Early Retirement Roadmap

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.
Stick around for the final regret — it's one even savvy retirees often miss.
🔔 If you found this episode helpful, please follow or subscribe & leave a review, or support me with a cup of coffee here. 
 🎥 When you’re not on the go, check out Mike’s Early Retirement Roadmap YouTube channel for more insights and inspiration.  And for my real life stories and experience in early retirement, check out my Youtube channel Early Retired & Real. 
🌐  Visit MikeUpland.com – Connect with Mike & explore retirement resources

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

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 to rediscover purpose and avoid feeling lost 💡✅ Why having structure & routine in retirement is crucial 📅✅ How to replace career achievements with new personal goals 🏅✅ The surprising impact of losing your work identity—and how to rebuild it 🎭✅ How to maintain social connections when your work network disappears 👥
I’ll also share my personal experience transitioning from my 30-year career to early retirement and the lessons I learned along the way!
🔔 If you found this helpful, please subscribe & leave a review, or support me with a cup of coffee here. 
🎥 When you’re not on the go, check out Mike’s Early Retirement Roadmap YouTube channel for more insights and inspiration.  And for my real life stories and experience in early retirement, check out my Youtube channel Early Retired & Real. 
🌐  Visit MikeUpland.com – Connect with Mike & explore retirement resources
🚀 Retirement isn’t the end—it’s a new beginning. Let’s make it amazing!

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.
What You’ll Learn:
How a market downturn at the wrong time can destroy your retirement plans
Why inflation silently eats away at your wealth over time
Key investing metrics like the CAPE ratio and Buffett Indicator
How to create a resilient early retirement strategy that lasts decades
🔔 If you found this episode helpful, please follow or subscribe & leave a review, or support me with a cup of coffee here. 
 🎥 When you’re not on the go, check out Mike’s Early Retirement Roadmap YouTube channel for more insights and inspiration.  And for my real life stories and experience in early retirement, check out my Youtube channel Early Retired & Real. 
🌐  Visit MikeUpland.com – Connect with Mike & explore retirement resources

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).
You’ll learn:
Why retirement feels unstructured or even empty for many
The #1 activity most retirees do daily (hint: it's not what they planned)
How to prepare emotionally, socially, and mentally — not just financially
The 3 characteristics of thriving retirees
Mike’s candid and honest sharing of his own retirement experiences
If you’re searching for early retirement advice, wondering how to build purpose after leaving work, or asking what makes a meaningful retirement, this episode is for you.
🔔 If you found this helpful, please subscribe & leave a review, or support me with a cup of coffee here. 
🎥 When you’re not on the go, check out Mike’s Early Retirement Roadmap YouTube channel for more insights and inspiration.  And for my real life stories and experience in early retirement, check out my Youtube channel Early Retired & Real. 
🌐  Visit MikeUpland.com – Connect with Mike & explore retirement resources.
 

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

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 independence, and smart investing, you won’t want to miss this!
🔔 If you found this helpful, please subscribe & leave a review, or support me with a cup of coffee here. 
🎥 When you’re not on the go, check out Mike’s Early Retirement Roadmap YouTube channel for more insights and inspiration.  And for my real life stories and experience in early retirement, check out my Youtube channel Early Retired & Real. 
🌐  Visit MikeUpland.com – Connect with Mike & explore retirement resources.

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

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 📅💰 in mind✅ How to maximize PTO payouts and avoid leaving money on the table 🏖️✅ How much notice to give (and why too much can backfire) 🚨✅ How to handle your boss’s reaction and preparation 🤯✅ What to expect from co-workers’ reactions and how to respond—from excitement to skepticism 🤔✅ The importance of planning ahead for a stress-free, rewarding exit 🚀
I’ll also share some of my personal experiences announcing my early retirement at 55. 
🔔 If you found this helpful, please subscribe & leave a review!🎥 When you’re not on the go, check out Mike’s Early Retirement Roadmap YouTube channel for more insights and inspiration.  And for my real life stories and experience in early retirement, check out my Youtube channel Early Retired & Real. 
☕ Enjoyed this show? Support me! Buy me a cup of coffee here! 🌐  Visit MikeUpland.com – Connect with Mike & explore retirement resources
🚀 Make your retirement announcement with confidence!

Scared to Retire? Overcome Your RETIREMENT FEARS!

