Early Retirement Roadmap

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.
#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
 
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🎥 Prefer a visual breakdown? Click here to watch this episode on my YouTube Channel: Early Retirement Roadmap.
🌐  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!
🎥 Early Retirement Roadmap is also available on YouTube! 
🌐  Visit MikeUpland.com – Connect with Mike & explore retirement resources 
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How Much Do You REALLY Need to Retire?

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 inflation, healthcare, and lifestyle choices on your savings 💸✅ Common mistakes that can derail your retirement 🚧✅ Smart strategies to make your money last 35+ years ⏳
I’ll also share my personal experience retiring at 55 years old, the lessons I learned along the way, and how you can create a plan that gives you true financial freedom.
👉 Want to stress-test your retirement plan? I highly recommend Boldin.com (think TurboTax for retirement planning) to model different financial scenarios and see if you're really ready.
🔔 Don’t forget to subscribe for more tips on early retirement! If you found this episode helpful, please leave a review—it really helps the show grow!
🎥 Watch the visual version of this episode on my YouTube channel: Early Retirement Roadmap.
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🌐  MikeUpland.com – Connect with Mike & explore retirement resources
🚀 Start planning your dream retirement today!
 
 

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

Are You REALLY Ready to Retire Early? This Checklist Will Tell You!
🚀 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 sustain a long retirement?🔹 Is your investment strategy strong enough to outpace inflation?🔹 Have you planned for health insurance and unexpected expenses?🔹 More importantly—are you mentally and emotionally ready for this big life change?
Mike breaks it all down and shares personal insights from his own early retirement journey—so you don’t have to figure it out alone. Plus, listen to the next episode, where we’ll dive deeper into how much you really need to retire early.
🎧 Subscribe now so you don’t miss it!
👉 Resources & Links:🔗 MikeUpland.com – Connect with Mike & explore retirement resources📺Watch Mike and this content on video here.☕ Enjoy the show? Support me! Buy me a cup of coffee here! ap for more insights
 

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

🚀 What if you could reclaim your time, health, and freedom—starting now?
In this episode of Early Retirement Roadmap, host Mike Upland, a seasoned early retiree, shares 10 powerful reasons why retiring early might be the smartest move you can make. From prioritizing your health to maximizing your time, he breaks down how early retirement can lead to a life of freedom, fulfillment, and opportunity.
🔹 Feeling stuck in the daily grind?🔹 Wondering if you can really afford to retire early?🔹 Dreaming of a life with no alarms and total flexibility?
Mike shares personal insights, expert advice, and mindset shifts to help you take control of your future. Whether you're already planning for early retirement or just starting to explore the idea, this episode is packed with actionable takeaways.
🎧 Next up: In the next episode, we’ll cover financial and non-financial signs that you’re ready to retire early, and after that, we’ll dive into how to determine how much you really need. Don’t miss it!
🎙️Enjoying the podcast? Help keep it going!☕Buy me a coffee here. 
📺 Watch Mike and this content on video here.  
 
👉 Connect with Mike at mikeupland.com and check out his YouTube channel Early Retirement Roadmap for even more tips.