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. 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, developing the right mindset, and finding purpose in retirement. You’ll hear candid discussions about the realities of early retirement, actionable tips for building wealth, and inspiring stories to help you navigate your own path to early retirement. 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 now to ensure you never miss an episode!
Thinking about early retirement? Here are 6 powerful reasons to retire early—covering retirement planning, financial freedom, health, and why waiting longer could cost more than money.
Whether you're close to retiring or just exploring the idea, these insights might change how you think about work, money, and time. Inspired by the popular topic “5 reasons to retire early,” this video takes it further—showing why waiting even one mo...
Think you need $1 million to retire? That Medicare covers everything? Or that your expenses will drop after you stop working?
In this episode of the Early Retirement Roadmap Podcast, I bust the top 10 retirement myths—with real data and practical advice. These are the beliefs that could seriously derail your plans and cost you thousands if you fall for them.
We’ll cover myths about:
🚨 Roth Conversion Warning: Miss This 2025 Window, Regret It FOREVER! In this episode, I break down why Roth conversions in 2025 are more important than ever—and how early retirees, those already retired, or those thinking about retirement could face massive tax regret if they don’t act soon.
Whether you're already in early retirement or planning to retire soon, you'll learn:
✅ Why the 2025 Roth conversion deadline is a critical ta...
Are you constantly worried about running out of money in retirement? You’re not alone—and the good news is, the truth might surprise you!
In this podcast, I reveal what most people get wrong about retirement spending, how rare it actually is to run out of money, and the real strategies that work—especially if you're retiring early. We’ll break down the 4% rule, portfolio withdrawal strategies, the guardrails approach, and real-worl...
Want to retire on $10K a month? This episode shows exactly how much you need saved in 2025 and beyond—factoring in taxes, healthcare, inflation, Social Security, and investment risk.
We’ll break down what it really takes to sustain $10,000 in monthly retirement income spending —whether you're aiming for early retirement, following the 4% rule (and why the 4% rule should really be used only as a very rough ballpark estimate), or jus...
⚠️ Are ACA subsidies really going away after 2025? If you're planning to retire early or already living off your investments, this could impact your healthcare costs in a big way. In this episode, I explain exactly what's happening with ACA subsidies in 2026—what's expiring, what's staying, and how you can still qualify for financial help through smart retirement planning and income strategies.
You’ll learn:
✅ What the “subsidy cli...
If you're in your 40s, 50s, or 60s, listen to this! In this podcast, I share 25 life lessons from people over 70 — timeless wisdom for navigating midlife, retirement planning, relationships, purpose, and happiness.
These life lessons are based on the powerful research of Dr. Karl Pillemer, author of 30 Lessons for Living, who interviewed over 1,000 older adults to uncover the most important advice they would pass on. I’ve distilled...
Many early retirees forget to factor in their adult children when planning retirement. From weddings and tuition to ongoing support, the financial impact can be substantial—especially when you no longer have a paycheck coming in. In this episode, I’ll walk you through how to plan for potential financial support, set healthy boundaries, and protect your own future—without guilt. Learn why planning ahead can be the difference between...
Should you claim Social Security early, wait until full retirement age, or delay until 70?
In this podcast, we walk through a real retirement case study and run the numbers to show how your claiming age affects your investments, taxes, and even your health insurance premiums.
📊 See why delaying may not always be the best choice—and how opportunity cost could erode your nest egg more than you realize.
💡 You’ll learn:
✅The real mat...
Want to pay WAY less for health insurance in early retirement? This follow-up to my previous very popular video (link below in watch next) shows how smart retirees legally slash ACA premiums by strategically managing their income. You'll learn how MAGI impacts subsidies, and see real scenarios using Healthcare.gov. Don’t overpay for healthcare—plan smarter and keep more of your money!
Is working longer really worth it?
In this episode, I break down 3 retirement stats and insights that could completely change the way you think about work, wealth, and health in retirement. If you're planning for early retirement, these numbers might just shift your whole retirement strategy.
Here's what you'll learn:
• Why 63.9 years is a critical number for your retirement health
• How the average person works 90,000 hours in the...
Are you wondering why it feels like everyone else is retiring early — and you're not? In this episode of Early Retirement Roadmap, we uncover the real reasons people delay early retirement, even when they have enough saved. Learn how to avoid the "one more year syndrome," stop chasing unrealistic retirement numbers, and discover 5 proven strategies to retire sooner than you think.
If you want to know how much you really need to ret...
What if you could save over $12,000 a year on healthcare—just by choosing the right account to withdraw from to fund your retirement? In this episode, I (early retiree and tax-planning nerd) break down the smartest way to structure your income before age 65 to maximize your ACA subsidy. You’ll learn why your taxable brokerage account might be your biggest retirement superpower, how MAGI works, and how to avoid the dreaded “coverage...
If you’re planning for retirement — or already enjoying your golden years — this episode is a must-listen. Dive into the five most common financial regrets retirees face, drawing from personal experience, hard-earned lessons, and recent data.
From not saving early enough to underestimating healthcare costs, I break down how you can sidestep these pitfalls and build a retirement that’s not just financially sound, but fulfilling.
Sti...
You’ve worked hard, saved diligently, and now retirement is here! But nobody warns you about the six major things that disappear the moment you leave the workforce. If you’re not prepared, these changes can hit harder than expected—but the good news? You can replace them with something even better!
In this episode of Early Retirement Roadmap, I’ll break down: ✅ The six things that vanish when you retire—and why they matter 🏆 ✅ How...
Planning for early retirement in 2025? Before you hand in your notice, this episode of Early Retirement Roadmap is your essential guide to navigating the biggest risks facing early retirees this year.
In it, I break down three critical threats — sequence of returns risk, rising inflation, and high market valuations, yes, even with the market downturn due to the Trump tariffs — and I share practical strategies to protect your retire...
Thinking about early retirement or already living it? This episode is your wake-up call — and your roadmap.
In this powerful and personal episode of The Early Retirement Roadmap, I talk about the retirement truths no one warns you about. Discover the real challenges behind the dream — from unexpected loneliness and identity loss to the surprising truth about pre-retirees' expectations vs. reality per a recent study by MassMutual (M...
Investing in index mutual funds sounds like a safe bet, right? Well, I thought so—until I got hit with an unexpected $17,000 tax bill.
In this episode of Early Retirement Roadmap, I break down the hidden tax trap in taxable mutual funds and why an ETF might be the smarter choice. Plus, I’ll share how tax-loss harvesting helped me fix my mistake and avoid future surprises. If you’re serious about early retirement, financial independ...
You’ve run the numbers, planned your finances, and dreamed of early retirement—but fear is still holding you back. You’re not alone! What if I run out of money? What about healthcare costs? Will I be bored? These fears are completely normal, and in this episode of Early Retirement Roadmap, I’ll help you tackle them head-on.
🌟 Here’s what you’ll learn: ✅ The #1 financial fear of early retirees—and how to overcome it 💸 ✅ How Monte ...
Planning to retire? Announcing your retirement isn’t as simple as picking a date and telling your boss—it’s about strategy, timing, and setting yourself up for success. In this episode of Early Retirement Roadmap, I’ll guide you through the complete retirement announcement process, so you can make a smooth, professional transition.
🌟 Here’s what we’ll cover: ✅ Choosing a date keeping tax benefits, health insurance, and bonuses 📅�...
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