Podcast

Episode Descriptions (By Order Listed in the Player)

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 72(t)—a little-known but completely legal loophole that allows penalty-free early withdrawals through SEPP (Substantially Equal Periodic Payments). This strategy could unlock your early retirement plans—but beware, the rules are strict and the risks are serious.

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 confidently and securely. From defining your retirement vision to setting a realistic retirement age, I cover everything you need to know for effective retirement planning.

6 Reasons to Retire AS SOON AS YOU CAN!

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. We’ll explore the opportunity cost of continued work, how your health and freedom are affected, and why arbitrary retirement goals may be holding you back from the financial independence you’ve already earned. I retired early at 55, and in this episode, I’ll share the reasons that finally made me take the leap—and how it’s changed my life, and that you should consider too.

The Top 10 Retirement Myths That Could Cost YOU Thousands!

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.

🚨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.

STOP Worrying About Running Out of Money in Retirement!

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 video, Mike reveals 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-world data that shows how most retirees end up with more money than they started with. Whether you're planning for early retirement or already living it, this episode will help you stop worrying and start living! Learn how to make your money last, without the stress.

How Much Do You REALLY Need to Retire on $10K a Month?

Want to retire on $10K a month? This episode goes over 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 just want a comfortable, worry-free lifestyle. You’ll also learn how to reduce your savings target without sacrificing your standard of living.

Will ACA Subsidies Disappear After 2025? What You NEED to Know!

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, Mike xplains 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.

If You’re in Your 40s, 50s, or 60s: 25 Life Lessons from 70+ Year-Olds

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. Mike has distilled those insights into 25 practical lessons tailored especially for those of us between ages 45 and 65. Whether you’re thinking about retirement, already retired, or simply looking to make the most of your next chapter, this episode is packed with real-world advice from those who’ve been there.

How Your Kids Can Derail Your Retirement (Unless You Plan for It)

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, Mike walks 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 peace and pressure in retirement.

Claim Social Security at 62, 67, or 70? The Answer May Surprise You!

In this video, 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.

How Early Retirees Can Pay WAY Less for Health Insurance!

Want to pay WAY less for health insurance in early retirement? This follow-up to Mike's previous very popular episode below The $12,900 Health Insurance Loophole for Early Retirees, shows how smart retirees legally slash ACA premiums by strategically managing how they are funding their retirement 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!

Retirement Stats That'll Make You Rethink Working Another Year

Is working longer really worth it?

In this episode, Mike breaks 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 and convince you of the value of retiring early.

Why You're Closer to Early Retirement Than You Think

Are you wondering why everyone else is retiring early — and how you can too? This episode reveals the real reasons people retire before 65 and how to fast-track your financial freedom. In this episode, Mike reveals why it seems like everyone else is retiring before you… and how you might be a lot closer to early retirement than you think.

The $12,900 Health Insurance Loophole for Early Retirees!

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, Mike (early retiree and tax-planning nerd) breaks 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 gap” in non-Medicaid expansion states. Perfect for anyone eyeing early retirement with a sharp eye on healthcare costs.

5 Retirement Regrets You’ll Want to Avoid

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.

What Vanishes When You Retire (And How to Get It Back!)

Discover how to design a purposeful, fulfilling life after leaving the 9-to-5. This podcast explores the hidden challenges of retirement—like losing identity, purpose, and routine—and shows you how to replace them with passion, health, and freedom. Perfect for anyone planning for early retirement or navigating life after work. Tune in for real stories, actionable tips, and a roadmap to your best chapter yet.

Thinking About Retiring Early in 2025? Think Again.

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 retirement portfolio. From building cash reserves to using TIPS bonds and dividend-paying ETFs, you'll learn how to retire with confidence even during market volatility.

Whether you're part of the FIRE movement or just ready to leave your 9–5, this episode will help you build a plan to retire early AND STAY retired.

The Retirement Wake-Up Call: What the Study AND My Story - Reveals!

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 (Mass Mutual).

How a Mutual Index Fund Cost Me $17K in Taxes (And How to Avoid This Mistake)

In this eye-opening episode of Early Retirement Roadmap, I share the surprising $17,000 tax bomb he never saw coming—and how you can avoid making the same costly mistake. Discover the hidden tax pitfalls of holding index mutual funds in taxable accounts, why ETFs might be a smarter choice, and how a simple switch and tax-loss harvesting strategy saved his portfolio (and sanity).

The Perfect Retirement Announcement: A Step-by-Step Guide

Ready to retire but unsure how to announce it without leaving money or goodwill on the table? In this actionable episode of the Early Retirement Roadmap podcast, host Mike Upland—an early retiree at 55—reveals step-by-step strategies to plan and execute a seamless retirement announcement. Discover how to pick the optimal retirement date (hint: year-end isn’t your only option!), maximize unused PTO, and avoid costly gaps in health insurance. Learn insider tips for navigating company policies, crafting a polished resignation letter, and handling reactions from bosses and colleagues—from enthusiastic supporters to skeptics.

Scared to Retire? Overcome Your RETIREMENT FEARS!

Are you ready to retire early but held back by fears of running out of money, healthcare costs, or losing your identity? In this empowering episode of the Early Retirement Roadmap podcast, Mike dives deep into the most common fears surrounding early retirement and shares actionable strategies to turn uncertainty into confidence. Discover how Monte Carlo simulations can stress-test your retirement portfolio against market crashes, ensuring your savings last decades. Learn why financial planners target an 80-85% success rate and how to balance safety with flexibility. Mike also tackles non-financial fears, including boredom, social isolation, and judgment from others, offering solutions like crafting intentional routines, pursuing passion projects, and building a supportive community.

