Early Retirement Roadmap

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!

Here is a link to the youtube version of this p...

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 📅�...

You’ve saved up, planned carefully, and are ready to enjoy your retirement—so what could possibly go wrong? In this episode of Early Retirement Roadmap, host Mike Upland reveals a critical mistake that could drain your retirement savings faster than you expect: Sequence of Returns Risk.

With today’s economic uncertainty—rising inflation, stock market volatility, and new tariffs shaking the financial landscape—understanding when you...

Thinking about early retirement but worried about health insurance? You’re not alone! Healthcare costs are one of the biggest reasons people delay retirement. But don’t let that stop you!

In this episode of Early Retirement Roadmap, I break down all your options for staying covered before Medicare, including: ✅ COBRA – Keep your employer’s plan (but at what cost?) 💼 ✅ ACA Marketplace Plans – Subsidies that can make coverage more a...

💰 Are you unknowingly making tax mistakes that could drain your retirement savings? In this episode of Early Retirement Roadmap, host Mike Upland breaks down the biggest retirement tax traps and how to avoid them.

📉 Learn how improper IRA and 401(k) withdrawals can push you into a higher tax bracket, trigger unexpected Social Security taxes, and even increase your Medicare premiums. We’ll also cover:

✅ The mistakes retirees make ...

Retirement planning isn’t one-size-fits-all, and the question of “How much money do I REALLY need?” can feel overwhelming. But don’t worry—I’ve got you covered!

In this episode of Early Retirement Roadmap, I’m diving deep into the essential factors that determine your retirement number, including: ✅ How to calculate your annual retirement spending 🔢 ✅ The 25x rule (and why it’s not enough for early retirees) 📊 ✅ The impact of inf...

🚀 You dream of ditching the 9-to-5 grind—but are you truly prepared to take the leap into early retirement? In this episode of Early Retirement Roadmap, host Mike Upland (early retiree at 55) walks you through the ultimate early retirement checklist—covering both financial and lifestyle readiness so you can retire with confidence.

🔹 Do you have enough savings to ...