Early Retirement Roadmap

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 – Su...

💰 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 c...

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 e...

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...

🚀 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...