The One Retirement Mistake that Could RUIN You!

In this episode, Mike discusses sequence of returns risk. Learn why withdrawing savings during market downturns (like the 2025 volatility fueled by tariffs, inflation, and economic uncertainty) can devastate your nest egg—even with careful planning. Discover 5 actionable strategies to protect your retirement, including cash buffers, flexible withdrawals, the bucket strategy, delaying Social Security, and generating side income. Perfect for pre-retirees or retirees seeking to safeguard their savings against market swings and inflation. Tune in to avoid costly mistakes and ensure your money lasts as long as you do! Subscribe to Early Retirement Roadmap on your favorite podcast platform or YouTube for expert tips on financial freedom.

Health Insurance Options for Early Retirement: What You NEED to Know

In this episode, Mike tackles a critical question for pre-65 retirees, what to do about Health Insurance. Discover actionable strategies to bridge the Medicare gap without draining your savings. Learn the pros and cons of COBRA, ACA Marketplace plans (with subsidy insights!), private insurance, short-term coverage, and part-time jobs offering benefits. Explore creative solutions like healthcare sharing programs, international insurance for expats, and maximizing Health Savings Accounts (HSAs) for tax-free medical expenses. Mike also emphasizes how prioritizing health—through stress reduction, exercise, and nutrition—can slash healthcare costs. Whether retiring at 55, 60, or earlier, this episode equips you with tools to navigate complex insurance choices, avoid financial pitfalls, and secure affordable coverage. Perfect for early retirees seeking clarity on COBRA costs, ACA subsidies, or creative alternatives like overseas plans. Subscribe to Early Retirement Roadmap on your favorite podcast platform or YouTube for expert tips on designing a worry-free retirement.

Retirement Tax Mistakes that Could Cost You Thousands

In this episode, Mike exposes retirement tax mistakes and how to avoid them. Learn how poor withdrawal strategies (like Bob and Linda’s $80,000 IRA mistake) trigger unnecessary taxes, inflate Medicare premiums, and tax up to 85% of Social Security benefits. Discover actionable tactics to optimize retirement income: blending withdrawals from traditional IRAs, Roth accounts, and taxable brokerage accounts to stay in lower tax brackets, leveraging Roth conversions, and using Qualified Charitable Distributions (QCDs) to slash RMDs. Dive into critical IRS rules for Required Minimum Distributions (RMDs) at 73, capital gains tax rates, and strategies like tax-loss harvesting. Perfect for retirees or pre-retirees aiming to maximize tax efficiency, reduce Social Security taxation, and avoid costly IRA withdrawal errors. Subscribe to Early Retirement Roadmap on your favorite podcast platform or YouTube for expert tips on turning retirement savings into lasting wealth!

How Much Do You REALLY Need to Retire?

In this episode, Mike answers the critical question: "How Much Money Do I REALLY Need to Retire?" Uncover actionable strategies to calculate your retirement number, avoid common pitfalls like inflation erosion, and balance lifestyle goals with financial security. Learn how the 4% rule and 25x expenses guideline work (and their limitations!), why healthcare costs and discretionary spending demand extra savings, and how to adjust withdrawal rates for 30-40+ year retirements. Discover tools like Boldin.com to stress-test your plan against market volatility, long-term care costs, and legacy goals. Mike shares real-world examples—from gas price inflation to Jane and John’s retirement scenarios—to illustrate key principles. Perfect for early retirees or planners seeking clarity on emergency funds, tax-efficient withdrawals, and validating their strategy with financial advisors. Subscribe to Early Retirement Roadmap on your favorite podcast platform or YouTube for step-by-step guidance on turning retirement dreams into reality.

Ready to Ditch the 9-to-5? Your Early Retirement Checklist

In this episode of Early Retirement Roadmap, Mike reveals the "Early Retirement Checklist" to assess if you’re truly ready to leave the 9-to-5 grind. Learn critical financial benchmarks like the 25x expenses rule, debt-free strategies, and why an emergency fund is vital to survive market downturns. Discover penalty-free income sources (Rule of 55, rental income, taxable accounts) and health insurance solutions (ACA subsidies, part-time work benefits). Beyond finances, Mike dives into non-financial readiness: crafting a purposeful retirement vision, emotional preparedness, and building a support network. Perfect for FIRE movement followers or anyone weighing early retirement risks—from aligning savings with travel goals to avoiding boredom and burnout. Subscribe to Early Retirement Roadmap on your favorite podcast platform or YouTube for actionable steps to thrive in your post-work life!

10 Powerful Reasons to Retire Early (Don't Wait Too Long!)

In this episode, Mike unveils "10 Powerful Reasons to Retire Early (Don't Wait Too Long!)". Discover why prioritizing health, reclaiming time, and escaping corporate stress are just the start. Mike shares personal insights from his 29-year Healthcare IT career, revealing how early retirement transformed his well-being, reignited passions, and freed him from migraines and insomnia. Learn to maximize vibrant years, craft a legacy built on memories (not meetings), and embrace financial freedom as a lifestyle—not just a savings goal. Perfect for anyone yearning to trade 9-5 grind for travel, hobbies, and purpose. Dive into actionable motivation to start planning now, avoid regret, and design a life aligned with what truly matters. Subscribe to Early Retirement Roadmap on your favorite podcast platform or YouTube for inspiration to leap into your next chapter!