte Carlo simulations, and probability of success can be useful—but they can also keep you working one more year. I retired at 55…
- Early Retirement Roadmap
I’m 57 & Retired: What I Actually Do All Day
Wondering when you retire, what you're going to do all day? And is that fear of being bored one of things holding you back from retiring? I’m 57 and retired…
- Early Retirement Roadmap
I Retired at 55: 10 Money Traps I Refuse to Fall For
I retired at 55, and these are 10 things I refuse to waste money on. Retirement doesn’t mean you stop spending money. It means you get more honest about what…
- Early Retirement Roadmap
Working Past 55? 6 Hidden Costs Most People Miss
Early retirement at 55 sounds like the dream — but after retiring early myself, I realized there are things I wish I had understood sooner about retirement…
- Early Retirement Roadmap
I Retired at 55: Here’s What I Wish I Did First
In this episode, I talk about the retirement strategy I wish I had seriously considered before leaving my career: easing into retirement instead of making it a…
- Early Retirement Roadmap
I'm 57 & Retired: America Feels Too Expensive.
Early retirement, retirement planning, cost of living, healthcare, insurance, and retiring in America are all starting to feel different than many of us…
- Early Retirement Roadmap
I’m 57 and Retired: 5 Things I Never Tell Anyone
Early retirement, retirement planning, and financial independence all require more than just money — they also require boundaries. I’m 57 and retired, and…
- Early Retirement Roadmap
I Retired at 55: My 7 Layers to Avoid Running Out of Money
Running out of money in retirement is one of the biggest fears. I retired at 55, and in this episode, I share the 7 layers I use to protect my retirement plan…
- Early Retirement Roadmap
My Gen X Retirement Doesn’t Look Like a Boomer’s
Gen X retirement won’t look like Boomer retirement. Here’s why retirement planning is changing for Generation X, from Social Security to health insurance…
- Early Retirement Roadmap
I Retired at 55: 10 Things You Need to Know
Early retirement, retirement planning, retired at 55, and what to know before retirement—here are 10 lessons I’ve learned after 17 months of early retirement…
- Early Retirement Roadmap
The Hidden Social Security Math That Changes Early Retirement
Social Security is a much bigger part of early retirement planning than most people realize. In this episode, I share early retirement planning tips on…
- Early Retirement Roadmap
Your Roth Conversion Window Closes Faster Than You Think
Early retirement planning tips matter a lot when it comes to Roth conversions. In this episode, I explain why your Roth conversion window can close faster than…
- Early Retirement Roadmap
Retiring Soon? Don’t Make this Mistake
Retiring soon? In this episode, I cover the biggest retirement planning mistake people make before retirement and the 7 things to figure out now, including…
- Early Retirement Roadmap
Your Net Worth is the Wrong Number
Early retirement planning is not just about net worth. In this episode, I break down the retirement number that matters more, plus ACA health insurance, taxes…
- Early Retirement Roadmap
I Retired at 55: 7 Early Retirement Mistakes I Missed
Early retirement planning tips from someone who actually did it: I retired at 55, and in this episode, I share 7 early retirement mistakes I missed so you can…
- Early Retirement Roadmap
How Much Do I Need to Retire Early? 5 Numbers That Tell You
How much do I need to retire early? In this episode, I walk through the five numbers that really determine whether early retirement works — including spending…
- Early Retirement Roadmap
Retire Now If You Can Answer Yes to These 6 Questions
Early retirement + retirement planning made simple: Can you retire now? In this episode, I share 6 questions to test your financial independence and retirement…
- Early Retirement Roadmap
Your First 5 Years of Retirement Decide Everything
Your first 5 retirement years decide everything—retirement planning, withdrawal strategy, taxes, health insurance, spending, purpose, relationships, and the…
- Early Retirement Roadmap
The Cash Runway Plan: Build It, Store It, Refill It
Build a cash runway for retirement so you’re not forced to sell stocks in a down market. Learn how many years you need, how to build it, where to hold it…
- Early Retirement Roadmap
ACA Subsidy Payback: The Tax-Time Trap
ACA subsidy payback at tax time? Form 8962 + 1095-A reconciliation can trigger a surprise bill when your MAGI ends up higher than expected. In this episode…
- Early Retirement Roadmap
Choppy Markets? Use This Retirement Defense Plan
Market volatility and choppy markets can wreck retirement plans—if you react the wrong way. In this episode, I share a simple framework to stay calm, avoid…
- Early Retirement Roadmap
ACA Premium Shock? Pay Less All Year
ACA premium shock for 2026? If your Marketplace/Obamacare health insurance premium jumped, this video shows 10 practical ways to pay less all year by…
- Early Retirement Roadmap
2026 401(k) & IRA Limits Are Up—But Maxing Out Can Backfire (3 Rules)
2026 401(k) and IRA contribution limits are rising from 2025—but maxing out can backfire if you’re planning early retirement. In this episode I break down 3…
- Early Retirement Roadmap
Monthly Dividend ETFs: The Paycheck Illusion (3 Tests to Avoid a Costly Mistake)
Monthly Dividend ETFs for retirement income can look like a paycheck—but it’s often an illusion. In this episode, I share 3 tests to avoid costly mistakes and…
- Early Retirement Roadmap
6 Levels of Retirement Wealth – Which Level Are You?
Wondering if you really have enough to retire? In this early retirement planning episode, I break down 6 levels of retirement wealth—from Survival to…
- Early Retirement Roadmap
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…
- Early Retirement Roadmap
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…
- Early Retirement Roadmap
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…
- Early Retirement Roadmap
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…
- Early Retirement Roadmap
🚨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…
- Early Retirement Roadmap
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…
- Early Retirement Roadmap
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…
- Early Retirement Roadmap
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…
- Early Retirement Roadmap
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…
- Early Retirement Roadmap
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…
- Early Retirement Roadmap
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 Retirement Roadmap
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…
- Early Retirement Roadmap
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…
- Early Retirement Roadmap
How to Tap Your IRA or 401(k) Early —NO IRS PENALTY! | Rule 72(t) Explained
Want early access to your 401(k) or IRA before age 59½ without getting slammed by the IRS 10% penalty? In this episode, I’ll walk you through the IRS Rule…
- Early Retirement Roadmap
Countdown to Retirement: Are You Really Ready to Take the Leap?
Are you really ready for retirement? As your retirement countdown begins, I reveal the critical steps you must take to ensure you're fully prepared to retire…