Podcast

Episode Descriptions (By Order Listed in the Player)

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!