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 Carlo simulations can give you confidence in your retirement plan 🔢✅ Why healthcare costs don’t have to be a dealbreaker 🏥✅ Eliminate debt for a stress-free retirement ✅✅ The secret to avoiding boredom and creating a fulfilling post-career life 🎨🌍✅ How to handle criticism from family & friends who don’t "get" early retirement 🤔
I’ll also share my personal experience retiring at 55 years old and how I knew for sure that I was ready.
👉 Links to Resources mentioned:
✅Boldin.com
✅Empower
✅Article: Best Retirement Calculators
✅ Watch my video on all your healthcare options prior to Medicare or listen to the podcast 
🔔 If you found this helpful, please subscribe & leave a review!
🎥 When you’re not on the go, check out Mike’s Early Retirement Roadmap YouTube channel for more insights and inspiration.  And for my real life stories and experience in early retirement, check out my Youtube channel Early Retired & Real. 
Support me by buying a cup of coffee here! ☕🌐  Visit MikeUpland.com – Connect with Mike & explore retirement resources
🚀 Your dream retirement is possible—don’t let fear hold you back!

The ONE Retirement Mistake That Could RUIN You!

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 withdraw from your investments is just as important as how much you withdraw.
Tune in as Mike breaks down:✅ Why withdrawing money during a market downturn can derail your retirement✅ The shocking impact of the 2008 crash on retirees—and why history may repeat itself✅ 5 powerful strategies to safeguard your nest egg, including the cash buffer strategy, flexible withdrawals, and the bucket method
Don’t let one mistake ruin your financial future! Whether you're planning for retirement or already there, this episode will help you make smart decisions to keep your money lasting as long as you do.
🎧 Listen now and take control of your retirement future!
🔔 Subscribe/Follow for more financial insights & leave a review if you found this episode helpful.
🎥 When you’re not on the go, check out Mike’s Early Retirement Roadmap YouTube channel for more insights and inspiration.  And for my real life stories and experience in early retirement, check out my Youtube channel Early Retired & Real. 
#RetirementPlanning #FinancialFreedom #EarlyRetirement #Investing #WealthManagement#SequenceOfReturns #SafeWithdrawalRate #StockMarketRisk #RetirementWithdrawals #EconomicUncertainty

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

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 affordable 💵✅ Private Insurance – Is it worth the higher cost? 🤔✅ Short-Term Plans – A risky but potentially viable bridge to Medicare ⏳✅ Part-Time Work with Benefits – Companies that offer insurance for fewer hours 🏢✅ Creative Solutions – Health sharing plans, expat insurance, and HSAs ✈️
 Plus, I’ll explain how taking care of your physical health can also protect your financial health in retirement!
👉 Resources & Links mentioned: 
 
1. COBRA Information - Click here to learn more about COBRA continuation coverage and eligibility requirements
 
2. Affordable Care Act (ACA) Marketplace: Click here to find out about ACA plans and check your eligibility for subsidies
 
3. Private Health Insurance - Compare private insurance options via ehealthinsurance.com or healthcare.com
 
4. Also, can go to ehealthinsurance.com to view short-term health insurance options too
 
5. Health sharing programs, Medishare, Zion Health & Christian Health Ministries
 
6. International health insurance options, Cigna Global & internationalinsurance.com
 
7. Click here for IRS Info about Health Savings Accounts
 
8. Click here for a list of employers that offer part-time jobs with health benefits
 
🎙️ If you found this podcast helpful, please subscribe & leave a review or support this new podcast show by buying me a cup of coffee here! 
🎥 Prefer a visual breakdown? Click here to watch this episode on my YouTube Channel: Early Retirement Roadmap. 
🎥 When you’re not on the go, for my real life stories and experience in early retirement, check out my Youtube channel Early Retired & Real. 
🌐  MikeUpland.com – Connect with Mike & explore retirement resources
🚀 Don’t let healthcare costs keep you from the retirement you deserve!

Retirement Tax Mistakes that Could Cost You Thousands!

💰 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 when withdrawing from their retirement accounts✅ How strategic withdrawals can lower your lifetime tax bill✅ What you MUST know about Required Minimum Distributions (RMDs)✅ How to use Roth Conversions and Qualified Charitable Distributions (QCDs) to reduce taxes✅ Case study: How Bob & Linda lost thousands—and what they should have done instead
Whether you're already retired or planning for the future, these tax-smart retirement strategies can help you keep more of your hard-earned money.
🎧 Listen now to avoid costly mistakes and make your retirement savings last longer!
🔗 Don’t forget to subscribe or follow, rate, and review so more people can benefit from these strategies!
🎥 When you’re not on the go, check out Mike’s Early Retirement Roadmap YouTube channel for more insights and inspiration.  And for my real life stories and experience in early retirement, check out my Youtube channel Early Retired & Real. 
🌐  Visit MikeUpland.com – Connect with Mike & explore retirement resources 
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