by Mike Upland
Welcome to the Early Retirement Roadmap podcast, your audio guide to preparing for and thriving in early retirement! If you’re dreaming of retiring early but feeling overwhelmed about where to start, or if you’re already retired and looking to make the most of your freedom, you’re in the right place. I’m your host Mike Upland, and I successfully retired at 55. Through this podcast, I share my personal early retirement journey—the victories, the challenges, and all the essential lessons I’ve learned along the way. Each episode delivers practical strategies and real-world insights on crucial topics like financial planning, developing the right mindset, and finding purpose in retirement. You’ll hear candid discussions about the realities of early retirement, actionable tips for building wealth, and inspiring stories to help you navigate your own path to early retirement. Whether you’re just starting to explore early retirement or fine-tuning your existing plans, this podcast provides the roadmap you need to build a financially secure and fulfilling post-career life. For visual guides and additional content, be sure to check out the Early Retirement Roadmap YouTube channel, where I share complementary videos and resources to support your early retirement journey. Your early retirement journey starts here—subscribe now to ensure you never miss an episode!
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Publishing Since
2/19/2025
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April 28, 2025
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 gap” in non-Medicaid expansion states. Perfect for anyone eyeing early retirement with a sharp eye on healthcare costs. 🔔 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 my Early Retirement Roadmap YouTube channel for more insights and inspiration. 🌐 Visit mikeupland.com – Connect with me & explore retirement resources including all my videos and blog articles.
April 22, 2025
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
April 14, 2025
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!
Ari Taublieb, CFP®, MBA
James Conole, CFP®
Benjamin Brandt CFP®, RICP®
Jason Parker
BiggerPockets
Audacy
Marketplace
Morningstar
Condé Nast Traveler
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